Name: 4420-74-0|(3-Mercaptopropyl)trimethoxysilane|98%
Brand: Ambeed
SKU: A165640
Rating: 94 (35 reviews)

1
[ 102-71-6 ]
[ 4420-74-0 ]
[ 29909-46-4 ]

Yield	Reaction Conditions	Operation in experiment
75%	With disodium hydrogenphosphate at 20℃; Inert atmosphere;	4 method four added at room temperature 3-thiol propyl trimethyl oxygen radical silane (196 mg, 0 . 001mol), triethanolamine (135 mg, 0 . 009mol) and 0.1% mole after sodium phosphate (catalyst), the nitrogen and room temperature stirring under the conditions of reaction 60-120 hours, the best for 100 hours, the stirring rate for 900-1150RPM, after the reaction with the propane in methylene chloride (1:1) at a low temperature of the mixed solvent (4 °C) recrystallization for three times, after crystallization is determined by nuclear magnetic resonance spectrum of the product, to obtain white solid, yield is about 75% ; when the reaction amplifying to 3-thiol propyl trimethyl oxygen radical silane (19.6g, 0 . 1mol), to yield 58-65%.
60%	In m-xylene Heating;
45.5%	In toluene at 110℃; for 30h;

	With hydroxide
	With potassium hydroxide In toluene at 20℃; for 4h; Dean-Stark;

Reference： [1]Current Patent Assignee: NATIONAL CHUNG CHENG UNIVERSITY - TWI522363, 2016, B Location in patent: Paragraph 0035; 0036
[2]Voloshin; Varzatskii; Vorontsov; Antipin; Lebedev; Belov; Strizhakova [Russian Chemical Bulletin, 2004, vol. 53, # 1, p. 92 - 98]
[3]Chen, Wen-Hao; Tseng, Yen-Ta; Hsieh, Shuchen; Liu, Wan-Chun; Hsieh, Chiung-Wen; Wu, Chin-Wei; Huang, Chen-Han; Lin, Hsing-Ying; Chen, Chao-Wen; Lin, Pei-Ying; Chau, Lai-Kwan [RSC Advances, 2014, vol. 4, # 87, p. 46527 - 46535]
[4]Voronkov,M.G. et al. [Journal of general chemistry of the USSR, 1975, vol. 45, p. 1618][Zhurnal Obshchei Khimii, 1975, vol. 45, p. 1649]
[5]Singh, Gurjaspreet; Rani, Sunita; Arora, Aanchal; Aulakh, Darpandeep; Wriedt, Mario [New Journal of Chemistry, 2016, vol. 40, # 7, p. 6200 - 6213]

2
[ 64456-54-8 ]
[ 4420-74-0 ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium methylate In methanol at 65℃; for 12h;
	With sodium methylate In methanol

Reference： [1]Srinivas, Venu; Nakajima, Yumiko; Sato, Kazuhiko; Shimada, Shigeru [Organic Letters, 2018, vol. 20, # 1, p. 12 - 15]
[2]Voronkov,M.G. et al. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1977, vol. 26, p. 1710 - 1713][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1977, vol. 26, p. 1849 - 1851]

3
[ 2530-87-2 ]
[ 4420-74-0 ]

Yield	Reaction Conditions	Operation in experiment
93.5%	With sodium sulfide; tetrabutyl-ammonium chloride; water; In toluene; at 88 - 92℃; for 4h;	This embodiment includes the following steps: To a 1000 ml three-necked flask equipped with a heating, stirring, cooling reflux device and a temperature measuring device, add 126 g of water and 61.6 g of 70% sodium sulfide (0.77 mol), and start stirring. After all dissolved, 4.5g of tetrabutylammonium chloride, 280g of toluene, and 139.0g (0.7mol) of chloropropyltrimethoxysilane were added in order, and the cooling and refluxing device was turned on. The temperature was raised to 88-92 C, and the reaction was held for 4 hours. After the reaction, the stirring was stopped, and the mixture was allowed to stand for 2 minutes. The organic layer was sampled and tracked by gas chromatography. The residual amount of chloropropyltriethoxysilane was 0.68%. The aqueous phase was separated. Distillate under reduced pressure and collect fractions at 110 to 115 C (absolute pressure 4kPa) to obtain 129 g of mercaptosilane coupling agent product.

Reference： [1]Patent: CN110483566,2019,A .Location in patent: Paragraph 0025-0027
[2]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1977,vol. 26,p. 1710 - 1713
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1977,vol. 26,p. 1849 - 1851
[3]Journal of Organic Chemistry,1978,vol. 43,p. 1687 - 1689

4
[ 2551-83-9 ]
[ 4420-74-0 ]

Reference： [1]Journal of Structural Chemistry,1987,vol. 28,p. 46 - 51
Zhurnal Strukturnoi Khimii,1987,vol. 28,p. 56 - 62

6
[ 2551-83-9 ]
[ 4420-74-0 ]
[ 35112-74-4 ]
[ 29055-11-6 ]

Reference： [1]Doklady Chemistry,1994,vol. 339,p. 205 - 207
Dokl. Akad. Nauk SSSR Ser. Khim.,1994,vol. 339,p. 62 - 64

7
[ 4420-74-0 ]
[ 1067-25-0 ]
[ 18971-71-6 ]
[ 161678-45-1 ]
C₂₄H₅₆O₁₂S₂Si₈ [ No CAS ]
[ 161678-44-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride In methanol at 20℃; for 504h; Yield given. Further byproducts given. Yields of byproduct given;

Reference： [1]Hendan, Benedikt J.; Marsmann, Heinrich C. [Journal of Organometallic Chemistry, 1994, vol. 483, # 1-2, p. 33 - 38]

8
[ 4420-74-0 ]
[ 1067-25-0 ]
[ 18971-71-6 ]
C₂₄H₅₆O₁₂S₂Si₈ [ No CAS ]
C₂₄H₅₆O₁₂S₂Si₈ [ No CAS ]
[ 161678-44-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride In methanol at 20℃; for 504h; Yield given. Further byproducts given. Yields of byproduct given;

Reference： [1]Hendan, Benedikt J.; Marsmann, Heinrich C. [Journal of Organometallic Chemistry, 1994, vol. 483, # 1-2, p. 33 - 38]

9
[ 4420-74-0 ]
[ 2155-96-6 ]
2-(3-trimethoxysilylpropyl)thioethyl-diphenylphosphine [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,1997,vol. 339,p. 38 - 43

10
[ 2127-03-9 ]
[ 4420-74-0 ]
2-((3-(trimethoxysilyl)propyl)dithio)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	In dichloromethane at 20℃; for 3h;
95%	In dichloromethane at 20℃; for 4h;

Reference： [1]Dufaud, Veronique; Davis, Mark E. [Journal of the American Chemical Society, 2003, vol. 125, # 31, p. 9403 - 9413]
[2]Nakamura, Tatsuya; Matsushita, Hisashi; Sugihara, Fuminori; Yoshioka, Yoshichika; Mizukami, Shin; Kikuchi, Kazuya [Angewandte Chemie - International Edition, 2015, vol. 54, # 3, p. 1007 - 1010][Angew. Chem., 2015, vol. 127, # 3, p. 1021 - 1024,4]

11
[ 4420-74-0 ]
[ 35112-74-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With 2,2'-dipyridyldisulphide In dichloromethane at 20℃; for 96h;
79.78%	With 2,2'-dipyridyldisulphide In dichloromethane at 20℃; for 96h; Inert atmosphere;	1 Example 1 Synthesis of 3,3′-bis (trimethoxysilylpropyl) disulfide (TMSPD) The method for preparing 3,3'-bis(trimethoxysilylpropyl)disulfide (TMSPD) of Example 1 is shown in Scheme 2 below.In a reflux condenser, nitrogen-connected three-necked round flask, add 20 mL of dichloromethane and 2 g of 2,2`-dithio -dipyridine and stir.4.45 g of excess (3-mercaptopropyl) trimethoxysilane was quickly added to the previously prepared solution using Syringe,The reaction is carried out at room temperature for 4 days.The reaction was extracted three times by mixing petroleum ether and distilled water.The extracted reaction was distilled under reduced pressure to remove the solvent, and dried in a vacuum oven at 60 to obtain 3,3'-bis (trimethoxysilylpropyl) disulfide (TMSPD, yield 79.78%)
36%	With bromopentacarbonylmanganese(I); oxygen In benzene at 20℃; for 2h; UV-irradiation; chemoselective reaction;

	With 2,2'-azobis(isobutyronitrile) at 90℃; for 1h;
	With 2,2-dithiopyridine In dichloromethane at 20℃;
76 %Spectr.	With cyclopentadienyl manganese tricarbonyl In benzene at 25℃; for 2.5h; Inert atmosphere; UV-irradiation;

Reference： [1]Dufaud, Veronique; Davis, Mark E. [Journal of the American Chemical Society, 2003, vol. 125, # 31, p. 9403 - 9413]
[2]Current Patent Assignee: KOREA INSTITUTE OF INDUSTRIAL TECHNOLOGY - KR2019/121040, 2019, A Location in patent: Paragraph 0165-0170
[3]Location in patent: experimental part Tan, Kheng Yee Desmond; Teng, Guan Foo; Fan, Wai Yip [Organometallics, 2011, vol. 30, # 15, p. 4136 - 4143]
[4]Parent, J. Scott; Sengupta, Saurav S. [Macromolecules, 2005, vol. 38, # 13, p. 5538 - 5544]
[5]Alauzun, Johan; Mehdi, Ahmad; Reye, Catherine; Corriu, Robert J. P. [Chemical Communications, 2006, # 3, p. 347 - 349]
[6]Location in patent: experimental part Tan, Kheng Yee Desmond; Kee, Jun Wei; Fan, Wai Yip [Organometallics, 2010, vol. 29, # 20, p. 4459 - 4463]

12
[ 4420-74-0 ]
3-mercaptopropylsilanetriol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
7%	In water Inert atmosphere;
	With hydrogenchloride at 20℃;
	With water

With hydrogenchloride In methanol; water at 20℃; for 72h;

A solution of 75 mLof anhydrous methanol and 2.5 mL of concentrated hydrochloric acid was placed in a two necked, round bottomed flask equipped with a condenser, an additional funnel, and a magnetic stir bar. To this solution was added dropwise a mixture of MPTMOS (7.37 g, 37.5 mmol) and methanol (15 mL) through the addition funnel over a period of 15 min with vigorous stirring. The stirring was continued for several hours until the solution had cooled to room temperature. The reaction mixture was kept at room temperature for another 3 days without stirring. After 3 days, di-n-butyltindilaurate (0.075g, 0.12 mmol) was added with stirring. The reaction was maintained at room temperature for another 7 days. Then, the solution was filtered, then the 1 were recrystallized in DMF/ether at room temperature to afford 1 (1.25g, 37%).

Reference： [1]Ma, Xiaoshuang; Tao, Furong; Zhang, Yang; Li, Tianduo; Raymo, Françisco M.; Cui, Yuezhi [Journal of Materials Chemistry A, 2017, vol. 5, # 27, p. 14343 - 14354]
[2]Liu, Chunqing; Huang, Yongqing; Naismith, Nathaniel; Economy, James; Talbott, Jonathan [Environmental Science and Technology, 2003, vol. 37, # 18, p. 4261 - 4268]
[3]Location in patent: scheme or table Chonkaew, Wunpen; Minghvanish, Withawat; Kungliean, Ulchulee; Rochanawipart, Nutthaya; Brostow, Witold [Journal of Nanoscience and Nanotechnology, 2011, vol. 11, # 3, p. 2018 - 2024]
[4]Liu, Lei; Lee, Su Jung; Lee, Myong Euy; Kang, Philjae; Choi, Moon-Gun [Tetrahedron Letters, 2015, vol. 56, # 12, p. 1562 - 1565]

13
[ 16068-37-4 ]
[ 4420-74-0 ]
polisilsesquioxane; monomer(s): 1,2 bis(triethoxysilyl)ethane; 3-mercaptopropyltrimethoxysilane [ No CAS ]

Reference： [1]Mendeleev Communications,2005,vol. 15,p. 168 - 170

14
sodium; 2-(pyridin-2-yldisulfanyl)-ethanesulfonate [ No CAS ]
[ 4420-74-0 ]
2-[3-(trimethoxysilyl)-propyldisulfanyl]-ethanesulfonic acid sodium salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74.7%	In methanol; acetic acid at 20℃;
74.7%	With acetic acid In methanol at 20℃;

Reference： [1]Lin; Lai; Huang; Song; Xu [Journal of the American Chemical Society, 2001, vol. 123, # 46, p. 11510 - 11511]
[2]Radu, Daniela R.; Lai, Cheng-Yu; Huang, Jianguo; Shu, Xu; Lin, Victor S.-Y. [Chemical Communications, 2005, # 10, p. 1264 - 1266]

15
[ 4813-57-4 ]
[ 4420-74-0 ]
polymer, radical telomerization, polymerization degree: 25; monomer(s): (3-mercaptopropyl)trimethoxysilane, 1 molar part; octadecyl acrylate, 30 molar parts [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With azobisisobutyronitrile In ethanol at 80℃; for 6h;

Reference： [1]Derakhshan, Mahnaz; Ansarian, Hamid R.; Rahman, M. Mizanur; Sakurai, Toshihiko; Takafuji, Makoto; Ihara, Hirotaka [Canadian Journal of Chemistry, 2005, vol. 83, # 10, p. 1792 - 1798]

16
[ 4420-74-0 ]
siloxane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrogenchloride In ethanol; triethoxyphenylsilane; water	11 Preparation of Co-Condensate from 10% MS in Phenyl Triethoxysilane Example 11 Preparation of Co-Condensate from 10% MS in Phenyl Triethoxysilane In a procedure similar to Example 2, 49.11 g (0.248 mol) of phenyl triethoxysilane (PTMS), 6.42 g (33 mmol) of 3-mercaptopropyl trimethoxysilane (MS), 100 mL of water and 26.8 mL (0.322 mol) of 12N hydrochloric acid were added to a 1 L separatory funnel with 560 mL of absolute ethanol. No phase separation occurred overnight. An additional 150 mL of water was added to give a milky suspension of the condensate. After settling overnight at ambient temperature, the lower phase was separated and vacuum dried to give ~95% yield of the expected co-condensation siloxane from the reactants.

