Name: 1438-82-0|1,1,1,3,3-Pentamethyldisiloxane|95% GC
Brand: Ambeed
SKU: A917895
Rating: 92 (35 reviews)

1
[ 106-92-3 ]
[ 1438-82-0 ]
[ 18044-44-5 ]

Yield	Reaction Conditions	Operation in experiment
94%	With pentakis(t-butyl isocyanide)iron In neat (no solvent) at 20℃; for 24h;
91%	With cobalt pivalate; 1-adamantanecarbonitrile In 1,2-dimethoxyethane at 50℃; for 23h;
	With platinum

Reference： [1]Sanagawa, Atsushi; Nagashima, Hideo [Organometallics, 2018, vol. 37, # 17, p. 2859 - 2871]
[2]Noda, Daisuke; Tahara, Atsushi; Sunada, Yusuke; Nagashima, Hideo [Journal of the American Chemical Society, 2016, vol. 138, # 8, p. 2480 - 2483]
[3]Plueddemann; Fanger [Journal of the American Chemical Society, 1959, vol. 81, p. 2632,2633]

2
[ 100-42-5 ]
[ 1438-82-0 ]
[ 3439-15-4 ]

Yield	Reaction Conditions	Operation in experiment
99%	With 1-adamantyl isocyanide; iron biscyclooctatetraene In neat (no solvent) at 20℃; for 23h; Glovebox; Inert atmosphere; Sealed tube;	27 Hydrosilylation of Various Alkenes with 1,1,3,3,3-pentamethyldisiloxane Using AdNC Ligand In a nitrogen-blanketed glove box, 2 mg (0.01 mmol) of Fe(COT)2 in Synthesis Example 2, 3 mg (0.02 mmol) of AdNC, 254 μL (1.3 mmol) of 1,1,3,3,3-pentamethyldisiloxane, and 115 μL (1.0 mmol) of styrene were added to a screw-top vial with a stirrer. The vial was closed, after which the contents were stirred at room temperature (RT) for 23 hours. After cooling, analysis was made by 1H-NMR spectroscopy to determine the structure and yield of the product. As a result, it was confirmed that the signal assigned to the reactant disappeared completely. Instead, a multiplet near 0.89 ppm indicative of the signal assigned to the desired product was observed, from which a yield was computed. The results are shown in Table 8.
99%	With 1-adamantyl isocyanide; iron(II) acetate at 80℃; for 3h; Inert atmosphere;	1 [Example 1] Hydrosilylation Reaction Using Iron Acetate and 1-Isocyanoadamantane [Example 1] Hydrosilylation Reaction Using Iron Acetate and 1-Isocyanoadamantane (0196) A 20 mL Schlenk flask was charged with 5 mg (0.03 mmol) of iron acetate (commercial product) as a catalyst precursor, 10 mg (0.06 mmol) of 1-isocyanoadamantane as a ligand, and 254 μL (1.3 mmol) of 1,1,3,3,3-pentamethyldisiloxane, which were stirred at 80° C. for 1 hour to activate the catalyst. (0197) After cooling, 115 μL (1.0 mmol) of styrene as a substrate was added, followed again by stirring at 80° C. for 3 hours. After cooling, 1.0 mmol of anisole as an internal standard was added to the reaction solution and stirred. A minute amount of the solution was dissolved in deuteronchloroform, passed through an alumina column to remove the catalyst, and analyzed by 1H-NMR spectroscopy to determine the structure and yield of the product. (It is noted that in the following Examples, a test sample was prepared according to the same procedure and analyzed by 1H-NMR spectroscopy.) (0198) As a result, it was confirmed that the signal assigned to the ethylene site of styrene as the reactant disappeared completely. Instead, a multiplet at 0.89 ppm indicative of the signal assigned to proton on silicon-adjoining carbon in the desired product, 1,1,3,3,3-pentamethyl-3-phenethyldisiloxane was observed. The results are shown in Table 1. (0199) 1H-NMR (396 MHz, CDCl3) δ: 0.07 (s, 6H), 0.09 (s, 9H), 0.86-0.92 (m, 2H), 2.61-2.68 (m, 2H), 7.13-7.33 (m, 5H)
98%	With bis(cyclooctatetraene)(1-isocyanoadamantane)iron; 1-adamantyl isocyanide In neat (no solvent) at 25℃; for 23h;

95%	With iron(II) pivalate; 1-adamantanecarbonitrile In neat (no solvent) at 50℃; for 3h;
95%	With pentakis(t-butyl isocyanide)iron In neat (no solvent) at 20℃; for 24h;
	In isopropyl alcohol Heating;
	In isopropyl alcohol
	With C₄₂H₆₄FeN₂Si₄ In 1,2-dimethoxyethane at 80℃; for 24h; Schlenk technique; Inert atmosphere;	6 [Example 6] Hydrosilylation Reaction of Styrene with 1,1,1,3,3-pentamethyldisiloxane Using Iron Complex C A 20-mL Schlenk tube equipped with a magnetic stirrer was heat dried while pumping to a vacuum of 5 Pa before its interior was purged with argon atmosphere. Into the Schlenk tube, iron complex C (7.7 mg, 0.01 mmol) was admitted as catalyst. To the tube, styrene (104 mg, 1.0 mmol) was added, after which 1,1,1,3,3-pentamethyldisiloxane (163 mg, 1.1 mmol) and dimethoxyethane (3.6 mg, 0.04 mmol) were added. The solution was stirred at 80° C. for 24 hours. The solution was cooled, to which anisole (108 mg, 1.0 mmol) was added as internal standard. By 1H-NMR spectroscopy, the geometry and yield of the product were determined. The results are shown as Entry 3 in Table 1
66 %Spectr.	With Pt single atoms supported microporous metal-organic frameworks In toluene at 110℃; for 24h; regioselective reaction;
	Stage #1: styrene; 1,1,1,3,3-pentamethyl-1,3-disiloxane at 60℃; Inert atmosphere; Stage #2: With 1,1,1,5,5,5-hexamethyl-3-(trimethylsiloxy)trisiloxanyl-3-methylene isocyanide at 60℃; for 12h; Inert atmosphere;	3 [Example 3] Hydrosilylation reaction of styrene and 1,1,1,3,3-pentamethyldisiloxane using an iron catalyst In a 100 mL three-necked flask,Add iron isopalmitate (283 mg, 0.5 mmol) and addIt was replaced with an argon atmosphere. Here,Styrene (5.21 g, 50 mmol),Add 1,1,1,3,3-pentamethyldisiloxane (9.65 g, 65 mmol) and addThe temperature was raised to 60 ° C. and the mixture was stirred. The isocyanide compound (678 mg, 2.0 mmol) synthesized in Example 2 was added thereto, and the mixture was stirred at 60 ° C. for 12 hours to produce an addition product having a GC yield of 44% and a dehydrogenation silylation product having a GC yield of 15%. I got the thing. The reaction formula is shown below.

Reference： [1]Current Patent Assignee: KYUSHU UNIVERSITY; SHIN-ETSU CHEMICAL CO., LTD. - US2017/260216, 2017, A1 Location in patent: Paragraph 0197; 0234-0235; 0238; 0275; 0285-0286; 0291; 0296
[2]Current Patent Assignee: KYUSHU UNIVERSITY; SHIN-ETSU CHEMICAL CO., LTD. - US2017/233417, 2017, A1 Location in patent: Paragraph 0196-0199
[3]Sunada, Yusuke; Noda, Daisuke; Soejima, Hiroe; Tsutsumi, Hironori; Nagashima, Hideo [Organometallics, 2015, vol. 34, # 12, p. 2896 - 2906]
[4]Noda, Daisuke; Tahara, Atsushi; Sunada, Yusuke; Nagashima, Hideo [Journal of the American Chemical Society, 2016, vol. 138, # 8, p. 2480 - 2483]
[5]Sanagawa, Atsushi; Nagashima, Hideo [Organometallics, 2018, vol. 37, # 17, p. 2859 - 2871]
[6]Andrianov,K.A. et al. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1967, p. 307 - 312][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1967, # 2, p. 321 - 329]
[7]Andrianov,K.A. et al. [Journal of Organometallic Chemistry, 1965, vol. 4, p. 360 - 370]
[8]Current Patent Assignee: KYUSHU UNIVERSITY; SHIN-ETSU CHEMICAL CO., LTD. - US10363551, 2019, B2 Location in patent: Paragraph 25; 26; 27
[9]Rivero-Crespo, Miguel; Oliver-Meseguer, Judit; Kapłońska, Klaudia; Kuśtrowski, Piotr; Pardo, Emilio; Cerón-Carrasco, José Pedro; Leyva-Pérez, Antonio [Chemical Science, 2020, vol. 11, # 31, p. 8113 - 8124]
[10]Current Patent Assignee: KYUSHU UNIVERSITY; SHIN-ETSU CHEMICAL CO., LTD. - JP2021/42177, 2021, A Location in patent: Paragraph 0100

3
[ 1438-82-0 ]
[ 1438-79-5 ]
[ 6231-68-1 ]

Yield	Reaction Conditions	Operation in experiment
93%	With C₂₉H₂₃Br₂CoN₂; trimethylsilylmethyllithium In toluene; pentane at 22℃; for 1h; Inert atmosphere;
79%	With cobalt pivalate; 1-adamantanecarbonitrile In 1,2-dimethoxyethane at 80℃; for 24h;

Reference： [1]Lee, Kangsang L. [Angewandte Chemie - International Edition, 2017, vol. 56, # 13, p. 3665 - 3669][Angew. Chem., 2017, # 129, p. 3719 - 3723]
[2]Noda, Daisuke; Tahara, Atsushi; Sunada, Yusuke; Nagashima, Hideo [Journal of the American Chemical Society, 2016, vol. 138, # 8, p. 2480 - 2483]
[3]Souchek,I. et al. [Doklady Chemistry, 1975, vol. 222, p. 305 - 307][Dokl. Akad. Nauk SSSR Ser. Khim., 1975, vol. 222, p. 128 - 131]

4
[ 1438-82-0 ]
[ 754-05-2 ]
[ 54222-74-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	With cobalt pivalate; 1-adamantyl isocyanide at 80℃; for 24h; Inert atmosphere;	36 Example 36] Hydrosilylation Reaction with Vinyltrimethylsilane Example 36] Hydrosilylation Reaction with Vinyltrimethylsilane (0253) A screw-top vial was charged with 8 mg (0.03 mmol) of cobalt pivalate in Synthesis Example 4 as a catalyst, 15 mg (0.09 mmol) of 1-isocyanoadamantane as a ligand, 254 μL (1.3 mmol) of 1,1,3,3,3-pentamethyldisiloxane, and 145 μL (1.0 mmol) of vinyltrimethylsilane. The contents were stirred at 80° C. for 24 hours. After cooling, analysis was made by 1H-NMR spectroscopy to determine the structure and yield of the product. As a result, it was confirmed that the signal assigned to the ethylene site of vinyltrimethylsilane as the reactant disappeared completely. Instead, the signal assigned to the desired product, 1,1,1,3,3-pentamethyl-3-(2-trimethylsilylethyl)disiloxane was observed, from which a yield was computed. The results are shown in Table 12. (0254) 1H-NMR (396 MHz, CDCl3) δ: -0.03 (s, 9H), 0.03 (s, 6H), 0.06 (s, 9H), 0.38 (s, 4H)

Reference： [1]Current Patent Assignee: KYUSHU UNIVERSITY; SHIN-ETSU CHEMICAL CO., LTD. - US2017/233417, 2017, A1 Location in patent: Paragraph 0253-0254
[2]Souchek,I. et al. [Doklady Chemistry, 1975, vol. 222, p. 305 - 307][Dokl. Akad. Nauk SSSR Ser. Khim., 1975, vol. 222, p. 128 - 131]

5
[ 826-62-0 ]
[ 1438-82-0 ]
[ 127683-85-6 ]

Reference： [1]Journal of Organometallic Chemistry,1991,vol. 402,p. 145 - 153

6
[ 1438-82-0 ]
[ 107-46-0 ]
[ 1873-88-7 ]
[ 107-51-7 ]
[ 141-62-8 ]
[ 2895-07-0 ]
[ 77606-50-9 ]

Reference： [1]Journal of Organometallic Chemistry,1982,vol. 238,p. 87 - 98

7
[ 78593-40-5 ]
[ 1438-82-0 ]
3-[(Z)-2-(1,1,3,3,3-Pentamethyl-disiloxanyl)-vinyl]-quinoline [ No CAS ]
3-[(E)-2-(1,1,3,3,3-Pentamethyl-disiloxanyl)-vinyl]-quinoline [ No CAS ]

Reference： [1]Chemistry Letters,1998,p. 443 - 444

8
[ 1438-82-0 ]
[ 536-74-3 ]
[ 208661-38-5 ]

Yield	Reaction Conditions	Operation in experiment
75%	With dimanganese decacarbonyl In decalin at 20℃; for 12h; Schlenk technique; Inert atmosphere; Irradiation; stereoselective reaction;
	With sodium iodide 1.) 0 deg C, 2 h; 2.) r.t., 2 h; Yield given. Multistep reaction;

Reference： [1]Liang, Hao; Ji, Yun-Xing; Wang, Rui-Han; Zhang, Zhi-Hao; Zhang, Bo [Organic Letters, 2019, vol. 21, # 8, p. 2750 - 2754]
[2]Mori, Atsunori; Takahisa, Eisuke; Kajiro, Hiroshi; Hirabayashi, Kazunori; Nishihara, Yasushi; Hiyama, Tamejiro [Chemistry Letters, 1998, # 5, p. 443 - 444]

9
[ 1438-82-0 ]
[ 332426-11-6 ]
dimethyl 3-[dimethyl(trimethylsiloxy)silyl]methyl-4-methyl-spiro[4,5]decane-1,1-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With NaB(3,5-(CF₃)2C₆H₃) In 1,2-dichloro-ethane at 20℃; for 0.666667h;

Reference： [1]Wang; Chakrapani; Stengone; Widenhoefer [Journal of Organic Chemistry, 2001, vol. 66, # 5, p. 1755 - 1760]

10
[ 1438-82-0 ]
[ 56428-93-4 ]

Yield	Reaction Conditions	Operation in experiment
99%	With Au/TiO₂ In lithium hydroxide monohydrate at 20℃; for 5h; Irradiation;	7 Example 7. Preparation of compound hydroxy-pentamethyldisiloxane In a 10 mL reaction flask, 5 mL of water was added, followed by 50 mM pentamethyldisiloxane and 0.25 mg of Au-TiO2, and magnetic stirring was performed at room temperature for 5 h under the induction of visible light.After the reaction finished, the catalyst was recovered by centrifugation, and 10 ml of ethyl acetate was added for extraction, and the extraction was performed twice.The organic phases were combined, and the organic phase was distilled under reduced pressure at 30 to 40 °C to remove the organic solvent,The target compound hydroxy-pentamethyldisiloxane (99% yield, 98% purity) was obtained by column chromatography using petroleum ether containing 10% ethyl acetate by volume. The gas-mass spectrogram of the product is shown in Figure 10, and the structural formula is as follows:
	hydrolysis;
	With wild-type cytochrome P₄₅₀ monooxygenase from Bacillus magaterium In aq. phosphate buffer; acetonitrile at 20℃; for 24h; Enzymatic reaction;

Reference： [1]Current Patent Assignee: UNIV XI AN JIAOTONG - CN114262341, 2022, A Location in patent: Paragraph 0067-0069
[2]Grzelka, Agnieszka; Chojnowski, Julian; Cypryk, Marek; Fortuniak, Witold; Hupfield, Peter C.; Taylor, Richard G. [Journal of Organometallic Chemistry, 2002, vol. 660, # 1, p. 14 - 26]
[3]Arnold, Frances H.; Bähr, Susanne; Brinkmann-Chen, Sabine; Garcia-Borràs, Marc; Houk, K. N.; Katsoulis, Dimitris E.; Roberts, John M. [Angewandte Chemie - International Edition, 2020, vol. 59, # 36, p. 15507 - 15511][Angew. Chem., 2020, vol. 132, # 36, p. 15637 - 15641,5]

11
[ 1438-82-0 ]
[ 111928-38-2 ]
[ 152595-28-3 ]

Yield	Reaction Conditions	Operation in experiment
98.8%	In toluene; xylene at 112℃; for 48h;

Reference： [1]Amako, Masaaki; Schinkel, Jonathan; Freiburger, Lee; Brook, Michael A. [Dalton Transactions, 2005, # 1, p. 74 - 81]

12
[ 887947-25-3 ]
[ 1438-82-0 ]
C₅₉H₆₉F₉O₉Si₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	In toluene; xylene at 20℃;

Reference： [1]Reddy, R. Amaranatha; Dantlgraber, Gert; Baumeister, Ute; Tschierske, Carsten [Angewandte Chemie - International Edition, 2006, vol. 45, # 12, p. 1928 - 1933]

13
CH₂=C(CH₃)CH₂O(EO)3CH₃ [ No CAS ]
[ 1438-82-0 ]
[ 719278-80-5 ]

Yield	Reaction Conditions	Operation in experiment
	With chloroplatinate In toluene at 70 - 110℃; for 3.5h;	1 Example 1 Example 1 [0043] A reaction was carried out at a Vi/SiH ratio of 1/1.2. [0044] In a flask, 218 g, i.e., 1 mole, of the polyether of the following formula (5) and 0.5 g of a 0.5% solution of chloroplatinic acid in toluene were placed, and heated to 70 degrees C. under a nitrogen flow. [CHEMMOL-00007] [0045] Then, 178 g, i.e., 1.2 moles, of the pentamethyldisiloxane of the formula (6) having a boiling point of 85 degrees C. were added dropwise at 70 degrees C. in 30 minutes. During the addition, the temperature in the flask rose to 90 degrees C. Subsequently, the temperature was raised to 110 degrees C. by heating and the reaction was allowed to continue at 110 degrees C. for 3 hours. [CHEMMOL-00008] [0046] The reaction solution thus obtained was subjected to distillation under a vacuum of about 10 mmHg to obtain 340 g of the polyethersilicone of the formula (7), hereinafter referred to as polyethersilicone A, was obtained. [CHEMMOL-00009]

Reference： [1]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD. - US2004/143128, 2004, A1 Location in patent: Page 3