Reference： [1]Current Patent Assignee: BRIDGESTONE CORPORATION - US2006/217473, 2006, A1

17
sodium; 2-(pyridin-2-yldisulfanyl)-ethanesulfonate [ No CAS ]
[ 4420-74-0 ]
2-[3-(trimethoxysilyl)-propyldisulfanyl]-ethanesulfonic acid sodium salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74.7%	In methanol at 20℃;	4 To synthesize the TPES-functionalized mesoporous silica (TPES-MCM), the well-developed cetyltrimethylammonium bromide (CTAB) surfactant-templated co-condensation method of tetraethoxysilane (TEOS) and organosiloxane precursors was modified by using compound 1 as the organosiloxane precursor, as shown in Scheme A. Synthesis of compound 1: 2,2?-Dipyridyl disulfide (8.82 g, 40.0 mmol) was dissolved in 50.0 mL of methanol; 1.6 mL of glacial acetic acid was added as catalyst. To this mixture, 2-mercaptoethanesulfonic acid sodium salt (3.82 g, 20.0 mmol) in 30.0 mL of methanol was added dropwise in 30 min with stirring. The reaction mixture was protected from light and stirred at ambient temperature overnight, followed by solvent evaporation under vacuum. The crude product was repurified by dissolving in a small amount of methanol, followed by ethyl ether precipitation and dried under vacuum to yield compound 1a. 5.14 g, yield=94.0%. 1H-NMR (300 MHz; DMSO-d6), ? 2.73 (m, 2H, CH2), 3.02 (m, 2H, CH2), 7.24 (d, 1H, ArH), 7.81 (m, 2H, ArH), 8.45 (d, 1H, ArH). To synthesize 2-[3-(trimethoxysilyl)-propyldisulfanyl]-ethanesulfonic acid sodium salt (1), compound 1a (1.36 g, 5.0 mmol) was dissolved in 20.0 mL of methanol with 1.0 mL of glacial acetic acid. To this mixture, (3-mercaptopropyl)trimethoxysilane (0.95 mL, 5.0 mmol) in 10.0 mL of methanol was added dropwise. The mixture was protected from light and stirred under nitrogen at room temperature overnight. The reaction mixture was quenched and solvent was evaporated under vacuum. The solid obtained was dissolved in a small amount of methanol, followed by ethyl ether precipitation. The purified product was collected by filtration and dried under vacuum. 5.14 g, yield=74.7%. 1H-NMR (300 MHz; D2O) ? 0.79 (t, 2H, CH2(1)), 1.83 (q, 2H, CH2(2)), 2.81 (t, 2H, CH2(3), 3.03 (t, 2H, CH2(5)), 3.27 (t, 2H, CH2(4)), 3.60 (s, 7H, OCH3). Sodium hydroxide (0.83 g, 20.84 mmol) was dissolved in 80.0 mL (5.0?103 mmol) of deionized water, and 1.53 g (4.17 mmol) CTAB was added while stirring continuously to get a clear solution, and then compound 1 (1.24 g, 3.46 mmol) was added. The reaction mixture was stirred at ambient temperature for two hours, followed by dropwise addition of TEOS (6.97 mL, 31.27 mmol). The mixture was stirred vigorously at room temperature for two days followed by heating at 90 C. for one day to improve the structural order. The as-synthesized TPES-MCM was filtered off, and then dried at 90 C. under vacuum for 10 h. To remove the surfactant template, 3.0 g of as-synthesized TPES-MCM was refluxed for 24 hours in 9.0 mL 37.4% HCl/324.0 mL MeOH.

Reference： [1]Current Patent Assignee: IOWA STATE UNIVERSITY OF SCIENCE AND TECHNOLOGY - US2005/107624, 2005, A1 Location in patent: Page/Page column 4-5

18
[ 558439-79-5 ]
[ 4420-74-0 ]
4-(3-trimethoxysilylpropylthiopentyloxy)phenylcarbamatomethyl-18-crown-6 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With dibenzoyl peroxide In chloroform for 120h; Heating / reflux;	2.3 20 g or 40 mmol of compound (Xb) synthesized in 2-2 are dissolved in 20 ml of chloroform. 7.85 g (40 mmol) of (3-mercaptopropyl)trimethoxysilane (Aldrich reference 13,561-7, C6H16O3SSi, MR=196.34), dissolved beforehand in 30 ml of chloroform, are added and the solution is brought to reflux for 5 days. 20 mg of benzoyl peroxide are added approximately every 20 hours. The reaction medium is subsequently brought to dryness by evaporation under vacuum to a constant weight. The yield is quantitative. 29 g of compound (XIIIa) are obtained.

Reference： [1]Current Patent Assignee: COMMISSARIAT A L'ENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES - US2005/143587, 2005, A1 Location in patent: Page/Page column 12

19
sodium sulfide anhydride [ No CAS ]
[ 2530-87-2 ]
[ 4420-74-0 ]

Yield	Reaction Conditions	Operation in experiment
79.9%	With hydrogen sulfide In methanol	2 ›Example[2] ›Example[2] 93.6 g (1.2 mole) of sodium sulfide anhydride was put into a 1-liter 4-mouth flask equipped with a stirrer, a reflux condenser, a thermometer, a gas blow-in tube(s) and a dripping funnel. 400 g of methanol was added to dissolve the sodium sulfide anhydride. After the dissolution was complete, 53.2 g (1.56 mol) of hydrogen sulfide was blown into the system for 2 hours at 30°-40° C. After the internal temperature was heated up to 70° C., 397.4 g (2.0 mol) of 3-chloropropyltrimethoxy silane was dripped through the dripping funnel and simultaneously 7.2 g (0.21 mol) of hydrogen sulfide was blown-in. The reaction was carried out for 1 hour at 65°-75° C. After completion of the dripping and the blowing-in, the temperature was kept at 60°-70° C. for 5 hours for aging. This reaction solution was cooled and sodium chloride was removed by means of filtering. At this time, the filtrate was analyzed using gas chromatography. As shown in the product ratio below, the amount of sulfide produced was small. After methanol was distilled away from the filtrate, vacuum distillation was carried out. 313.7 g of 3-mercaptopropyltrimethoxy silane was obtained. The yield was 79.9%.

Reference： [1]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD. - US5840952, 1998, A

20
[ 51826-90-5 ]
[ 4420-74-0 ]

Yield	Reaction Conditions	Operation in experiment
89.4%		3 ›Example[3] ›Example[3] 351 g of 3-mercaptopropyltrimethoxy silane was obtained in the same manner as in Example 1 except for the fact that 485.8 g (2.0 mol) of 3-bromopropyltrimethoxy silane was used instead of the 3-chloropropyltrimethoxy silane in Example 1. The yield was 89.4%.
87.2%		6 ›Example[6] ›Example[6] 342.3 g of 3-mercaptopropyltrimethoxy silane was obtained in the same manner as in Example 1 except for the fact that 485.8 g (2.0 mol) of 3-bromopropyltrimethoxy silane was used instead of the 3-chloropropyltrimethoxy silane in Example 4. The yield was 87.2%.

Reference： [1]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD. - US5840952, 1998, A
[2]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD. - US5840952, 1998, A

21
triphenyl-tin hydroxide [ No CAS ]
[ 4420-74-0 ]
triisopropanolamine [ No CAS ]
[ 101538-44-7 ]

Yield	Reaction Conditions	Operation in experiment
79%	With potassium hydroxide In toluene	3 Production of compound No. 9 of the invention (third process) EXAMPLE 3 Production of compound No. 9 of the invention (third process) A 300 cc four-necked flask equipped with a stirrer, a thermometer and an azeotropical dehydrator having a reflux condenser was charged with 1.96 g (0.01 mole) of 3-mercaptopropyltrimethoxysilane and 100 ml of toluene, and the silane compound was well dissolved. With stirring, solution of 3.67 g (0.01 mole) of triphenyltin hydroxide in 50 ml of toluene as added dropwise, and the mixture was azeotropically dehydrated to synthesize triphenyltin thiopropyltrimethoxysilane. The reaction mixture was then cooled, and 1.91 g (0.01 mole) of triisopropanolamine and 0.05 g of potassium hydroxide were added. While the mixture was stirred at 50° to 70° C. for 2 hours, the resulting methanol was removed as an azeortrope with toluene. After hot filtration, the filtrate was concentrated to give 6.3 g of a white solid. Recrystallization from a mixture of ethanol and toluene gave 5.1 g (yield 79%) of 1-(3-triphenylstannylthiopropyl)-3,7,10-trimethylsilatrane as white crystals having a melting point of 153.5° to 154.0° C.

Reference： [1]Current Patent Assignee: NITTO KASEI CO.,LTD. - US4654368, 1987, A

22
[ 52995-76-3 ]
[ 4420-74-0 ]
C₁₃H₃₀O₆SSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium methylate In tetrahydrofuran at 0 - 20℃; for 1.33333h;	1 EXAMPLE 1; A 500 mL flask dried in an oven was equipped with a reflux condenser. To the flask were added 16.9 g (0.0861 mol) of (3-mercaptopropyl)trimethoxysilane and 150 mL of tetrahydrofuran under nitrogen atmosphere. The flask was cooled with ice water and stirred for 10 min after adding 35.9 mL (0.0861 mol) of 2.40 M sodium methoxide solution. 15.0 g (0.0820 mol) of tris(ethylene glycol)methyl ether chloride was added for 10 min and the temperature was increased to room temperature. The mixture was stirred for 1 hr at room temperature and the product was filtered. The solvent was removed at normal pressure and the residue was distilled in vacuum to obtain 25.4 g of the compound 1 (yield: 90%). Compound 1: b.p. 146.5° C./0.5 mmHg; 1H NMR (CDCl3, 300 MHz), δ (ppm) 0.70 (t, J=7.9 Hz, 2 H, SiCH2), 1.60-1.70 (m, 2 H, SiCH2CH2), 2.52 (t, J=7.5 Hz, 2 H, SiCH2CH2CH2), 2.66 (t, J=7.2 Hz, 2 H, SCH2CH2O), 3.34 (s, 3 H, CH3O), 3.52 (s, 9 H, CH3OSi), 3.50-3.63 (m, 10 H, CH2O).
90%	Stage #1: 3-(trimethoxysilyl)-1-propanethiol With sodium methylate In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: 1-chloro-3,6,9-trioxadecane In tetrahydrofuran at 0 - 20℃; for 1.16667h;	1 Example 1; [Show Image] A 500 mL flask dried in an oven was equipped with a reflux condenser. To the flask were added 16.9 g (0.0861 mol) of (3-mercaptopropyl)trimethoxysilane and 150 mL of tetrahydrofuran under nitrogen atmosphere. The flask was cooled with ice water and stirred for 10 min after adding 35.9 mL (0.0861 mol) of 2.40 M sodium methoxide solution. 15.0 g (0.0820 mol) of tris(ethylene glycol)methyl ether chloride was added for 10 min and the temperature was increased to room temperature. The mixture was stirred for 1 hr at room temperature and the product was filtered. The solvent was removed at normal pressure and the residue was distilled in vacuum to obtain 25.4 g of the compound 1 (yield: 90 %). Compound 1: b.p. 146.5 °C/0.5 mmHg; 1H NMR (CDCl3, 300 MHz), δ (ppm) 0.70 (t, J = 7.9 Hz, 2 H, SiCH2), 1.60-1.70 (m, 2 H, SiCH2CH2), 2.52 (t, J = 7.5 Hz, 2 H, SiCH2CH2CH2), 2.66 (t, J = 7.2 Hz, 2 H, SCH2CH2O), 3.34 (s, 3 H, CH3O), 3.52 (s, 9 H, CH3OSi), 3.50-3.63 (m, 10 H, CH2O).

Reference： [1]Current Patent Assignee: KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY - US2007/43232, 2007, A1 Location in patent: Page/Page column 3-4
[2]Current Patent Assignee: KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY - EP1762571, 2007, A1 Location in patent: Page/Page column 5

23
[ 4420-74-0 ]
[ 112-26-5 ]
C₁₈H₄₂O₈S₂Si₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium methylate; In tetrahydrofuran; at 0 - 20℃; for 1.83333h;Heating / reflux;	EXAMPLE 4; A 500 mL flask dried in an oven was equipped with a reflux condenser. To the flask were added 29.9 g (0.141 mol) of (3-mercaptopropyl)trimethoxysilane and 250 mL of tetrahydrofuran under nitrogen atmosphere. The flask was cooled with ice water and stirred for 10 min after adding 58.9 mL (0.141 mol) of 2.40 M sodium methoxide solution. 12.0 g (0.0643 mol) of <strong>[112-26-5]1,2-bis(2-chloroethoxy)ethane</strong> was added for 10 min and the temperature was increased to room temperature. The mixture was stirred for 1 hr at room temperature and refluxed for 30 min. After separating the product by filtration, the solvent was removed at normal pressure. The residue was distilled in vacuum to obtain 28.0 g of the compound 4 (yield: 86%). Compound 4: b.p. 185-7 C./0.5 mmHg; 1H NMR (CDCl3, 400 MHz), delta (ppm) 0.69 (t, J=8.2 Hz, 4 H, SiCH2), 1.60-1.68 (m, 4 H, SiCH2CH2), 2.51 (t, J=7.1 Hz, 4 H, SiCH2CH2CH2), 2.64 (t, J=7.1 Hz, 4 H, SCH2CH2O), 3.51 (s, 18 H, CH3OSi), 3.56 (s, 4 H, SCH2CH2OCH2), 3.57 (t, 7.1 Hz, 4 H, SCH2CH2O).
86%		Example 4; [Show Image] A 500 mL flask dried in an oven was equipped with a reflux condenser. To the flask were added 29.9 g (0.141mol) of (3-mercaptopropyl)trimethoxysilane and 250 mL of tetrahydrofuran under nitrogen atmosphere. The flask was cooled with ice water and stirred for 10 min after adding 58.9 mL (0.141 mol) of 2.40 M sodium methoxide solution. 12.0 g (0.0643 mol) of <strong>[112-26-5]1,2-bis(2-chloroethoxy)ethane</strong> was added for 10 min and the temperature was increased to room temperature. The mixture was stirred for 1 hr at room temperature and refluxed for 30 min. After separating the product by filtration, the solvent was removed at normal pressure. The residue was distilled in vacuum to obtain 28.0 g of the compound 4 (yield: 86 %). Compound 4: b.p. 185-7 C/0.5 mmHg; 1H NMR (CDCl3, 400 MHz), delta (ppm) 0.69 (t, J = 8.2 Hz, 4 H, SiCH2), 1.60-1.68 (m, 4 H, SiCH2CH2), 2.51 (t, J = 7.1 Hz, 4 H, SiCH2CH2CH2), 2.64 (t, J = 7.1 Hz, 4 H, SCH2CH2O), 3.51 (s, 18 H, CH3OSi), 3.56 (s, 4 H, SCH2CH2OCH2), 3.57 (t, 7.1 Hz, 4 H, SCH2CH2O).

Reference： [1]Patent: US2007/43232,2007,A1 .Location in patent: Page/Page column 4
[2]Patent: EP1762571,2007,A1 .Location in patent: Page/Page column 6

24
[ 4420-74-0 ]
[ 676-58-4 ]
γ-mercaptopropyldimethylmethoxysilane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	In tetrahydrofuran at 0℃; for 1h;
	In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;	3 Example 3 Synthesis of 3,3′-bis (monomethoxydimethylsilylpropyl) disulfide (MMSPD) The method for preparing 3,3'-bis (monomethoxydimethylsilylpropyl) disulfide (MMSPD) of Example 3 is shown in Scheme 4 below.Connect the condenser, Ar injection tube, and thermometer to a 250 mL three-neck round flask, and mix 3-mercaptopropyltrimethoxysilane and Tetrahydrofuran at 0 °C in a round flask. CH3MgCl-tetrahydrofuran solution is added drop wise dropwise for 1 hour.After dropping CH3OH drop-wise at low temperature, dilute with Tetrahydrofuran-diethyl ether solution (1: 8).The product was filtered and washed several times with diethyl ether to remove diethyl ether under reduced pressure distillation. The product was dried at 100 °C. in a vacuum oven to synthesize (3-mercaptoproryl)monomethoxydimethylsilane

Reference： [1]Dayal, Smita; Li, Jun; Li, Ying-Syi; Wu, Hongqiao; Samia, Anna C. S.; Kenney, Malcolm E.; Burda, Clemens [Photochemistry and Photobiology, 2008, vol. 84, # 1, p. 243 - 249]
[2]Current Patent Assignee: KOREA INSTITUTE OF INDUSTRIAL TECHNOLOGY - KR2019/121040, 2019, A Location in patent: Paragraph 0179-0181; 0184

25
[ 79-77-6 ]
[ 4420-74-0 ]
[ 804565-48-8 ]

Yield	Reaction Conditions	Operation in experiment
80%	With 1,8-diazabicyclo[5.4.0]undec-7-ene at 25 - 30℃; for 72h;	1.b To a well-stirred mixture of (3-ionone (10.00 g, 52.1 mmol) and DBU (79.20 mg, 0. 52 mmol) was rapidly added at 25-30° (cooling bath: 15°) 3-mercaptopropyl- trimethoxysilane (10.21 g from ABCR, 52.1 mmol). After 72h, the reaction mixture was poured onto a cold stirred 5% aqueous HCl solution and extracted twice with EtzO. The organic phases were washed (H2O, saturated aqueous NaHC03 solution and saturated aqueous NaCl solution), dried (Na2SO4), filtered and concentrated. The crude extract was dried 1 h at 65-70°/1 Pa to gave 18.00 g of thioether (pale yellow oil, containing by 'H-NMR ca. 10% of p-ionone, yield = 80%). 'H-NNR : 0.74 (dt, J=3.5 and 8.5, 2H), 0.94 (s, 3H), 1.15 (s, 3H), 1. 35-1. 74 (m, 6H), 1.80 (s, 3H), 1.91 (m, 2H), 2.17 (s, 3H), 2.58 (m, 2H), 2. 88 (dd, J=3.5 and 18. 0,1H), 3.28 (dd, J=8.0 and 18.0, 1H), 3.56 (s, 9H), 3.99 (dd, J=3.5 and 8. 0,1H) 3C-NMR : 206.6 (s), 139.9 (s); 131.6 (s), 53.2 (t), 50.5 (q), 39. 8 (t), 38.1 (d), 37.0 (t), 35.8 (s), 33.7 (t), 30.7 (q), 28.3 (q), 27.9 (q), 22.8 (t), 22.4 (q), 19.3 (t), 8.8 (t)

Reference： [1]Current Patent Assignee: SAFBON WATER SERVICE (HOLDING) INC - WO2005/41908, 2005, A1 Location in patent: Page/Page column 21

26
[ 78-10-4 ]
[ 4420-74-0 ]
silica gel [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With cetyltrimethylammonium bromide; NaOH In water cetyltrimethylammonium bromide dissolved in H2O, NaOH added, stirred at 80°C, tetraethoxysilane and (3-mercaptopropyl)trimethoxysilane added, kept at 80°c for 2 h; filtered, washed with H2O, dried in air at 80°C, EtOH soln. of HCl added, stirred at 60°C for 24 h, centrifuged, washed with H2O, dried in air at 150°C for 24 h; monitored by XRD;
	With n-Dodecylamine In water; acetonitrile at 60℃; for 18h;	The microporous silica was synthesized as described previously by our group in the literature [21]. Briefly, a suspension was prepared from n-dodecylamine, distilled water, acetonitrile, with Si(OC2H5)4 and Si(OMe)3(C3H7S) as the silica-hydride donors and then stirred for 18 h at 60 °C. Hereafter, the mixture was cooled, filtered and extracted with absolute ethanol to remove the template. Finally, the solid was air-dried at 80 °C.

Reference： [1]Chen, Hongmin; He, Junhui [Dalton Transactions, 2009, # 33, p. 6651 - 6655]
[2]Hu, Wenbin; Xie, Huilin; Yue, Hangbo; Prinsen, Pepijn; Luque, Rafael [Catalysis Communications, 2017, vol. 97, p. 51 - 55]

27
[ 98474-79-4 ]
[ 4420-74-0 ]
C₃₃H₃₄N₆O₉SSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With dibutyltin dilaurate In tetrahydrofuran at 20℃; for 8h; Dry environment;	9 Example 9; Compound I; 52.2 g of TDI trimer was dissolved in 400 mL of anhydrous tetrahydrofuran (THF), and the solution was added to a mixture of 19.6 g of γ-mercapto- propyltrimethoxysilane and 0.07 g of dibutyltin dilaurate (DBTDL). The resultant solution was stirred for 8 hs at room temperature under a dry environment. Subsequently, THF was removed with reduced pressure distillation and 66.77 g of compound I was obtained, with a yield of 93%. The compound I has a formula of [Show Image] Elemental analysis of C33H34NsO9SSi: measured value (calculated value)%: C 55.03(55.15), H 4.65(4.74), N 11.59(11.70), O 19.92(20.05), S 4.35(4.46), Si 3.79(3-90);1HNMR(δ/ppm): 2.35(m,1H), 2.8(q, 2H), 3.2(q, 2H),3.55(s, 1H), 6.9(t, 1H), 7.02(q,1H), 7.26(m,1H), 7.5(m, 1H), 7.9(s,1H), 8.0(s, 1H).

Reference： [1]Current Patent Assignee: Zhang, Qunchao; Wang, Decai - EP2157094, 2010, A1 Location in patent: Page/Page column 8

28
[ 118-48-9 ]
[ 4420-74-0 ]
[ 1253793-85-9 ]

Yield	Reaction Conditions	Operation in experiment
94%	With potassium carbonate In ethyl acetate at 20℃; for 23h; Inert atmosphere; chemoselective reaction;

Reference： [1]Temperini, Andrea; Annesi, Diego; Testaferri, Lorenzo; Tiecco, Marcello [Tetrahedron Letters, 2010, vol. 51, # 41, p. 5368 - 5371]

29
[ 4420-74-0 ]
[ 108-24-7 ]
[ 64456-54-8 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium carbonate In ethyl acetate at 20℃; for 9h; Inert atmosphere; chemoselective reaction;
	With potassium carbonate In acetonitrile at 20℃; for 12h;	For example, the manufacturing method of the mercaptoalkylsilatrane derivative of the present invention begins with providing one equivalent weight of (3-mercaptopropyl)trimethoxysilane (MPTMS) solution, and then a potassium carbonate solution of about 2.5 equivalent weights and about 10 milliliters (ml) of acetonitrile are added in the MPTMS solution. Afterward, about 3 equivalent weights of acetic anhydride is added in, such that a chemical reaction between the acetic anhydride and the MPTMS undergoes in room temperature for 12 hours. After the reaction is completed, the resulting mixture is evaporated to dryness, follows by using dichloromethane (DCM) to re-dissolve the solid, and then a filtering step is performed on the resulting solution.

Reference： [1]Temperini, Andrea; Annesi, Diego; Testaferri, Lorenzo; Tiecco, Marcello [Tetrahedron Letters, 2010, vol. 51, # 41, p. 5368 - 5371]
[2]Current Patent Assignee: NATIONAL CHUNG CHENG UNIVERSITY - US2014/296552, 2014, A1 Location in patent: Paragraph 0033

30
[ 4420-74-0 ]
[ 1314886-02-6 ]
[ 1314886-16-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In acetone at 80℃; for 5h;	14 Example 14 A mixture of 4-(N-methylperfluorobutanesulfonamidomethyl)-4'- chloromethylbiphenyl (0.005 mol, 2.64 g), HS(CH2)3Si(OMe)3 (0.00525 mol, 1.03 g), K2CO3 (0.0075 mol, 1.03 g), and acetone was heated at 80°C for 5 hr. After evaporation of the volatiles, ethyl acetate was added to re-dissolve the product. Then filtration was used to remove the salt. Evaporation of solvent gave the desired product.

Reference： [1]Current Patent Assignee: 3M CO - WO2011/87717, 2011, A1 Location in patent: Page/Page column 25

31
[ 4420-74-0 ]
[ 947-42-2 ]
[ 1415933-86-6 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran at 0 - 20℃; for 22h;	8 Diphenylsilanediol (5 g), tetrahydrofuran (THF, 4 g) and mercaptopropyltrimethoxysilane (MPTS, 30 g) were placed in a 100 mL 3-neck round bottom flask with a stir bar and reflux condenser. The flask was kept at +0°C, while ammonia (~1 g) was bubbled in. The reaction was allowed to proceed for 4 hours at 0°C, followed by 18 hours warming to room temperature. When GC/MS was run, a peak corresponding to l,5-bis(mercaptopropyl)-l,l,5,5-tetramethoxy-3,3-diphenyltrisiloxane was seen, along with unreacted excess MPTS.

Reference： [1]Current Patent Assignee: PIBOND OY - WO2012/172176, 2012, A2 Location in patent: Page/Page column 16

32
[ 4420-74-0 ]
[ 107-05-1 ]
[ 1430074-50-2 ]

Yield	Reaction Conditions	Operation in experiment
76.2%	Stage #1: 3-chloroprop-1-ene With magnesium In tetrahydrofuran at 20℃; Inert atmosphere; Stage #2: 3-(trimethoxysilyl)-1-propanethiol In tetrahydrofuran at 20℃; Inert atmosphere;	2.3 Preparation of mercaptopropylmethyldiallylsilane (M1) General procedure: A 250mL three-necked round-bottomed flask with an addition funnel, reflux condenser, and a stir bar was charged with allylmagnesium chloride (100.0mmol) in 100mL of anhydrous THF. Mercaptopropylmethyldimethoxysilane (3.00g, 16.67mmol) in 30mL THF was then slowly dropped into the allylmagnesium chloride solution via the addition funnel for over 30min, and the mixture was stirred at room temperature overnight. When the reaction was completed, the reaction was quenched with methanol and then filtered. The organic phase was dried over anhydrous magnesium sulfate. After the solvent was evaporated under vacuum, the residue was further purified by using column chromatography on silica gel with ether/hexane at 1/9 (v/v) as eluent to yield M1 as colorless liquid (2.35g, yield: 78.3%). 1H NMR (300MHz, CDCl3, ppm): δ=0.02 (s, -SiCH3, 3H), 0.65-0.70 (m, -SiCH2-, 2H), 1.34-1.37 (t, -SH, J=7.9Hz, 1H), 1.57-1.63 (m, -SiCH2CH=CH2, 4H), 1.64-1.68 (m, -CH2CH2SH, 2H), 2.51-2.57 (m, -CH2SH, 2H), 4.85-4.92 (m, -CH2CH=CH2, 4H), 5.74-5.84 (m, -CH2CH=CH2, 2H); 13C NMR (75MHz, CDCl3, ppm): δ=-5.90, 12.20, 21.16, 25.52, 28.52, 113.30, 134.31; 29Si NMR (59.60MHz, CDCl3, ppm): δ=0.80; MS: 199.08 [M+-H]. FT-IR (KBr, cm-1): ν=3076, 2959, 2917, 2881, 2558, 1629, 1419, 1253, 1157, 992. Anal. Calc. for C10H20SSi, C, 59.93; H, 10.06; S, 16.00%. Found: C, 59.89; H, 9.96; S, 15.75%.

Reference： [1]Xue, Lei; Yang, Zhizhou; Wang, Dengxu; Wang, Yike; Zhang, Jie; Feng, Shengyu [Journal of Organometallic Chemistry, 2013, vol. 732, p. 1 - 7]

33
[ 4420-74-0 ]
[ 1443919-53-6 ]
[ 1443919-61-6 ]

Yield	Reaction Conditions	Operation in experiment
99%	With 2,2-dimethoxy-2-phenylacetophenone In methanol at 90℃; UV-irradiation;

Reference： [1]Sassi, Mauro; Mascheroni, Luca; Ruffo, Riccardo; Salamone, Matteo M.; Pagani, Giorgio A.; Mari, Claudio M.; D'Oorazio, Giuseppe; La Ferla, Barbara; Beverina, Luca [Organic Letters, 2013, vol. 15, # 14, p. 3502 - 3505]

34
[ 444315-18-8 ]
[ 4420-74-0 ]
C₃₆H₈₂O₁₅SSi₉ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With 2,2-dimethoxy-2-phenylacetophenone In tetrahydrofuran for 0.166667 - 0.5h; UV-irradiation;	Compound 8 General procedure: All reactions were conducted in the presence of air. Mono(vinyl)-substituted T8 (1) and the appropriate thiol were added to 1 ml THF in a 5 ml bottle equipped with a stir. The bottle was irradiated for 10-30 min and the reaction was monitored by FTIR. When the reaction was complete, the reaction mixture was concentrated via rotary evaporation and methanol was added to precipitate the product, which was then separated by filtration and dried under vacuum.