14
CH₂=C(CH₃)CH₂O(EO)4CH₃ [ No CAS ]
[ 1438-82-0 ]
[ 719278-82-7 ]

Yield	Reaction Conditions	Operation in experiment
	With chloroplatinate In toluene at 70 - 110℃; for 3.5h;	3 Example 3 Example 3 [0052] A reaction was carried out at a Vi/SiH ratio of 1/1.2. [0053] In a flask, 262 g, i.e., 1 mole, of the polyether of the formula (10) and 0.5 g of a 0.5% solution of chloroplatinic acid in toluene were placed, and heated to 70 degrees C. under a nitrogen flow. [CHEMMOL-00012] [0054] Then, 178 g, i.e., 1.2 moles, of the same pentamethyldisiloxane of the formula (6) as the one used in Example 1 having a boiling point of 85 degrees C. were added dropwise at 70 degrees C. in 30 minutes. During the addition, the temperature in the flask rose to 90 degrees C. Subsequently, the temperature was raised to 110 degrees C. by heating and the reaction was allowed to continue at 110 degrees C. for 3 hours. [0055] The reaction solution thus obtained was subjected to vacuum distillation to obtain 370 g of the polyethersilicone of the formula (11), hereinafter referred to as polyethersilicone C, was obtained. [CHEMMOL-00013]

Reference： [1]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD. - US2004/143128, 2004, A1 Location in patent: Page 4

15
[ 402860-20-2 ]
[ 1438-82-0 ]
[ 402860-21-3 ]

Yield	Reaction Conditions	Operation in experiment
96%	With nitrogen In toluene	4-Benzyloxy-benzoic acid (R)-1-methyl-6-(1,1,3,3,3-pentamethyl-disiloxanyl)hexyl ester (34) 4-Benzyloxy-benzoic acid (R)-1-methyl-6-(1,1,3,3,3-pentamethyl-disiloxanyl)hexyl ester (34) Nitrogen gas was bubbled through the solution of 4-benzyloxybenzoic acid (r)-1-methyl-hex-5-enyl ester (32) (1 equi.) And 1,1,1,3,3-pentamethyldisiloxane (33) (1.2 equi.) In toluene (10 ml/mmole) for 15 min. Pt catalyst (0.001 equi.) Was added to the reaction mixture and nitrogen bubbling was continued for another 15 min. The reaction mixture was stirred at 55 c for 24 h, cooled to room temperature, quenched with water, extracted with ethyl acetate:hexane (1:1), washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (5% EtOAc/hexanes) afforded 4-benzyloxy-benzoic acid (R)-1-methyl-6-(1,1,3,3,3-pentamethyl-disiloxanyl) hexyl ester (34) a white solid (96%).
96%	With nitrogen In toluene	4-Benzyloxy-benzoic acid (R)-1-methyl-6-(1,1,3,3,3-pentamethyl-disiloxanyl) -hexyl ester (34) 4-Benzyloxy-benzoic acid (R)-1-methyl-6-(1,1,3,3,3-pentamethyl-disiloxanyl) -hexyl ester (34) Nitrogen gas was bubbled through the solution of 4-benzyloxybenzoic acid (R)-1-methyl-hex-5-enyl ester (32) (1 equi.) and 1,1,1,3,3-pentamethyldisiloxane (33) (1.2 equi.) in toluene (10 mL/mmole) for 15 min. Pt catalyst (0.001 equi.) was added to the reaction mixture and nitrogen bubbling was continued for another 15 min. The reaction mixture was stirred at 55 C. for 24 h, cooled to room temperature, quenched with water, extracted with ethyl acetate:hexane (1:1), washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (5% EtOAc/hexanes) afforded 4-benzyloxy-benzoic acid (R)-1-methyl-6-(1,1,3,3,3-pentamethyl-disiloxanyl) -hexyl ester (34) a white solid (96%).

Reference： [1]Current Patent Assignee: CITIZEN WATCH CO LTD - US2003/17278, 2003, A1
[2]Current Patent Assignee: CITIZEN WATCH CO LTD - US2003/17278, 2003, A1

16
[ 1438-82-0 ]
[ 105857-45-2 ]
2,2,8,8-tetramethyl-5-[(pentamethyldisiloxanyl)methyl]-3,7-dioxa-2,8-disilanonane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In isopropyl alcohol	1 EXAMPLE 1 EXAMPLE 1 Into a flask equipped with a stirrer, thermometer, dropping funnel, reflux condenser, and oil bath were introduced 0.06 part of a solution prepared by dissolving 0.5 part of chloroplatinic acid in 25 parts of isopropanol, and 53.4 parts of 2-methylene-1,3- bis(trimethylsiloxy)propane. Stirring was then initiated and the liquid in the flask was heated to 70° C. 29.6 Parts of 1,1,3,3,3-pentamethyldisiloxane was added dropwise to the flask from the dropping funnel over a period of 15 minutes, while appropriately cooling the liquid reaction mixture to maintain the liquid temperature at 80°-90° C. After completion of the addition, stirring was continued for 1 hour at a liquid temperature of 90° C. Upon analysis by gas chromatography, it was ascertained that the peak due to 1,1,3,3,3-pentamethyldisiloxane had disappeared. After the reaction mixture was allowed to cool, a fraction having a boiling point of 96°-98° C./3 Torr was taken by vacuum distillation, thereby obtaining 68.4 parts of 1-(2-trimethylsiloxymethyl-3-trimethylsiloxypropyl)-1,1,3,3,3-pentamethyldisiloxane in a colorless, transparent liquid state (yield 90%). As a result of analysis by gas chromatography, the purity of this product was found to be 97%.

Reference： [1]Current Patent Assignee: MOMENTIVE PERFORMANCE MATERIALS HOLDINGS INC. - US5059707, 1991, A

17
1,3-bis(trimethylsiloxy)-2-(2-propenyloxy)methyl-2-methylpropane [ No CAS ]
[ 1438-82-0 ]
2-(3'-pentamethyldisiloxanylpropyloxy)methyl-2-methylpropan-1,3-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In isopropyl alcohol	1 2-(3'-pentamethyldisiloxanylpropyloxy)methyl-2-methylpropan-1,3-diol Example 1 2-(3'-pentamethyldisiloxanylpropyloxy)methyl-2-methylpropan-1,3-diol A solution (4 μl) of chloroplatinic acid (1 g) dissolved in isopropanol (20 ml) and 1,3-bis(trimethylsiloxy)-2-(2-propenyloxy)methyl-2-methylpropane (1.0 g, 3.3 mmols) were heated with stirring in a flask in nitrogen atmosphere, followed by dropwise dropping pentamethyldisiloxane (0.73 g, 4.8 mmols) at 80°C, further agitating the mixture for 2 hours at 80°C, and distilling the reaction mixture to obtain a fraction of a b.p. of 150°C/10 mmHg (colorless, transparent liquid, 1.19 g, yield 80%). The results of 1H-NMR, IR and mass spectra of this product are described below and the product was confirmed to be a siloxane compound having the following structural formula: 1H-NMR(CDCl3): δ (ppm) 0.06 (Si-Me3, s, 33H) 0.56 (-CH2-Si, m, 2H) 0.86 (CH3-C≡, s, 3H) 1.58 (-CH2-, m, 2H) 3.17 (-CH2-, s, 2H) 3.33 (-CH2-, t, 2H) 3.40 (-CH2-, s, 4H) IR (KBr) νmax 2970cmmin1 (C-H) 1120~1050cmmin1 (Si-O) MS m/e: 452 (M+)

Reference： [1]Current Patent Assignee: CHISSO CORPORATION - EP277816, 1988, A1

18
[ 1438-82-0 ]
[ 1005177-03-6 ]

Yield	Reaction Conditions	Operation in experiment
97%	With tetrapropoxysilane; tris(pentafluorophenyl)-borane In toluene at 20℃; for 0.416667h;

Reference： [1]Thompson, David B.; Brook, Michael A. [Journal of the American Chemical Society, 2008, vol. 130, # 1, p. 32 - 33]

19
1-(4-allyloxy-3-methoxyphenyl)-4,4-dimethylpentane-1,3-dione [ No CAS ]
[ 1438-82-0 ]
[ 148794-57-4 ]

Yield	Reaction Conditions	Operation in experiment
68.4%	In toluene at 100 - 105℃; for 6h;	2.1 0.5 mg of hydrogen hexachloroplatinate (IV) hexahydrate was added to a mixture of 2.5 g of 1-(3-methoxy-4-allyloxyphenyl)-3-tert-butyl-1,3-propanedione, 1.7 g of 1,1,1,3,3-pentamethyldisiloxane, and 20 ml of toluene and reacted for 6 hours at 100-105°C while being stirred. After the completion of the reaction, toluene was removed under a reduced pressure and the residual was separated and purified by means of silica gel column chromatography (eluted with 2 v/v% ethyl acetate-hexane mixture) to obtain 2.6 g of a colorless oil-like substance. The yield was 68. 4%. λmax : 335 nm (ε = 24090), mass spectrum M+m/e 438

Reference： [1]Current Patent Assignee: SHISEIDO COMPANY LIMITED - EP1944012, 2008, A1 Location in patent: Page/Page column 18

20
[ 1438-82-0 ]
[ 1072942-91-6 ]
[ 1072942-80-3 ]

Yield	Reaction Conditions	Operation in experiment
50%	In xylene at 100℃; for 6h;	3 To a mixture of compound Q9 (5.5 g; 0.016 mol) and 4.83 ml pentamethyltrisiloxane (0.024 mol) in 100 ml xylene 10 drops of Karstedt's catalyst were added and the resulting mixture was heated at 1000C for 6 h. After cooling to RT the solvent was evaporated in vacuo and the residue was purified by column chromatography (using hexane as eluent). Yield: 4 g (50%). Rf = 0.87(hexane-acetone 10:0.4). λmaxi = 306 nm, εmaxi = 16180; λmaX2 = 345 nm, εmaX2 = 14924.1H-NMR (CDCI3): 0.09 (s, 9H, 3 CH3), 0.13 (s, 6H, 2 CH3), 0.59 (dd, J = 14.8 and 8.9 Hz, IH, C3 -H), 0.79 (dd, J= 14,8 and 4.8 Hz, IH, C3 -H), 1.01 (d, J= 6.6 Hz, 3H, CH3), 1.33 (m, IH, C4-H), 1.44 (m, 2H, C3-H and C5'-H), 1.52 (m, 2H, C2-H and C6-H), 1.80 (m-d, J= 12.9 Hz, IH, C4-H), 1.90 (m-d, J= 12.5 Hz, 2H, C3-H and C5-H), 1.97 (m-d, ,J= 12.6 Hz, 2H, C2- H and C6-H), 2.16 (m, IH, C2 -H), 2.58 (m, IH, Cr-H), 2.60 (dd, J= 13.0 and 8.3 Hz, IH, Cr-H), 2.83 (dd, J= 13.0 and 6.5 Hz, IH, Cf-H), 7.07 (d, J= 1.6 Hz, IH, C5-H), 7.49 (dd, J = 6.5 and 3.0 Hz, 2H, C5-H and C6-H), 7.96 (dd, J= 6.5 and 3.0 Hz, 2H, C4-H. and C7-H), 8.13 (d, J= 1.6 Hz, IH, C3-H), 11.34 (s, IH, OH)."C-NMR (CDCl3): 1.32 (CH3), 1.39 (C:H3), 1.99 (3 CH3), 22.70 (CH3), 26.12 (C-4"), 26.90 (C-3" and C-5"), 29.48 (C-2"'), 34.58 (C-2"), 34.62 (C-6"), 41.44 (C-I "'), 43.77 (C-I"), 116.78 (C-3), 117.59 (C-4' and C-7'), 124.79 (C-2), 127.42 (C-5' and C-6'), 130.80 (C-5), 131.31 (C- 6), 138.97 (C-4), 142.73(C-3a' and C-7a'), 146.11 (Cl).

Reference： [1]Current Patent Assignee: ISDIN SA - WO2008/131921, 2008, A1 Location in patent: Page/Page column 83; 85-86

21
CH₂=C(CH₃)CH₂O(EO)4CH₃ [ No CAS ]
[ 1438-82-0 ]
None [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dihydrogen hexachloroplatinate In toluene at 70 - 110℃; for 3.5h;	1 262 g (1 mole) of a polyether having the structure CH2C(CH3) CH2O(EO)4CH3 and 0.5 g of a 0.5 mass % toluene solution of chloroplatinic acid were weighed out in a flask, and heated to 70° C. in a current of nitrogen.At 70° C., 178 g (1.2 moles) of pentamethyldisiloxane (Me3SiOSiMe2H, bp. 85° C.) was dripped in over 30 minutes. At this time, the temperature of the reaction system rose to 90° C. The temperature was then raised to 110° C., and maintained at 110° C. for 3 hours to complete the reaction.After performing a reduced pressure strip of excess pentamethyldisiloxane, 390 g of a polyether silicone A was obtained.

Reference： [1]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD. - US7547797, 2009, B2 Location in patent: Page/Page column 4

22
[ 1438-82-0 ]
[ 96220-75-6 ]
None [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dihydrogen hexachloroplatinate In toluene at 70 - 110℃; for 3.5h;	2 248 g (1 mole) of a polyether having the structure CH2CH CH2O(EO)4CH3 and 0.5 g of a 0.5 mass % toluene solution of chloroplatinic acid were weighed out in a flask, and heated to 70° C. in a current of nitrogen.At 70° C., 178 g (1.2 moles) of pentamethyldisiloxane (Me3SiOSiMe2H, bp. 85° C.) was dripped in over 30 minutes. At this time, the temperature of the reaction system rose to 85° C. The temperature was then raised to 110° C., and maintained at 110° C. for 3 hours to complete the reaction.After performing a reduced pressure strip of excess pentamethyldisiloxane, 370 g of a polyether silicone B was obtained.

Reference： [1]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD. - US7547797, 2009, B2 Location in patent: Page/Page column 4

23
[ 1438-82-0 ]
CH₂=C(CH₃)CH₂O(EO)5CH₃ [ No CAS ]
None [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dihydrogen hexachloroplatinate In toluene at 70 - 110℃; for 3.5h;	3 306 g (1 mole) of a polyether having the structure CH2C(CH3)CH2O(EO)5CH3 and 0.5 g of a 0.5 mass % toluene solution of chloroplatinic acid were weighed out in a flask, and heated to 70° C. in a current of nitrogen.At 70° C., 178 g (1.2 moles) of pentamethyldisiloxane (Me3SiOSiMe2H, bp. 85° C.) was dripped in over 30 minutes. At this time, the temperature of the reaction system rose to 90° C. The temperature was then raised to 110° C., and maintained at 110° C. for 3 hours to complete the reaction.After performing a reduced pressure strip of excess pentamethyldisiloxane, 440 g of a polyether silicone C was obtained.

Reference： [1]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD. - US7547797, 2009, B2 Location in patent: Page/Page column 4-5

24
[ 1438-82-0 ]
[ 132388-53-5 ]
None [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dihydrogen hexachloroplatinate In toluene at 70 - 110℃; for 3.5h;	4 292 g (1 mole) of a polyether having the structure CH2CHCH2O(EO)5CH3 and 0.5 g of a 0.5 mass % toluene solution of chloroplatinic acid were weighed out in a flask, and heated to 70° C. in a current of nitrogen.At 70° C., 178 g (1.2 moles) of pentamethyldisiloxane (Me3SiOSiMe2H, bp. 85° C.) was dripped in over 30 minutes. At this time, the temperature of the reaction system rose to 85° C. The temperature was then raised to 110° C., and maintained at 110° C. for 3 hours to complete the reaction.After performing a reduced pressure strip of excess pentamethyldisiloxane, 420 g of a polyether silicone D was obtained.

Reference： [1]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD. - US7547797, 2009, B2 Location in patent: Page/Page column 5

25
[ 1438-82-0 ]
[ 78-08-0 ]
[ 1242030-56-3 ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: 1,1,1,3,3-pentamethyl-1,3-disiloxane; Triethoxyvinylsilane In hexane at 20℃; for 0.0833333h; Stage #2: With tris(pentafluorophenyl)borate In hexane; toluene for 0.0833333h;
89%	Stage #1: 1,1,1,3,3-pentamethyl-1,3-disiloxane; Triethoxyvinylsilane In hexane at 20℃; for 0.0833333h; Stage #2: With tris(pentafluorophenyl)borate In hexane; toluene

Reference： [1]Grande, John B.; Thompson, David B.; Gonzaga, Ferdinand; Brook, Michael A. [Chemical Communications, 2010, vol. 46, # 27, p. 4988 - 4990]
[2]Keddie, Daniel J.; Grande, John B.; Gonzaga, Ferdinand; Brook, Michael A.; Dargaville, Tim R. [Organic Letters, 2011, vol. 13, # 22, p. 6006 - 6009]

26
[ 1438-82-0 ]
[ 2550-04-1 ]
[ 1242030-58-5 ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: 1,1,1,3,3-pentamethyl-1,3-disiloxane; allyltriethoxysilane In dichloromethane at 20℃; for 0.0833333h; Stage #2: With tris(pentafluorophenyl)borate In dichloromethane; toluene for 0.05h;
85%	With tris(pentafluorophenyl)borate In hexane; toluene for 2h; Sealed tube; Inert atmosphere;	4.3.1. Synthesis of 1 Allyltrimethoxysilane (5.0328 g, 31.017 mmol) was added to a 500 mL oven-dried round-bottomedflask. Dry hexanes (~10 mL) were added to the reaction and the flask was capped and flushed withnitrogen. BCF catalyst solution (110 L, 0.0365 g/mL toluene, 7.84 103 mmol) was added beforeslowly adding in excess pentamethyldisiloxane (22.7582 g, 153.401 mmol). After 2 h the reaction wasshown to be complete by 1H NMR and ~1.5 g of neutral alumina was added to the flask to remove theBCF. The solution was left to stir for ~1 h before filtering the product through Celite and rinsing withhexane. Hexanes were removed under reduced pressure, yielding 14.6443 g of 1 (85% yield). 1H NMR(CDCl3, 600 MHz): 6.13 (dd, 1H, J = 14.8, 20.4 Hz), 5.93 (dd, 1H, J = 3.8, 14.8 Hz), 5.74 (dd, 1H, J = 3.8,20.4 Hz), 1.57 (d, 2H, J = 7.9 Hz), 0.19-0.05 (m, 46H) ppm

Reference： [1]Grande, John B.; Thompson, David B.; Gonzaga, Ferdinand; Brook, Michael A. [Chemical Communications, 2010, vol. 46, # 27, p. 4988 - 4990]
[2]Zheng, Sijia; Liang, Shuai; Chen, Yang; Brook, Michael A. [Molecules, 2019, vol. 24, # 22]