Reference： [1]Li, Liguo; Xue, Lei; Feng, Shengyu; Liu, Hongzhi [Inorganica Chimica Acta, 2013, vol. 407, p. 269 - 273]

35
[ 930-68-7 ]
[ 4420-74-0 ]
[ 1492897-14-9 ]

Yield	Reaction Conditions	Operation in experiment
81%	With C₃₃H₄₃FeN₄O₂S In pentane at 40℃; for 18h;

Reference： [1]Alt, Isabel; Rohse, Philipp; Plietker, Bernd [ACS Catalysis, 2013, vol. 3, # 12, p. 3002 - 3005]

36
[ 4420-74-0 ]
[ 1118-46-3 ]
C₂₂H₅₄O₉S₃Si₃Sn [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
4.3 g	Stage #1: 3-(trimethoxysilyl)-1-propanethiol With lithium hydride In tetrahydrofuran at 25℃; for 1.5h; Schlenk technique; Stage #2: Trichlorbutylstannan In tetrahydrofuran at 65℃; for 1.5h; Schlenk technique;	1 Modifier 5 is represented by Formula M5 below and was prepared as follows To a 100 mL, Schlenk flask was charged 50 ml tetrahydrofuran (THF), 360 mg (45.25 mmol) lithium hydride, and subsequently, 4.0 g (20.37 mmol) gamma-mercaptopropyl (methyl) dimethoxysilane PI from the ABCR GmbH. The reaction mixture was stirred for .5 hours at 25°C. Then a solution of n-butyl tiichloro stannane (1.915 g (6.79 mmol)) in 10 g THF was then added drop wise to the Schlenk ilask. The reaction mixture was warmed up to 65°C and kept at this temperature for 1.5 hours. Subsequently the THF solvent was removed under vacuum (reduced pressure) from the resulting mixture at room temperature and the residue was dissolved in 50 niL pentane. Precipitated lithium chloride was separated from the reaction product dissolved, in the pentane by filtration. The peotane solvent was removed under vacuum (under reduced pressure). The resulting colorless liquid solution proved, to be pure per NMR, and therefore no further purification was necessary. A yield of 4.3 g (5.5 mmol) of modifier M5 was obtained. 1H-NMR (400 MHz, 23°C, C6D6); δ = 3.42 (s, 27H, SiOCH3), 2.93 (t, 6H, S-CH2CH2CH2-Si), 1.93 (m, 6H, CH2CH2CH2-Si), 1.47 (m, 2H, SnCH2CH2CH2CH3), 1.44 (m, 2H, SnCH2CH2CH2CH3), 1.18 (m, 2H, SnCH2CH2CH2CH3), 0.80 (t, 3H, SnCH2CH2CH2CH3), 0.77(t, 6H, S-CH2CH2CH2-Si) ppm; 13C (101 MHz, 23°C, C6D6): δ = 50.34 (OCH3), 31.56 (S-CH2CH2CH2-Si), 28.28 (SCH2CH2CH2-Si), 27.58 (SnCH2CH2CH2CH3), 26.16 (SnCH2CH2CH2CH3), 13.48 (SnCH2CH2CH2CH3), 9.08 (S-CH2CH2CH2-Si) ppm.

Reference： [1]Current Patent Assignee: TRINSEO S.A. - WO2014/40639, 2014, A1 Location in patent: Page/Page column 59

37
[ 4420-74-0 ]
[ 18162-48-6 ]
[ 1416804-31-3 ]

Yield	Reaction Conditions	Operation in experiment
20.7 g	With triethylamine In cyclohexane at 20 - 60℃; for 27h; Schlenk technique;	3.M2 Modifier 2 is represented by Formula M2 below and was prepared as follows A 500 mL Schlenk flask was charged with 100 g cyclohexane, 8.6 g (85 mmol.) triethylamine and 13.12 g (80 mmol) gamma-mercaptopropyl trimethoxy silane [Silquest A-1.89] from, the Cromton GmbH. 24.91 g (165 mmol) tert-butyl dimethyl chloro silane were diluted with 170 g cyclohexane and. the resulting solution is then, added drop wise to the Schlenk flask. Immediately a white triethylammonium chloride precipitated. The suspension was stirred for about 24 hours at room temperature and. for another three hours at 60 °C. The white precipitate was subsequently separated by filtration. The resulting colorless solution was distilled in. the vacuum, to yield 20.7 g (67.7 mmol) of modifier M2.

Reference： [1]Current Patent Assignee: TRINSEO S.A. - WO2014/40639, 2014, A1 Location in patent: Page/Page column 55; 56

38
[ 4420-74-0 ]
[ 683-18-1 ]
dibutyltinbis(mercaptopropyltrimethoxysilane) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-(trimethoxysilyl)-1-propanethiol With lithium hydride In tetrahydrofuran at 25℃; for 2h; Schlenk technique; Stage #2: dibutyltin chloride In tetrahydrofuran at 65℃; for 1.25h; Schlenk technique;	1 Modifier 5 is represented by Formula M5 below and was prepared as follows To a 100 mL, Schlenk flask was charged 50 ml tetrahydrofuran (THF), 360 mg (45.25 mmol) lithium hydride, and subsequently, 4.0 g (20.37 mmol) gamma-mercaptopropyl (methyl) dimethoxysilane PI from the ABCR GmbH. The reaction mixture was stirred for .5 hours at 25°C. Then a solution of n-butyl tiichloro stannane (1.915 g (6.79 mmol)) in 10 g THF was then added drop wise to the Schlenk ilask. The reaction mixture was warmed up to 65°C and kept at this temperature for 1.5 hours. Subsequently the THF solvent was removed under vacuum (reduced pressure) from the resulting mixture at room temperature and the residue was dissolved in 50 niL pentane. Precipitated lithium chloride was separated from the reaction product dissolved, in the pentane by filtration. The peotane solvent was removed under vacuum (under reduced pressure). The resulting colorless liquid solution proved, to be pure per NMR, and therefore no further purification was necessary. A yield of 4.3 g (5.5 mmol) of modifier M5 was obtained. 1H-NMR (400 MHz, 23°C, C6D6); δ = 3.43 (s, 18H, SiOCH3), 2.87 (t, 4H, S-CH2CH2CH2-Si), 1.98 (m, 4H, CH2CH2CH2-Si), 1.64 (m, 4H, SnCH2CH2CH2CH3), 1.30 (m, 8H, SnCH2CH2CH2CH3), 0.88 (t, 6H, SnCH2CH2CH2CH3), 0.78(t, 4H, S-CH2CH2CH2-Si) ppm; 13C (101 MHz, 23°C, C6D6): δ = 50.34 (OCH3), 28.59 (S-CH2CH2CH2-Si), 28.68 (SCH2CH2CH2-Si), 30.79 (SnCH2CH2CH2CH3), 27.04 (SnCH2CH2CH2CH3), 17.88 (SnCH2CH2CH2CH3), 13.73 (SnCH2CH2CH2CH3), 9.25 (S-CH2CH2CH2-Si) ppm.

Reference： [1]Current Patent Assignee: TRINSEO S.A. - WO2014/40639, 2014, A1 Location in patent: Page/Page column 59; 60

39
[ 24424-99-5 ]
[ 4420-74-0 ]
[ 1253793-79-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In acetonitrile at 20℃; for 12h;	Furthermore, the manufacturing method of the mercaptoalkylsilatrane derivative of the present invention in the third preferred embodiment is, for example, to provide the (3-mercaptopropyl)trimethoxysilane solution of about 1 equivalent weight at first, and add in the potassium carbonate solution of about 2.5 equivalent weights and about 10 milliliter (ml) of acetonitrile into the (3-mercaptopropyl)trimethoxysilane solution. Afterward, an acid anhydride solution of t-butoxycarbonyl of about 1.2 equivalent weights is added in, such that a chemical reaction between acid anhydride and (3-mercaptopropyl)trimethoxysilane undergoes in room temperature for 12 hours. After the reaction is completed, the resulting mixture is evaporated to dryness, follows by using dichloromethane to re-dissolve the solid, and then a filtering step is performed on the resulting solution. Afterward, the filtrate is extracted by using a sodium carbonate (Na2CO3) solution to obtain a mercaptoalkylsilane compound having a protecting group of t-butoxycarbonyl.

Reference： [1]Current Patent Assignee: NATIONAL CHUNG CHENG UNIVERSITY - US2014/296552, 2014, A1 Location in patent: Paragraph 0042

40
[ 4420-74-0 ]
[ 28920-43-6 ]
C₂₁H₂₆O₅SSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In acetonitrile at 20℃; for 36h;	Furthermore, the manufacturing method of the mercaptoalkylsilatrane derivative of the present invention in the fourth preferred embodiment is, for example, to provide the (3-mercaptopropyl)trimethoxysilane solution of about 1 equivalent weight at first, and add in the potassium carbonate solution of about 2.5 equivalent weights and about 10 milliliter (ml) of acetonitrile into the (3-mercaptopropyl)trimethoxysilane solution. Afterward, a solution of 9-fluorenylmethoxycarbonyl chloride of about 2 equivalent weights is added, such that a chemical reaction between fluorenylmethoxycarbonyl chloride and (3-mercaptopropyl)trimethoxysilane undergoes in room temperature for 36 hours. After the reaction is completed, the resulting mixture is evaporated to dryness, follows by using dichloromethane to re-dissolve the solid, and then a filtering step is performed on the resulting solution. Afterward, the filtrate is extracted by using a 10% sodium bicarbonate solution to obtain a silane compound having a protecting group of 9-fluorenylmethoxycarbonyl.

Reference： [1]Current Patent Assignee: NATIONAL CHUNG CHENG UNIVERSITY - US2014/296552, 2014, A1 Location in patent: Paragraph 0045

41
[ 4420-74-0 ]
[ 76-83-5 ]
C₂₅H₃₀O₃SSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In acetonitrile at 20℃; for 12h;	Furthermore, the manufacturing method of the mercaptoalkylsilatrane derivative of the present invention in the second preferred embodiment is, for example, to provide the (3-mercaptopropyl)trimethoxysilane solution of about 1 equivalent weight at first, and add in the potassium carbonate solution of about 2.5 equivalent weights and about 10 milliliter (ml) of acetonitrile into the (3-mercaptopropyl)trimethoxysilane solution. Afterward, a solution of about 1.2 equivalent weights of triphenylmethyl chloride is added in, such that a chemical reaction between triphenylmethyl chloride and (3-mercaptopropyl)trimethoxysilane undergoes in room temperature for 12 hours. After the reaction is completed, the resulting mixture is evaporated to dryness, follows by using dichloromethane (DCM) to re-dissolve the solid, and then a filtering step is performed on the resulting solution. Afterward, the filtrate is extracted by using pentane to obtain a mercaptoalkylsilane compound having a protecting group of triphenylmethyl.

Reference： [1]Current Patent Assignee: NATIONAL CHUNG CHENG UNIVERSITY - US2014/296552, 2014, A1 Location in patent: Paragraph 0039

42
[ 4420-74-0 ]
C₈H₁₅N₂⁽¹⁺⁾*C₃H₃O₂^(1-) [ No CAS ]
C₈H₁₅N₂⁽¹⁺⁾*C₉H₁₉O₅SSi^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With diisopropylamine In methanol at 20℃; for 20h;	1 Synthesis of reactive ionic liquid (13) Acrylic acid monomer (0.0125 mol) was dropped into a 5.0 g solution of an equimolar amount of 1-butyl-3-methylimidazolium hydrogencarbonate (solvent:methanol/water=3:2 mixture; concentration: 50 mass%; 0.0125 mol) inan ice bath. During the dropping, generation of bubbles was observed. The reaction solution was returned to roomtemperature 30 minutes later, and was stirred for 6 hours. Then, the solvent was evaporated under a reduced pressure.After the evaporation, methanol (super dehydrated; manufactured by Wako Pure Chemical Industries, Ltd.) was added,and then evaporated under a reduced pressure. Thus, an ionic liquid monomer was obtained by the acid ester method.Subsequently, 2.10 g (10.0 mmol) of the obtained ionic liquid monomer and 1.87 mL (10.1 mmol) of 3-mercaptopropyltrimethoxysilanewere dissolved in 20 mL of methanol (super dehydrated). 10 mol% of diisopropylamine with respect tothe 3-mercaptopropyltrimethoxysilane was added to the solution as a catalyst. Then, the solution was stirred at roomtemperature for 20 hours. By evaporation of the reaction solution, reactive ionic liquid (13) represented by the formulabelow was obtained.

Reference： [1]Current Patent Assignee: Sumitomo Riko (in: Sumitomo Electric); SUMITOMO ELECTRIC INDUSTRIES, LTD.; KYUSHU UNIVERSITY - EP2832736, 2015, A1 Location in patent: Paragraph 0082

43
[ 1072-62-4 ]
[ 15214-89-8 ]
[ 4420-74-0 ]
C₁₃H₂₉NO₇S₂Si*C₅H₈N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		0.96 mL (10 mmol) of ethylimidazole and 2.07 g (10 mmol) of 2-acrylamide-2-methylpropane sulfonic acid werestirred in 40 mL of acetone at room temperature for 2 hours. Unreacted portion of 2-acrylamide-2-methylpropane sulfonicacid was removed by filtration. The filtrate was subjected to evaporation, and thus a viscous liquid compound wasobtained. 3.00 g (10 mmol) of the obtained compound and 1.87 mL (10.1 mmol) of 3-mercaptopropyltrimethoxysilanewere dissolved in 20 mL of methanol (super dehydrated; manufactured by Wako Pure Chemical Industries, Ltd.), and4 mol% of diisopropylamine with respect to the 3-mercaptopropyltrimethoxysilane was further added to the solution. Thesolution was stirred at room temperature for 20 hours. By evaporation of the solvent, ionic liquid (24) was obtained.

Reference： [1]Patent: EP2832736,2015,A1 .Location in patent: Paragraph 0092

44
[ 4420-74-0 ]
[ 3637-26-1 ]
C₁₇H₃₇NO₈S₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With diisopropylamine; In methanol; at 20℃; for 16h;	25 mL (0.148 mol) of dimethylaminoethyl methacrylate was dissolved in 100 mL of acetone. A solution of 13mL (0.148 mol) of propane sultone in 20 mL of acetone was dropped into the dimethylaminoethyl methacrylate solutionunder a nitrogen atmosphere. The mixed solution was stirred at room temperature for 14 hours. Then, a white precipitatewas collected by filtration, and further was dried under a reduced pressure. Thus, a monomer was obtained. Next, 10mmol of the obtained monomer and 10.1 mmol of 3-mercaptopropyltrimethoxysilane were dissolved in 50 mL of methanol.4 mol% of diisopropylamine was further added to the solution. The solution was stirred at room temperature for 16 hours.By evaporation of the reaction solution, ionic liquid (26) was obtained. The ionic liquid was stored with trifluoroethanolmixed.

Reference： [1]Patent: EP2832736,2015,A1 .Location in patent: Paragraph 0094

45
[ 4420-74-0 ]
[ 69655-76-1 ]
C₆₄H₁₅₂O₃₆S₈Si₁₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
Ca.100%	With 2,2-dimethoxy-2-phenylacetophenone; In tetrahydrofuran; at 20℃; for 0.25h;UV-irradiation; Inert atmosphere;	General procedure: In a vial, OVS (0.5g, 0.79mmol), 1.0equiv (to ?Vi goups) of 3?mercaptopropylmethyldimethoxysilane (1.14g, 6.33mmol) and 2wtpercent of DMPA were dissolved in the minimal amount of anhydrous THF under the argon condition. The mixture was irradiated with stirring for 15min with UV light at room temperature. The solvent was evaporated in vacuo and then washed by distilled methanol to obtain SQ?[SiMe(OMe)2]8 as a viscous pale yellow oil (1.64g, yield ?100percent). SQ?[SiMe(OMe)2]8 can also be prepared without DMPA after 90min of irradiation.

Reference： [1]Journal of Organometallic Chemistry,2015,vol. 783,p. 49 - 54

46
[ 1484-13-5 ]
[ 4420-74-0 ]
9-(2-((3-(trimethoxysilyl)propyl)thio)ethyl)-9H-carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With 1-hydroxycyclohexyl phenyl ketone; In tetrahydrofuran; for 4h;UV-irradiation;	To a dry 100 ml round bottom flask, 3-mercaptopropyltrimethoxysilane(10 g, 50.4 mmol) and 9-vinyl carbazole (9.74 g, 50.4 mmol) were dissolved in 10 ml of dry THF. To this solution, photoinitiator Igracure 184 (0.1 g) was dissolved. After 3 freeze thaw cycles, the solution was irradiated with a365 nm UV lamp at a distance of 10 cm for 4 hours with stirring. 9-(2-((3-(trimethoxysilyl)propyl)thio)ethyl)-9H-carbazole (CzTMS) was obtained through flash column chromatography with THF. (19.68 g, 98% yield).

Reference： [1]Journal of Nanoscience and Nanotechnology,2017,vol. 17,p. 5562 - 5565
[2]Chemistry - A European Journal,2014,vol. 20,p. 12773 - 12776

47
[ 931-53-3 ]
[ 4420-74-0 ]
[ 762-21-0 ]
diethyl 2-((cyclohexylimino)methylene)-3-(3-(trimethoxysilyl)propylthio)succinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	In dichloromethane at 20℃; for 3h;	4.1. General procedure for the preparation of 4a-h (exemplified to 4a) General procedure: To a magnetically stirred solution of ethanethiol (0.06 g, 1.0 mmol) and DMAD (0.14 g, 1.0mmol) in CH2Cl2 (5 mL) was added, tert-butyl isocyanide (0.08 g, 1.0 mmol). The mixture wasstirred for 3 h at room temperature. After completion of the reaction as indicated by TLC, thesolvent was removed under vacuum. The obtained residue was chromatographed on a silica gelcolumn using a mixture of n-hexane and AcOEt (4:1) as eluent to yield 4a as a yellow oil (0.20 g,72%).

Reference： [1]Sarvary, Afshin; Shaabani, Shabnam; Ghanji, Nasim; Shaabani, Ahmad [Journal of Sulfur Chemistry, 2015, vol. 36, # 2, p. 117 - 123]

48
[ 2399-48-6 ]
[ 4420-74-0 ]
C₁₄H₂₈O₆SSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21.8 g	With 2,2'-azobis(isobutyronitrile); In ethyl acetate; for 24h;Inert atmosphere; Reflux;	Under an argon atmosphere, <strong>[2399-48-6]tetrahydrofurfuryl acrylate</strong> (manufactured byTokyo Kasei Kogyo Co., Ltd.) 10.0 g (64 mmol) of 3-mercaptopropyltrimethoxysilane (Shin-Etsu Chemical Co., Ltd.) 12.5 g (64 mmol) and azobisbutyronitrile (manufactured by Nacalai Tesque) 210 mg (1.2 mmol) were dissolvedin dehydrated ethyl acetate 60 ml, was heated under reflux for 24 hours. Underreduced pressure to remove ethyl acetate, the No2-8 compound is a compound ofthe present invention was obtained 21.8 g.
21.8 g	With 2,2'-azobis(isobutyronitrile); In ethyl acetate; for 24h;Inert atmosphere; Reflux;	Under an argon atmosphere,Tetrahydrofurfuryl acrylate10.0 g (64 mmol) (manufactured by Tokyo Chemical Industry Co., Ltd.)Was added 3-mercaptopropyltrimethoxysilane12.5 g (64 mmol) of a catalyst (Shin-Etsu Chemical Co., Ltd.)And azobisisobutyronitrile(Manufactured by Nacalai Tesque)210 mg (1.2 mmol)Was dissolved in 60 ml of dehydrated ethyl acetate,And heated under reflux for 24 hours.By removing the ethyl acetate under reduced pressure,21.8 g of the compound of No 1-8 as the compound of the present invention was obtained.

Reference： [1]Patent: JP2015/218139,2015,A .Location in patent: Paragraph 0030
[2]Patent: JP2018/115171,2018,A .Location in patent: Paragraph 0027

49
[ 17119-11-8 ]
[ 4420-74-0 ]
C₂₂H₄₈O₃SSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With 2,2'-azobis(isobutyronitrile) at 120℃; for 60h; Sealed tube;	5 Reaction of vinylidene double bond terminated 1-octene dimer (C16=) and (3-mercaptopropyl)trimethoxysilane Example 5 Reaction of vinylidene double bond terminated 1-octene dimer (C16=) and (3-mercaptopropyl)trimethoxysilane Vinylidene double bond terminated 1-octene dimer (C16=) (5.0 grams, 22.28 mmol, MW: 224.43, 1.0 equivalent), (3-mercaptopropyl)trimethoxysilane (5.25 grams, 26.73 mmole, MW: 196.34, 1.2 equivalent) and 2,2'-azobis(2-methylpropionitrile) (AIBN) (0.365 grams, 2.23 mmol, MW: 164.0, 0.1 equivalent) were charged in a 25 milliliter thick sealed glass reactor. After addition, the reaction mixture was stirred for 60 hours at 120° C. The reaction was then stopped and cooled down to room temperature. The unreacted (3-mercaptopropyl)trimethoxysilane and high boiling component were distilled by air bath oven at 180° C. under vacuum for 1 hour. The 1H NMR showed the conversion of vinylidene double bond and the formation of thioether linkage (-CH2-S-CH2-). The final product was determined by 1H NMR. Yield: 5.0 grams (53%). 1H NMR (CDCl3): 3.57 (9H, s), 2.49 (4H, m), 1.69-1.54 (3H, m) 1.27 (22H, m), 0.89 (6H, t), 0.75 (2H). IR: (cm-1): 2925, 2854, 1458, 1378, 1340, 1302, 1247, 1191, 1090, 815.

Reference： [1]Current Patent Assignee: EXXON MOBIL CORP - US9422499, 2016, B2 Location in patent: Page/Page column 25; 26

50
[ 3194-70-5 ]
[ 4420-74-0 ]
2,4-diamino-6-{2-[3-(trimethoxysilyl)propylthio]ethyl}-1,3,5-triazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	In methanol at 65℃; for 1h;	1 Synthesis of 2,4-diamino-6- {2- [3- (trimethoxysilyl) propylthio] ethyl} -1,3,5-triazine In a 500 mL flask, 27.4 g (200.0 mmol) of 2,4-diamino-6-vinyl-1,3,5-triazine,39.3 g (200.0 mmol) of 3-mercaptopropyltrimethoxysilane and 200 mL of methanol were added,To prepare a reaction solution.While stirring this reaction solution,The reaction was carried out at 65 ° C. for 1 hour,The reaction solution was concentrated under reduced pressure,64.7 g (yield 97%) of white crystals were obtained.

Reference： [1]Current Patent Assignee: ZEON CORPORATION; SHIKOKU CHEMICALS CORPORATION - JP2016/37457, 2016, A Location in patent: Paragraph 0022

51
[ 827027-31-6 ]
[ 4420-74-0 ]
[2-{3-(3-trimethoxysilylpropylthio)propionyloxy}ethyl]-N,N,N-trimethylammonium bistrifluoromethanesulfonimide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96.4%	In acetonitrile at 20℃; for 5h;	4 Synthesis of [2-{3-(3-trimethoxysilylpropylthio)propionyloxy}ethyl]-N,N,N-trimethylammonium bistrifluoromethanesulfonimide The resulting [2- (acryloyloxy) ethyl] trimethylammonium bistrifluoromethanesulfonimide 53. 6g (122.3 mmol) was dissolved in 46.6 g of acetonitrile and 3-trimethoxysilane Propylpropanethiol 24. Og (122. 3 mmol), And allowed to react at room temperature for 5 hours. Then, the extract was concentrated to dryness to give [2-{3-(3-trimethoxysilylpropylthio)propionyloxy}ethyl]-N,N,N-trimethylammonium bistrifluoromethanesulfonimide 74. 9 g (yield 96.4%)

Reference： [1]Current Patent Assignee: Sumitomo Chemical (w/o Dongwoo Fine-Chem); SUMITOMO CHEMICAL COMPANY LIMITED - CN103596965, 2016, B Location in patent: Paragraph 0087-0089; 0091

52
[ 676257-10-6 ]
[ 4420-74-0 ]
N-[2-{3-(3-trimethoxysilylpropylthio)-2-methylpropionyloxy}ethyl]-N,N,N-trimethylammonium bis(trifluoromethanesulfonyl)imide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96.7%	In acetonitrile at 20℃; for 5h;	5 Syntheisi of N-[2-{3-(3-trimethoxysilylpropylthio)-2-methylpropionyloxy}ethyl]-N,N,N-trimethylammonium bis(trifluoromethanesulfonyl)imide The resulting methacryloyl choline bis-trifluoromethanesulfonimide was obtained55.3 g (122.3 mmol)Dissolved in 47.7 g of acetonitrile,3-Trimethoxysilylpropanethiol 24. lg (122. 3 mmol) was added,And allowed to react at room temperature for 5 hours.The mixture was concentrated to dryness to give N-[2-{3-(3-trimethoxysilylpropylthio)-2-methylpropionyloxy}ethyl]-N,N,N-trimethylammonium bis(trifluoromethanesulfonyl)imide 76. 8 g (yield 96.7%).

Reference： [1]Current Patent Assignee: Sumitomo Chemical (w/o Dongwoo Fine-Chem); SUMITOMO CHEMICAL COMPANY LIMITED - CN103596965, 2016, B Location in patent: Paragraph 0093-0095; 0097

53
[ 131-17-9 ]
[ 4420-74-0 ]
bis(7-trimethoxysilyl-4-thioheptyl)phthalate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12.9 g	With Irgacure 1173; for 0.05h;UV-irradiation;	5.0 g (20.3 mmol) of ortho<strong>[131-17-9]diallyl phthalate</strong> and 7.97 g (40.6 mmol) of 3-mercaptopropyltrimethoxysilane were mixed. 100 mg of Irgacure 1173 (manufactured by Ciba Specialty Chemicals) was added as a photopolymerization initiator to the resulting solution, and ultraviolet light (365 nm, 5 mW / cm ) was irradiated with a high pressure mercury lamp while stirring the solution The reaction was carried out for 3 minutes. The reaction solution was concentrated under reduced pressure to obtain 12.9 g of bis (7-trimethoxysilyl-4-thioheptyl) phthalate (compound (1)).

Reference： [1]Patent: JP6083888,2017,B2 .Location in patent: Paragraph 0051

54
allyl polyether [ No CAS ]
[ 4420-74-0 ]
C₃₀H₆₄O₁₄SSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tertiary butyl per-2-ethylhexanoate In tetrahydrofuran at 65℃; for 2h;	1 I. Production of Surface-Treated Powder (Production by Production Example 1) Surface hydrophilization treatment of the titanium oxide powder was performed according to the following procedures (A) and (B). (A) Preparation of Surface Treatment Agent (Alkoxysilane Containing Sulfur Atoms and Polyether Group) Into a 1 liter three-necked flask equipped with a stirrer, a thermometer, an ester adapter and a Dimroth condenser, a compound represented by the following formula (9) 4.2 g of alkoxysilane containing a mercapto group represented, 12.6 g of a compound having a polyether group and an allyl group represented by the following formula (10), and 36.5 g of THF (tetrahydrofuran), and then stirring 1 g of PERBUTYL-O [t-butylperoxy-2-ethylhexanoate manufactured by NOF CORPORATION] was added and aging was carried out at 65 ° C. for 2 hours.

Reference： [1]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD. - JP5910530, 2016, B2 Location in patent: Paragraph 0066

55
[ 4420-74-0 ]
2,2'-azobis[N-(2-propenyl)-2-methylpropionamide] [ No CAS ]
2,2'-azobis[2-methyl-N-(3-(3-(trimethoxysilyl)propylthio)propyl)propionamide] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2,2’-azobis(4-methoxy-2,4-dimethyl)valeronitrile In toluene at 35℃; for 2h; Inert atmosphere;	2 In a recovery flask, 2,2'-azobis [N - (2-propenyl) -2-methylpropionamide] (VF-096 manufactured by Wako Pure Chemical Industries, Ltd.), 33.5 g of 3-mercaptopropyltrimethoxysilane (manufactured by Tokyo Chemical Industry Co., Ltd.) 0.66 g of 2,2'-azobis (4-methoxy-2,4-dimethylvaleronitrile) (V-70 manufactured by Wako Pure Chemical Industries, Ltd.) and 50 g of toluene were placed and while stirring with a magnetic stirrer The flask was purged with nitrogen for 20 minutes and sealed tightly. Then, the reaction solution was placed in a water bath kept at 35 ° C., and reacted for 2 hours with stirring. The resulting reaction product was concentrated by an evaporator and purified by column chromatography.

Reference： [1]Current Patent Assignee: TOYO TIRE CORPORATION - JP5946758, 2016, B2 Location in patent: Paragraph 0033

56
[ 4420-74-0 ]
[ 1025-15-6 ]
1,3,5-tris [3-[[3-(trimethoxysilyl)propyl]thio]propyl]isocyanurate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With 2,2'-azobis(isobutyronitrile); at 110℃; for 5h;	In a 100 mL flask equipped with a thermometer, 24.9 g (100 mmol) of 1,3,5-<strong>[1025-15-6]triallyl isocyanurate</strong>,And 58.9 g (300 mmol) of (3-mercaptopropyl) trimethoxysilane were placed,After adding 200 mg (1.22 mmol) of azobisisobutyronitrile thereto, the reaction was carried out at 110 C. for 5 hours with stirring. The obtained reaction mixture was cooled to obtain 83.8 g (100% yield) of the title isocyanurate compound as a pale yellow liquid.