27
[ 1438-82-0 ]
[ 2530-83-8 ]
[ 1242030-61-0 ]
[ 1242030-62-1 ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 4988 - 4990
[2]Dalton Transactions,2010,vol. 39,p. 9369 - 9378

28
N-(3,4-dimethylphenyl)-N-(4-methoxyphenyl)-3,4-dimethylaniline [ No CAS ]
[ 1438-82-0 ]
[ 1259383-66-8 ]

Yield	Reaction Conditions	Operation in experiment
95%	With tris(pentafluorophenyl)borate In toluene at 20℃; for 0.333333h;

Reference： [1]Kamino, Brett A.; Grande, John B.; Brook, Michael A.; Bender, Timothy P. [Organic Letters, 2011, vol. 13, # 1, p. 154 - 157]

29
[ 1438-82-0 ]
[ 386258-95-3 ]
[ 1259383-68-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	With tris(pentafluorophenyl)borate In toluene at 20℃; for 0.333333h;

Reference： [1]Kamino, Brett A.; Grande, John B.; Brook, Michael A.; Bender, Timothy P. [Organic Letters, 2011, vol. 13, # 1, p. 154 - 157]

30
[ 1438-82-0 ]
[ 13050-56-1 ]
[ 1259383-70-4 ]

Yield	Reaction Conditions	Operation in experiment
96%	With tris(pentafluorophenyl)borate In toluene at 20℃; for 0.333333h;

Reference： [1]Kamino, Brett A.; Grande, John B.; Brook, Michael A.; Bender, Timothy P. [Organic Letters, 2011, vol. 13, # 1, p. 154 - 157]

31
[ 1438-82-0 ]
C₁₃H₂₂OSi [ No CAS ]
[ 1067-25-0 ]
[ 1254985-33-5 ]
C₁₂H₂₂O₂Si₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tris(pentafluorophenyl)borate In hexane; toluene at 20℃;

Reference： [1]Location in patent: experimental part Grande, John B.; Gonzaga, Ferdinand; Brook, Michael A. [Dalton Transactions, 2010, vol. 39, # 39, p. 9369 - 9378]

32
[ 1438-82-0 ]
C₉H₂₄O₄Si₂ [ No CAS ]
1,1,1,5,5,5-hexamethyl-3-propyl-3-[(trimethylsilyl)oxy]trisiloxane [ No CAS ]
[ 107-51-7 ]
[ 1067-25-0 ]
[ 1254985-33-5 ]

Reference： [1]Dalton Transactions,2010,vol. 39,p. 9369 - 9378

33
[ 1438-82-0 ]
[ 2530-83-8 ]
[ 1242030-61-0 ]
[ 1242030-62-1 ]
C₁₃H₃₂O₆Si₃ [ No CAS ]

Reference： [1]Dalton Transactions,2010,vol. 39,p. 9369 - 9378

34
[ 1438-82-0 ]
[ 14867-28-8 ]
[ 1254985-45-9 ]

Yield	Reaction Conditions	Operation in experiment
87.5%	With tris(pentafluorophenyl)borate In hexane; toluene at 20℃;

Reference： [1]Gonzaga, Ferdinand; Grande, John B.; Brook, Michael A. [Chemistry - A European Journal, 2012, vol. 18, # 5, p. 1536 - 1541]

35
[ 1438-82-0 ]
[ 375856-97-6 ]
C₁₉H₃₂O₄Si₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2,6-di-tert-butyl-4-methyl-phenol In toluene; xylene at 20℃;	a-V-4 Synthesis Example a-V-4 Synthesis of Silicone Compound: I = m = n = 0, X1 = CH3, X3 = 3--(3-methoxy-4-methacyloxyphenyl)propyl group in the Chemical Structure 1 Drip 4.11 parts of the compound a-IV (3-methoxy-4-methacryloxy arylbenzene), 0.007 parts of a stabilizer (2,6-di-t-butyl-4-methylphenol), 10 parts of toluene, and 0.032 parts of xylene solution of 2 % by weight platinum / 1,3-divinyl-l,1,3,3-tetramethyl disiloxane complex (manufactured by Sigma-Aldrich Co.) to a solution of 2.5 parts of methyl hydrogen silicone compound (pentamethyl disiloxane) and 2.5 parts of toluene at room temperature in about 60 minutes while stirring followed by reaction one night. Thereafter, distill away the solvent with a reduced pressure, conduct stripping treatment for two hours with a reduced pressure of 10 mmHg at 40 °C and confirm disappearance of absorption (2155 cm-1 of Si-H in infra-red absorption spectrum to obtain 6.99 parts of the target silicone compound a-M12. The infra-red absorption spectrum graph is shown as Fig. 3M.

Reference： [1]Current Patent Assignee: RICOH CO LTD - EP2520579, 2012, A2 Location in patent: Page/Page column 33

36
[ 1438-82-0 ]
[ 1395396-58-3 ]
[ 1402226-18-9 ]

Yield	Reaction Conditions	Operation in experiment
74%	With platinum⁽⁰⁾-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In 5,5-dimethyl-1,3-cyclohexadiene; toluene for 2h; Reflux;
74%	With platinum⁽⁰⁾-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In 5,5-dimethyl-1,3-cyclohexadiene; toluene for 2h; Reflux;	7 [Synthesis of N-N'-bis(1,9-di(1,1,1,3,3, pentamethylcyclohexanyl)nonane-5-yl)perylene-3,4,9,10-tetracarboxylic acid bisimide (compound (2-44) ((2), m=0, n=1))] Perylene-3,4,9,10-tetracarboxylic acid bis(1,8-nonadiene-5-ylimide) (compound (10), m = 1, n = 1) and 1.19 g (8.1 mmol) of 1,1,1,3,3-pentamethyl disiloxane were dissolved in 30 ml of toluene, and 10 µl of a Karsted catalyst (2.1At%, a solution in xylene) was added to the solution thus obtained, which was then refluxed for 2 hours. The resultant solution was cooled to room temperature, and the solvent was distilled off under reduced pressure. Then, the red residue thus obtained was purified by silica gel column chromatography (eluent: hexane: ethyl acetate=10 :1). The crude product thus obtained was dissolved in dichloromethane and re-precipitated with methanol. The precipitate thus obtained was separated by filtration. Thus, 1.29 g (1.05 mol) of a red powder was obtained as an intended compound (2-44). A yield of the compound (2-44) was 74%. Values obtained by instrumental analysis of the compound (2-44) are shown below. [0096] Compound (2-44): 1H NMR (400 MHz, CDCl3) δ = 8.68 (d, br, 4H, J = 8.0 Hz), 8.62 (d, 4H, J = 8.0 Hz), 5.16 (tt, 2H, J = 9.2, 6.0 Hz), 2.18-2.29 (m, 4H), 1.80-1.91 (m, 4H), 1.19-1.42 (m, 16H), 0.47 (dd, 8H, J = 8.8, 7.2 Hz), -0.01 ppm (s, 36H), -0.04 ppm (s, 24H); IR (ATR): v = 2958, 1697, 1651, 1594, 1338, 1254, 1044, 837, cm-1; Exact Mass: 1226.58; Molecular Weight: 1228.17m/z[M+]: 1226.87 (82%), 1227.89 (100%), 1228.88 (83%), 1229.88 (43%), 1230.87 (37%)
	With platinum⁽⁰⁾-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In 5,5-dimethyl-1,3-cyclohexadiene; toluene at 20℃;

Reference： [1]Funahashi, Masahiro; Sonoda, Akinari [Journal of Materials Chemistry, 2012, vol. 22, # 48, p. 25190 - 25197]
[2]Current Patent Assignee: KAGAWA UNIVERSITY - EP2695885, 2014, A1 Location in patent: Paragraph 0094-0095
[3]Funahashi, Masahiro; Takeuchi, Nozomi; Sonoda, Akinari [RSC Advances, 2016, vol. 6, # 22, p. 18703 - 18710]

37
[ 1438-82-0 ]
[ 4286-85-5 ]
[ 85316-45-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	In hexane at 20℃; for 2h;	14A 4,4-Diphenyl-1-butene (compound 1, 0.40 mmol) and pentamethyl disiloxane (0.6 mmol) were dissolved in hexane (2.0 ml), added with poly (methylphenylsilane)-supported platinum (200 mg, 5.5 mol %) prepared in Example 10A and stirred at 20° C. for 2 hr. The filtrate was washed with hexane after separation from catalyst, concentrated, and purified by silica gel column chromatography using hexane as an eluting solvent. (4,4-Diphenylbutyl) pentamethyl disiloxane was obtained as oil without color (140 mg (98%)) and 1,1-diphenyl butane was obtained (2 mg (yield 2%)).(4,4-Diphenylbutyl) pentamethyl disiloxane: 1H-NMR (CDCl3) δ=0.11-0.04 (sx2, 15H), 0.47-0.61 (m, 2H), 1.20-1.39 (m, 2H), 2.06 (dt, J=7.7 Hz), 3.90 (t, 1H, J=7.7 Hz), 7.06-7.29 (m, 10 H)

Reference： [1]Current Patent Assignee: JAPAN SCIENCE AND TECHNOLOGY AGENCY - US8318967, 2012, B2 Location in patent: Page/Page column 21-22

38
[ 1438-82-0 ]
[ 142-29-0 ]
1-cyclopentyl-1,1,3,3,3-pentamethyldisiloxane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With C₄₀H₇₂Co₂N₈ In neat (no solvent) at 50℃; for 24h;
80%	With C₂₂H₃₄FeO₂Si₄ at 80℃; for 3h; Inert atmosphere; Schlenk technique;	9 [Example 9] : Hydrosilylation of cyclopentene with 1,1,1,3,3-pentamethyldisiloxane. A magnetic stirrer was added to a 20 mL shrink tube and heated and dried under reduced pressure to 5 Pa. Subsequently, the inside of the Schlenk tube was replaced with an argon atmosphere. Iron complex A (25 mg, 0.05 mmol) was added as a catalyst to the Schlenk tube. The cyclopentene(44.2 μL, 0.5 mmol) was added to the solution, and 1,1,1,3,3-pentamethyldisiloxane (97.6 μL, 0.5 mmol) was added thereto.C & lt; / RTI & gt; for 3 hours. After cooling, anisole was added as an internal standard,OneThe 1 H-NMR spectrum was measured,The crude and yield were determined. The results are shown in Table 2 as entry 3.
73%	With C₂₁H₃₄FeO₂Si₄ at 80℃; for 3h; Inert atmosphere;

18%

With tert-butylisonitrile; iron biscyclooctatetraene at 80℃; for 3h; Inert atmosphere; Glovebox;

23 Example 23 In a nitrogen-blanketed glove box, 26 mg (0.10 mmol) of Fe(COT)2 in Synthesis Example 2, 23 μL (0.20 mmol) of t-BuNC, 254 μL (1.3 mmol) of 1,1,3,3,3-pentamethyldisiloxane, and 88 μL (1.0 mmol) of cyclopentene were added to a screw-top vial with a stirrer. The vial was closed, after which the contents were stirred at 80° C. for 3 hours. After cooling, analysis was made by 1H-NMR spectroscopy to determine the structure and yield of the product. As a result, it was confirmed that the signal assigned to the ethylene site of cyclopentene as the reactant diminished. Instead, a multiplet near 0.86 ppm indicative of the signal assigned to proton on silicon-adjoining carbon in the desired product was observed, from which a yield was computed. The results are shown in Table 5. 1H-NMR (396 MHz, CDCl3) δ: 0.02 (s, 6H), 0.06 (s, 9H), 1.20-1.36 (m, 2H), 0.83-0.92 (m, 1H), 1.50-1.57 (m, 4H), 1.66-1.85 (m, 2H)

Reference： [1]Sanagawa, Atsushi; Nagashima, Hideo [Organometallics, 2018, vol. 37, # 17, p. 2859 - 2871]
[2]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD.; KYUSHU UNIVERSITY - KR2015/125983, 2015, A Location in patent: Paragraph 0198-0200
[3]Sunada, Yusuke; Tsutsumi, Hironori; Shigeta, Keisuke; Yoshida, Ryota; Hashimoto, Toru; Nagashima, Hideo [Dalton Transactions, 2013, vol. 42, # 48, p. 16687 - 16692]
[4]Current Patent Assignee: KYUSHU UNIVERSITY; SHIN-ETSU CHEMICAL CO., LTD. - US2017/260216, 2017, A1 Location in patent: Paragraph 0197; 0271; 0272-0273

39
[ 74-85-1 ]
[ 1438-82-0 ]
[ 6231-60-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With C₂₂H₃₄FeO₂Si₄ In toluene at 20℃; for 16h; Inert atmosphere; Schlenk technique;	12 [Example 12] Hydrosilylation of ethylene with 1,1,1,3,3-pentamethyldisiloxane. A magnetic stirrer was added to a 20 mL shrink tube and heated and dried under reduced pressure to 5 Pa. Then, the inside of the shrink tube was filled with argonIt replaced the crisis. The iron complex A (5 mg, 0.01 mmol) was added as a catalyst to the Schlenk tube and dissolved in toluene (2 mL).To this solution, 1,1,1,3,3-pentamethyldisiloxane (195.2 μL, 1.0 mmol) was added. After the obtained solution was freeze-deaerated,The inside of the Lenk tube was replaced with an ethylene atmosphere. Subsequently, the solution was stirred at room temperature for 16 hours, and then toluene was distilled off under reduced pressure. The 1 H-NMR spectrum was measured to determine the structure and yield of the product. The reaction mixture was concentrated under reduced pressure(5 Pa, room temperature) to obtain 160 mg (0.91 mmol) of purified product. The results are shown in Table 3 as entry 2. The structure of the obtained silane was confirmed by 1H, 13C, and 29Si-NMR spectra.
91%	With C₂₁H₃₄FeO₂Si₄ In toluene at 20℃; for 5h; Schlenk technique;
55 %Spectr.	With C₁₇H₂₈O₂RuS₂Si₂ at 80℃; for 16h; Schlenk technique; Inert atmosphere;	20 5) Ruthenium complex Hydrosilylation reaction with B[Example 20] Hydrosilylation of ethylene with 1,1,1,3,3-pentamethyldisiloxaneA magnetic stirrer was added to a 20 mL shrink tube and heated and dried under reduced pressure to 5 Pa. Subsequently, the inside of the Schlenk tube was replaced with an argon atmosphere. The ruthenium complex B (14 mg, 0.03 mmol) was added as a catalyst to the Schlenk tube. To this was added 1,1,1,3,3-pentamethyldisiloxane (195.2 μL, 1.0 mmol). After the obtained solution was freeze-deaerated, the inside of the Schlenk tube was replaced with an ethylene atmosphere. Thereafter, the solution was stirred at 80 DEG C for 16 hours. After cooling, anisole was added as an internal standard, and 1 H-NMR spectrum was measured to determine the structure and yield of the product (yield: 55%).

Reference： [1]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD.; KYUSHU UNIVERSITY - KR2015/125983, 2015, A Location in patent: Paragraph 0209-0211
[2]Sunada, Yusuke; Tsutsumi, Hironori; Shigeta, Keisuke; Yoshida, Ryota; Hashimoto, Toru; Nagashima, Hideo [Dalton Transactions, 2013, vol. 42, # 48, p. 16687 - 16692]
[3]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD.; KYUSHU UNIVERSITY - KR2015/121721, 2015, A Location in patent: Paragraph 0231-0233

40
[ 111-67-1 ]
[ 1438-82-0 ]
C₁₃H₃₂OSi₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With C₂₂H₃₄FeO₂Si₄ at 80℃; for 3h; Inert atmosphere; Schlenk technique;	3 [Example 3] Hydrosilylation of 2-octene with 1,1,1,3,3-pentamethyldisiloxane A magnetic stirrer was added to a 20 mL shrink tube and heated and dried under reduced pressure to 5 Pa. Then, the inside of the shrink tube was filled with argonIt replaced the crisis. The iron complex A (15 mg, 0.03 mmol) was added as a catalyst to the Schlenk tube. To this was added 2-octene (156.3 [mu] L,1.0 mmol) was added, followed by 1,1,1,3,3-pentamethyldisiloxane (195.2 μL, 1.0 mmol). After cooling, anisole (108.6 μL, 1.0 mmol, the same amount is used hereinafter) was added as an internal standard,The & lt; 1 & gt; H-NMR spectrum was measured to determine the structure and yield of the product. The reaction mixture was purified by distillation (8 Pa, 70 ) to obtain the desired product (195 mg, 0.75 mmol). The structure of the obtained compound was confirmed by 1H, 13C, and 29Si-NMR spectra. These results are shown in Table 1 as the entry 1.
80%	With C₂₁H₃₄FeO₂Si₄ at 80℃; for 3h; Inert atmosphere;
6%	With Cyclohexyl isocyanide; iron biscyclooctatetraene In neat (no solvent) at 80℃; for 3h; Inert atmosphere; Sealed tube;	19 [Example 19] Hydrosilylation of 2-octene with 1,1,3,3,3-pentamethyldisiloxane Reaction was carried out according to the same procedure as in Example 3 aside from using 157 μL (1.0 mmol) of 2-octene instead of styrene. As a result, it was confirmed that the signal assigned to the ethylene site of 2-octene as the reactant diminished. Instead, a multiplet at 0.51 ppm indicative of the signal assigned to proton on silicon-adjoining carbon in the desired product was observed, from which a yield was determined. The results are shown in Table 4. 1H-NMR (396 MHz, CDCl3) δ: 0.03 (s, 6H), 0.06 (s, 9H), 0.50 (t, J=7.7 Hz, 2H), 0.88 (t, J=6.8 Hz, 3H), 1.19-1.34 (m, 12H)

Reference： [1]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD.; KYUSHU UNIVERSITY - KR2015/125983, 2015, A Location in patent: Paragraph 0179-0181
[2]Sunada, Yusuke; Tsutsumi, Hironori; Shigeta, Keisuke; Yoshida, Ryota; Hashimoto, Toru; Nagashima, Hideo [Dalton Transactions, 2013, vol. 42, # 48, p. 16687 - 16692]
[3]Current Patent Assignee: KYUSHU UNIVERSITY; SHIN-ETSU CHEMICAL CO., LTD. - US2017/260216, 2017, A1 Location in patent: Paragraph 0197; 0235; 0263-0264; 0270

41
[ 1438-82-0 ]
[ 591-87-7 ]
[ 98485-26-8 ]
[ 70693-47-9 ]
[ 64185-06-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 55 %Spectr. 2: 9 %Spectr. 3: 44 %Spectr.	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; biphenyl In ⁽²⁾H₈-toluene at 40℃; for 3h; Sealed tube; Inert atmosphere;	4.5 Experimental procedure of the hydrosilylation of AA with MM′H₁ and spectral data of the product (Table2, entry 1) To a stirred mixture of dehydrated toluene-d8 (50.0μL), AA (110mg 1.07mmol), MM′H1 (147mg, 0.970mmol) and biphenyl (15.5mg, 0.101mmol) in a 0.5mL sealed tube were added chloro(1,5-cyclooctadiene)iridium(I) dimer (1.70mg, 2.53μmol) under argon. The reaction mixture was gradually heated to 40°Cand stirred for 3h giving a hydrosilylation product, MM′R0.551R0.092R0.033R0.185.