Reference： [1]Patent: JP2017/8017,2017,A .Location in patent: Paragraph 0044

57
[ 4420-74-0 ]
[ 229162-26-9 ]
1,3,4,6-tetrakis[3-[[3-(trimethoxysilyl)propyl]thio]propyl]glycoluril [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With 2,2'-azobis(isobutyronitrile) at 60℃; for 3h;	1 Synthesis of 1,3,4,6-tetrakis [3 - [[3- (trimethoxysilyl) propyl] thio] propyl] glycoluril 3.02 g (10.0 mmol) of 1,3,4,6-tetraallyl glycoluril and 7.85 g (40.0 mmol) of (3-mercaptopropyl) trimethoxysilane were placed in a 100 mL flask equipped with a thermometer, After adding 192 mg (1.2 mmol) of azobisisobutyronitrile thereto, the reaction was carried out at 60 ° C. for 3 hours with stirring. The obtained reaction mixture was cooled and concentrated under reduced pressure to obtain 10.8 g (yield 99%) of a colorless transparent liquid.

Reference： [1]Current Patent Assignee: SHIKOKU CHEMICALS CORPORATION - JP2017/8017, 2017, A Location in patent: Paragraph 0038

58
[ 4420-74-0 ]
(8S,9S)-9-[2-(N-methyl)pyridinium](9-desoxy)epicinchonidine tetrafluorobate [ No CAS ]
(8S,9S)-9-[2-(N-methyl)pyridinium](9-desoxy)(11-(3-(trimethoxysilylpropylthio)epi-10,11-dihydrocinchonidine))tetrafluoroborate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With 2,2'-azobis(isobutyronitrile) In chloroform for 24h; UV-irradiation;	9 Example 9 (8S,9S)-9-[2-(N-methyl)pyridinium]-(9-desoxy)-(11-(3-(trimethoxysilylpropylthio)-epi-10, 11-dihydrocinchonidine tetrafluoroborate (XI) Example 9 (8S,9S)-9-[2-(N-methyl)pyridinium]-(9-desoxy)-(11-(3-(trimethoxysilylpropylthio)-epi-10, 11-dihydrocinchonidine tetrafluoroborate (XI) (0082) (8S,9S)-9-[2-(N-methyl)pyridinium]-(9-desoxy)-epi-cinchonidine tetrafluoroborate (IX) (0.4 g, 0.76 mmol) was dissolved in CHCl3 (4 mL), to which was added (3-mercaptopropil)trimetoxisilane (0.142 mL, 0.76 mmol) and the stirred mixture was irradiated with uv light from a mercury vapor lamp for 24 h. The solvent and other volatile compounds were removed in vacuo, giving the title compound as a viscous orange oil (0.509 g, 96%) that was immobilized to the solid support. (0083) MS (ESI): calculated for C32H45N4O4SSi\| 611.30, observed value 611.27.

Reference： [1]Current Patent Assignee: UNIVERSIDADE DE EVORA - US2016/236184, 2016, A1 Location in patent: Paragraph 0082; 0083

59
[ 4420-74-0 ]
[chloro(phenyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone [ No CAS ]
(2,4,6-trimethylbenzoyl)phenylthiophosphinic acid S-(3-(trimethoxysilyl)propyl) ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With triethylamine In toluene at 20℃; for 1h;	2,4,6-trimethylbenzoyl)phenylthiophosphinic acid S-(3-(trimethoxysilyl)propyl) ester (9) To a mixture of (3-mercaptopropyl)trimethoxysilane (3.25mL, 17.5mmol), triethylamine (4.80mL, 34.5mmol) and anhydrous toluene (50mL), which was stirred at room temperature, the solution of 7 (5.30g, 17.2mmol) in toluene (20mL) was added and the resulting suspension was stirred at this temperature for 1h. The reaction mixture was washed with distilled water (30mL), 1% (w/w) aqueous citric acid solution (3×25mL) then with 2% aqueous Na2CO3 solution (2×25mL), again with distilled water (25mL) and was then dried over anhydrous Na2SO4. After evaporation of the solvent, the residual oil was purified by column chromatography on silica gel, using CH2Cl2-AcOEt (gradient 0-20% AcOEt) as the eluent. The purification gave product 9 in the form of a colourless oil (4.09g, 8.8mmol, 51%). (0069) 1H NMR (400MHz, CDCl3): δ=0.65-0.69 (m, 2H), 1.70-1.74 (m, 2H), 2.12 (s, 6H), 2.26 (s, 3H), 2.83-2.89 (m, 2H), 3.50 (s, 9H), 6.81 (s, 2H), 7.47-7.50 (m, 2H), 7.55-7.57 (m, 1H), 7.87-7.91 (m, 2H), ppm. (0070) 13C NMR (75MHz, CDCl3): δ=8.8, 19.9, 21.4, 21.2, 24.6 (d, J=4.5Hz), 31.5 (d, J=3Hz), 50.5, 128.4, 128.9 (d, 3J=30.8Hz), 132.4 (d, 2J=9.8Hz), 133.1 (d, 4J=3Hz), 135.0, 135.6 (d, 1J=47.3Hz), 140.7, 214.6 (d, J=73.5Hz), ppm. HRMS (ESI): m/z calcd. for C7H9Br2N2 [M+H]+ 343.8108, found 343.8105.

Reference： [1]Roszkowski, Piotr; Sahin, Melahat; Ayalur-Karunakaran, Santhosh; Gammer, Christoph; Schlögl, Sandra; Kern, Wolfgang; Krawczyk, Krzysztof K. [Polymer, 2017, vol. 129, p. 207 - 220]

60
[ 4420-74-0 ]
[ 130-95-0 ]
C₂₆H₄₀N₂O₅SSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2,2-dimethoxy-2-phenylacetophenone In chloroform at 20℃; for 27h; Schlenk technique; Inert atmosphere; UV-irradiation;	Preparation of quinine- and quinidine-functionalized trimethoxysilanes (I-QN and I-QD) General procedure: According to the reported method [1],into a 25 mL Schlenk flask charged with quinine or quinidine (1.62 g, 5.0 mmol), 2,2-dimethoxy-2-phenylacetophenone (0.026 g) asa photoinitiator, and chloroform (5.0 mL) was added (3-mercaptopropyl)trimethoxylsilane (1.00 g, 5.0 mmol). The resulting mixturewas stirred at room temperature for 10 min while the reaction system was purged with nitrogen. Under the nitrogen atmosphere, thereaction mixture was irradiated for 27 h with a UV lamp. After evaporation of the solvent and volatile components under a reducedpressure, the corresponding functionalized trimethoxysilane (I-QN or I-QD) was obtained in high purity (by 1H NMR measurement)and was used without further purification in the next step.

Reference： [1]Cao, Shi-Xuan; Wang, Jia-Xi; He, Zheng-Jie [Chinese Chemical Letters, 2018, vol. 29, # 1, p. 201 - 204]

61
[ 4420-74-0 ]
[ 56-54-2 ]
C₂₆H₄₀N₂O₅SSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2,2-dimethoxy-2-phenylacetophenone In chloroform at 20℃; for 27h; Schlenk technique; Inert atmosphere; UV-irradiation;	Preparation of quinine- and quinidine-functionalized trimethoxysilanes (I-QN and I-QD) General procedure: According to the reported method [1],into a 25 mL Schlenk flask charged with quinine or quinidine (1.62 g, 5.0 mmol), 2,2-dimethoxy-2-phenylacetophenone (0.026 g) asa photoinitiator, and chloroform (5.0 mL) was added (3-mercaptopropyl)trimethoxylsilane (1.00 g, 5.0 mmol). The resulting mixturewas stirred at room temperature for 10 min while the reaction system was purged with nitrogen. Under the nitrogen atmosphere, thereaction mixture was irradiated for 27 h with a UV lamp. After evaporation of the solvent and volatile components under a reducedpressure, the corresponding functionalized trimethoxysilane (I-QN or I-QD) was obtained in high purity (by 1H NMR measurement)and was used without further purification in the next step.

Reference： [1]Cao, Shi-Xuan; Wang, Jia-Xi; He, Zheng-Jie [Chinese Chemical Letters, 2018, vol. 29, # 1, p. 201 - 204]

62
1-vinyl-3-dodecyl-3H-imidazol-1-ium bromide [ No CAS ]
[ 4420-74-0 ]
C₂₆H₅₃N₂O₃SSi⁽¹⁺⁾*Br^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79.2%	With (2,4,6-trimethylbenzoyl)diphenylphosphine oxide In chloroform at 20℃; for 24h; UV-irradiation; Darkness;	4 Example 4 Weigh 4mmol γ-mercaptopropyltrimethoxysilane in 10mL aluminum foil wrapped quartz round bottom flask, then add 4mmol of 1-vinyl-3-dodecyl imidazolium bromide liquid, TPO and 1mL of anhydrous Chloroform, of which TPO was added in an amount of 3% of the amount of 1-vinyl-3-dodecyl imidazolium bromide ionic liquid; stirred at a speed of 200rpm, purged with argon for 5min, Placed at room temperature under the power of 45W UV lamp (365nm), irradiation 24h, the reaction was completed, the solvent was removed in a vacuum oven at 40 ° C to give a yellow waxy product 1.29g, which is the target imidazole ionic liquid silane coupling agent, 79.2% rate.Referring to FIG. 5, it can be seen from FIG. 5 that the structure of the ionic liquid silane coupling agent prepared in Example 4 is as shown in FIG. 1.

Reference： [1]Current Patent Assignee: XIAN UNIVERSITY OF SCIENCE & TECHNOLOGY - CN106432319, 2017, A Location in patent: Paragraph 0047; 0048; 0049

63
[ 4420-74-0 ]
[ 1211992-00-5 ]
C₁₄H₂₉N₂O₃SSi⁽¹⁺⁾*Cl^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.49 g	With 2,2-dimethoxy-2-phenylacetophenone In methanol at 20℃; for 18h; UV-irradiation; Darkness;	5 Example 5 Weigh 5mmol γ-mercaptopropyltrimethoxysilane in 10mL aluminum foil wrapped quartz round-bottomed flask, then add 5mmol of 1-allyl-3-ethyl imidazolium ionic liquid, benzoin dimethyl ether and 0.5 mL anhydrous methanol, wherein the amount of benzoin dimethyl ether is 1% 2-allyl-3-ethyl imidazolium ionic liquid; stirring at 300rpm, purged with argon for 5min, remove the aluminum foil , At room temperature under the power of 15W UV lamp (365nm), irradiation 18h, the reaction was completed in a vacuum oven at 40 to remove the solvent to give a yellow viscous liquid 1.49g, which is the target imidazole ionic liquid silane coupling Agent.Referring to FIG. 6, it can be seen from FIG. 6 that the structure of the ionic liquid silane coupling agent prepared in Example 5 is as shown in FIG. 1.

Reference： [1]Current Patent Assignee: XIAN UNIVERSITY OF SCIENCE & TECHNOLOGY - CN106432319, 2017, A Location in patent: Paragraph 0050; 0051; 0052

64
1-allyl-3-butylimidazolium tetrafluoroborate [ No CAS ]
[ 4420-74-0 ]
C₁₆H₃₃N₂O₃SSi⁽¹⁺⁾*BF₄^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81.2%	With (2,4,6-trimethylbenzoyl)diphenylphosphine oxide In acetonitrile at 20℃; for 24h; UV-irradiation; Darkness;	6 Example 6 Take 5mmol γ-mercaptopropyltrimethoxysilane in 10mL aluminum foil wrapped quartz round bottom flask, then add 5mmol of 1-allyl-3-butylimidazolium tetrafluoroborate ionic liquid, TPO and 0.7mL Anhydrous acetonitrile, wherein TPO is added in an amount of 3% of the amount of 1-allyl-3-butylimidazolium tetrafluoroborate ionic liquid; stirring at 400rpm, purging with argon for 5min, removing Aluminum foil paper, placed at room temperature under the power of 50W UV lamp (365nm), irradiation 24h, the reaction was completed, the solvent was removed in a vacuum oven at 40 to give a yellow viscous liquid 1.97g, which is the target imidazolium ionic liquid silane Coupling agent, yield 81.2%.Referring to FIG. 7, it can be seen from FIG. 7 that the structure of the ionic liquid silane coupling agent prepared in Example 6 is as shown in FIG. 1.

Reference： [1]Current Patent Assignee: XIAN UNIVERSITY OF SCIENCE & TECHNOLOGY - CN106432319, 2017, A Location in patent: Paragraph 0053; 0054; 0056

65
1-vinyl-3-methylimidazolium chloride [ No CAS ]
[ 4420-74-0 ]
C₁₂H₂₅N₂O₃SSi⁽¹⁺⁾*Cl^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53.4%	With 2,2-dimethoxy-2-phenylacetophenone In methanol at 20℃; for 12h; UV-irradiation; Darkness;	1 Example 1 Take 4mmol γ-mercaptopropyltrimethoxysilane in 10mL aluminum foil wrapped quartz round bottom flask, and then 4 mmol of 1-vinyl-3-methylimidazolium chloride ionic liquid, benzoin dimethyl ether and 0.5 mL of anhydrous methanol were added, and , The amount of bisbenzaldehyde was 2% of the amount of the 1-vinyl-3-methylimidazolium chloride ionic liquid substance; Speed stirring, purged with argon 5min, remove the aluminum foil paper, placed at room temperature under the power of 15W UV lamp (365nm), according to Shot 12h, the reaction was completed, and then in a vacuum oven at 40 to remove the solvent (methanol) to give a yellow viscous liquid 0.73g, that is As the target imidazole ionic liquid silane coupling agent, the yield was 53.4%.2, it can be seen from Figure 2, the structure of the ionic liquid silane coupling agent prepared in Example 1 shown in Figure 1 Show structure.

Reference： [1]Current Patent Assignee: XIAN UNIVERSITY OF SCIENCE & TECHNOLOGY - CN106432319, 2017, A Location in patent: Paragraph 0038; 0039; 0040

66
[ 4420-74-0 ]
[ 34311-88-1 ]
C₁₃H₂₇N₂O₃SSi⁽¹⁺⁾*Br^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66.3%	With (2,4,6-trimethylbenzoyl)diphenylphosphine oxide In methanol at 20℃; for 24h; UV-irradiation; Darkness;	2 Example 2 Weigh 4mmol γ-mercaptopropyltrimethoxysilane in 10mL aluminum foil wrapped quartz round bottom flask, and then added 4mmol of 1-vinyl-3-ethyl bromide imidazolium ionic liquid, 2,4,6-tris Methylbenzoyl-diphenylphosphine oxide (TPO) and 0.5 mL of anhydrous methanol, TPO added in an amount of 2% of the amount of 1-vinyl-3-ethylimidazolium bromide ionic liquid; Speed stirring, purged with argon 5min, remove the aluminum foil paper, placed at room temperature at a power of 50W UV lamp (365nm), irradiation 24h, and then in a vacuum oven at 40 to remove the solvent (methanol), to give a yellow viscous Liquid 0.95g, which is the target imidazole ionic liquid silane coupling agent, a yield of 66.3%.Referring to FIG. 3, it can be seen from FIG. 3 that the structure of the ionic liquid silane coupling agent prepared in Example 2 is as shown in FIG. 1.