Reference： [1]Igarashi, Masayasu; Matsumoto, Tomohiro; Kobayashi, Toshiaki; Sato, Kazuhiko; Ando, Wataru; Shimada, Shigeru; Hara, Masanao; Uchida, Hiroshi [Journal of Organometallic Chemistry, 2014, vol. 752, p. 141 - 146]

42
[ 1438-82-0 ]
[ 1402226-21-4 ]
[ 1402226-22-5 ]

Yield	Reaction Conditions	Operation in experiment
	With platinum⁽⁰⁾-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 180℃; Inert atmosphere;	9 [Synthesis of N-N'-bis(4-(1,9-di(1,1,1,3,3,5,5-heptamethyl trisiloxanyl)nonane-5-yloxy) phenyl)perylene-3,4,9,10-tetracarboxylic acid bisimide (compound (2-46) ((2), m = 0, n = 3))] Example 9 [Synthesis of N-N'-bis(4-(1,9-di(1,1,1,3,3,5,5-heptamethyl trisiloxanyl)nonane-5-yloxy) phenyl)perylene-3,4,9,10-tetracarboxylic acid bisimide (compound (2-46) ((2), m = 0, n = 3))] A 200 ml-capacity three neck flask containing a stirring bar and connected to a condenser was sufficiently dried. Then, a nitrogen atmosphere was established in the flask, N-N'-di(1,12-tridecadiene-7-yl)perylene-3,4,9,10,tetracarboxylic acid bisimide (10) (n = 3) (0.3 g, 4.35 * 10-4 mol) and 1,1,1,3,3,pentamethyl siloxane (0.32 g, 21.75 * 10-4 mol) were introduced into the flask, and toluene (50 ml) was further added to the mixture thus obtained to dissolve them. The solution thus obtained was stirred while placing the flask in an oil bath (180°C). When the solution became a homogeneous mixture, a Karstedt catalyst (10 μl) was added to the solution, and the mixture thus obtained was further stirred for half a day. When generation of an intended compound was recognized by thin-layer chromatography, the solvent was distilled off under reduced pressure, and the compound was purified by flash chromatography on silica gel (hexane : ethyl acetate = 20:1), (hexane : ethyl acetate =10:1), (hexane : ethyl acetate = 5 : 1) and re-precipitated with CH2Cl2. Thus, intended N-N'-bis(4-(1,9,-di(1,1,1,3,3,5,5-heptamethyl trisiloxanyl)nonane-5-yloxy)phenyl)perylene-3,4,9,10-tetracarboxylic acid bisimide (compound (2-46) ((2), m = 0, n = 3)) was obtained. Values obtained by instrumental analysis values of the compound (2-46) are shown below. Values obtained by instrumental analysis of compound (2-46): 1H NMR (400 MHz, CDCl3) δ = 8.64 (d, br, 4H), 8.62 (d, 4H, 7.6 Hz), 5.18 (m, 2H), 2.3-2.2 (m, 4H), 1.9-1.8 (m, 4H), 1.4-1.8 (m, 7H), 1.2-1.4 (m, 22H), 0.8 (t, 3H, 6.0 Hz), 0.4 (m, 8H), -0.01 (s, 30H), -0.02 (s, 30H), IR (ATR): v = 2922, 1649, 1337, 1249, 1044, 835 cm-1 Exact Mass: 1338.70; Molecular Weight: 1340.38 m/z[M+]: 1337.97 (100%), 1338.98 (69%), 1339.93 (57%), 1340.94 (56%), 1341.93 (57%)

Reference： [1]Current Patent Assignee: KAGAWA UNIVERSITY - EP2695885, 2014, A1 Location in patent: Paragraph 0115-0117

43
[ 1438-82-0 ]
[ 1191457-71-2 ]
[ 1573019-39-2 ]
[ 1573019-37-0 ]

Yield	Reaction Conditions	Operation in experiment
	With platinum⁽⁰⁾-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 75℃; for 0.5h; Inert atmosphere;	1 Synthesis Example 2 General procedure: In 1 liter of a separable flask equipped with a nitrogen gas introducing tube, a thermometer, a Dimroth condenser and a dropping funnel were charged 143 g (0.25 mol) of an epoxy group-containing fluorene compound havingmethallyl group obtained in Example 1 and represented by the following general formula (4),200 g of toluene, and 0.05 g of tris(1,3-divinyl-1,1,3,3-tet- ramethyl-disiloxane)-diplatinum(0) (Karstedt catalyst) which contains 2% by weight of platinum, then, to the mixture was gradually added dropwise 74 g (0.5 mol) of pentamethyldisiloxane at 75° C. This dropwise addition required for 30 minutes. After completion of the dropwise addition, themixture was matured at 75° C. for 5 hours.10052] After completion of the maturing, the reaction mixture was analyzed by gas chromatography, and confirmed tobe a pentamethyldisiloxane remaining amount of 2% or less.10053] The reaction mixture was concentrated under reduced pressure by a rotary evaporator at 80° C./0.6 kPa, to obtain 210 g of a colorless solid. This product was analyzed by infrared absorption spectrometry and ‘H nuclear magnetic resonance spectrometry, and confirmed that the product was a fluorene compound into which a siloxane has been incorporated by reacting the methallyl group portion and Si--H, represented by the following structural formula (7),This product was analyzed by ‘H nuclear magnetic resonance spectrometry, a purity of the a adduct was 98%, and the isomer (f3 adduct) represented by the following structural formula (8),

Reference： [1]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD. - US2014/66636, 2014, A1 Location in patent: Paragraph 0051-0054

44
[ 1438-82-0 ]
[ 1573019-26-7 ]
[ 1573019-31-4 ]

Yield	Reaction Conditions	Operation in experiment
210 g	With platinum⁽⁰⁾-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 75℃; for 0.5h; Inert atmosphere;	2 Synthesis Example 2 In 1 liter of a separable flask equipped with a nitrogen gas introducing tube, a thermometer, a Dimroth condenser and a dropping funnel were charged 143 g (0.25 mol) of an epoxy group-containing fluorene compound havingmethallyl group obtained in Example 1 and represented by the following general formula (4),200 g of toluene, and 0.05 g of tris(1,3-divinyl-1,1,3,3-tet- ramethyl-disiloxane)-diplatinum(0) (Karstedt catalyst) which contains 2% by weight of platinum, then, to the mixture was gradually added dropwise 74 g (0.5 mol) of pentamethyldisiloxane at 75° C. This dropwise addition required for 30 minutes. After completion of the dropwise addition, themixture was matured at 75° C. for 5 hours.10052] After completion of the maturing, the reaction mixture was analyzed by gas chromatography, and confirmed tobe a pentamethyldisiloxane remaining amount of 2% or less.10053] The reaction mixture was concentrated under reduced pressure by a rotary evaporator at 80° C./0.6 kPa, to obtain 210 g of a colorless solid. This product was analyzed by infrared absorption spectrometry and ‘H nuclear magnetic resonance spectrometry, and confirmed that the product was a fluorene compound into which a siloxane has been incorporated by reacting the methallyl group portion and Si--H, represented by the following structural formula (7),This product was analyzed by ‘H nuclear magnetic resonance spectrometry, a purity of the a adduct was 98%, and the isomer (f3 adduct) represented by the following structural formula (8),

Reference： [1]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD. - US2014/66636, 2014, A1 Location in patent: Paragraph 0051; 0052; 0053

45
[ 1438-82-0 ]
[ 1622149-25-0 ]
[ 1622149-27-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	With platinum 1,3-divinyl-1,1,3,3-tetramethyldisiloxane In 5,5-dimethyl-1,3-cyclohexadiene; toluene at 20℃; for 2.5h; Inert atmosphere;	2-Bromo-3-(4-pentamethyldisiloxy-butyl)thiophene (1a) To a solution of 5a (0.68 g, 3.2 mmol) in 4 mL toluene were added pentamethyldisiloxane (0.74 mL, 3.8 mmol) and (1,1,3,3-tetramethyl-1,3-divinyldisiloxane)platinum(0) (2 wt% xylene solution, 5 mg). After stirring the mixture was at room temperature for 2.5 h, the resulting reaction mixture was subjected to column chromatography on silica gel to afford 1.27 g of 1a (>99%).
2.5 g	With platinum⁽⁰⁾-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In 5,5-dimethyl-1,3-cyclohexadiene at 20℃; for 0.0833333h; Inert atmosphere; Schlenk technique;

Reference： [1]Mori, Atsunori; Ide, Kenji; Tamba, Shunsuke; Tsuji, Satoru; Toyomori, Yuka; Yasuda, Takeshi [Chemistry Letters, 2014, vol. 43, # 5, p. 640 - 642]
[2]Fujita, Keisuke; Sumino, Yugo; Ide, Kenji; Tamba, Shunsuke; Shono, Keisuke; Shen, Jian; Nishino, Takashi; Mori, Atsunori; Yasuda, Takeshi [Macromolecules, 2016, vol. 49, # 4, p. 1259 - 1269]

46
[ 1438-82-0 ]
[ 1622149-26-1 ]
[ 1622149-28-3 ]

Yield	Reaction Conditions	Operation in experiment
93%	With platinum 1,3-divinyl-1,1,3,3-tetramethyldisiloxane In 5,5-dimethyl-1,3-cyclohexadiene; toluene at 20℃; for 2.5h; Inert atmosphere;	2-Bromo-3-(4-pentamethyldisiloxy-butyl)thiophene (1a) General procedure: To a solution of 5a (0.68 g, 3.2 mmol) in 4 mL toluene were added pentamethyldisiloxane (0.74 mL, 3.8 mmol) and (1,1,3,3-tetramethyl-1,3-divinyldisiloxane)platinum(0) (2 wt% xylene solution, 5 mg). After stirring the mixture was at room temperature for 2.5 h, the resulting reaction mixture was subjected to column chromatography on silica gel to afford 1.27 g of 1a (>99%).

Reference： [1]Mori, Atsunori; Ide, Kenji; Tamba, Shunsuke; Tsuji, Satoru; Toyomori, Yuka; Yasuda, Takeshi [Chemistry Letters, 2014, vol. 43, # 5, p. 640 - 642]

47
[ 637-69-4 ]
[ 1438-82-0 ]
1-(4-methoxyphenylethyl)-1,1,3,3,3-pentamethyldisiloxane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With bis(cyclooctatetraene)(1-isocyanoadamantane)iron; 1-adamantyl isocyanide In neat (no solvent) at 40℃; for 23h;
96%	With 1-adamantyl isocyanide; iron biscyclooctatetraene In neat (no solvent) at 50℃; for 23h; Inert atmosphere; Glovebox; Sealed tube;	27 Hydrosilylation of 4-methoxystyrene with 1,1,3,3,3-pentamethyldisiloxane General procedure: In a nitrogen-blanketed glove box, 2 mg (0.01 mmol) of Fe(COT)2 in Synthesis Example 2, 3 mg (0.02 mmol) of AdNC, 254 μL (1.3 mmol) of 1,1,3,3,3-pentamethyldisiloxane, and 115 μL (1.0 mmol) of styrene were added to a screw-top vial with a stirrer. The vial was closed, after which the contents were stirred at room temperature (RT) for 23 hours. After cooling, analysis was made by 1H-NMR spectroscopy to determine the structure and yield of the product. As a result, it was confirmed that the signal assigned to the reactant disappeared completely. Instead, a multiplet near 0.89 ppm indicative of the signal assigned to the desired product was observed, from which a yield was computed. The results are shown in Table 8.
92%	With iron(II) pivalate; 1-adamantanecarbonitrile In neat (no solvent) at 30℃; for 24h;

Reference： [1]Sunada, Yusuke; Noda, Daisuke; Soejima, Hiroe; Tsutsumi, Hironori; Nagashima, Hideo [Organometallics, 2015, vol. 34, # 12, p. 2896 - 2906]
[2]Current Patent Assignee: KYUSHU UNIVERSITY; SHIN-ETSU CHEMICAL CO., LTD. - US2017/260216, 2017, A1 Location in patent: Paragraph 0197; 0260; 0284-0286; 0318-0319
[3]Noda, Daisuke; Tahara, Atsushi; Sunada, Yusuke; Nagashima, Hideo [Journal of the American Chemical Society, 2016, vol. 138, # 8, p. 2480 - 2483]

48
[ 111-66-0 ]
[ 1438-82-0 ]
1,1,1,3,3-pentamethyl-3-octyl-disiloxane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With tert-butylisonitrile; [Fe(mesityl)(μ-mesityl)]₂ In neat (no solvent) at 80℃; for 16h; Inert atmosphere; Sealed tube;	1 Hydrosilylation of 1-octene with 1,1,3,3,3-pentamethyldisiloxane Using Isocyanide Ligand A screw-top vial was charged with 15 mg (0.025 mmol) of [Fe(mesityl) (μ-mesityl)]2 in Synthesis Example 1, 11 μL (0.10 mmol) of tBuNC, 98 μL (0.5 mmol) of 1,1,3,3,3-pentamethyldisiloxane, and 78 μL (0.5 mmol) of 1-octene. The vial was closed, after which the contents were stirred at 80° C. for 16 hours. After cooling, 1.0 mmol of anisole as an internal standard was added to the reaction solution and stirred. A minute amount of the solution was dissolved in deuterochloroform, passed through an alumina column to remove the catalyst, and analyzed by 1H-NMR spectroscopy to determine the structure and yield of the product. It is noted that in the following Examples, a test sample was prepared according to the same procedure and analyzed by 1H-NMR spectroscopy. As a result, it was confirmed that the signal assigned to the ethylene site of 1-octene as the reactant disappeared completely. Instead, a multiplet near 0.50 ppm indicative of the signal assigned to proton on silicon-adjoining carbon in the desired product, 1,1,1,3,3-pentamethyl-3-octyldisiloxane was observed, from which a yield was determined. The results are shown in Table 1. 1H-NMR (396 MHz, CDCl3) δ: 0.03 (s, 6H), 0.06 (s, 9H), 0.50 (t, J=7.7 Hz, 2H), 0.88 (t, J=6.8 Hz, 3H), 1.19-1.34 (br, 12H)
96%	With (<SUP>TF</SUP>APDI)Co(2-ethylhexanoate)<SUB>2</SUB> In neat (no solvent) at 23℃; for 1h;
96%	With C₄₀H₇₂Co₂N₈ In neat (no solvent) at 50℃; for 24h;

94%	With 2,6-bis(1-(2,6-dimethylphenylimino)ethyl)pyridine; (cyclooctatetraene)tris(1-isocyanoadamantane)iron In neat (no solvent) at 80℃; for 23h;
90%	With cobalt pivalate; 1-adamantanecarbonitrile In 1,2-dimethoxyethane at 80℃; for 36h;
90%	With nickel 2-ethylhexanoate; 1,4-bis(2,6-diisopropylphenyl)-2,3-dimethyl-1,4-diazabuta-1,3-diene In neat (no solvent) at 23℃; for 6h; regioselective reaction;
80%	With C₂₂H₃₄FeO₂Si₄ at 80℃; for 3h; Inert atmosphere; Schlenk technique;	7 [Example 7] Hydrosilylation of 1-octene with 1,1,1,3,3-pentamethyldisiloxane. A magnetic stirrer was added to a 20 mL shrink tube, After heating and drying under reduced pressure to 5 Pa, The inside of the Schrenk tube was replaced with an argon atmosphere. The iron complex A (15 mg, 0.03 mmol) was added as a catalyst to the Schlenk tube. 1-Octene (156.3 μL, 1.0 mmol) was added thereto, Further, 1,1,1,3,3-pentamethyldisiloxane (195.2 μL, 1.0 mmol) was added thereto, The solution was stirred at 80 for 3 hours. After cooling, Anisole was added as an internal standard, and a & lt; 1 & gt; H-NMR spectrum was measured. The structure and yield of the product were determined. The results are shown in Table 2 as entry 1.
74%	With tert-butylisonitrile; cobalt(II) acetate at 80℃; for 24h; Inert atmosphere;	22 [Example 22] Hydrosilylation Reaction of 1-Octene [Example 22] Hydrosilylation Reaction of 1-Octene (0224) A screw-top vial was charged with 5 mg (0.03 mmol) of cobalt acetate (commercial product) as a catalyst, 5 mg (0.06 mmol) of t-butyl isocyanide as a ligand, 254 μL (1.3 mmol) of 1,1,3,3,3-pentamethyldisiloxane, and 157 μL (1.0 mmol) of 1-octene. The vial was closed, after which the contents were stirred at 80° C. for 24 hours. After cooling, analysis was made by 1H-NMR spectroscopy to determine the structure and yield of the product. As a result, it was confirmed that the signal assigned to the ethylene site of 1-octene as the reactant disappeared completely. Instead, a triplet at 0.51 ppm indicative of the signal assigned to proton on silicon-adjoining carbon in the desired product, 1,1,1,3,3-pentamethyl-3-octyldisiloxane was observed, from which a yield was computed. The results are shown in Table 6. (0225) 1H-NMR (396 MHz, CDCl3) δ: 0.03 (a, 6H), 0.06 (s, 9H), 0.50 (t, J=7.7 Hz, 2H), 0.88 (t, J=6.8 Hz, 3H), 1.19-1.34 (br, 12H)
15 %Spectr.	With C₂₂H₃₄O₂RuSi₄ at 80℃; for 3h; Schlenk technique; Inert atmosphere;	7 [Example 7]The hydrosilylation of 1-octene with 1,1,1,3,3-pentamethyldisiloxane A magnetic stirrer was added to a 20 mL shrink tube and heated and dried under reduced pressure to 5 Pa. Subsequently, the inside of the Schlenk tube was replaced with an argon atmosphere. To the Schlenk tube was added ruthenium complex A (8 mg, 0.015 mmol) as a catalyst. 1-octene (78.2 μL, 0.5 mmol) was added thereto, and 1,1,1,3,3-pentamethyldisiloxane (97.6 μL, 1.0 mmol) was added thereto.And stirred for 3 hours.
99 %Spectr.	With cobalt(II) acetate; 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene In neat (no solvent) at 80℃; for 24h; Inert atmosphere; Sealed tube;	4 [Example 1] Hydrosilylation Using Iron Pivalate and 1,3-dimesitylimidazol-2-ylidene (Abbreviated as IMes, Hereinafter) [Example 1] Hydrosilylation Using Iron Pivalate and 1,3-dimesitylimidazol-2-ylidene (Abbreviated as IMes, Hereinafter) (0215) A screw-top vial was charged with 8 mg (0.03 mmol) of iron pivalate in Synthesis Example 1 as a catalyst precursor, 18 mg (0.06 mmol) of IMes as a NHC ligand, 254 μL (1.3 mmol) of 1,1,3,3,3-pentamethyldisiloxane, and 157 μL (1.0 mmol) of 1-octene. The vial was closed, after which the contents were stirred at 80° C. for 24 hours. Thereafter, 1.0 mmol of anisole as an internal standard was added to the reaction solution and stirred. A minute amount of the solution was dissolved in deuterochloroform, passed through alumina to remove the catalyst, and analyzed by 1H-NMR spectroscopy. In the following Examples, a test sample was prepared according to the same procedure and analyzed by 1H-NMR spectroscopy. As a result, it was confirmed that the signal assigned to the ethylene site of 1-octene as the reactant disappeared completely. Instead, a multiplet at 0.51 ppm indicative of the signal assigned to proton on silicon-adjoining carbon in the desired product, 1,1,1,3,3-pentamethyl-3-octyldisiloxane was observed, from which a yield was computed. The results are shown in Table 1. The yield computed from the 1H-NMR data was 65%. [Example 4] Change of Ligand from Example 3 (0218) Reaction was carried out according to the same procedure as in Example 3 aside from using 23 mg (0.06 mmol) of IPr instead of IMes. As a result, it was confirmed that the signal assigned to the reactant disappeared completely. Instead, a multiplet at 0.51 ppm indicative of the signal assigned to the desired product was observed, from which a yield was computed. The results are shown in Table 1. The yield computed from the 1H-NMR data was at least 99%.
99 %Chromat.	With C₇₇H₇₀N₂OPtSi₂ In toluene at 80℃; for 5h; Inert atmosphere; Sealed tube; regioselective reaction;
	With platinum doped titanium oxide In toluene at 20℃; for 6h;	6 Examples 6 to 10: Production of organosilicon compound by hydrosilylation reaction using platinum-supported catalyst Pentamethyldisiloxane and 1-octene were reacted in toluene solvent at room temperature for 6 hours using each of the platinum-supported catalysts 1 to 5 prepared in Examples 1 to 5 as a catalyst.Each platinum-supported catalyst was used so that the amount of platinum was 0.01 mol% (100 ppm) based on pentamethyldisiloxane.When the product mixture after the reaction was analyzed by 29 Si NMR, no raw material substrate was detected and only the hydrosilylation product was detected. In the case of Example 9 and Example 10, the product mixture after the reaction was analyzed by gas chromatography, and the yields of the hydrosilylation products were 9% and 14%, respectively.
	With C₂₈H₃₄CoN₃O₄⁽¹⁺⁾*C₅H₇O₂^(1-) In tetrahydrofuran at 80℃; for 8h; Sealed tube;

Reference： [1]Current Patent Assignee: KYUSHU UNIVERSITY; SHIN-ETSU CHEMICAL CO., LTD. - US2017/260216, 2017, A1 Location in patent: Paragraph 0197; 0228-0233; 0262; 0270; 0292-0294; 0299-0300
[2]Schuster, Christopher H.; Diao, Tianning; Pappas, Iraklis; Chirik, Paul J. [ACS Catalysis, 2016, vol. 6, # 4, p. 2632 - 2636]
[3]Sanagawa, Atsushi; Nagashima, Hideo [Organometallics, 2018, vol. 37, # 17, p. 2859 - 2871]
[4]Sunada, Yusuke; Noda, Daisuke; Soejima, Hiroe; Tsutsumi, Hironori; Nagashima, Hideo [Organometallics, 2015, vol. 34, # 12, p. 2896 - 2906]
[5]Noda, Daisuke; Tahara, Atsushi; Sunada, Yusuke; Nagashima, Hideo [Journal of the American Chemical Society, 2016, vol. 138, # 8, p. 2480 - 2483]
[6]Pappas, Iraklis; Treacy, Sean; Chirik, Paul J. [ACS Catalysis, 2016, vol. 6, # 7, p. 4105 - 4109]
[7]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD.; KYUSHU UNIVERSITY - KR2015/125983, 2015, A Location in patent: Paragraph 0192-0194
[8]Current Patent Assignee: KYUSHU UNIVERSITY; SHIN-ETSU CHEMICAL CO., LTD. - US2017/233417, 2017, A1 Location in patent: Paragraph 0224-0225
[9]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD.; KYUSHU UNIVERSITY - KR2015/121721, 2015, A Location in patent: Paragraph 0186-0187; 0195
[10]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD.; KYUSHU UNIVERSITY - US2017/260215, 2017, A1 Location in patent: Paragraph 0215; 0218
[11]Zak; Bołt; Kubicki; Pietraszuk [Dalton Transactions, 2018, vol. 47, # 6, p. 1903 - 1910]
[12]Current Patent Assignee: NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY - JP2018/131424, 2018, A Location in patent: Paragraph 0040
[13]Gutiérrez-Tarriño, Silvia; Concepción, Patricia; Oña-Burgos, Pascual [European Journal of Inorganic Chemistry, 2018, vol. 2018, # 45, p. 4867 - 4874]

49
[ 1438-82-0 ]
[ 111-81-9 ]
[ 1731-86-8 ]

Reference： [1]Organometallics,2015,vol. 34,p. 2896 - 2906

50
[ 405-99-2 ]
[ 1438-82-0 ]
1,1,1-3,3-pentamethyl-3-(2-(4-fluorophenyl)ethyl)disiloxane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With bis(cyclooctatetraene)(1-isocyanoadamantane)iron; 1-adamantyl isocyanide In neat (no solvent) at 50℃; for 23h;
92%	With iron(II) pivalate; 1-adamantanecarbonitrile In neat (no solvent) at 50℃; for 3h;
89%	With tert-butylisonitrile; iron biscyclooctatetraene In neat (no solvent) at 50℃; for 23h; Inert atmosphere; Sealed tube;	15 [Example 11] Hydrosilylation of Styrene with 1,1,3,3,3-pentamethyldisiloxane (Change of Reaction Conditions from Example 3) General procedure: A screw-top vial was charged with 8 mg (0.03 mmol) of Fe(COT)2 in Synthesis Example 2, 7 μL (0.06 mmol) of tBuNC, 254 μL (1.3 mmol) of 1,1,3,3,3-pentamethyldisiloxane and 115 μL (1.0 mmol) of styrene. The vial was closed, after which the contents were stirred at 50° C. for 23 hours. After cooling, analysis was made by 1H-NMR spectroscopy to determine the structure and yield of the product. As a result, it was confirmed that the signal assigned to the reactant disappeared completely. Instead, a multiplet near 0.89 ppm indicative of the signal assigned to the desired product was observed, from which a yield was determined. The results are shown in Table 3.

Reference： [1]Sunada, Yusuke; Noda, Daisuke; Soejima, Hiroe; Tsutsumi, Hironori; Nagashima, Hideo [Organometallics, 2015, vol. 34, # 12, p. 2896 - 2906]
[2]Noda, Daisuke; Tahara, Atsushi; Sunada, Yusuke; Nagashima, Hideo [Journal of the American Chemical Society, 2016, vol. 138, # 8, p. 2480 - 2483]
[3]Current Patent Assignee: KYUSHU UNIVERSITY; SHIN-ETSU CHEMICAL CO., LTD. - US2017/260216, 2017, A1 Location in patent: Paragraph 0197; 0260; 0285-0286

51
[ 1438-82-0 ]
[ 5664-17-5 ]
1-(3-cyclohexylprop-1-en-2-yl)-1,1,3,3,3-pentamethyldisiloxane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With supported gold nanoparticles on TiO₂ In 1,2-dichloro-ethane at 65℃; for 2h; regioselective reaction;

Reference： [1]Kidonakis, Marios; Stratakis, Manolis [Organic Letters, 2015, vol. 17, # 18, p. 4538 - 4541]

52
[ 1438-82-0 ]
[ 98-83-9 ]
1,1,1-3,3-pentamethyl-3-(2-phenylpropyl)disiloxane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With Cyclohexyl isocyanide; cobalt pivalate at 80℃; for 3h; Inert atmosphere;	57 [Example 57] Hydrosilylation Reaction Using Cobalt Pivalate and Cyclohexyl Isocyanide [Example 57] Hydrosilylation Reaction Using Cobalt Pivalate and Cyclohexyl Isocyanide (0284) A screw-top vial was charged with 3 mg (0.01 mmol) of cobalt pivalate in Synthesis Example 4 as a catalyst, 3 μL (0.03 mmol) of cyclohexyl isocyanide as an isocyanide ligand, 254 μL (1.3 mmol) of 1,1,3,3,3-pentamethyldisiloxane as a hydrosilane, and 130 μL (1.0 mmol) of α-methylstyrene. The contents were stirred at 80° C. for 3 hours. After cooling, analysis was made by 1H-NMR spectroscopy to determine the structure and yield of the product. As a result, it was confirmed that the signal assigned to the reactant disappeared completely. Instead, a multiplet near 2.92 ppm indicative of the signal assigned to proton on silicon-adjoining carbon in the desired product was observed, from which a yield was computed. The results are shown in Table 19.
98%	With cobalt pivalate; 1-adamantanecarbonitrile In neat (no solvent) at 80℃; for 6h;
96%	With C₄₀H₇₂Co₂N₈ In neat (no solvent) at 50℃; for 24h;

> 99 %Spectr.	With cobalt pivalate; tert-butylisonitrile In neat (no solvent) at 80℃; for 3h;
> 97 %Spectr.	With (π-Me₅C₅)Si⁺B(C₆F₅)₄^- In 1,2-dichloro-ethane at 80℃; for 1h; Inert atmosphere;
	With trityl tetrakis(pentafluorophenyl)borate In dichloromethane-d2 at 20℃; for 0.166667h;	2 EXAMPLE 2 148 mg (1.00 mmol) of pentamethyldisiloxane in 0.5 ml of d2-dichloromethane are mixed with a solution of 118 mg (1.00 mmol) of α-methylstyrene in 0.5 ml of d2-dichloromethane and a solution of 1.0 mg (1.0 μmol, 0.11 mol %) of trityl tetraakis(pentafluorophenyl)borate in 0.5 ml of d2-dichloromethane is added. After a reaction time of 10 min, the reaction is stopped by adding one drop of pyridine. 1H-NMR spectroscopic investigation shows quantitative conversion with formation of the hydrosilylation product Ph-CH(CH3)-CH2-Si(CH3)2-O-Si(CH3)3.
	With ethyl trimethylsilyl ether; [(π-Me₅C₅)Si]B(C₆F₅)₄ In dichloromethane-d2 at 60℃; for 1h; Inert atmosphere;	1 EXAMPLE 1 A mixture of 239 mg (2.02 mmol) of α-methylstyrene and 300 mg (2.02 mmol) of pentamethyldisiloxane is admixed under an inert gas atmosphere (argon) with a solution of 1.8 mg (2.14 μmol) of the compound (π-Me5C5)Si+ B(C6F5)4- and 4.8 mg (0.041 mmol) of ethoxytrimethylsilane in 540 mg of dideuterodichloromethane with shaking and allowed to stand at 25° C. for 8 days. The reaction mixture is examined by NMR spectroscopy after this time: α-methylstyrene and pentamethyldisiloxane are present in an unchanged amount, and no hydrosilylation product can be detected. The catalyst (π-Me5C5)Si+ B(C6F5)4- is detectable in an unchanged amount by NMR spectroscopy (singlet at δ=2.2 ppm). The sample is subsequently heated at 60° C. for 1 hour and then examined again by NMR spectroscopy: formation of the hydrosilylation product, 1,1,1,3,3-pentamethyl-3-(2-phenylpropyl)disiloxane, conversion >99%.

Reference： [1]Current Patent Assignee: KYUSHU UNIVERSITY; SHIN-ETSU CHEMICAL CO., LTD. - US2017/233417, 2017, A1 Location in patent: Paragraph 0284
[2]Noda, Daisuke; Tahara, Atsushi; Sunada, Yusuke; Nagashima, Hideo [Journal of the American Chemical Society, 2016, vol. 138, # 8, p. 2480 - 2483]
[3]Sanagawa, Atsushi; Nagashima, Hideo [Organometallics, 2018, vol. 37, # 17, p. 2859 - 2871]
[4]Noda, Daisuke; Tahara, Atsushi; Sunada, Yusuke; Nagashima, Hideo [Journal of the American Chemical Society, 2016, vol. 138, # 8, p. 2480 - 2483]
[5]Fritz-Langhals, Elke [Organic Process Research and Development, 2019, vol. 23, # 11, p. 2369 - 2377]
[6]Current Patent Assignee: WACKER CHEMIE AG - US2019/382421, 2019, A1 Location in patent: Paragraph 0063; 0065
[7]Current Patent Assignee: WACKER CHEMIE AG - US2020/55880, 2020, A1 Location in patent: Paragraph 0063-0069

53
[ 1438-82-0 ]
[ 7399-49-7 ]
1,1,1-3,3-pentamethyl-3-(2-(2-tolyl)propyl)disiloxane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With cobalt pivalate; 1-adamantanecarbonitrile In neat (no solvent) at 80℃; for 24h;

Reference： [1]Noda, Daisuke; Tahara, Atsushi; Sunada, Yusuke; Nagashima, Hideo [Journal of the American Chemical Society, 2016, vol. 138, # 8, p. 2480 - 2483]

54
[ 111-67-1 ]
[ 1438-82-0 ]
1,1,1,3,3-pentamethyl-3-octyl-disiloxane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With C₄₀H₇₂Co₂N₈ In neat (no solvent) at 50℃; for 24h;
94%	With cobalt pivalate; 1-adamantanecarbonitrile In 1,2-dimethoxyethane at 80℃; for 36h;
83%	With cobalt pivalate; [1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene at 80℃; for 24h; Inert atmosphere;	15 [Example 15] Hydrosilylation of 2-octene with 1,1,3,3,3-pentamethyldisiloxane Using Cobalt Pivalate and IMes [Example 15] Hydrosilylation of 2-octene with 1,1,3,3,3-pentamethyldisiloxane Using Cobalt Pivalate and IMes (0229) A reactor was charged with 8 mg (0.03 mmol) of cobalt pivalate in Synthesis Example 3, 18 mg (0.06 mmol) of IMes, 254 μL (1.3 mmol) of 1,1,3,3,3-pentamethyldisiloxane, and 157 μL (1.0 mmol) of 2-octene, which were stirred at 80° C. for 24 hours. After cooling, analysis was made by the internal standard method to find a substrate conversion of at least 99% and formation of 1,1,1,3,3-pentamethyl-3-octyldisiloxane in a yield of 83%.

79%

With tert-butylisonitrile; cobalt(II) acetate at 80℃; for 24h; Inert atmosphere;

23 [Example 22] Hydrosilylation Reaction of 1-Octene [Example 22] Hydrosilylation Reaction of 1-Octene (0224) A screw-top vial was charged with 5 mg (0.03 mmol) of cobalt acetate (commercial product) as a catalyst, 5 mg (0.06 mmol) of t-butyl isocyanide as a ligand, 254 μL (1.3 mmol) of 1,1,3,3,3-pentamethyldisiloxane, and 157 μL (1.0 mmol) of 1-octene. The vial was closed, after which the contents were stirred at 80° C. for 24 hours. After cooling, analysis was made by 1H-NMR spectroscopy to determine the structure and yield of the product. As a result, it was confirmed that the signal assigned to the ethylene site of 1-octene as the reactant disappeared completely. Instead, a triplet at 0.51 ppm indicative of the signal assigned to proton on silicon-adjoining carbon in the desired product, 1,1,1,3,3-pentamethyl-3-octyldisiloxane was observed, from which a yield was computed. The results are shown in Table 6. (0225) 1H-NMR (396 MHz, CDCl3) δ: 0.03 (a, 6H), 0.06 (s, 9H), 0.50 (t, J=7.7 Hz, 2H), 0.88 (t, J=6.8 Hz, 3H), 1.19-1.34 (br, 12H)

Reference： [1]Sanagawa, Atsushi; Nagashima, Hideo [Organometallics, 2018, vol. 37, # 17, p. 2859 - 2871]
[2]Noda, Daisuke; Tahara, Atsushi; Sunada, Yusuke; Nagashima, Hideo [Journal of the American Chemical Society, 2016, vol. 138, # 8, p. 2480 - 2483]
[3]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD.; KYUSHU UNIVERSITY - US2017/260215, 2017, A1 Location in patent: Paragraph 0229
[4]Current Patent Assignee: KYUSHU UNIVERSITY; SHIN-ETSU CHEMICAL CO., LTD. - US2017/233417, 2017, A1 Location in patent: Paragraph 0224-0225

55
[ 1438-82-0 ]
[ 76487-56-4 ]
C₂₃H₃₄O₅Si₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With platinum⁽⁰⁾-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 75℃; for 48h; Inert atmosphere;	Liquid crystal siloxane compounds 1A-4A and 1B-4B: General procedure: To a degassed solution of compound 4M (0.26 g, 0.0008 mol) and pentamethylhydrodisiloxane (0.14 g, 0.0009 mol) in 10 mL of dry and freshly distilled toluene was added divinyltetramethyldimethylsiloxyl (2.5 mg) as catalyst. The reaction mixture was stirred at 75 °C under nitrogen for 48 h. After the solvent being evaporated, the residue was purified by column chromatography (silica gel, using n-hexane/ethyl acetate as an eluent) to yield 0.33 g (76 %) of white crystals.

Reference： [1]Chen, Cheng-Chih; Lin, Chih-Hung [Asian Journal of Chemistry, 2016, vol. 28, # 6, p. 1270 - 1274]

56
[ 1438-82-0 ]
[ 76487-57-5 ]
C₂₄H₃₆O₅Si₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With platinum⁽⁰⁾-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 75℃; for 48h; Inert atmosphere;	Liquid crystal siloxane compounds 1A-4A and 1B-4B: General procedure: To a degassed solution of compound 4M (0.26 g, 0.0008 mol) and pentamethylhydrodisiloxane (0.14 g, 0.0009 mol) in 10 mL of dry and freshly distilled toluene was added divinyltetramethyldimethylsiloxyl (2.5 mg) as catalyst. The reaction mixture was stirred at 75 °C under nitrogen for 48 h. After the solvent being evaporated, the residue was purified by column chromatography (silica gel, using n-hexane/ethyl acetate as an eluent) to yield 0.33 g (76 %) of white crystals.