Reference： [1]Current Patent Assignee: XIAN UNIVERSITY OF SCIENCE & TECHNOLOGY - CN106432319, 2017, A Location in patent: Paragraph 0041; 0042; 0043

67
[ 2155-94-4 ]
[ 4420-74-0 ]
(1-dimethylamino-4-thiahept-7-yl)trimethoxysilane [ No CAS ]
(1-dimethylamino-2-methyl-3-thiahex-6-yl)trimethoxysilane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With azobis(2-cyanobutane) at 80 - 85℃; for 3h; Overall yield = 12.4 g;	1 [Example 1] mixer,Reflux,Into a flask equipped with a dropping funnel and a thermometer,78.5 g (0.400 mol) of 3-mercaptopropyltrimethoxysilane were charged, and the mixture was heated to 80 ° C.After the internal temperature stabilized,42.5 g (0.499 mol) of dimethylallylamine,A mixture of 3.9 g (0.019 mol) of 2,2'-azobis (2-methylbutyronitrile) was added dropwise over 2 hours, and the mixture was stirred at 85 ° C. for 1 hour.The reaction solution was distilled,12.4 g of a fraction having a boiling point of 121 to 122 ° C./0.4 kPa was obtained.

Reference： [1]Current Patent Assignee: SHIN-ETSU CHEMICAL CO., LTD. - JP2016/141623, 2016, A Location in patent: Paragraph 0032; 0033

68
[ 4420-74-0 ]
8Na⁽¹⁺⁾*H⁽¹⁺⁾*H₂O*O₃₄PW₉^(9-) [ No CAS ]
[ 1643-19-2 ]
3C₁₆H₃₆N⁽¹⁺⁾*C₁₂H₂₈O₃S₄Si₄⁽⁶⁺⁾*O₃₄PW₉^(9-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	Stage #1: 3-(trimethoxysilyl)-1-propanethiol; 8Na⁽¹⁺⁾H⁽¹⁺⁾H₂O*O₃₄PW₉^(9-) With hydrogenchloride In water; acetonitrile Stage #2: tetrabutylammomium bromide In water; acetonitrile at 20℃; for 0.5h;	Synthesis of (Bu₄N)₃[A-PW₉O₃₄(HS(CH₂)₃SiO)₃(Si(CH₂)₃SH)] (2) In the 200 mL solvent mixture ofacetonitrile/water (150/50 v/v), (3-mercaptopropyl) trimethoxysilane (744 mL,4.0 mmol) was added. Then the solution was acidified with 5 mL of 6 M aqueous HCl followed by slow additionof the precursor 1 (2.7 g (1.0 mmol)). The solution was then concentrated to 60 mL by heating over a water bath. Tetrabutylammonium bromide (3.0 g, 9.3 mmol) was added to this and stirred for 30 min at RT and the precipitates formed were collected on a medium frit and washed with water, ethanol and diethyl ether, and dried under vacuum.

Reference： [1]Narkhede, Nilesh; Uttam, Bhawna; Rao, Chebrolu Pulla [Inorganica Chimica Acta, 2018, vol. 483, p. 337 - 342]

69
[ 4420-74-0 ]
[ 67881-98-5 ]
2-(2-(trimethoxysilylpropylthio)isobutyryloxy)ethylphosphorylcholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With diisopropylamine In ethanol at 20℃; for 24h;	6 Synthesis Example 6 Synthesis of 2-(2-(trimethoxysilylpropylthio)isobutyryloxy)ethylphosphorylcholine In a screw tube, 3.0 g of 2-methacryloyloxyethyl phosphorylcholine (manufactured by NOF CORPORATION) represented by the formula (M), 20 ml of ethanol,2.0 g of 3-mercaptopropyltrimethoxysilane represented by the formula (N)And 0.04 g of diisopropylamine were added and reacted at room temperature for 24 hours.After completion of the reaction, decantation was carried out using hexane and THF to obtain white 2-(2-(trimethoxysilylpropylthio)isobutyryloxy)ethylphosphorylcholine represented by formula (O) ( Yield 3.9 g, yield 80%).

Reference： [1]Current Patent Assignee: NOF CORPORATION - JP2015/110534, 2015, A Location in patent: Paragraph 0076

70
[ 2155-94-4 ]
[ 4420-74-0 ]
(1-dimethylamino-4-thiahept-7-yl)trimethoxysilane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27.9 g	With 2,2'-azobis(isobutyronitrile) at 80℃; for 24h; Inert atmosphere;	5 Example 5 Under an argon atmosphere, 328 mg (2 mmol) of azobisisobutyronitrile (available from NACALAI TESQUE, INC.) was dissolved in a mixture of 8.5 g (100 mmol) of dimethylallylamine (available from Tokyo Chemical Indus try Co., Ltd.) and 19.6 g (100 mmol) of 3-mercaptopropy- ltrimethoxysilane (available from Shin-Etsu Chemical Co., Ltd.), the inside of the reaction system was replaced with argon gas bubbled through the solution, and then, the solution was heated and stirred for 24 hours at 80° C. to obtain 27.9 g of a compound (D) in which a 3-dimethylam- inopropyl group was bonded to a 3-(trimethoxysilyl)propyl group through a thioether bond. In ‘H-NMR measurement, disappearance of signals (5.11 to 5.21 and 5.78 to 5.93 ppm) attributed to protons of the allyl group of dimethylallylamine being a raw material was confirmed.

Reference： [1]Current Patent Assignee: OSAKA GAS CO LTD - US2018/362552, 2018, A1 Location in patent: Paragraph 0126; 0127

71
[ 2439-35-2 ]
[ 4420-74-0 ]
C₁₃H₂₉NO₅SSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34.2 g	With 2,2'-azobis(isobutyronitrile); In ethyl acetate; at 80℃; for 24h;Inert atmosphere;	Under an argon atmosphere, 328 mg (2 mmol) of azobisisobutyronitrile (available from NACALAI TESQUE, INC.) was dissolved in a mixture of 14.3 g (100 mmol) of 2-(dimethylamino)ethyl acrylate (available from Tokyo Chemical Industry Co., Ltd.), 19.6 g (100 mmol) of 3-mer- captopropyltrimethoxysilane (available from Shin-Etsu Chemical Co., Ltd.), and 100 ml of dehydrated ethyl acetate, the inside of the reaction system was replaced with argon gas bubbled through the solution, and then, the solution was heated and stirred for 24 hours at 80 C., afier which ethyl acetate was removed to obtain 34.2 g of a compound (E) in which an acrylic group of 2-(dimethylamino)ethyl acrylate was bonded to a 3-(trimethoxysilyl)propyl group through a thioether bond. In ?H-NMR measurement, disappearance of signals (5.80, 6.16, and 6.43 ppm) attributed to protons of the acrylic group of 2-(dimethylamino)ethyl acrylate being a raw material was confirmed.

Reference： [1]Patent: US2018/362552,2018,A1 .Location in patent: Paragraph 0131; 0132

72
[ 2867-47-2 ]
[ 4420-74-0 ]
C₁₄H₃₁NO₅SSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32.9 g	With 2,2'-azobis(isobutyronitrile) In ethyl acetate at 80℃; for 24h; Inert atmosphere;	7 Example 7 Under an argon atmosphere, 328 mg (2 mmol) of azobisisobutyronitrile (available from NACALAI TESQUE, INC.) was dissolved in a mixture of 15.7 g (100 mmol) of 2-(dimethylamino)ethyl methacrylate (available from Wako Pure Chemical Industries, Ltd.), 19.6 g (100 mmol) of 3-mercaptopropyltrimethoxysilane (available from Shin-Etsu Chemical Co., Ltd.), and 100 ml of dehydrated ethyl acetate, the inside of the reaction system was replaced with argon gas bubbled through the solution, and then, the solution was heated and stirred for 24 hours at 80° C., after which ethyl acetate was removed to obtain 32.9 g of a compound (F) in which a methacrylic group of 2-(dimethylamino)ethyl methacrylate was bonded to a 3-(trimethoxysilyl)propyl group through a thioether bond.In 1H-NMR measurement, disappearance of signals (5.75 and 6.11 ppm) attributed to protons of the methacrylic group of 2-(dimethylamino)ethyl methacrylate being a raw material was confirmed.

Reference： [1]Current Patent Assignee: OSAKA GAS CO LTD - US2018/362552, 2018, A1 Location in patent: Paragraph 0136; 0137

73
[ 3845-76-9 ]
[ 4420-74-0 ]
C₁₄H₃₂N₂O₄SSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34.2 g	With 2,2'-azobis(isobutyronitrile); In ethyl acetate; at 80℃; for 24.0h;Inert atmosphere;	Under an argon atmosphere, 328 mg (2 mmol) of azobisisobutyronitrile (available from NACALAI TESQUE, INC.) was dissolved in a mixture of 15.6 g (100 mmol) of <strong>[3845-76-9]N-[3-(dimethylamino)propyl]acrylamide</strong> (available from Wako Pure Chemical Industries, Ltd.), 19.6 g (100 mmol) of 3-mercaptopropyltrimethoxysilane (available from ShinEtsu Chemical Co., Ltd.), and 100 ml of dehydrated ethyl acetate, the inside of the reaction system was replaced with argon gas bubbled through the solution, and then, the solution was heated and stirred for 24 hours at 80 C. under an argon atmosphere, afier which ethyl acetate was removed to obtain 34.2 g of a compound (G) in which an acrylic group of <strong>[3845-76-9]N-[3-(dimethylamino)propyl]acrylamide</strong> was bonded to a 3-(trimethoxysilyl)propyl group through a thioether bond. In ?H-NMR measurement, disappearance of signals (5.60, 6.05, and 6.21 ppm) attributed to protons of the acrylic group of <strong>[3845-76-9]N-[3-(dimethylamino)propyl]acrylamide</strong> being a raw material was confirmed.

Reference： [1]Patent: US2018/362552,2018,A1 .Location in patent: Paragraph 0141; 0142

74
[ 4420-74-0 ]
[ 5205-93-6 ]
C₁₅H₃₄N₂O₄SSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35.6 g	With 2,2'-azobis(isobutyronitrile) In ethyl acetate at 80℃; for 24h; Inert atmosphere;	9 Example 9 Under an argon atmosphere, 328 mg (2 mmol) of azobisisobutyronitrile (available from NACALAI TESQUE, INC.) was dissolved in a mixture of 17.0 g (100 mmol) of N-[3-(dimethylamino)propyl]methacrylamide (available from Tokyo Chemical Industry Co., Ltd.), 19.6 g (100 mmol) of 3-mercaptopropyltrimethoxysilane (available from Shin-Etsu Chemical Co., Ltd.), and 100 ml of dehydrated ethyl acetate, the inside of the reaction system was replaced with argon gas bubbled through the solution, and then, the solution was heated and stirred for 24 hours at 80° C. under an argon atmosphere, after which ethyl acetate was removed to obtain 35.6 g of a compound (H) in which a methacrylic group of N-[3-(dimethylamino)propyl]meth- acrylamide was bonded to a 3-(trimethoxysilyl)propyl group through a thioether bond.In 1H-NMR measurement, disappearance of signals (5.30 and 5.74 ppm) attributed to protons of the methacrylic group of N-[3-(dimethylamino)propyl]methacrylamide being a raw material was confirmed.

Reference： [1]Current Patent Assignee: OSAKA GAS CO LTD - US2018/362552, 2018, A1 Location in patent: Paragraph 0146; 0147

75
[ 4420-74-0 ]
[ 1067-33-0 ]
dibutyltinbis(mercaptopropyltrimethoxysilane) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 40℃; for 1.0h;Inert atmosphere;	Dibutyltinbis(mercaptopropyltrimethoxysilane) (hereafter referred to as Command Cure Tin 1 or CC Tin 1) was created by reaction of dibutyltindiacetate (DBTDA) with mercaptopropyltrimethoxysilane in a 1:2 stoichiometric ratio. After mixing the reactants, the headspace was purged with nitrogen gas and stored at 40 degrees Celsius for one hour. After storing, the mixture was placed into a vacuum chamber to a pressure of at least 0.5 in. Hg to boil the acetic acid from the mixture. Using a 5 cfm dual stage vacuum pump with a dry ice cold trap, the vacuum was held until all boiling ceased.

Reference： [1]Patent: US2019/55363,2019,A1 .Location in patent: Paragraph 0052

76
[ 2439-35-2 ]
[ 4420-74-0 ]
C₁₅H₃₁NO₇SSi [ No CAS ]

Reference： [1]Patent: US2018/362552,2018,A1

77
[ 4420-74-0 ]
[ 1506-76-9 ]
[ 121-44-8 ]
C₁₀₂H₉₀O₂₄S₆Si₆^(6-)*6C₆H₁₅N*6H⁽¹⁺⁾ [ No CAS ]

Reference： [1]Chemical Communications,2019,vol. 55,p. 6066 - 6069

78
[ 4420-74-0 ]
C₃₃H₅₅F₂₁O₁₂Si₁₀ [ No CAS ]
C₅₁H₁₀₃F₂₁O₂₁S₃Si₁₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With 2,2'-azobis(isobutyronitrile) In tetrahydrofuran at 80℃; for 6h; Inert atmosphere;	1 Example 1 Tris (dimethylvinylsiloxy) heptatrifluoropropyl incomplete POSS (0.112 g, 0.084 mmol) and 2,2′-azobisisobutyronitrile (AIBN) (0.0007 g, 0.0038 mmol) in anhydrous tetrahydrofuran (THF) (0.75 g) ml) solution under a nitrogen atmosphere was added 3-mercaptopropyltrimethoxysilane (0.23 ml, 1.26 mmol). After reacting the reaction solution at 80 ° C. for 6 hours, volatile components were distilled off under reduced pressure. The obtained residue was purified by HPLC to obtain a colorless semi-solid product 1.Obtained at a rate of 78% (0.0903 g, 0.047 mmol) (FIGS. 1 and 2).