Reference： [1]Chen, Cheng-Chih; Lin, Chih-Hung [Asian Journal of Chemistry, 2016, vol. 28, # 6, p. 1270 - 1274]

57
[ 1438-82-0 ]
[ 76487-58-6 ]
C₂₅H₃₈O₅Si₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With platinum⁽⁰⁾-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 75℃; for 48h; Inert atmosphere;	Liquid crystal siloxane compounds 1A-4A and 1B-4B: To a degassed solution of compound 4M (0.26 g, 0.0008 mol) and pentamethylhydrodisiloxane (0.14 g, 0.0009 mol) in 10 mL of dry and freshly distilled toluene was added divinyltetramethyldimethylsiloxyl (2.5 mg) as catalyst. The reaction mixture was stirred at 75 °C under nitrogen for 48 h. After the solvent being evaporated, the residue was purified by column chromatography (silica gel, using n-hexane/ethyl acetate as an eluent) to yield 0.33 g (76 %) of white crystals. 1H NMR (CDCl3, δ, ppm): 0.0 (m, 15H, -Si-CH3), 0.53 (m, 2H, -Si-CH2-CH2-), 1.50-2.20 (m, 8H, -CH2-), 3.80 (s, 3H, -O-CH3), 4.03 (t, 2H, -O-CH2-), 6.92 (m, 4H, aromatic protons), 7.10 (m, 2H, aromatic protons), 8.11 (m, 2H, aromatic protons).

Reference： [1]Chen, Cheng-Chih; Lin, Chih-Hung [Asian Journal of Chemistry, 2016, vol. 28, # 6, p. 1270 - 1274]

58
[ 1438-82-0 ]
[ 73376-32-6 ]
C₂₂H₃₂O₅Si₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With platinum⁽⁰⁾-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 75℃; for 48h; Inert atmosphere;	Liquid crystal siloxane compounds 1A-4A and 1B-4B: General procedure: To a degassed solution of compound 4M (0.26 g, 0.0008 mol) and pentamethylhydrodisiloxane (0.14 g, 0.0009 mol) in 10 mL of dry and freshly distilled toluene was added divinyltetramethyldimethylsiloxyl (2.5 mg) as catalyst. The reaction mixture was stirred at 75 °C under nitrogen for 48 h. After the solvent being evaporated, the residue was purified by column chromatography (silica gel, using n-hexane/ethyl acetate as an eluent) to yield 0.33 g (76 %) of white crystals.

Reference： [1]Chen, Cheng-Chih; Lin, Chih-Hung [Asian Journal of Chemistry, 2016, vol. 28, # 6, p. 1270 - 1274]

59
[ 1112-39-6 ]
[ 1438-82-0 ]
[ 2895-07-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid	1 1,1,1,3,3,3-hexamethyldisiloxane was mixed with 1,1,3,3-tetramethyldisiloxane in a molar ratio of 1: 1, adding concentrated sulfuric acid under total hydrolysis 1h to give 1,1,1,3,3-pentamethyldisiloxane. Mixing 1,1,1,3,3-pentamethyldisiloxane and dimethyldimethoxysilane in a molar ratio of 1: 1, adding concentrated sulfuric acid for total hydrolysis 1 ~ 3h. After distillation, fractions of 135 ° C were collected to give the 1,1,1,3,3,5,5-heptamethyltrisiloxane product.

Reference： [1]Current Patent Assignee: SHANGHAI CHUQING NEW MAT TECH - CN105384763, 2016, A Location in patent: Paragraph 0015; 0016

60
[ 2155-94-4 ]
[ 1438-82-0 ]
C₁₃H₃₃NO₄SSi₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: N,N-dimethyl-2-propen-1-amine; 1,1,1,3,3-pentamethyl-1,3-disiloxane In toluene at 60 - 80℃; for 8h; Stage #2: With 1,3-propanesultone In toluene at 20℃;	1 Hydrogen polyorganosiloxane (0.1 mol) of the following structural formula (6) was added dropwise to a toluene solution of dimethylallylamine (0.1 mol) at 60 to 80 ° C., and the reaction was completed by stirring at this temperature for 8 hours , And the solvent was removed by an evaporator to obtain a colorless transparent liquid (silicone modified tertiary amine). Thereafter, the resultant liquid (silicone-modified tertiary amine) was dropped into a toluene solution of 1,3-propane sultone while stirring in a water bath, and a white solid was precipitated by stirring at room temperature overnight. This was filtered and washed with toluene and acetone to obtain a white solid represented by the following structural formula (7).

Reference： [1]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD. - JP2015/59092, 2015, A Location in patent: Paragraph 0040

61
[ 1438-82-0 ]
[ 872-05-9 ]
ndecyl-Si(Me)2-OSiMe₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With C₄₈H₆₀N₄O₈Pt⁽²⁺⁾*2NO₃^(1-) In toluene at 80℃; for 1h; Inert atmosphere; Schlenk technique;	4.4. General procedure for the hydrosilylation reaction General procedure: To a 25 ml Schlenk flask, 1 mmol of hydrosilane, 1 mmol of olefin(or 2 mmol of olefin for compound 12 and 1.3 mmol of olefin for compound 13), 2 ml of anhydrous toluene and 0.001 mol% of complex1 or 2 (solution in toluene) were added under argon atmosphere.The mixture was heated at 80 °C for definite time. The progress of reactions was examined by GC or GC-MS analysis. Afterthe reaction was complete, the solvent and all volatiles wereremoved under reduced pressure to give products 3-19.
52%	With 2C₄H₉O^(1-)Ni⁽²⁺⁾(x)KCl In tetrahydrofuran at 20℃; for 4h; Glovebox; Inert atmosphere;

Reference： [1]Walczak, Anna; Stachowiak, Hanna; Kurpik, Gracjan; Kaźmierczak, Joanna; Hreczycho, Grzegorz; Stefankiewicz, Artur R. [Journal of Catalysis, 2019, vol. 373, p. 139 - 146]
[2]Buslov, Ivan; Song, Fang; Hu, Xile [Angewandte Chemie - International Edition, 2016, vol. 55, # 40, p. 12295 - 12299][Angew. Chem., 2016, vol. 128, p. 12483 - 12487]

62
[ 22065-57-2 ]
[ 1438-82-0 ]
ethyl 2-(1,1,3,3,3-pentamethyldisiloxanyl)-2-phenylacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With copper(I) trifluoromethanesulfonate benzene; 6-[(R)-1-(1-naphthyl)ethyl]-3,9-ditosyl-3,6,9,15-tetraazabicyclo[9,3,1]pentadeca-1⁽¹⁵⁾,11,13-triene In 1,2-dichloro-ethane at 20℃; for 18h; Inert atmosphere; Schlenk technique;	Representative procedure for the synthesis of compounds 3 General procedure: Under Ar atmosphere, a solution of L1 or L3 (0.0044 mmol) and [(CuOTf)2*C6H6)](0.002 mmol) in 1,2-dichloroethane (1.0 mL) was stirred for 1h at rt. The silane 2 (0.6mmol) was added, followed by the slow addition during 1.5 h of a solution of thediazocompound 1 (0.2 mmol) in 1,2-dichloroethane (1.0 mL) using a syringe pump. Theresulting mixture was stirred at this temperature until disappearance of the startingmaterial (checked by TLC analysis). The solvent was removed under vacuum. Theresulting residue was purified by flash column chromatography (SiO2, hexanes:ethylacetate) to afford 3.

Reference： [1]Tseberlidis, Giorgio; Caselli, Alessandro; Vicente, Rubén [Journal of Organometallic Chemistry, 2017, vol. 835, p. 1 - 5]

63
[ 1438-82-0 ]
[ 87061-56-1 ]
1-[1,2-bis (triethoxysilyl)ethyl]-1,1,3,3,3-pentamethyldisiloxane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44.5 g	With platinum⁽⁰⁾-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 60℃; for 1h;	4 Synthesis of 1- [1,2-bis (triethoxysilyl)] ethyl-1,1,3,3,3-pentamethyldisiloxane In a flask equipped with a stirrer, a reflux condenser, a dropping funnel and a thermometer, 35.3 g (0.1 mol) of 1,2-bis (triethoxysilyl) ethylene, 0.07 g of a toluene solution of platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex was charged and heated to 60° After the internal temperature stabilized, 1,1,1,3,3-pentamethyldisiloxane 14.8 g ( 0.1 mol) was added dropwise over 1 hour, and the mixture was stirred at that temperature for 1 hour. The reaction solution was distilled to obtain 44.5 g of a fraction having a boiling point of 143 ° -146 ° C./0.4 kPa

Reference： [1]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD. - JP2016/155771, 2016, A Location in patent: Paragraph 0032

64
[ 1438-82-0 ]
[ 53998-34-8 ]
1-[1,2-bis(methyldimethoxysilyl)ethyl]-1,1,3,3,3-pentamethyldisiloxane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33.2 g	With platinum⁽⁰⁾-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 60℃; for 1h;	5 Synthesis of 1-[1,2-bis(methyldimethoxysilyl)ethyl]-1,1,3,3,3-pentamethyldisiloxane Into a flask equipped with a stirrer, a reflux condenser, a dropping funnel and a thermometer, 23.6 g (0.1 mol) of 1,2-bis (methyldimethoxysilyl) ethylene, 0.07 g of a toluene solution of a platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex was charged and heated to 60 ° C. It was heated. After the internal temperature was stabilized, 14.8 g (0.1 mol) of 1,1,1,3,3-pentamethyldisiloxane was added dropwise over 1 hour and the mixture was stirred at that temperature for 1 hour. The reaction solution was distilled to obtain 33.2 g of a fraction having a boiling point of 115 ° -116 ° C./0.4 kPa

Reference： [1]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD. - JP2016/155771, 2016, A Location in patent: Paragraph 0034

65
[ 1438-82-0 ]
[ 18236-41-4 ]
1-[1,2-bis(trimethoxysilyl)ethyl]-1,1,3,3,3-pentamethyl disiloxane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37.2 g	With platinum⁽⁰⁾-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 60℃; for 1h;	1 Synthesis of 1- [1,2-bis (trimethoxysilyl)] ethyl-1,1,3,3,3-pentamethyldisiloxane A flask equipped with a stirrer, a reflux condenser, a dropping funnel and a thermometer was charged with 26.8 g (0.1 mol) of 1,2-bis (trimethoxysilyl) ethylene, A toluene solution of platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex was added And heated to 60 ° C. did. After the internal temperature was stabilized, 14.8 g of 1,1,1,3,3-pentamethyldisiloxane ( 0.1 mol) was added dropwise over 1 hour, and the mixture was stirred at that temperature for 1 hour. The reaction solution was distilled, A fraction with a boiling point of 123-124 ° C / 0.4 kPa 37.2 g were obtained

Reference： [1]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD. - JP2016/155771, 2016, A Location in patent: Paragraph 0026

66
[ 1438-82-0 ]
2-(3-allyl-5-(4-methoxyphenyl)furan-2-yl)benzo[d]oxazole [ No CAS ]
2-(5-(4-methoxyphenyl)-3-(3-(1,1,3,3,3-pentamethyldisiloxanyl)propyl)furan-2-yl)benzo[d]oxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With platinum⁽⁰⁾-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene at 20℃; for 24h; Inert atmosphere; Sealed tube;	(21) 2-{5-(4-methoxyphenyl)-3-[3-(pentamethyldisiloxanyl)propyl]-2-furyl}-1,3-benzoxazole (7a) A 10-mL screw-top test tube equipped with a Teflon-coated magnetic stirrer bar was charged with terminal alkene 6a (33.1mg, 0.10 mmol), disiloxane (24 μL, 0.12 mmol), and anhyd THF(0.50 mL). To the solution was added a 2 wt% solution of Karstedt catalyst [(1,1,3,3-tetramethyl-1,3-divinyldisiloxane)platinum(0)] [Pt(dvds)] in xylene (Aldrich; 2.2 μL, 0.1 μmol, 0.1mol%) at r.t., and the mixture was stirred at r.t. for 24 h. The resulting mixture was then treated with H2O. The mixture was partitioned between Et2O (2 mL) and H2O (2 mL) three times. The combined organic extracts were dried (Na2SO4) and filtered,and the filtrate was concentrated under reduced pressure. The crude product was purified by column chromatography[silica gel, 100% hexane to hexane-Et2O (5:1)] to afford a pale yellow oil; yield: 33.2 mg (0.069 mmol, 69%); Rf = 0.40 (hexane-Et2O, 5:1); IR (ATR): 2956, 1613, 1563, 1532, 1492, 1453, 1251,1175, 1036, 839, 804, 758, 745, 689, 667, 624 cm-1. 1H NMR(400 MHz, CDCl3): δ = 7.82-7.75 (m, 3 H), 7.60-7.53 (m, 1 H),7.37-7.29 (m, 2 H), 6.96 (d, J = 8.8 Hz, 2 H), 6.63 (s, 1 H), 3.86 (s,3 H), 3.03 (t, J = 7.6 Hz, 2 H), 1.81-1.72 (m, 2 H), 0.72-0.65 (m, 2H), 0.07 (s, 6 H), 0.05 (s, 9 H). 13C NMR (100 MHz, CDCl3): δ =160.1, 156.5, 156.2, 150.0, 142.1, 137.1, 134.5, 126.3, 124.7,124.6, 122.8, 119.9, 114.3, 110.4, 107.9, 55.5, 29.2, 23.8, 18.4,2.1, 0.5. HRMS (DART+): m/z [M + H]+ calcd for C26H34NO4Si2:480.2026; found: 480.2025.

Reference： [1]Miyagawa, Naoki; Murase, Yuki; Okano, Kentaro; Mori, Atsunori [Synlett, 2017, vol. 28, # 9, p. 1106 - 1110]

67
[ 498-66-8 ]
[ 1438-82-0 ]
1-(1,1,3,3,3-pentamethyldisiloxanyl)-2-norbornene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With iron(II) pivalate; [1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene In neat (no solvent) at 80℃; for 24h; Inert atmosphere;	12 [Example 12] Hydrosilylation of 2-norbornene with 1,1,3,3,3-pentamethyldisiloxane Using Cobalt Pivalate and IMes [Example 12] Hydrosilylation of 2-norbornene with 1,1,3,3,3-pentamethyldisiloxane Using Cobalt Pivalate and IMes (0226) A reactor was charged with 8 mg (0.03 mmol) of cobalt pivalate in Synthesis Example 3, 18 mg (0.06 mmol) of IMes, 254 μL (1.3 mmol) of 1,1,3,3,3-pentamethyldisiloxane, and 94 mg (1.0 mmol) of 2-norbornene, which were stirred at 80° C. for 24 hours. After cooling, analysis was made by the internal standard method to find a substrate conversion of at least 99% and formation of 1-(1,1,3,3,3-pentamethyldisiloxanyl)-2-norbornene in a yield of 80%.

Reference： [1]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD.; KYUSHU UNIVERSITY - US2017/260215, 2017, A1 Location in patent: Paragraph 0226

68
[ 498-66-8 ]
[ 1438-82-0 ]
1-(bicyclo[2.2.1]hept-2-yl)-1,1,3,3,3-pentamethyldisiloxane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With cobalt pivalate; [1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene In neat (no solvent) at 80℃; for 24h; Inert atmosphere;	28 [Example 28] Hydrosilylation Reaction of 2-norbornene with 1,1,3,3,3-pentamethyldisiloxane Using Cobalt Pivalate and IMes [Example 28] Hydrosilylation Reaction of 2-norbornene with 1,1,3,3,3-pentamethyldisiloxane Using Cobalt Pivalate and IMes (0245) A screw-top vial was charged with 3 mg (0.01 mmol) of cobalt pivalate in Synthesis Example 3 as a catalyst, 6 mg (0.02 mmol) of IMes as a NHC ligand, 254 μL (1.3 mmol) of 1,1,3,3,3-pentamethyldisiloxane as a hydrosilane, and 94 mg (1.0 mmol) of 2-norbornene. The contents were stirred at 80° C. for 24 hours. After cooling, analysis was made by 1H-NMR spectroscopy to determine the structure and yield of the product. As a result, it was confirmed that the signal assigned to the reactant disappeared completely. Instead, a multiplet at 0.49 ppm indicative of the signal assigned to proton on silicon-adjoining carbon in the desired product was observed, from which a yield was computed. The results are shown in Table 4.

Reference： [1]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD.; KYUSHU UNIVERSITY - US2017/260215, 2017, A1 Location in patent: Paragraph 0244; 0245

69
[ 1438-82-0 ]
[ 3710-30-3 ]
[ 111-66-0 ]
1,8-bis(1,1,3,3,3-pentamethyl-disiloxanyl)octane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 60% 2: 40%	With iron(II) pivalate; [1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene at 80℃; for 24h; Inert atmosphere;	14 [Example 14] Hydrosilylation of 1,7-octadiene with 1,1,3,3,3-pentamethyldisiloxane Using Iron Pivalate and IMes [Example 14] Hydrosilylation of 1,7-octadiene with 1,1,3,3,3-pentamethyldisiloxane Using Iron Pivalate and IMes (0228) A reactor was charged with 8 mg (0.03 mmol) of iron pivalate in Synthesis Example 1, 18 mg (0.06 mmol) of IMes, 254 μL (1.3 mmol) of 1,1,3,3,3-pentamethyldisiloxane, and 151 μL (1.0 mmol) of 1,7-octadiene, which were stirred at 80° C. for 24 hours. After cooling, analysis was made by the internal standard method to find a substrate conversion of at least 99% and formation of 1,8-bis(1,1,3,3,3-pentamethyl-disiloxanyl)octane in a yield of 60% and a single end hydrogenated product, octene in a yield of 40%.

Reference： [1]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD.; KYUSHU UNIVERSITY - US2017/260215, 2017, A1 Location in patent: Paragraph 0228

70
[ 1438-82-0 ]
[ 3710-30-3 ]
1,8-bis(1,1,3,3,3-pentamethyl-disiloxanyl)octane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With cobalt pivalate; 1-adamantyl isocyanide at 80℃; for 24h; Inert atmosphere;	39 Example 36] Hydrosilylation Reaction with Vinyltrimethylsilane Example 36] Hydrosilylation Reaction with Vinyltrimethylsilane (0253) A screw-top vial was charged with 8 mg (0.03 mmol) of cobalt pivalate in Synthesis Example 4 as a catalyst, 15 mg (0.09 mmol) of 1-isocyanoadamantane as a ligand, 254 μL (1.3 mmol) of 1,1,3,3,3-pentamethyldisiloxane, and 145 μL (1.0 mmol) of vinyltrimethylsilane. The contents were stirred at 80° C. for 24 hours. After cooling, analysis was made by 1H-NMR spectroscopy to determine the structure and yield of the product. As a result, it was confirmed that the signal assigned to the ethylene site of vinyltrimethylsilane as the reactant disappeared completely. Instead, the signal assigned to the desired product, 1,1,1,3,3-pentamethyl-3-(2-trimethylsilylethyl)disiloxane was observed, from which a yield was computed. The results are shown in Table 12. (0254) 1H-NMR (396 MHz, CDCl3) δ: -0.03 (s, 9H), 0.03 (s, 6H), 0.06 (s, 9H), 0.38 (s, 4H)
60%	With cobalt pivalate; [1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene at 80℃; for 24h; Inert atmosphere;	13 [Example 13] Hydrosilylation of 1,7-octadiene with 1,1,3,3,3-pentamethyldisiloxane Using Cobalt Pivalate and IMes [Example 13] Hydrosilylation of 1,7-octadiene with 1,1,3,3,3-pentamethyldisiloxane Using Cobalt Pivalate and IMes (0227) A reactor was charged with 8 mg (0.03 mmol) of cobalt pivalate in Synthesis Example 3, 18 mg (0.06 mmol) of IMes, 254 μL (1.3 mmol) of 1,1,3,3,3-pentamethyldisiloxane, and 151 μL (1.0 mmol) of 1,7-octadiene, which were stirred at 80° C. for 24 hours. After cooling, analysis was made by the internal standard method to find a substrate conversion of at least 99% and formation of 1,8-bis(1,1,3,3,3-pentamethyl-disiloxanyl)octane in a yield of 60% and an isomerized compound, octadiene in a yield of 5%.

Reference： [1]Current Patent Assignee: KYUSHU UNIVERSITY; SHIN-ETSU CHEMICAL CO., LTD. - US2017/233417, 2017, A1 Location in patent: Paragraph 0253-0254
[2]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD.; KYUSHU UNIVERSITY - US2017/260215, 2017, A1 Location in patent: Paragraph 0227

71
[ 1066-35-9 ]
[ 10519-96-7 ]
[ 1438-82-0 ]

Yield	Reaction Conditions	Operation in experiment
1.2 kg	In tetrahydrofuran; at 20℃; for 1h;Large scale;	Take prepared <strong>[10519-96-7]potassium trimethylsilanolate</strong> 1.12kg in 2L of anhydrous tetrahydrofuran, was added dropwise with stirring dimethylchlorosilane1kg, dropwise, room temperature reaction 1h, filtered, concentrated, extracted with ether, dried and concentrated to give a high purity of 98% or more of pentamethyl disiloxane 1.2kg.

Reference： [1]Patent: CN107235996,2017,A .Location in patent: Paragraph 0018

72
[ 1438-82-0 ]
[ 5356-85-4 ]
1,2-bis(1,1,1,3,5,5,5-heptamethyltrisiloxan-3-yl)ethane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With 1-adamantyl isocyanide; cobalt(II) acetate at 80℃; for 24h; Inert atmosphere;	32 Example 32 Example 32 (0243) (0244) A screw-top vial was charged with 5 mg (0.03 mmol) of cobalt acetate, 10 mg (0.06 mmol) of 1-isocyanoadamantane, 353 μL (1.3 mmol) of 1,1,1,3,5,5,5-heptamethyltrisiloxane, and 249 mg (1.0 mmol) of 1,1,1,3,5,5,5-heptamethyl-3-vinyltrisiloxane. The vial was closed, after which the contents were stirred at 80° C. for 24 hours. After cooling, analysis was made by 1H-NMR spectroscopy to determine the structure and yield of the product. As a result, it was confirmed that the signal assigned to the ethylene site of 1,1,1,3,5,5,5-heptamethyl-3-vinyltrisiloxane as the reactant disappeared completely. Instead, a singlet at 0.35 ppm indicative of the signal assigned to proton on silicon-adjoining carbon in the desired product, 1,2-bis(1,1,1,3,5,5,5-heptamethyltrisiloxan-3-yl)ethane was observed, from which a yield was computed. The results are shown in Table 10. (0245) 1H-NMR (396 MHz, CDCl3) δ: 0.00 (s, 12H), 0.09 (s, 36H), 0.35 (s, 4H)

Reference： [1]Current Patent Assignee: KYUSHU UNIVERSITY; SHIN-ETSU CHEMICAL CO., LTD. - US2017/233417, 2017, A1 Location in patent: Paragraph 0243-0245

73
[ 498-66-8 ]
[ 1438-82-0 ]
1-(1,1,3,3,3-pentamethyldisiloxanyl)norbornane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With cobalt pivalate; 1-adamantyl isocyanide at 80℃; for 24h; Inert atmosphere;	37 Example 36] Hydrosilylation Reaction with Vinyltrimethylsilane Example 36] Hydrosilylation Reaction with Vinyltrimethylsilane (0253) A screw-top vial was charged with 8 mg (0.03 mmol) of cobalt pivalate in Synthesis Example 4 as a catalyst, 15 mg (0.09 mmol) of 1-isocyanoadamantane as a ligand, 254 μL (1.3 mmol) of 1,1,3,3,3-pentamethyldisiloxane, and 145 μL (1.0 mmol) of vinyltrimethylsilane. The contents were stirred at 80° C. for 24 hours. After cooling, analysis was made by 1H-NMR spectroscopy to determine the structure and yield of the product. As a result, it was confirmed that the signal assigned to the ethylene site of vinyltrimethylsilane as the reactant disappeared completely. Instead, the signal assigned to the desired product, 1,1,1,3,3-pentamethyl-3-(2-trimethylsilylethyl)disiloxane was observed, from which a yield was computed. The results are shown in Table 12. (0254) 1H-NMR (396 MHz, CDCl3) δ: -0.03 (s, 9H), 0.03 (s, 6H), 0.06 (s, 9H), 0.38 (s, 4H)

Reference： [1]Current Patent Assignee: KYUSHU UNIVERSITY; SHIN-ETSU CHEMICAL CO., LTD. - US2017/233417, 2017, A1 Location in patent: Paragraph 0255-0256

74
[ 100-42-5 ]
[ 1438-82-0 ]
[ 3439-15-4 ]
[ 73727-41-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 73% 2: 27%	With 1-adamantyl isocyanide; nickel diacetate at 80℃; for 24h; Inert atmosphere;	43 [Example 42] Hydrosilylation Reaction of Styrene with 1,1,3,3,3-Pentamethyldisiloxane Using Nickel Acetate and t-Butyl Isocyanide [Example 42] Hydrosilylation Reaction of Styrene with 1,1,3,3,3-Pentamethyldisiloxane Using Nickel Acetate and t-Butyl Isocyanide (0264) A screw-top vial was charged with 5 mg (0.03 mmol) of nickel acetate (commercial product), 5 mg (0.06 mmol) of t-butyl isocyanide, 254 μL (1.3 mmol) of 1,1,3,3,3-pentamethyldisiloxane, and 115 μL (1.0 mmol) of styrene. The vial was closed, after which the contents were stirred at 80° C. for 24 hours. After cooling, analysis was made by 1H-NMR spectroscopy to determine the structure and yield of the product. As a result, it was confirmed that the signal assigned to the reactant diminished. Instead, there were observed a multiplet near 0.89 ppm indicative of the signal assigned to proton on silicon-adjoining carbon in 1,1,1,3,3-pentamethyl-3-phenethyldisiloxane, a doublet at 1.36 ppm indicative of the signal assigned to proton on β-position carbon in 1,1,1,3,3-pentamethyl-3-(1-phenylethyl)-disiloxane having silicon added at α-position, and a quartet at 2.16 ppm indicative of the signal assigned to proton on silicon-adjoining carbon, from which yields were computed. The results are shown in Table 14. (0265) α-adduct, 1H-NMR (396 MHz, CDCl3) δ: -0.01 (s, 3H), 0.00 (s, 3H), 0.02 (s, 9H), 1.36 (d, J=7.6 Hz, 2H), 2.16 (q, J=7.6 Hz, 2H), 7.06-7.11 (m, 3H), 7.17 (t, J=7.6 Hz, 2H)
1: 6% 2: 31%	With tert-butylisonitrile; nickel diacetate at 80℃; for 24h; Inert atmosphere;	42 [Example 42] Hydrosilylation Reaction of Styrene with 1,1,3,3,3-Pentamethyldisiloxane Using Nickel Acetate and t-Butyl Isocyanide [Example 42] Hydrosilylation Reaction of Styrene with 1,1,3,3,3-Pentamethyldisiloxane Using Nickel Acetate and t-Butyl Isocyanide (0264) A screw-top vial was charged with 5 mg (0.03 mmol) of nickel acetate (commercial product), 5 mg (0.06 mmol) of t-butyl isocyanide, 254 μL (1.3 mmol) of 1,1,3,3,3-pentamethyldisiloxane, and 115 μL (1.0 mmol) of styrene. The vial was closed, after which the contents were stirred at 80° C. for 24 hours. After cooling, analysis was made by 1H-NMR spectroscopy to determine the structure and yield of the product. As a result, it was confirmed that the signal assigned to the reactant diminished. Instead, there were observed a multiplet near 0.89 ppm indicative of the signal assigned to proton on silicon-adjoining carbon in 1,1,1,3,3-pentamethyl-3-phenethyldisiloxane, a doublet at 1.36 ppm indicative of the signal assigned to proton on β-position carbon in 1,1,1,3,3-pentamethyl-3-(1-phenylethyl)-disiloxane having silicon added at α-position, and a quartet at 2.16 ppm indicative of the signal assigned to proton on silicon-adjoining carbon, from which yields were computed. The results are shown in Table 14. (0265) α-adduct, 1H-NMR (396 MHz, CDCl3) δ: -0.01 (s, 3H), 0.00 (s, 3H), 0.02 (s, 9H), 1.36 (d, J=7.6 Hz, 2H), 2.16 (q, J=7.6 Hz, 2H), 7.06-7.11 (m, 3H), 7.17 (t, J=7.6 Hz, 2H)

Reference： [1]Current Patent Assignee: KYUSHU UNIVERSITY; SHIN-ETSU CHEMICAL CO., LTD. - US2017/233417, 2017, A1 Location in patent: Paragraph 0264-0266
[2]Current Patent Assignee: KYUSHU UNIVERSITY; SHIN-ETSU CHEMICAL CO., LTD. - US2017/233417, 2017, A1 Location in patent: Paragraph 0264-0265

75
[ 100-42-5 ]
[ 1438-82-0 ]
[ 100-41-4 ]
[ 3439-15-4 ]
[ 73727-41-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 51% 2: 37%	With dirhodium tetraacetate at 80℃; for 24h; Inert atmosphere;	2 [Comparative Example 2] Hydrosilylation Reaction of Styrene with 1,1,3,3,3-Pentamethyldisiloxane Using Rhodium Acetate Dimer Alone [Comparative Example 2] Hydrosilylation Reaction of Styrene with 1,1,3,3,3-Pentamethyldisiloxane Using Rhodium Acetate Dimer Alone (0276) A screw-top vial was charged with 8 mg (0.015 mmol) of rhodium acetate dimer, 254 μL (1.3 mmol) of 1,1,3,3,3-pentamethyldisiloxane, and 115 μL (1.0 mmol) of styrene. The vial was closed, after which the contents were stirred at 80° C. for 24 hours. After cooling, analysis was made by 1H-NMR spectroscopy to determine the structure and yield of the product. As a result, it was confirmed that the signal assigned to styrene as the reactant disappeared completely. Instead, a multiplet at 0.89 ppm indicative of the signal assigned to the product was observed, from which a yield was computed. The yield of the desired product was 51%, whereas 37% of a product having silicon added at α-position and 12% of ethylbenzene were detected as by-products.

Reference： [1]Current Patent Assignee: KYUSHU UNIVERSITY; SHIN-ETSU CHEMICAL CO., LTD. - US2017/233417, 2017, A1 Location in patent: Paragraph 0276

76
[ 106-86-5 ]
[ 1438-82-0 ]
[ 10194-04-4 ]

Reference： [1]Dalton Transactions,2018,vol. 47,p. 1903 - 1910

77
[ 100-42-5 ]
[ 1438-82-0 ]
[ 100-41-4 ]
[ 3439-15-4 ]
(E)-[1-(phenyl)-2-(1,1,3,3,3-pentamethyldisiloxane)]ethene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 18 %Spectr. 2: 17 %Spectr.	With C₃₈H₅₈N₂RuSi₄ In neat (no solvent) at 25℃; for 23h; Schlenk technique; Inert atmosphere;	11 [Working Example 11] Hydrosilylation Reaction Using Ruthenium Complex F A magnetic stirrer was placed in a 20 mE Schlenk tube and the tube was dried by heating under a reduced pressure of 5 Pa, after which the tube interior was purged with argon.Ruthenium Complex F (2.3 mg, 0.003 mmol) was added as the catalyst to this Schlenk tube. Styrene (104 mg, 1.0 mmol) was added thereto, followed by 1,1,1 ,3,3-pentameth- yldisiloxane (163 mg, 1.1 mmol), and the resulting solution was stirred at 25° C. for 23 hours. Afier cooling of thesolution, anisole (108 mg, 1.0 mmol) was added as an internal reference, the ‘H-NMR spectrum was measured, and the structure and yield of the product were determined. These results are shown as Entry 5 in Table 1.
1: 39 %Spectr. 2: 28 %Spectr. 3: 28 %Spectr.	With C₄₂H₆₄N₂RuSi₄ In neat (no solvent) at 25℃; for 23h; Schlenk technique; Inert atmosphere;	8 [Working Example 8] Hydrosilylation ReactionUsing Ruthenium Complex B A magnetic stirrer was placed in a 20 mE Schlenk tube and the tube was dried by heating under a reduced pressure of 5 Pa, after which the tube interior was purged with argon. Ruthenium Complex B (2.4 mg, 0.003 mmol) was added asthe catalyst to this Schlenk tube. Styrene (104 mg, 1.0 mmol) was added thereto, followed by 1,1,1 ,3,3-pentameth- yldisiloxane (163 mg, 1.1 mmol), and the resulting solution was stirred at 25° C. for 23 hours. After cooling of the solution, anisole (108 mg, 1.0 mmol) was added as aninternal reference, the ‘H-NMR spectrum was measured, and the structure and yield of the product were determined. These results are shown as Entry 2 in Table 1.

Reference： [1]Current Patent Assignee: KYUSHU UNIVERSITY; SHIN-ETSU CHEMICAL CO., LTD. - US9884316, 2018, B2 Location in patent: Page/Page column 30; 31; 32
[2]Current Patent Assignee: KYUSHU UNIVERSITY; SHIN-ETSU CHEMICAL CO., LTD. - US9884316, 2018, B2 Location in patent: Page/Page column 30; 31; 32

78
[ 1438-82-0 ]
[ 83953-73-5 ]
cholesteryl 4-[3-(1,1,3,3,3-pentamethyldisiloxanyl)propoxy]benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	With platinum⁽⁰⁾-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In 5,5-dimethyl-1,3-cyclohexadiene; toluene at 20℃; for 24h; Inert atmosphere;	Cholesteryl 4-[3-(1,1,3,3,3-pentamethyldisiloxanyl)propoxy]benzoate D-n (n=2) The siloxane-based LCs (D and E) were prepared by means of a typical hydrosilylation of the vinyl-bearing substituted compound (C) with siloxane compounds having a Si-H bond using a platinum catalyst. Pt(dvs) in xylene solution (0.12 g, 0.32 mmol) was added to a solution of C (1.4 g, 2.5 mmol) and 1,1,1,3,3-pentamethyldisiloxane (0.64 g, 6.7 mmol) in dry toluene (50 mL). The resulting solution was stirred under argon at room temperature for 24 h. To the reaction mixture was added 200 mL of ethyl acetate. The residue was diluted in 300 mL of ethyl acetate. The organic layer was washed with water two times and brine once, and dried over sodium sulfate. Then, the solution was evaporated to dryness in a vacuum. The residue was purified by column chromatography over silica gel using dichloromethane/hexane (1:4) as the eluent to afford colorless crystals. Yield : 0.66 g (38 %) 1H-NMR (CDCl3) : δ (ppm) 7.95 (d, J = 8.6 Hz, 2H), 6.87 (d, J = 8.6 Hz, 2H), 5.39 (d, J = 4.1 Hz, 1H), 4.85-4.74 (m, 1H), 3.94 (t, J = 6.8 Hz, 2H), 2.42 (d, J = 7.7 Hz, 2H), 2.04-0.92 (m, 28H), 1.04 (s, 3H), 0.90 (d, J = 6.5 Hz, 3H), 0.85 (d, J = 6.3 Hz, 3H), 0.84 (d, J = 6.3 Hz, 3H), 0.66 (s, 3H), 0.65-0.56 (m, 2H), 0.06 (s, 6H), 0.05 (s, 9H).

Reference： [1]Katsuki, Kaito; Kaneko, Kosuke; Kaneko, Kimiyoshi; Kato, Riki; Miyamoto, Nobuyoshi; Hanasaki, Tomonori [Journal of Organometallic Chemistry, 2019, vol. 886, p. 34 - 39]

79
[ 1438-82-0 ]
[ 16709-86-7 ]
C₁₀H₂₇ClOSi₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With C₄₈H₆₀N₄O₈Pt⁽²⁺⁾*2NO₃^(1-) In toluene at 80℃; for 2h; Inert atmosphere; Schlenk technique;	4.4. General procedure for the hydrosilylation reaction General procedure: To a 25 ml Schlenk flask, 1 mmol of hydrosilane, 1 mmol of olefin(or 2 mmol of olefin for compound 12 and 1.3 mmol of olefin for compound 13), 2 ml of anhydrous toluene and 0.001 mol% of complex1 or 2 (solution in toluene) were added under argon atmosphere.The mixture was heated at 80 °C for definite time. The progress of reactions was examined by GC or GC-MS analysis. Afterthe reaction was complete, the solvent and all volatiles wereremoved under reduced pressure to give products 3-19.