Reference： [1]Current Patent Assignee: KYOTO INSTITUTE OF TECHNOLOGY - JP2019/189564, 2019, A Location in patent: Paragraph 0070; 0071; 0072

79
[ 870-23-5 ]
[ 2487-90-3 ]
[ 4420-74-0 ]

Yield	Reaction Conditions	Operation in experiment
88.2%	Stage #1: prop-2-ene-1-thiol at 62 - 64℃; for 0.5h; Inert atmosphere; Stage #2: trimethoxysilane In methanol at 72 - 75℃; for 2h;	1.2; 2.2 (2) Hydrosilylation reaction Under nitrogen protection, 150 g of allyl mercaptan and 0.4 g of anti-sulfur poisoning platinum catalyst were added to the three-necked flask, and the activation treatment was performed at 62-64 ° C for 30 minutes under stirring;260 g of trimethoxyhydrosilane and 65 g of methanol were added dropwise to the mixture after the activation treatment, and the reaction was incubated at 72 to 75 ° C for 2 hours. The remaining ≤ 1% of allyl mercaptan was detected by gas chromatography, and the reaction was stopped;Unreacted trimethoxyhydrosilane and by-product tetramethoxysilane under reduced pressure,346.86g of colorless and transparent 3-mercaptopropyltrimethoxysilane product was obtained by distillation under reduced pressure.Product yield was 88.2%. Gas chromatography analysis showed that the product content was 98.42%.

Reference： [1]Current Patent Assignee: JIANGXI CHENGUANG NEW MAT - CN110724159, 2020, A Location in patent: Paragraph 0026; 0032-0036; 0041-0043

80
[ 4420-74-0 ]
[ 1025-15-6 ]
C₁₈H₃₁N₃O₆SSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With triethylamine In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; Cooling with ice;	Synthesis of Crosslinker-Functionalized Nanosilica. The surface modification process offunctionalizing SiO2 nanoparticles by grafting the auxiliary crosslinking agent is shown in Figure 1.The mixture solution of 3.92 g MPTMS (0.02 mol), 0.23 g TEA and THF is slowly dropped into thesolution of 4.98 g TAIC (0.02 mol) dissolved in 10 mL THF solvent, stirred under nitrogen protectionin ice-water bath for 5 min, and then naturally warmed to ambient temperature. The liquid product(MTAIC) with 76% yield will be obtained after reacting in thermal insulation for 24 h. By means ofultrasonic dispersion treatment for 30 min, 10 g dried nanosilica was uniformly blended into 100 mLethanol solution (3:1), after which the MTAIC is instilled with the solution being controlled on pH = 4by diluted hydrochloric acid. The obtained suspension is washed and filtered with ethanol for 3 timesand then dried in vacuum at 60 C to finally achieve the functionalized TAIC-s-SiO2 nanomaterial.

Reference： [1]Fu, Yu-Wei; Zhang, Yong-Qi; Sun, Wei-Feng; Wang, Xuan [Molecules, 2020, vol. 25, # 17]

81
[ 4420-74-0 ]
tetraallylcarborane [ No CAS ]
C₃₈H₉₂B₁₀O₁₂S₄Si₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	In hexane for 1h; UV-irradiation;	1. Synthesis of compound 4 A quartz test tube equipped with a magnetic stirrer was loaded with 12 ml of hexane, 0.2 g (0.65 mmol) of tetraallylcarborane, and 0.98 ml (5.2 mmol) of 3-mercaptopropyltrimethoxysilane. Then reaction was initiated by UV radiation. The stirring was continued for 1 hour. The solvent was distilled off on a rotary vacuum evaporator at a temperature of 50 °C/ 360 mbar. Excess of 3-mercaptopropyltrimethoxysilane was removed at a temperature of 100° C/1 mbar. The yield of the product was 0.31 g (95%).1H NMR (500.13 MHz, C6D6, ppm): δ 3.55 (s, 36H, -OCH3); 2.9-0.7 (6H, B-H); 2.69-2.67 (m, 4H, -CH2-S-); (m, 4H, -S-CH2-); 2.48-2.45 (t, 4H, -S-CH2-); 2.19-2.17 (t, 4H, -CH2-S-); 2.03-1.85 (m, 16H, -CH2-); 1.61-1.56 (m, 4H, Ccarb-CH2-); 1.22-1.19 (m, 4H, B-CH2-); 0.94-0.91 (m, 4H, -CH2-Si-); 0.88-0.85 (m, 4H, -CH2-Si-). 13C NMR (125.47 MHz, C6D6, ppm): δ 72.46, 49.99, 35.68, 35.19, 34.97, 34.87, 30.94, 30.49, 29.70, 23.42, 23.30, 14.69, 8.77.29Si NMR (99.36 MHz, C6D6, ppm): δ -42.42, -42.47. 11B NMR (160.46 MHz, C6D6, ppm): δ 18.21, 0.23, -5.72, -11.17, -16.15. IR (ν/cm-1): 2585 (ν B-H). Elemental analysis: Found %: C, 41.86; H, 8.53; B, 9.95; S, 11.76; Si, 10.28; Calculated for C38H92B10O12S4Si4 %: C, 41.88; H, 8.51; B, 9.92; O, 17.62; S, 11.77; Si, 10.31.HRMS (ESI) m/z calcd. for C38H92B10O12S4Si4 [(M+nNH4)+]: 1108.58, found 1107.58; [(M+nNa)+]: 1113.54, found 1112.54.

Reference： [1]Anisimov, Anton A.; Kononova, Elena G.; Möller, Martin; Minyaylo, Ekaterina O.; Muzafarov, Aziz M.; Ol'shevskaya, Valentina A.; Peregudov, Alexander S.; Shchegolikhina, Olga I.; Zaitsev, Andrei V. [Journal of Organometallic Chemistry, 2020, vol. 928]

82
[ 4420-74-0 ]
9,9-bis(6-allyloxy-2-naphthyl)fluorene [ No CAS ]
9,9-bis{6-[3-(3-trimethoxysilylpropylthio)propoxy]-2-naphthyl}fluorene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-(trimethoxysilyl)-1-propanethiol; 9,9-bis(6-allyloxy-2-naphthyl)fluorene In toluene for 0.5h; Stage #2: With V-601 In toluene at 80℃; for 10h;	1 In a 1,000 ml eggplant flask, 159.2 g of 9,9-bis (6-allyloxy-2-naphthyl) fluorene (manufactured by Osaka Gas Chemical Co., Ltd.), After adding 141.4 g of 3-mercaptopropyltrimethoxysilane (MPTMS) and 300 ml of special grade toluene and stirring for 30 minutes to completely dissolve the mixture, the polymerization initiator (V-601) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) 2.3 g was added, and the mixture was reacted at 80 ° C. for 10 hours. Then, the solvent and the remaining MPTMS were distilled off under reduced pressure to obtain a viscous liquid.

Reference： [1]Current Patent Assignee: OSAKA GAS CO LTD - JP2020/180063, 2020, A Location in patent: Paragraph 0099-0102

83
[ 4420-74-0 ]
N-butyl-4-(4-maleimidostyryl)-1,8-naphthalimide [ No CAS ]
N-butyl-4-(3-(trimethoxysilyl-propylthio)styryl)-1,8-naphthalimide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	In ethanol at 20℃;	3.4. Synthesis of N-Butyl-4-(3-(Trimethoxysilyl-Propylthio)Styryl)-1,8-Naphthalimide (CSP) To prepare CSP as an FSN precursor, as depicted in Figure 1, previous thiol sensor N-butyl-4-(4-maleimidostyryl)-1,8-naphthalimide (CS) (Figure S1) [28], was used. In a typical procedure, in anoven-dried 25 mL round-bottom flask, CS was taken (0.2 g, 0.5 mmol) in 10 mL EtOH.Then, 3-Mercaptopropyl)trimethoxysilane (MPTMS, Sigma-Aldrich, 1.96 g, 10 mmol) was added tothe system, and the resultant mixture was stirred for 2 h at room temperature. The reaction mixturewas concentrated under high vacuum to a trace amount and hexane was poured to recrystallize theproduct yellow powder CSP. Yield 0.26 g, 81%. 1H-NMR (400 Hz, DMSO-d6): 9.01 (d, J = 8.0 Hz,1H), 8.54 (d, J = 8.2 Hz, 1H), 8.50 (d, J = 8.0 Hz, 1H), 8.29 (d, J = 8.2 Hz, 1H), 8.28 (d, J = 16.0 Hz, 1H),7.99 (d, J = 7.8 Hz, 2H), 7.93 (dd, J = 8.0, 7.8 Hz, 1H), 7.65 (d, J = 16.0 Hz, 1H), 7.35 (d, J = 7.8 Hz, 2H),4.10 (t, 2H), 4.04 (t, 2H), 3.45 (s, 9H), 2.47 (m, 2H), 1.62 (m, 2H), 1.39 (m, 2H) 1.35 (m, 2H), 0.91 (t, 3H),0.71 (m, 2H) ppm. HRMS (ESI, m/z): [M+ H]+ 644.81; found, 645.2. Anal. Calcd for CSP C34H36N2O7SSi:C, 63.33, H, 5.63; N, 4.34; CSP0.5H2O: C34H37N2O7.5SSi; found: C, 62.46; H, 5.70; N, 4.21.

Reference： [1]Chang, Cheng-Chung; Wu, Hsing-Ju [Molecules, 2020, vol. 25, # 23]

84
[ 4420-74-0 ]
[ 1688-69-3 ]
C₁₅H₂₇NO₄SSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-(trimethoxysilyl)-1-propanethiol; p-allyloxyaniline In toluene for 0.166667h; Stage #2: With triethylamine In toluene at 40℃; for 4h; Inert atmosphere;	1.S5; 2.S5; 3.S5; 4.S5 Step S5: Add Intermediate 10, γ-mercaptopropyltrimethoxysilane and toluene into the reaction kettle, stir at 300r/min for 10min, then blow in nitrogen to exhaust the air at a temperature of 40°C Under the conditions, add triethylamine to react for 4h to prepare Intermediate 11. Dissolve cyanuric chloride in acetone, add Intermediate 8, and perform the reaction at a speed of 150r/min and a temperature of 40. After 3h, intermediate 11 was added, and the reaction was carried out at a temperature of 80°C to obtain intermediate 12. Nano silica, ethanol, and deionized water were added to the reaction kettle. At a frequency of 3MHz, After ultrasonic treatment for 10 minutes, the pH value was adjusted to 4, the intermediate 12 was added, and the reaction was carried out for 1 hour at a temperature of 100° C., and the filtrate was removed by filtration to prepare an antioxidant.

Reference： [1]Current Patent Assignee: JIANGSU JIYI NEW MAT - CN113004331, 2021, A Location in patent: Paragraph 0023; 0032; 0038-0039; 0045-0046; 0052-0053; 0059

85
3-ethyl-3-[(allyloxy)methyl]oxetane [ No CAS ]
[ 4420-74-0 ]
C₁₅H₃₂O₅SSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	at 20℃; for 0.666667h; Irradiation;	2 Example 2 Place 1.56g (10mmol) of compound 1-a and 1.96g (10mmol) of mercaptopropyltrimethoxysilane in a 30mL beaker, mix and stir for 10min until the system is uniform, then place the beaker with magneton at the wavelength at room temperature It was irradiated vertically downward under a 365nm mercury lamp for 30min (continuous stirring during irradiation, the distance between the beaker and the mercury lamp was 10cm, and the mercury lamp intensity was 100mW/cm2) to obtain compound 2 with a yield of 99%.

Reference： [1]Current Patent Assignee: HUBEI GURUN TECHNOLOGY CO LTD - CN113336787, 2021, A Location in patent: Paragraph 0154-0157

86
[ 4420-74-0 ]
C₁₁H₂₀O₂ [ No CAS ]
C₁₇H₃₆O₅SSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	at 20℃; for 0.666667h; Irradiation;	5 Put 1.84g (10mmol) of compound 5-a and 2.66g (10mmol) of 4-trimethoxysilylpropane-1-thiol in a 30mL beaker, mix and stir for 10min until the system is uniform, and then it will become magnetic at room temperature. The sub-beaker was placed under a 365nm mercury lamp and irradiated vertically downward for 30min (continuous stirring during irradiation, the distance between the beaker and the mercury lamp was 10cm, and the mercury lamp intensity was 100mW/cm2) to obtain compound 5 with a yield of 99%.

Reference： [1]Current Patent Assignee: HUBEI GURUN TECHNOLOGY CO LTD - CN113336787, 2021, A Location in patent: Paragraph 0166; 0170-0172

87
[ 4420-74-0 ]
C₇H₁₂O₂ [ No CAS ]
C₁₃H₂₈O₅SSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	at 20℃; for 0.666667h; Irradiation;	6 Put 1.28g (10mmol) of compound 6-a and 1.96g (10mmol) of mercaptopropyltrimethoxysilane in a 30mL beaker, mix and stir for 10min until the system is uniform, then place the beaker with magnets at 365nm at room temperature Under the mercury lamp, irradiate vertically downward for 30min (continuous stirring during irradiation, the distance between the beaker and the mercury lamp is 10cm, and the mercury lamp intensity is 100mW/cm2) to obtain compound 6 with a yield of 99%.

Reference： [1]Current Patent Assignee: HUBEI GURUN TECHNOLOGY CO LTD - CN113336787, 2021, A Location in patent: Paragraph 0173; 0177-0179

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	4420-74-0	MDL No. :	MFCD00004901
Formula :	C₆H₁₆O₃SSi	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UUEWCQRISZBELL-UHFFFAOYSA-N
M.W :	196.34	Pubchem ID :	20473
Synonyms :

Num. heavy atoms :	11
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	6
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	50.01
TPSA :	66.49 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) :	-6.57 cm/s

[ CAS No. 4420-74-0 ] {[proInfo.proName]}

Quality Control of [ 4420-74-0 ]

Related Doc. of [ 4420-74-0 ]

Product Details of [ 4420-74-0 ]

Calculated chemistry of [ 4420-74-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 4420-74-0 ]

Application In Synthesis of [ 4420-74-0 ]

[ 4420-74-0 ] Synthesis Path-Downstream 1~87

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Log Po/w (iLOGP) :	2.51
Log Po/w (XLOGP3) :	1.3
Log Po/w (WLOGP) :	1.18
Log Po/w (MLOGP) :	-0.27
Log Po/w (SILICOS-IT) :	-0.38
Consensus Log Po/w :	0.87

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Log S (ESOL) :	-1.48
Solubility :	6.5 mg/ml ; 0.0331 mol/l
Class :	Very soluble
Log S (Ali) :	-2.3
Solubility :	0.992 mg/ml ; 0.00505 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.7
Solubility :	3.95 mg/ml ; 0.0201 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.69

Signal Word:	Danger	Class:	3
Precautionary Statements:	P210-P261-P264-P270-P272-P273-P280-P301+P312+P330-P302+P352-P312-P333+P313-P391-P501	UN#:	1993
Hazard Statements:	H225-H302-H317-H411-H372	Packing Group:	Ⅲ
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
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:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
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