Reference： [1]Walczak, Anna; Stachowiak, Hanna; Kurpik, Gracjan; Kaźmierczak, Joanna; Hreczycho, Grzegorz; Stefankiewicz, Artur R. [Journal of Catalysis, 2019, vol. 373, p. 139 - 146]

80
[ 6628-00-8 ]
[ 1438-82-0 ]
C₁₄H₃₃NOSi₂ [ No CAS ]
C₁₄H₃₃NOSi₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With platinum⁽⁰⁾-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 60℃; for 24h; Schlenk technique; Inert atmosphere;	2.3. Functionalization of M2H with nitrogen-containing compounds General procedure: M2H was functionalized with organic compounds containing anitrogen atom by hydrosilylation performed in the presence ofKarstedt's catalyst. Reactions were carried out in a clean and drySchlenk flask under dry argon atmosphere. Molar ratio of Si-Hgroups from the siloxane to CH2CH-CH2- or CH2CH- groupsfrom the nitrogen-containing organic compound equal to 1:1.5 wasapplied. The excess of organic compound over the Si-H groups inthe siloxane was used to ensure that all Si-H groups weresubstituted.In a typical run, 0.0085 mol (1.5 ml) of M2H and 0.0255 mol ofnitrogen-containing organic compound (Naa: 3.46 ml, Nap: 3.74 ml,Nach: 3.69 ml, 4VP: 2.76 ml, 2VP: 2.75 ml) in toluene (3.0 ml) wereused. The reactions were catalyzed by 0.17106 mol of Pt introducedinto the system from Karstedt's catalyst. The reaction temperaturewas controlled at 60 C for 24 h. Gas chromatograms (GC)and FTIR spectra of the initial reaction mixture as well as thesamples withdrawn after 1, 3 and 24 h of the process were recorded.Based on GC, changes in the concentrations of the reagents (M2H, the organic compound) were determined, whereas themeasured FTIR spectra served as the basis for establishing thedisappearance of the Si-H groups from the systems. After the reactions,toluene was removed by rotary evaporation. Then theremaining mixture was subjected to vacuum distillation in order todistill off the unreacted N-containing compound. This method wassufficient to separate siloxane functionalized by Nach from theexcess of Nach. In the case of M2H/Naa, M2H/Nap and M2H/2VP systems,separation by column chromatography on silica gel using aseluent hexane/dichloromethane mixture, ethyl acetate and hexane/ethyl acetate mixture, respectively was additionally performed. Itwas, however, inefficient in the isolation of M2H/2VP product.Additionally, in order to facilitate interpretation of gas chromatograms,the reaction between M2H and Naa was carried out by thedescribed procedure, but using excessive amount of the siloxane(Si-H: CH2CH-CH2- groups molar ratio equal to 1:0.5).

Reference： [1]Chechelska-Noworyta, Aleksandra; Owińska; Hasik, Magdalena [Journal of Organometallic Chemistry, 2019, vol. 898]

81
[ 1438-82-0 ]
[ 1111-74-6 ]
[ 993-07-7 ]

Yield	Reaction Conditions	Operation in experiment
	With (π-Me₅C₅)Si⁺B(C₆F₅)₄^- In dichloromethane-d2 at 20℃; for 0.75h; Inert atmosphere;	1 Example 1: Disproportionation of 1,1,1,2,2-pentamethyldisiloxane in the Presence of (π-Me₅C₅)Si⁺B(C₆F₅)₄^- All working steps were conducted under Ar. 296 mg (2.00 mmol) of pentamethyldisiloxane were dissolved in 1.0 ml of d2-dichloromethane and a solution of 1.8 mg (0.0021 mmol, 0.11 mol %) of (π-Me5C5)Si+B(C6F5)4- was added at 20° C. The reaction was monitored by NMR spectroscopy. After 45 minutes, the reactant pentamethyldisiloxane was no longer detectable by NMR spectroscopy and the NMR shows the formation of higher molecular weight siloxanes comprising H groups. The silanes dimethylsilane and trimethylsilane were formed in the molar ratio of 70:30. Conversion=95%

Reference： [1]Current Patent Assignee: WACKER CHEMIE AG - US2019/345175, 2019, A1 Location in patent: Paragraph 0061-0062

82
[ 1438-82-0 ]
C₅H₁₆O₄Si₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With oxygen; ozone In dichloromethane at -90.16℃;	EXPERIMENTAL General procedure: Silane hydrotrioxides were prepared at a temperatureof 183 K by passing a cooled ozone-oxygen mixturethrough a 0.038-0.2 M solution of the correspondingsilane in CH2Cl2. The ozonation time was3-14 min. The concentrations of hydrotrioxides andtriphenylphosphite ozonide were determined accordingto the standard procedure with triphenylphosphine[17]. NMR spectra were recorded on a Varian Mercury-500 spectrometer, which allows recording spectraat low temperatures down to 183 K.

Reference： [1]Khalitova; Grabovskii; Kabal’nova [High Energy Chemistry, 2019, vol. 53, # 6, p. 435 - 437][Khim. Vys. Energ., 2019, vol. 53, # 6, p. 438 - 440,3]

83
[ 1438-82-0 ]
C₁₈H₁₅BF₂O₂ [ No CAS ]
C₂₃H₃₁BF₂O₃Si₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With platinum⁽⁰⁾-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 20℃; for 24h;	General method for synthesis of siloxane DBMBF2 derivatives by hydrosililation reaction. A mixture of corresponding hydridsilane, allyl-DBMBF2 and Karstedt catalyst (30 μL) in toluene(20 mL) was stirred at room temperature for 24 h. After the reaction was complete a solvent wasremoved by rotor evaporator. The residue was purified by column chromatography on silica(toluene or a mixture toluene:chloroform were used as an eluent).

Reference： [1]Kononevich, Yuriy N.; Belova, Anastasia S.; Sazhnikov, Viacheslav A.; Safonov, Andrey A.; Ionov, Dmitry S.; Volodin, Alexander D.; Korlyukov, Alexander A.; Muzafarov, Aziz M. [Tetrahedron Letters, 2020, vol. 61, # 31]

84
[ 1438-82-0 ]
C₁₉H₁₇BF₂O₃ [ No CAS ]
C₂₄H₃₃BF₂O₄Si₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With platinum⁽⁰⁾-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 20℃; for 24h;	General method for synthesis of siloxane DBMBF2 derivatives by hydrosililation reaction. A mixture of corresponding hydridsilane, allyl-DBMBF2 and Karstedt catalyst (30 μL) in toluene(20 mL) was stirred at room temperature for 24 h. After the reaction was complete a solvent wasremoved by rotor evaporator. The residue was purified by column chromatography on silica(toluene or a mixture toluene:chloroform were used as an eluent).

Reference： [1]Kononevich, Yuriy N.; Belova, Anastasia S.; Sazhnikov, Viacheslav A.; Safonov, Andrey A.; Ionov, Dmitry S.; Volodin, Alexander D.; Korlyukov, Alexander A.; Muzafarov, Aziz M. [Tetrahedron Letters, 2020, vol. 61, # 31]

85
[ 1438-82-0 ]
[ 2489-86-3 ]
C₁₈H₂₈OSi₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	With platinum⁽⁰⁾-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene for 24h; Inert atmosphere;	Mono-Naph (5) A solution of 1-allylnaphthalene 3 (0.1 g, 0.6 mmol),pentamethyldisiloxane 4 (0.1 g, 0.67 mmol) and Karstedt′s catalyst (0.3mol% [Pt]) in dry toluene (10 mL) was stirred under argon atmosphere for24 h. After the reaction was complete the solvent was removed under reduced pressure and the productwas purified by column chromatography on silica with hexane as an eluent to give compound 5 (0.04g). Yield: 25%. 1H NMR (400 MHz, CDCl3): δ 0.07 (s, 15H, Si-CH3), 0.69-0.73 (t, 2H, Si-CH2-CH2),1.77-1.86 (m, 2H, CH2-CH2-CH2), 3.10-3.14 (t, 2H, CH2-CH2-Ar), 7.34-7.36 (d, 1H, J = 6.9 Hz, Ar),7.41-7.44 (t, 1H, Ar), 7.47-7.54 (m, 2H, Ar), 7.72-7.74 (d, 1H, J = 8.1 Hz, Ar), 7.87-7.88 (d, 1H, J =7.1 Hz, Ar), 8.06-8.08 (d, 1H, J = 8.2 Hz, Ar). 13C NMR (101 MHz, CDCl3): δ 0.4, 1.9, 18.8, 24.8,36.9, 123.9, 125.3, 125.5, 125.6, 125.9, 126.4, 128.7, 131.9, 133.9, 138.9. 29Si NMR (79 MHz,CDCl3): δ -48.1, 7.4. IR (KBr): 3070, 3052, 3014, 2962, 2940, 2904, 2877, 1402, 1257, 1173, 1058, 967, 874,845, 813, 795, 759, 695 cm-1.

Reference： [1]Alfimov, M. V.; Anisimov, A. A.; Belova, A. S.; Ionov, D. S.; Kononevich, Yu. N.; Muzafarov, A. M.; Safonov, A. A.; Sazhnikov, V. A.; Shchegolikhina, O. I. [Tetrahedron, 2021, vol. 93]

86
[ 2768-02-7 ]
[ 1438-82-0 ]
[ 1242030-56-3 ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: (vinyl)trimethoxylsilane With tris(pentafluorophenyl)borate In toluene Inert atmosphere; Stage #2: 1,1,1,3,3-pentamethyl-1,3-disiloxane In toluene for 0.333333h; Inert atmosphere;	2.3.1. Synthesis of Vinyltris(pentamethyldisiloxanyl)silane (V2) A 100 mL oven-dried, round-bottomed flask was purged under nitrogen for 10 min(Figure 1). Vinyltrimethoxysilane (1.56 g, 10.5 mmol), dry toluene (2 mL), and B(C6F5)3catalyst (0.67 mL of 10 mg mL1 solution, 0.016 mmol) were added, and the mixturewas stirred under nitrogen. The desired hydrosilane, for example, pentamethyldisiloxane(PMDS) for V2 (6.25 g, 42.1 mmol) was added dropwise, using a needle and syringe,in a slight stoichiometric excess (4.0 equivalent for V2 based on the 3 alkoxy groups);subsequent drops were added only once bubbling had ceased for a total addition time of~20 min. Neutral alumina (~0.1 g) was added to the flask after stirring for 1 h to quenchthe B(C6F5)3 catalyst. The solution was gravity filtered and the alumina was rinsed withhexanes, followed by rotary evaporation of the combined liquid fractions to remove solvent.Rotary evaporation was sufficient to remove residual pentamethyldisiloxane in the case ofV2. Yields V2 4.81 g (84%).V2: 1H-NMR (CDCl3, 600 MHz): 5.98-5.87 (m, 3H), 0.09 (m, 45H) ppm. GCMS-EI[M-CH3]+ m/z at 529 (13), 367 (17), 341 (23), 221 (55), 41 (45), 73 (55).

Reference： [1]Brook, Michael A.; Lusterio, Adrien [Molecules, 2021, vol. 26, # 16]

87
[ 1438-82-0 ]
10-allyl-3-(1-(4-(tert-butyl)phenyl)-1H-phenanthro[9,10-d]imidazol-2-yl)-10H-phenothiazine [ No CAS ]
3-(1-(4-(tert-butyl)phenyl)-1H-phenanthro[9,10-d]imidazol2-yl)-10-(3-(1,1,3,3,3-pentamethyldisiloxanyl)propyl)-10H-phenothiazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: 1,1,1,3,3-pentamethyl-disiloxane; 10-allyl-3-(1-(4-(tert-butyl)phenyl)-1H-phenanthro[9,10-d]imidazol-2-yl)-10H-phenothiazine In toluene Inert atmosphere; Stage #2: With platinum⁽⁰⁾-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In 5,5-dimethyl-1,3-cyclohexadiene; toluene at 20℃; for 12h; Inert atmosphere;	3-(1-(4-(Tert-butyl)phenyl)-1H-phenanthro[9,10-d]imidazol2-yl)-10-(3-(1,1,3,3,3-pentamethyldisiloxanyl)propyl)-10Hphenothiazine (Mono-PIPTZ): Under N2 atmosphere, the intermediate PIPTZ (0.33 g, 0.56 mmol) and 1,1,1,3,3-pentamethyldisiloxane (0.1 mL, 0.68 mmol) were dissolved in 20 mL of ultra-dry toluene. After the reaction mixture became transparent and clear, 5 μL of catalyst (platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex; 0.10 M solution in xylenes) was added using a syringe. The reaction mixture was stirred at room temperature for 12 h. Solvent was evaporated under vacuum, and the crude product was purified by column chromatography using petroleum ether/dichloromethane/ethyl acetate (10:10:1, v/v/v) as eluent to obtain the compound Mono-PIPTZ as yellow solid (0.326 g, 79%). m.p.: > 280 °C. 1H NMR (500 MHz, CDCl3, δ, ppm): 8.84 (br, 1H), 8.72 (d, J = 8.4 Hz, 1H), 8.66 (d, J = 8.4 Hz, 1H), 7.70 (t, J = 7.4 Hz, 1H), 7.60 (d, J = 7.8 Hz, 1H), 7.58 (d, J = 8.3 Hz, 2H), 7.47-7.44 (m, 1H), 7.38 (d, J = 8.3 Hz, 2H), 7.22 (d, J = 4.7 Hz, 3H), 7.14 (s, 1H), 7.08 (t, J = 7.4 Hz, 1H), 7.00 (d, J = 7.4 Hz, 1H), 6.85 (t, J = 7.4 Hz, 1H), 6.76 (d, J = 8.3 Hz, 1H), 6.66 (d, J = 8.6 Hz, 1H), 3.75 (t, J = 7.2 Hz, 2H), 1.78-1.71 (m, 2H), 1.43 (s, 9H), 0.56 (t, J = 8.5 Hz, 2H), 0.0 (s, 9H), -0.01 (s, 6H). 13C NMR (126 MHz, CDCl3, δ, ppm): 127.2, 126.5, 126.2, 125.4, 125.3, 125.2, 125.1, 124.3, 123.6, 122.8, 122.1, 121.1, 120.9, 120.6, 118.9, 113.4, 112.6, 48.6, 33.1, 29.5, 18.6, 13.3, 0.01, -1.01, -1.67. HRMS: Calcd. for C45H49N3OSSi2, 736.3208 [M + H]+; Found: 736.3209. Error = 0.2378 ppm.

Reference： [1]Guo, Yongchun; Li, Debao; Su, Ruige; Yu, Tianzhi; Zhang, Chen; Zhao, Jiaqin; Zhao, Yuling [Journal of Molecular Structure, 2022, vol. 1262]

88
[ 1438-82-0 ]
2-(9-allyl-9H-carbazol-3-yl)-1-(4-(tert-butyl)phenyl)-1H-phenanthro[9,10-d]imidazole [ No CAS ]
1-(4-(tert–butyl)phenyl)-2-(9-(3-(1,1,3,3,3-pentamethyldisiloxanyl)propyl)-9H-carbazol-3-yl)-1H-phenanthro[9,10-d]imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	Stage #1: 1,1,1,3,3-pentamethyl-disiloxane; 2-(9-allyl-9H-carbazol-3-yl)-1-(4-(tert-butyl)phenyl)-1H-phenanthro[9,10-d]imidazole In toluene Inert atmosphere; Stage #2: With platinum⁽⁰⁾-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In 5,5-dimethyl-1,3-cyclohexadiene; toluene at 20℃; for 12h; Inert atmosphere;	3-(1-(4-(Tert-butyl)phenyl)-1H-phenanthro[9,10-d]imidazol2-yl)-10-(3-(1,1,3,3,3-pentamethyldisiloxanyl)propyl)-10Hphenothiazine (Mono-PIPTZ): General procedure: Under N2 atmosphere, the intermediate PIPTZ (0.33 g, 0.56 mmol) and 1,1,1,3,3-pentamethyldisiloxane (0.1 mL, 0.68 mmol) were dissolved in 20 mL of ultra-dry toluene. After the reaction mixture became transparent and clear, 5 μL of catalyst (platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex; 0.10 M solution in xylenes) was added using a syringe. The reaction mixture was stirred at room temperature for 12 h. Solvent was evaporated under vacuum, and the crude product was purified by column chromatography using petroleum ether/dichloromethane/ethyl acetate (10:10:1, v/v/v) as eluent to obtain the compound Mono-PIPTZ as yellow solid (0.326 g, 79%).

Reference： [1]Guo, Yongchun; Li, Debao; Su, Ruige; Yu, Tianzhi; Zhang, Chen; Zhao, Jiaqin; Zhao, Yuling [Journal of Molecular Structure, 2022, vol. 1262]

Type	HazMat fee for 500 gram (Estimated)
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CAS No. :	1438-82-0	MDL No. :	MFCD00053658
Formula :	C₅H₁₆OSi₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XUKFPAQLGOOCNJ-UHFFFAOYSA-N
M.W :	148.35	Pubchem ID :	6327260
Synonyms :

Num. heavy atoms :	8
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	43.31
TPSA :	9.23 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.47 cm/s

[ CAS No. 1438-82-0 ] {[proInfo.proName]}

Quality Control of [ 1438-82-0 ]

Related Doc. of [ 1438-82-0 ]

Product Details of [ 1438-82-0 ]

Calculated chemistry of [ 1438-82-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1438-82-0 ]

Application In Synthesis of [ 1438-82-0 ]

[ 1438-82-0 ] Synthesis Path-Upstream 1~3

[ 1438-82-0 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Log Po/w (iLOGP) :	2.75
Log Po/w (XLOGP3) :	2.45
Log Po/w (WLOGP) :	1.82
Log Po/w (MLOGP) :	1.16
Log Po/w (SILICOS-IT) :	-1.59
Consensus Log Po/w :	1.32

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Log S (ESOL) :	-2.17
Solubility :	1.0 mg/ml ; 0.00674 mol/l
Class :	Soluble
Log S (Ali) :	-2.29
Solubility :	0.765 mg/ml ; 0.00516 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.74
Solubility :	2.67 mg/ml ; 0.018 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.46

Signal Word:	Danger	Class:	3
Precautionary Statements:	P501-P240-P210-P233-P243-P241-P242-P280-P370+P378-P303+P361+P353-P403+P235	UN#:	1993
Hazard Statements:	H225	Packing Group:	Ⅱ
GHS Pictogram:

Precautionary Statements-General
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Code	Phrase
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P378
P380	Evacuate area.
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
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P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling