[ CAS No. 17865-11-1 ] {[proInfo.proName]}

Name: 17865-11-1|(4-(Trimethylsilyl)phenyl)boronic acid|95%
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SKU: A294038
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Quality Control of [ 17865-11-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 17865-11-1 ]

SDS Specification

Alternatived Products of [ 17865-11-1 ]

Product Details of [ 17865-11-1 ]

CAS No. :	17865-11-1	MDL No. :	MFCD00093348
Formula :	C₉H₁₅BO₂Si	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NRPZMSUGPMYBCQ-UHFFFAOYSA-N
M.W :	194.11	Pubchem ID :	1710
Synonyms :

Calculated chemistry of [ 17865-11-1 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	59.25
TPSA :	40.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.62 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.63
Log Po/w (WLOGP) :	-0.09
Log Po/w (MLOGP) :	1.26
Log Po/w (SILICOS-IT) :	-1.09
Consensus Log Po/w :	0.54

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.91
Solubility :	0.239 mg/ml ; 0.00123 mol/l
Class :	Soluble
Log S (Ali) :	-3.13
Solubility :	0.144 mg/ml ; 0.000741 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.56
Solubility :	0.538 mg/ml ; 0.00277 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.45

Safety of [ 17865-11-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 17865-11-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 17865-11-1 ]
Downstream synthetic route of [ 17865-11-1 ]

[ 17865-11-1 ] Synthesis Path-Upstream 1~5

1
[ 17865-11-1 ]
[ 67665-47-8 ]

Reference： [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 22, p. 6696 - 6700[2] Angew. Chem., 2018, vol. 130, p. 6806 - 6810,5
[3] Angewandte Chemie - International Edition, 2018, vol. 57, # 22, p. 6696 - 6700[4] Angew. Chem., 2018, vol. 130, p. 6806 - 6810,5

2
[ 6999-03-7 ]
[ 17865-11-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.5 h; Inert atmosphere Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃; Stage #3: With water In tetrahydrofuran; hexane; ethyl acetate	l-Bromo-4-(trimethylsilyl)benzene (25 g, 0.10 mol) was added to a 1-bulb flask and an argon atmosphere was established. After adding tetrahydrofuran (500 mL), the mixture was stirred at -78 ⁰C for 10 minutes. After adding n-BuLi (2.5 M in hexane, 43.6 mL, 0.10 mol) dropwise, the mixture was stirred for 1 hour and 30 minutes at -78 0C. Then, trimethyl borate (13.6 mL, 0.11 mol) was added at -78 ⁰C. After stirring for 30 minutes at -78 ⁰C, the mixture was stirred at room temperature for 4 hours. After the reaction was completed, extraction was performed using distilled water and EA. The organic layer was dried with MgSO₄ and the solvent was removed using a rotary evaporator. Pure Compound A (18 g, 85percent) was separated by column chromatography using hexane and EA as an eluent.

Reference： [1] Patent: WO2010/140801, 2010, A1, . Location in patent: Page/Page column 18
[2] Macromolecules, 2003, vol. 36, # 7, p. 2327 - 2332
[3] Organic and Biomolecular Chemistry, 2003, vol. 1, # 9, p. 1609 - 1624

3
[ 5419-55-6 ]
[ 106-37-6 ]
[ 17865-11-1 ]

Reference： [1] Patent: US6034089, 2000, A,

4
[ 75-77-4 ]
[ 5419-55-6 ]
[ 106-37-6 ]
[ 17865-11-1 ]

Reference： [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 22, p. 6696 - 6700[2] Angew. Chem., 2018, vol. 130, p. 6806 - 6810,5

5
[ 75-77-4 ]
[ 106-37-6 ]
[ 17865-11-1 ]

Reference： [1] Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2816 - 2819

[ 17865-11-1 ] Synthesis Path-Downstream 1~87

1
[ 13101-40-1 ]
[ 17865-11-1 ]
3-bromo-5-chloro-4'-(trimethylsilyl)biphenyl [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,1999,p. 451 - 458

2
[ 126-30-7 ]
[ 17865-11-1 ]
[ 574755-28-5 ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 16648 - 16653
Angew. Chem.,2018,vol. 130,p. 16890 - 16895,6
[2]Chemical Communications,2012,vol. 48,p. 1538 - 1540
[3]Organic Letters,2020,vol. 22,p. 2756 - 2760
[4]Organic Letters,2019,vol. 21,p. 6347 - 6351
[5]Organic and Biomolecular Chemistry,2003,vol. 1,p. 1609 - 1624
[6]Angewandte Chemie - International Edition,2008,vol. 47,p. 4866 - 4869
[7]Angewandte Chemie - International Edition,2011,vol. 50,p. 7022 - 7026

3
[ 6999-03-7 ]
[ 17865-11-1 ]

Yield	Reaction Conditions	Operation in experiment
85%		l-Bromo-4-(trimethylsilyl)benzene (25 g, 0.10 mol) was added to a 1-bulb flask and an argon atmosphere was established. After adding tetrahydrofuran (500 mL), the mixture was stirred at -78 0C for 10 minutes. After adding n-BuLi (2.5 M in hexane, 43.6 mL, 0.10 mol) dropwise, the mixture was stirred for 1 hour and 30 minutes at -78 0C. Then, trimethyl borate (13.6 mL, 0.11 mol) was added at -78 0C. After stirring for 30 minutes at -78 0C, the mixture was stirred at room temperature for 4 hours. After the reaction was completed, extraction was performed using distilled water and EA. The organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. Pure Compound A (18 g, 85%) was separated by column chromatography using hexane and EA as an eluent.

Reference： [1]Patent: WO2010/140801,2010,A1 .Location in patent: Page/Page column 18
[2]Macromolecules,2003,vol. 36,p. 2327 - 2332
[3]Organic and Biomolecular Chemistry,2003,vol. 1,p. 1609 - 1624

4
[ 19057-50-2 ]
[ 17865-11-1 ]
(3'',4'',5'',6''-tetrakis(4'-(trimethylsilyl)-[1,1'-biphenyl]-4-yl)-[1,1':4',1'':2'',1''':4''',1''''-quinquephenyl]-4,4''''-diyl)bis(trimethylsilane) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 177 - 186
[2]Angewandte Chemie - International Edition,2003,vol. 42,p. 5329 - 5333
[3]Chemical Communications,2017,vol. 53,p. 8679 - 8682

5
[ 2789-89-1 ]
[ 17865-11-1 ]
[ 647851-32-9 ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 5798 - 5805

6
[ 18014-00-1 ]
[ 17865-11-1 ]
[ 635321-73-2 ]

Reference： [1]Macromolecules,2003,vol. 36,p. 8240 - 8245

7
[ 17865-11-1 ]
[ 136118-19-9 ]
(3'',4'',5'',6''-tetrakis(4'-(trimethylsilyl)-[1,1'-biphenyl]-4-yl)-[1,1':4',1'':2'',1''':4''',1''''-quinquephenyl]-4,4''''-diyl)bis(trimethylsilane) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 5798 - 5805

8
[ 17865-11-1 ]
5,11,17,23-tetrakisiodo-25,26,27,28-tetradecoxycalix[4]arene [ No CAS ]
5,11,17,23-tetrakis(4-trimethylsilylphenyl)-25,26,27,28-tetradecyloxycalix[4]arene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 2816 - 2819

9
[ 17865-11-1 ]
[ 583-53-9 ]
(2'-bromobiphenyl-4-yl)trimethylsilane [ No CAS ]

Reference： [1]Organic Letters,2005,vol. 7,p. 3717 - 3720
[2]Angewandte Chemie - International Edition,2018,vol. 57,p. 6696 - 6700
Angew. Chem.,2018,vol. 130,p. 6806 - 6810,5

10
[ 877993-05-0 ]
[ 17865-11-1 ]
C₇₆H₉₄O₆Si₄ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 940 - 946

11
[ 699119-05-6 ]
[ 17865-11-1 ]
[ 871114-85-1 ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 6348 - 6354

12
[ 871114-86-2 ]
[ 17865-11-1 ]
[ 871114-87-3 ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 6348 - 6354

13
[ 610-94-6 ]
[ 17865-11-1 ]
[ 180577-88-2 ]

Reference： [1]Macromolecules,2005,vol. 38,p. 9933 - 9938

14
[ 573-17-1 ]
[ 17865-11-1 ]
9-(4-(trimethylsilyl)phenyl)phenanthrene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 6880 - 6886

15
[ 98-88-4 ]
[ 17865-11-1 ]
[ 17933-83-4 ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 6880 - 6886

16
C₉₈H₁₇₃BrO₃₈ [ No CAS ]
[ 17865-11-1 ]
C₁₀₇H₁₈₆O₃₈Si [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 6082 - 6083

17
[ 883970-41-0 ]
[ 17865-11-1 ]
1,3,5-tris[2'-(4''-(4'''-trimethylsilyl)phenyl)biphenyl]benzene [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 3033 - 3036

18
[ 17865-11-1 ]
[ 1625-89-4 ]

Reference： [1]Synlett,2007,p. 1913 - 1916
[2]ChemCatChem,2019,vol. 11,p. 3933 - 3940

19
[ 22445-41-6 ]
[ 17865-11-1 ]
(3’,5’-dimethyl-[1,1‘-biphenyl]-4-yl)trimethylsilane [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 10272 - 10275
[2]Advanced Synthesis and Catalysis,2020,vol. 362,p. 2637 - 2641

20
[ 1002327-84-5 ]
[ 17865-11-1 ]
thioacetic acid S-[5''-(acetylsulfanyl)methyl-4-(trimethylsilanyl)[1,1':4',1'']terphenyl-3''-yl]methyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 10272 - 10275

21
[ 577-19-5 ]
[ 17865-11-1 ]
[ 723749-58-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In dimethoxyetane; water; at 80℃; for 3h;	2-Nitro- (4'-trimethylsilyl-biphenyl 2-Bromo-nitrobenzene (0.86g), 4-(trimethylsilyl) phenylboronic acid (LG) and bis- (triphenylphosphine)-palladiumdichloride (0.3g) were dissolved in dimethoxyetane (35ML) and then a solution of sodium bicarbonate (1.3g) dissoved in water (5ML) was added dropwise. The mixture was heated for 3 hours (80C bath temperature), cooled to room temperature, poured on to ethyl acetate: water: 1 : 1 (300ML) and suction filtered. The organic phase was separated, dried over sodium sulfate and the solvent was removed. The resultant residue (1.58g of a dark oil) was chromatographed on silica gel (eluent : hexane: ethyl acetate: : 4: 1) to yield a yellow oil (1.12g). This compound was used in Step B.

Reference： [1]Patent: WO2004/58723,2004,A1 .Location in patent: Page 87; 88

22
[ 589-87-7 ]
[ 17865-11-1 ]
[ 17908-91-7 ]

Yield	Reaction Conditions	Operation in experiment
78.7%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water;Heating / reflux;	Example 2; Alternatively, cyclo-hexa(diphenyl-4-methylphenylamine) (Compound (9)) can be prepared from steps A to H as described in example (1) above followed by steps J to M as described below; (J) Compound (10) 4-Bromo-4'-(Trimethvlsilvl)biphenyl; To a solution of 1-bromo-4-iodobenzene (14.14g, 50mmol), 4-(trimethylsilyl)phenyl boronic acid (9.71g, 50mmol) and Pd(PPh3)4 (2.31g, 2.0mmol) in degassed 1,4-dioxane (100ml) was added a solution of potassium carbonate (16.6g, 120mmol) in degassed water (50ml). The mixture was refluxed under a nitrogen atmosphere until the reaction was complete (according to HPLC analysis).The reaction mixture was then washed with distilled water and brine and then dried over MgSO4 before being filtered through a silica plug. The crude product was purified by flash column chromatography (silica gel 60; 9:1, hexane:dichloromethane) followed by recrystallisation from methanol to yield a colourless crystalline solid (12.01g, 78.7%)greater than 99% pure by HPLC.

Reference： [1]Patent: WO2006/10555,2006,A1 .Location in patent: Page/Page column 26-27
[2]Advanced Synthesis and Catalysis,2020,vol. 362,p. 2637 - 2641

23
[ 19493-44-8 ]
[ 17865-11-1 ]
[ 916433-89-1 ]

Yield	Reaction Conditions	Operation in experiment
62%	With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); di-tert-butyl((trimethylsilyl)methyl)phosphine; In 1,4-dioxane; at 20℃; for 12h;	Example 9 In this example, 1-(4-trimethylsilanyl-phenyl)-isoquinoline is synthesized from 1-chloro-isoquinoline and 4-trimethylsilyl-butylphenylboronic acid. 15.0 g (0.07727 mol) of 4-trimethylsilyl-butylphenylboronic acid, 10.11 g (0.0618 mol) 1-chloro-isoquinoline, 15.11 g (0.0464 mol) of cesium carbonate, 0.71 g (0.000775 mol) of tris(dibenzylideneacetone) dipalladium (0), 0.43 g (0.00185 mol) of di-tert-butyl-trimethylsilylmethyl-phosphine and 100 ml of dioxane were stirred at room temperature for 12 hours. The reaction mixture was filtered and the solvent was removed under vacuum. The resulting mixture was purified by chromatography on silica gel with eluent petroleum ether/ethyl ether at 10/0.5. Yield of 1-(4-trimethylsilanyl-phenyl)-isoquinoline was 10.63 g (62%) as colorless solid with m.p. 93.45 C. 1H NMR (CDCl3) 0.30 (s, 9H, Me3Si), 7.45-7.70 (m, 7H, arom-H), 7.85 (s, 1H, arom-H), 8.15 (s, 1H, arom-H), 8.51 (s, 1H, arom-H). Anal. Calcd. for C18H19NSi: C, 77.93; H, 6.90; N, 5.05. Found: C, 77.68; H, 6.95; N, 4.97.
62%	With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); di-tert-butyl((trimethylsilyl)methyl)phosphine; In 1,4-dioxane; at 20℃; for 12h;	15.0 g (0.07727 mol) of 4-trimethylsilyl-phenylboronic acid, 10.11 g (0.0618 mol) 1-chloro-isoquinoline, 15.11 g (0.0464 mol) of cesium carbonate, 0.71 g (0.000775 mol) of tris(dibenzylideneacetone) dipalladium (0), 0.43 g (0.00185 mol) of di-tert-butyl-trimethylsilylmethyl-phosphane and 100 ml of dioxane were stirred at room temperature for 12 hr. The reaction mixture was filtered and the solvent was removed under vacuum. The resulting mixture was purified by chromatography on silica gel using petroleum ether/ethyl ether (10/0.5) as eluent. Yield of 1-(4-trimethylsilanyl-phenyl)-isoquinoline was 10.63 g (62%) as a colorless solid with m.p. 93.45 C. 1H NMR (CDCl3) 0.30 (s, 9H, Me3Si), 7.45-7.70 (m, 7H, arom-H), 7.85 (s, 1H, arom-H), 8.15 (s, 1H, arom-H), 8.51 (s, 1H, arom-H). Anal. Found: C, 77.68; H, 6.95; N, 4.97.

Reference： [1]Patent: US2006/281923,2006,A1 .Location in patent: Page/Page column 6
[2]Patent: US2008/74033,2008,A1 .Location in patent: Page/Page column 8

24
[ 3510-66-5 ]
[ 17865-11-1 ]
5-methyl-2-(4-trimethylsilanyl-phenyl)-pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); benzyl(di-tert-butyl)phosphane; In 1,4-dioxane; at 20℃; for 12h;	Example 11 In this example, a method of forming 5-methyl-2-(4-trimethylsilanyl-phenyl)-pyridine is shown. 15.0 g (0.0773 mol) of 4-trimethylsilyl-butylphenylboronic acid, 11.96 g (0.0695 mol) of 2-bromo-5-methyl-pyridine, 15.11 g (0.0464 mol) of cesium carbonate, 0.71 g (0.000776 mol) of tris(dibenzylideneacetone) dipalladium (0), 0.43 g (0.00182 mol) of benzyl-di-tert-butyl-phosphine and 100 ml of dioxane were stirred at room temperature for 12 hours. The reaction mixture was filtered and the solvent was removed under vacuum. The resulting mixture was purified by distillation in vacuum. Yield of 5-methyl-2-(4-trimethylsilanyl-phenyl)-pyridine was 8.05 g (48%) as yellow solid with b.p. at 111-114 C./0.02 mm and m.p. 66.07 C. 1H NMR (CD2Cl2) 2.15 (s, 3H, Me) 7.45-8.50 (m, 7H, arom-H). Anal. Calcd. for C15H19NSi: C, 74.63; H, 7.93; N, 5.80. Found: C, 74.34; H, 7.86; N, 5.85. The structure has been confirmed by X-ray analysis.
48%	With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); benzyl(di-tert-butyl)phosphane; In 1,4-dioxane; at 20℃; for 12h;	15.0 g (0.0773 mol) of 4-trimethylsilyl-phenylboronic acid, 11.96 g (0.0695 mol) of 2-bromo-5-methyl-pyridine, 15.11 g (0.0464 mol) of cesium carbonate, 0.71 g (0.000776 mol) of tris(dibenzylideneacetone) dipalladium (0), 0.43 g (0.00182 mol) of benzyl-di-tert-butyl-phosphane and 100 ml of dioxane were stirred at room temperature for 12 hr. The reaction mixture was filtered and the solvent was removed under 1 mm vacuum. The resulting mixture was purified by distillation in vacuum. Yield of 5-methyl-2-(4-trimethylsilanyl-phenyl)-pyridine was 8.05 g (48%) as a yellow solid with b.p. 111-114 C./0.02 mm and m.p. 66.07 C. 1H NMR (CD2Cl2) 2.15 (s, 3H, Me) 7.45-8.50 (m, 7H, arom-H). Anal. Found: C, 74.34; H, 7.86; N, 5.85. The structure was confirmed by X-ray analysis.

Reference： [1]Patent: US2006/281923,2006,A1 .Location in patent: Page/Page column 7
[2]Patent: US2008/74033,2008,A1 .Location in patent: Page/Page column 9

25
[ 100125-12-0 ]
[ 17865-11-1 ]
[ 1032392-95-2 ]

Reference： [1]Chemistry - A European Journal,2008,vol. 14,p. 933 - 943

26
3,8-bis(4-bromo-2'-pyridyl)-4,7-phenanthroline [ No CAS ]
[ 17865-11-1 ]
[ 1049037-41-3 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 11013 - 11022

27
[ 74137-36-3 ]
[ 17865-11-1 ]
[ 1200799-36-5 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 17768 - 17770

28
[ 1008788-37-1 ]
[ 17865-11-1 ]
[ 1200040-32-9 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 17655 - 17666

29
[ 1219633-30-3 ]
[ 17865-11-1 ]
[ 1219633-31-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 65℃; for 16h;	Step 2: Preparation of ethyl 4-[4-(trimethylsilyl)phenv?-5,6-dihvdro-2/-/- pyran-3-carboxylate. A flask containing ethyl 4-[(trifluoromethyl)sulfonyl]oxy}- 3,6-dihydro-2H-pyran-3-carboxylate isolated from the previous step (1.98 g, 5.8 mMol), (trimethylsilyl)phenylboronic acid (1.26 g, 6.51 mMol), tetrakis(triphenylphosphine)palladium(0) (0.752 g, 0.65 mMol), potassium carbonate (2.88 g, 20.8 mMol), and tetrahydrofuran (30 ml_) was heated to 650C for 16 hours. The reaction was concentrated and the crude product was purified by silica gel chromatography (Gradient: 10 to 50% ethyl acetate in heptane) to give ethyl 4-[4-(trimethylsilyl)phenyl]-5,6-dihydro-2H-pyran-3- carboxylate in an approximately 2:1 molar ratio with materials from the boronic acid reagent, as an oil. Yield: 1.32 g, <4.34 mMol, <67%. LCMS m/z 305.0 (M+1 ). 1H NMR (400 MHz, CHLOROFORM-d), product peaks only, delta 0.28 (s, 9 H), 0.90 (t, J=7.2 Hz, 3 H), 2.54 (m, 2 H), 3.95 (m, 4 H), 4.50 (t, J=2.6 Hz, 2 H), 7.16 (d, J=8.1 Hz, 2 H), 7.51 (d, J=7.9 Hz, 2 H).

Reference： [1]Patent: WO2010/38167,2010,A1 .Location in patent: Page/Page column 59

30
[ 51507-18-7 ]
[ 17865-11-1 ]
[ 1251532-41-8 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 4506 - 4509

31
4-(trimethylsilyl)phenylboronic acid MIDA ester [ No CAS ]
[ 17865-11-1 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 4728 - 4731

32
[ 17865-11-1 ]
[ 197969-58-7 ]
[ 1257582-69-6 ]

Yield	Reaction Conditions	Operation in experiment
62%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; at 100℃; for 5h;	2,7-Dibromo-9,9'-dimethylfluorene (30 g, 0.078mol), Compound A (15.3 g, 0.078 mol) and tetrakis(triphenylphosphine)palladium (2.73 g, 0.23 mmol) were added to a 2-bulb flask. After stirring while adding toluene, 2 M potassium carbonate and ethanol were added. After refluxing at 100 0C for 5 hours, the mixture was cooled to room temperature when the reaction was completed. Then, after extracting with distilled water and EA, the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. Pure Compound B (22 g, 62% was separated by column chromatography using hexane and EA as an eluent.

Reference： [1]Patent: WO2010/140801,2010,A1 .Location in patent: Page/Page column 18

33
[ 3460-24-0 ]
[ 17865-11-1 ]
[ 1244947-52-1 ]

Reference： [1]Journal of Physical Chemistry B,2010,vol. 114,p. 12765 - 12776

34
[ 95970-08-4 ]
[ 17865-11-1 ]
[ 1325176-75-7 ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 8259 - 8261

35
[ 7511-49-1 ]
[ 17865-11-1 ]
[ 1333127-72-2 ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 9995 - 9997

36
[ 17865-11-1 ]
[ 552839-06-2 ]
[ 1338246-91-5 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 5838 - 5841

37
[ 79-38-9 ]
[ 17865-11-1 ]
[ 2972-91-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With [1,4-bis(diphenylphosphino)butane] palladium(ll) dichloride; cesium fluoride; In 1,4-dioxane; water; at -196 - 100℃; for 2h;Inert atmosphere;	To the reaction vessel was added dichloro [1,4-bis (diphenylphosphino) butane]30.2 mg (0.05 mmol) of palladium, 194 mg (1.0 mmol) of 4- (trimethylsilyl) phenylboronic acid and 304 mg (2.0 mmol) of cesium fluoride were added and after purging with argon, 2 mL of 1,4- 0.1 mL (5.6 mmol) was added. The mixture was cooled to -196 C., 466 mg (4.0 mmol) of chlorotrifluoroethylene was added, and the mixture was sealed under an argon stream and heated to 100 C. and stirred for 2 hours. After the reaction, the mixture was filtered and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography to obtain 201 mg of 1-trifluorovinyl-4- (trimethylsilyl) benzene (yield: 87%).

Reference： [1]Patent: JP5833392,2015,B2 .Location in patent: Paragraph 0083-0085
[2]Organic Letters,2012,vol. 14,p. 3454 - 3457

38
[ 94569-84-3 ]
[ 17865-11-1 ]
[ 1400812-80-7 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 16753 - 16758,6

39
[ 6630-33-7 ]
[ 17865-11-1 ]
[ 1422011-56-0 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 928 - 931

40
[ 615-42-9 ]
[ 17865-11-1 ]
[ 1394123-87-5 ]

Yield	Reaction Conditions	Operation in experiment
93%	With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide; In diethylene glycol dimethyl ether; water; at 95℃; for 15h;Inert atmosphere;	Comparative Synthesis Example 3 <Synthesis of 4,4'-bis(2,2'-bipyridin-6-yl)-1,1':2',1'-terphenyl (comparative compound 3)> 1,2-Diiodobenzene (20 g), 4-trimethylsilylphenylboronic acid (25 g), sodium hydroxide (7.4 g), tetrakis(triphenylphosphine)palladium(0) (3.6 g), diethylene glycol dimethyl ether (240 ml), and water (60 ml) were added to a nitrogen-substituted reaction vessel. The mixture was heated, and stirred at 95C for 15 hours. Water (100 ml) was added after cooling the mixture to room temperature, and the organic layer was collected by separation. The organic layer was washed two times with water (100 ml), dried over anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was purified by column chromatography (support: silica gel, eluent: n-hexane) to obtain a white powder of 4,4'-bi(trimethylsilyl)-1,1':2',1'-terphenyl (21.1 g; yield 93%).
93%	With tetrakis(triphenylphosphine) palladium(0); In diethylene glycol dimethyl ether; water; at 95℃; for 15h;	Example 3 <Synthesis of 4,4'-bis(2,2'-bipyridin-5-yl)-1,1':2',1'-terphenyl (compound 10)> 1,2-Diiodobenzene (20 g), 4-trimethylsilylphenylboronic acid (25 g), sodium hydroxide (7.4 g), tetrakis(triphenylphosphine)palladium(0) (3.6 g), diethylene glycol dimethyl ether (240 ml), and water (60 ml) were added to a nitrogen-substituted reaction vessel. The mixture was heated, and stirred at 95C for 15 hours. After cooling the mixture to room temperature, water (100 ml) was added, and the organic layer was collected by separation. The organic layer was washed two times with water (100 ml), dried over anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was purified by column chromatography (support: silica gel, eluent: n-hexane) to obtain a white powder of 4,4'-bis(trimethylsilyl)-1,1':2',1'-terphenyl (21.1 g; yield 93%).

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 10356 - 10360
Angew. Chem.,2015,vol. 127,p. 10497 - 10502
[2]Patent: EP2679581,2014,A1 .Location in patent: Paragraph 0162
[3]Patent: EP2679582,2014,A1 .Location in patent: Paragraph 0110

41
[ 496850-09-0 ]
[ 17865-11-1 ]
methyl 4-amino-3-chloro-5-fluoro-6-(4-(trimethylsilyl)phenyl)picolinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With trisodium tris(3-sulfophenyl)phosphine; palladium diacetate; cesium fluoride; In water; acetonitrile; at 150℃; for 0.0833333h;Microwave irradiation;	Example 47 Preparation of methyl 4-amino-3-chloro-5-fluoro-6-(4-(trimethylsilyl)phenyl)picolinate [0366] <strong>[17865-11-1](4-(trimethylsilyl)phenyl)boronic acid</strong> (540 mg, 2.8 mmol, 1.1 equiv) were combined in a 20 mL vial followed by cesium fluoride (420 mg, 2.8 mmol, 1.1 equiv), palladium acetate (28 mg, 0.13 mmol, 0.05 equiv), and sodium 3,3?,3?-phosphinetriyltribenzenesulfonate (140 mg, 0.25 mmol, 0.10 equiv). A 3:1 mixture of water: acetonitrile (7.2 mL) was added and the resulting brown mixture was capped and placed in a Biotage Initiator microwave reactor for 5 min at 150 C., with external IR-sensor temperature monitoring from the side of the vessel. The cooled reaction mixture was diluted with water (150 mL) and extracted with dichloromethane (5×60 mL). The combined organic layers were dried (magnesium sulfate), gravity filtered, and concentrated by rotary evaporation. The residue was purified by silica gel column chromatography (33% ethyl acetate in hexanes) to afford the title compound as a pale yellow powder (700 mg, 79%): mp 148-150 C.; 1H NMR (300 MHz, CDCl3) delta 7.86 (m, 2H), 7.62 (m, 2H), 4.88 (br s, 2H), 3.98 (s, 3H), 0.29 (s, 9H); ESIMS m/z 353 ([M+H]+).

Reference： [1]Patent: US2014/274696,2014,A1 .Location in patent: Paragraph 0366; 0367

42
[ 1365727-53-2 ]
[ 17865-11-1 ]
C₃₇H₄₈O₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With tetrakis(triphenylphosphine) palladium(0); In propan-1-ol;Reflux;	General procedure: To a solution of 5 (200 mg, 0.40 mmol) in 1-propanol (15 ml)was added arylboronic acid (0.40 mmol) and the mixture was stirredfor 15 min at ambient temperature followed by addition of Pd(0)(PPh3)4 (22 mg, 5% mmol) and aq. solution of 2 M Na2CO3(5 ml). The reaction mixture was heated under reflux for 12-14 h. After cooling, water (5 ml) was added and the mixture waspartitioned with EtOAc (3 10 ml). The combined organic extractswere washed with aq. solution of 5% Na2CO3 (3 10 ml), dried(Na2SO4) and evaporated in vacuo. The residue was purified on ashort SiO2 column using hexane: EtOAc (3:2) as eluent to givethe desired product.

Reference： [1]Steroids,2015,vol. 101,p. 43 - 50

43
[ 373-52-4 ]
[ 17865-11-1 ]
(4-(fluoromethyl)phenyl)trimethylsilane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With dmap; 1,10-Phenanthroline; (1,2-dimethoxyethane)dichloronickel(II); potassium carbonate; In 1,4-dioxane; 1,2-dimethoxyethane; at 70℃; for 24h;	To a 25 mL reaction tube was added 175 mg (0.9 mmol) of 4-trimethylsilylbenzeneboronic acid, 6.6 mg (5 mol%Mol% refers to the percentage of molar ratio of NiCl2 · DME to compound B) NiCl2 · DME (dimethylethyl ether chlorideNickel), 5.4 mg (5 mol%, mol% refers to the percentage of phen and the molar ratio of compound B) phen (1,10 &), 7.4 mg (5 mol%, mol% is the percentage of DMAP and compound B molar) DMAP (4-dimethylamineYl) pyridine), 166 mg (1.2 mmol) of K2CO3, 2 mL of ethylene glycol dimethyl ether, 1.7 mL of 1,4-dioxane,(Concentration: 2M, 0.6 mmol) of the uL CH2FBr was stirred at 70 C for 24 hours,The rate was 82%, the purity was identified by hydrogen spectrum greater than 95%

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 9079 - 9083
Angew. Chem.,2015,vol. 127,p. 9207 - 9211,5
[2]Patent: CN106278847,2017,A .Location in patent: Paragraph 0097; 0098; 0099

44
[ 556-96-7 ]
[ 17865-11-1 ]
(3’,5’-dimethyl-[1,1‘-biphenyl]-4-yl)trimethylsilane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene;Inert atmosphere; Reflux;	A 250 ml round flask was charged with 1-bromo-3,5-dimethylbenzene (6 g, 32.4 mmol), <strong>[17865-11-1](4-(trimethylsilyl)phenyl)boronic acid</strong> (9.44 g, 48.6 mmol), K2C03 solution (18 g in 10 ml water),ethanol 10 ml, toluene 50 ml. The mixture was bubbled with argon for 10 mm, then Pd(PPh3)4(1 .87 g, 1.62 mmol) was added. The resulting mixture was treated with liquid nitrogen bath. Af40 ter three times freeze-pump-thaw procedure, the mixture was refluxed overnight. The reactionwas monitored by TLC. After the reaction finished, the mixture was washed with deionized water and the water layer was extracted with ethyl acetate (10 ml X 2). The combined organic layer was dried over MgSO4, filtered and concentrated. The crude product was purified by chromatography to afford compound 123. Colorless oil (yield = 95%)

Reference： [1]Patent: WO2015/121785,2015,A1 .Location in patent: Page/Page column 39; 41; 42

45
C₃₇H₂₂BrN [ No CAS ]
[ 17865-11-1 ]
C₄₆H₃₅NSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene;Inert atmosphere; Reflux;	Pitching 100 mL flask was charged with intermediate (12) 0.5 g (0.892 mmol), (4 - (trimethylsilyl) phenyl) boronic acid ((4 - (trimethylsilyl) phenyl) boronic acid), 0.208 g (1.07 mmol) and Pd (PPh3 ) was introduced into 52 mg of 4 (0.045 mmol) was dissolved in Toluene 6 mL EtOH and 3 mL under a nitrogen atmosphere, was added a 2M K2CO3 solution 0.9 mL was stirred under reflux. After completion of the reaction, the reaction was cooled to room temperature and added to 5 mL H2O. Drying the mixture and then extracted two times with MC 20 mL extract with Na2SO4, filtered and concentrated under a reduced pressure. Purification of the resulting compound was purified by silica gel column chromatography to obtain a compound of a light green solid (5-96, HSB-08-035) 0.27 g (Yield: 48%).

Reference： [1]Patent: KR2015/137230,2015,A .Location in patent: Paragraph 0673; 0674; 0675; 0676

46
4-bromo-5,6-dimethylindene [ No CAS ]
[ 17865-11-1 ]
4-(4-trimethylsilylphenyl)-5,6-dimethylindene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; triphenylphosphine; In 1,2-dimethoxyethane; water; for 12h;Reflux;	In 500ml flask, after the 4-trimethylsilyl boronic acid 8.35g and (43.0mmol) and the solution was added to the dimethoxyethane 200ml, potassium phosphate 11.4g (53.7mmol), water 30ml, 4- bromo -5, 6-dimethyl indene 6.00g (26.8mmol), triphenylphosphine 0.352g (1.34mmol), PdCl2 (PPh3) added 2 0.472g the (0.672mmol) in the order, and the mixture was stirred under reflux for 12 hours. It was added water 200ml and cooled to room temperature. The organic phase was separated and the aqueous phase was extracted twice with ethyl acetate 200 ml, and mixed the resultant organic phase was washed with brine, the organic phase dried with sodium sulfate added thereto. Filter the sodium sulfate, the solvent was distilled off under reduced pressure and purified by silica gel column, 4-yellow liquid 4.20 g (53% yield) of indene - (4-trimethylsilyl-phenyl) - 5,6-dimethyl Obtained.

Reference： [1]Patent: JP2015/172037,2015,A .Location in patent: Paragraph 0065; 0138

47
[ 45738-35-0 ]
[ 17865-11-1 ]
4-(4-trimethylsilylphenyl)indene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; triphenylphosphine; In 1,2-dimethoxyethane; water; for 12h;Reflux;	in 500ml flask, after the solution was added 4-trimethylsilyl boronic acid 10.0g and (51.5mmol) dimethoxyethane 200ml, potassium phosphate 27.3g(128mmol), water 100ml, 4- bromoindene 8.37g ( 43.0mmol), triphenylphosphine 0.22 g of (0.86 mmol), PdCl 2 (PPh 3 ) 2 added 0.300g the(0.430mmol) in the order, and the mixture was stirred under reflux for 12 hours. It was added water 100ml and cooled to room temperature. Theorganic phase was separated and the aqueous phase was extracted twice with ethyl acetate 100 ml, and mixed the resultant organic phase waswashed with brine, the organic phase dried with sodium sulfate added thereto. Filter the sodium sulfate, the solvent was distilled off under reducedpressure and purified by silica gel column, 4- (4-trimethylsilyl-phenyl) - - to give a yellow liquid 9.0 g (79% yield) of indene.
79%	With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; triphenylphosphine; In 1,2-dimethoxyethane; water; for 12h;Reflux;	In a 500 ml flask, 10.0 g (51.5 g) of 4-trimethylsilylphenylboronic acid Mmol) and dimethoxyethane (200 ml) were added to make a solution, then potassium phosphate 27.3 G (128 mmol), water 100 ml, 4-bromoindene 8.37 g (43.0 mmo L), triphenylphosphine 0.22 g (0.86 mmol), PdCl 2 (PPh 3 ) 2 0.300 g (0.430 mmol) were sequentially added and stirred and refluxed for 12 hours.To room temperature And 100 ml of water was added. After separating the organic phase, the aqueous phase was washed with 100 ml of ethyl acetate Times, extract the obtained organic phases, wash with brine, add sodium sulfate and dry the organic phase I let it dry. The sodium sulfate was filtered, the solvent was distilled off under reduced pressure, and the residue was purified on a silica gel column, 9.0 g (yield 79%) of a yellow liquid of 4- (4-trimethylsilyl-phenyl) -indene was obtained.
79%	With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; triphenylphosphine; In 1,2-dimethoxyethane; water; for 12h;Reflux;	After adding 10.0 g (51.5 mmol) of 4-trimethylsilylphenylboronic acid and 200 ml of dimethoxyethane to a 500 ml flask, 27.3 g (128 mmol) of potassium phosphate, 100 ml of water, 8.37 g of 4-bromoindene 0.22 g (0.86 mmol) of triphenylphosphine and 0.300 g (0.430 mmol) of PdCl 2 (PPh 3) 2 were sequentially added, and the mixture was stirred and refluxed for 12 hours. After cooling to room temperature, 100 ml of water was added. After separating the organic phase, the aqueous phase was extracted twice with 100 ml of ethyl acetate and the resulting organic phases were combined, washed with brine, dried over sodium sulfate, and the organic phase was dried. The sodium sulfate was filtered, the solvent was distilled off under reduced pressure, and the residue was purified with a silica gel column to obtain 9.0 g (yield 79%) of a yellow liquid of 4- (4-trimethylsilylphenyl)indene.

79%

With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; triphenylphosphine; In water; for 12h;Reflux;

After adding 10.0 g (51.5 mmol) of 4-trimethylsilylphenylboronic acid and 200 ml of dimethylethane to a 500 ml flask, 27.3 g (128 mmol) of potassium phosphate, 100 ml of water, 8.37 g of 4-bromoindene (43 0.22 g (0.86 mmol) of triphenylphosphine and 0.300 g (0.430 mmol) of PdCl2(PPh3)2 were sequentially added, and the mixture was stirred and refluxed for 12 hours. After cooling to room temperature, 100 ml of water was added. After separation of the organic phase, the aqueous phase was extracted twice with 100 ml of ethyl acetate and the resulting organic phases were combined, washed with brine, sodium sulfate was added and the organic phase was dried. The sodium sulfate was filtered, the solvent was distilled off under reduced pressure, and the residue was purified with a silica gel column to obtain 9.0 g (yield 79%) of a yellow liquid of 4-(4-trimethylsilylphenyl)indene.

Reference： [1]Patent: JP2015/172037,2015,A .Location in patent: Paragraph 0150
[2]Patent: JP2015/63515,2015,A .Location in patent: Paragraph 0140
[3]Patent: JP6051738,2016,B2 .Location in patent: Paragraph 0140
[4]Patent: JP6015306,2016,B2 .Location in patent: Paragraph 0141

48
[ 88-12-0 ]
[ 383-62-0 ]
[ 17865-11-1 ]
ethyl 2,2-difluoro-4-(2-oxopyrrolidin-1-yl)-4-(4-(trimethylsilyl)phenyl)butanoate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 12270 - 12274
Angew. Chem.,2016,vol. 128,p. 12458 - 12462,5

49
C₃₂H₁₈Br₂ [ No CAS ]
[ 17865-11-1 ]
C₅₀H₄₄Si₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; toluene; for 24h;Reflux;	About 2.0 g (about 3.6 mmol) of Intermediate D (IntermediateD was synthesized with reference to Tetrahedron Letters 38 (1997) 741-744 byMark D. Clayton and Peter W. Rabideau), about 1.5 g (about 7.9 mmol) ofIntermediate E, about 208 mg (about 0.18 mmol) oftetrakis(triphenylphosphine)palladium (Pd(PPh3)4, and about 8 ml (about 16 mmol)of 2M potassium carbonate (K2CO3) solution were dissolved in about 10 ml oftoluene and about 15 ml of tetrahydrofuran (THF), and the solution was refluxedfor about 24 hours. When the reaction wasterminated, the solvent was evaporated and removed. The resultant was washedrespectively with about 500 ml of ethylacetate and about 500 ml of water. Thenan organic layer was collected and dried using anhydrous magnesium sulfate.Then the resultant was isolated by silica chromatography to obtain about 1.1 g ofCompound 33 (yield: about 44%).
44%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; toluene; for 24h;Reflux;	Intermediate D (Intermediate D, synthesized by application of Mark D. Clayton and Peter W. Rabideau, Tetrahedron Letters 38 (1997) 741-744) (2.0 g, 3.6 mmol)Intermediate E (1.5 g, 7.9 mmol), tetrakis triphenylphosphine palladium (Pd (PPh3) 4 (208 mg, 0.18 mmol)And a 2M aqueous potassium carbonate (K2CO3) solution (8 ml, 16 mmol)And dissolved in toluene (10 ml) and tetrahydrofuran THF (15 ml), respectively, and the mixture was refluxed for 24 hours. After completion of the reaction, the solvent was removed by evaporation, and then 500 ml of ethyl acetate and 500 ml of water were added and washed. The organic layer was collected and dried over anhydrous magnesium sulfate. Subsequently, the resultant was separated by silica chromatography to obtain 1.1 g (yield: 44%) of Compound 33.

Reference： [1]Patent: KR2015/20644,2015,A .Location in patent: Paragraph 0275-0277
[2]Patent: KR2015/20645,2015,A .Location in patent: Paragraph 0273-0277

50
[ 1753-75-9 ]
[ 17865-11-1 ]
5-(4-trimethylsilylphenyl)benzo[c][1,2,5]thiadiazole [ No CAS ]

Reference： [1]Inorganic Chemistry,2016,vol. 55,p. 8446 - 8458

51
[ 19821-80-8 ]
[ 17865-11-1 ]
(2',6'-dibromo-[1,1'-biphenyl]-4-yl)trimethylsilane [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 15539 - 15542

52
[ 17865-11-1 ]
[ 102687-65-0 ]
(E)-trimethyl(4-(3,3,3-trifluoro-1-propen-1-yl)phenyl)silane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With tris-(dibenzylideneacetone)dipalladium(0); sodium carbonate; tri tert-butylphosphoniumtetrafluoroborate; In tetrahydrofuran; water; at 20℃; for 12h;Inert atmosphere; Sealed tube;	Under an argon atmosphere,To the reaction vessel, 97 mg (0.5 mmol) of 4- (trimethylsilyl) phenylboronic acid,2.3 mg (0.0025 mmol) of tris (dibenzylideneacetone) dipalladium,2.9 mg (0.01 mmol) of tri-tert-butylphosphonium tetrafluoroborate,286 mg (1 mmol) of sodium carbonate decahydrate,0.5 mL (0.75 mmol) of a 1.5 M solution of (E) -1-chloro-3,3,3-trifluoropropene in tetrahydrofuran,0.5 mL of tetrahydrofuran and 0.18 mL of distilled water were added.After closing the reaction vessel,And the mixture was stirred at room temperature for 12 hours.The mixture was purified by silica gel column chromatography (hexane)(E) -trimethyl (4- (3,3,3-trifluoro-1-propen-1-yl) phenyl) silane120 mg (colorless liquid, yield 98%) was obtained

Reference： [1]Patent: JP2016/179968,2016,A .Location in patent: Paragraph 0083; 0084

53
[ 1231645-50-3 ]
[ 17865-11-1 ]
4-(4-trimethylsilylphenyl)-5-methylindene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; triphenylphosphine; In 1,2-dimethoxyethane; water; for 12h;Reflux;	4.82 g (24.8 mmol) of 4-trimethylsilylphenylboronic acid and 30 ml of dimethoxyethane were added to a 200 ml flask to prepare a solution, Potassium phosphate 8.12 g (38.2 mmol), water 30 ml, 4.00 g (19.1 mmol) of 4-bromo-5-methyl-indene, 0.250 g (0.956 mmol) of triphenylphosphine, 0.330 g (0.478 mmol) of PdCl 2 (PPh 3) 2 were sequentially added, 12 hours stirring It was refluxed. After cooling to room temperature, 30 ml of water was added. After separating the organic phase, the aqueous phase was extracted with ethyl acetate Extract twice with 30 ml and mix the resulting organic phases, wash with brine, add sodium sulfate The organic phase was dried.The sodium sulfate was filtered and the solvent was distilled off under reduced pressure to give a silica gel colored And purified with a yellow liquid of 4- (4-trimethylsilyl-phenyl) -5-methyl-indene 3.90 g (yield 73%) of a body was obtained.

Reference： [1]Patent: JP2015/63515,2015,A .Location in patent: Paragraph 0062; 0134

54
[ 17865-11-1 ]
[ 125114-77-4 ]
7-(4-trimethylsilylphenyl)-1-indanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; triphenylphosphine; In 1,2-dimethoxyethane; water; for 12h;Reflux;	To a 400 ml flask, p-trimethylsilylphenylboronic acid (11.2 g, 59.6 mmol) and DME (80 ml) were added to make a solution, and further potassium phosphate (20.4 g, 96.0 mmol), water 20 ml, 7-bromo- -indanone (10.0 g, 48.0 mmol), triphenylphosphine (246 mg, 0.960 mmol) and PdCl2(PPh3)2 (335 mg, 0.480 mmol) were added and stirred under reflux for 12 hours. After cooling to room temperature, 200 ml of water was added and the aqueous phase was extracted twice with 200 ml of ethyl acetate. The organic phase was collected, dried over sodium sulfate, and the solvent was distilled off to obtain a crude product. furtherPurification with a silica gel column (petroleum ether) gave 12.0 g (yield 90%) of 7-(4-trimethylsilylphenyl)-1-indanone.

Reference： [1]Patent: JP6051738,2016,B2 .Location in patent: Paragraph 0166

55
[ 17865-11-1 ]
[ 171408-84-7 ]
2,7-bis-(4-(trimethylsilyl)phen-1-yl)-9,9’-spirobifluorene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 2060 - 2069

56
[ 1798-06-7 ]
[ 17865-11-1 ]
C₁₇H₂₀O₂Si [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 4429 - 4434

57
4-Bromo-2-methyl indene [ No CAS ]
[ 17865-11-1 ]
2-methyl-4-(4-trimethylsilylphenyl)indene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; triphenylphosphine; In 1,2-dimethoxyethane; water; for 12h;Reflux;	After adding 4-trimethylsilylphenylboronic acid (2.23 g, 11.4 mmol) and 20 ml of DME to a 100 ml flask, 20 ml of an aqueous solution of potassium phosphate (6.08 g, 28.6 mmol), 2-methyl-4-bromoindene (2.00 g, 9.56 mmol), triphenylphosphine (0.0500 g, 0.190 mmol) and Pd(PPh3)2Cl2 (0.0670 g, 0.095 mmol) were sequentially added and stirred and refluxed for 12 hours. After cooling to room temperature, 20 ml of water was added. After separating the organic phase, the aqueous phase was extracted twice with 20 ml of ethyl acetate and the resulting organic phases were combined, washed with brine, and sodium sulfate was added to dry the organic phase. The sodium sulfate was filtered, the solvent was distilled off under reduced pressure, and the residue was purified with a silica gel column (petroleum ether) 1.20 g (yield 45%) of a yellow liquid of 2-methyl-4-(4-trimethylsilylphenyl)indene was obtained.

Reference： [1]Patent: JP6015306,2016,B2 .Location in patent: Paragraph 0054; 0133

58
[ 23680-84-4 ]
[ 17865-11-1 ]
6,7-dimethoxy-2-(4-(trimethylsilyl)phenyl)quinazolin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With potassium phosphate; [1,1?-bis(di-cyclohexylphosphino)ferrocene]dichloropalladium (II); In 1,4-dioxane; at 100℃; for 16h;Inert atmosphere;	General procedure: 2-Chloro-6,7-dimethoxyquinazolin-4-amine (1) (150 mg, 1.0 eq and 0.627 mmol), aryl boronic acid (150 mol%), and K3PO4 (300 mol%) in anhydrous 1,4-dioxane (6 mL) were added in a dry screw-capped vial that was equipped with a stirring bar. The vial was flushed with argon gas for a few minutes and [PdCl2(dcpf)] (0.08 eq, 8 mol%) was added. The vial was sealed with a teflon-lined cap and the mixture was heated at 100 C with stirring for 16h. The mixture was cooled, filter through celite pad, the solvent was evaporated under reduced pressure and dried under high vacuum. Resulted crude compound was dissolved in ethyl acetate, washed with water, brine solution and dried over anhydrous Na2SO4. The organic layer was concentrated under reduced pressure. The crude product, which was loaded into a silica column packed in CH2Cl2. Sequential elution with pet-ether, followed by 2-5% MeOH in CH2Cl2, afforded the requisite compounds; Yields 45-96.4% this was further dried under high vacuum to remove traces of solvent. (See specific compound headings below for details).

Reference： [1]Synthetic Communications,2017,vol. 47,p. 1142 - 1150

59
[ 75-45-6 ]
[ 17865-11-1 ]
[ 343957-95-9 ]

Yield	Reaction Conditions	Operation in experiment
82%	With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; hydroquinone; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 110℃; for 48h;Inert atmosphere; Sealed tube;	General procedure: To a 25 ml sealed tube were added anhydrous K2CO3 (powder, 4.0 equiv.), hydroquinone (2.0 equiv.), Pd2(dba)3 (2.5 mol%), Xantphos (7.5 mol%) and ArB(OH)2 (0.3 or 0.5 mmol) or Ar-Beg (0.3 or 0.5 mmol) under argon. A solution of ClCF2H in 1,4-dioxane (2.0 M, 1.5 ml for 0.3 mmol scale or 2.5 ml for 0.5 mmol scale, 10 equiv.) and fresh distilled 1,4-dioxane (1.0 ml for 0.3 mmol scale or 2.5 ml for 0.5 mmol scale) were added subsequently. The sealed tube was screw capped and heated to 110 C (oil bath). After stirring for 48 h, the reaction was cooled to room temperature and fluorobenzene (1.0 equiv.) was added. The yield was determined by 19F NMR before working up. The reaction mixture was then diluted with ethyl acetate, filtered through a pad of Celite and concentrated. The residue was purified with silica gel chromatography to provide the desired product.

Reference： [1]Nature Chemistry,2017,vol. 9,p. 918 - 923

60
[ 151588-82-8 ]
[ 17865-11-1 ]
C₁₇H₂₁FSi [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 4480 - 4483

61
[ 76-09-5 ]
[ 17865-11-1 ]
[ 1186026-67-4 ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 16648 - 16653
Angew. Chem.,2018,vol. 130,p. 16890 - 16895,6
[2]Journal of the American Chemical Society,2017,vol. 139,p. 12386 - 12389

62
[ 17865-11-1 ]
[ 67665-47-8 ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 6696 - 6700
Angew. Chem.,2018,vol. 130,p. 6806 - 6810,5
[2]Angewandte Chemie - International Edition,2018,vol. 57,p. 6696 - 6700
Angew. Chem.,2018,vol. 130,p. 6806 - 6810,5

63
[ 17865-11-1 ]
[ 13132-25-7 ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 2013 - 2019
[2]Green Chemistry,2019,vol. 21,p. 4971 - 4975

64
[ 16657-07-1 ]
[ 17865-11-1 ]
4-(4-trimethylsilylphenyl)indene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; triphenylphosphine; In 1,2-dimethoxyethane; water; at 90℃; for 4h;	In a 200 mL glass reaction vessel,16 g (75.4 mmol) of tripotassium phosphate, 42 mL of distilled water, 42 mL of 1,2-dimethoxyethane (DME), 5.0 g (25.8 mmol) of 4-trimethylsilylphenylboronic acid,4.19 g (21.5 mmol) of 7-bromo-1 H-indene,420 mg (0.60 mmol) of dichlorobis (triphenylphosphine) palladium and 313 mg (1.19 mmol) of triphenylphosphine were sequentially added, followed by heating under reflux at 90 C. for 4 hours. After being released to room temperature, the reaction solution was poured into 50 mL of distilled water, transferred to a separating funnel, and extracted three times with hexane. The hexane solution was washed with saturated brine and steamAfter washing three times with distilled water, drying with sodium sulfate, sodium sulfate was filtered, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, hexane / diisopropyl ether = 20: 1)To obtain 5.69 g (yield: 100%) of 4- (4-trimethylsilylphenyl) indene as a colorless oil.

Reference： [1]Patent: JP2016/50189,2016,A .Location in patent: Paragraph 0086; 0152

65
[ 1493-03-4 ]
[ 17865-11-1 ]
[ 343957-95-9 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium dihydrogenphosphate; tetrakis(triphenylphosphine) palladium(0); bis[2-(diphenylphosphino)phenyl] ether; In tetrahydrofuran; water; toluene; at 60℃; for 24h;Inert atmosphere;	General procedure: Tetrakis (triphenylphosphine) palladium (0)(34.7 mg, 0.03 mmol, 10 mol%),DPEphos (16.2 mg, 0.03 mmol, 10 mol%),4- (ethoxycarbonyl) phenylboronic acid (58.2 mg, 0.3 mmol),In a mixture obtained by adding potassium phosphate (127.5 mg, 0.6 mmol) to toluene (3 mL),Water (300 muL) and difluoroiodomethane in THF (1.0-1.5 M, 0.45 mmol) were added.Added at room temperature under an argon atmosphere.After completion of the addition, the reaction solution is heated to 60 C.The mixture was stirred at the same temperature for 24 hours.Then cool to room temperature,Water was added to stop the reaction.After stopping the reaction, extract with ether,The ether layer is washed with brine,It was dried over anhydrous magnesium sulfate.After filtration, the solvent was distilled off under reduced pressure,A crude product was obtained.The resulting crude product isPurification using silica gel chromatography gave the desired product(42.0 mg, 70% yield).

Reference： [1]ACS Catalysis,2019,vol. 9,p. 417 - 421
[2]Patent: JP2019/156773,2019,A .Location in patent: Paragraph 0068; 0069; 0072

66
[ 201230-82-2 ]
[ 17865-11-1 ]
[ 257887-58-4 ]
2,2-difluoro-4-(triisopropylsilyl)-1-(4-(trimethylsilyl)phenyl)but-3-yn-1-one [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 1031 - 1036

67
[ 201230-82-2 ]
(((1-(3-bromo-3,3-difluoroprop-1-yn-1-yl)cyclopentyl)oxy)methyl)benzene [ No CAS ]
[ 17865-11-1 ]
4-(1-(benzyloxy)cyclopentyl)-2,2-difluoro-1-(4-(trimethylsilyl)phenyl)but-3-yn-1-one [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 1031 - 1036

68
[ 144930-50-7 ]
[ 17865-11-1 ]
(4-(mesitylsulfonyl)phenyl)trimethylsilane [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 974 - 979

69
[ 1127-76-0 ]
[ 17865-11-1 ]
C₂₁H₂₄Si [ No CAS ]
C₂₁H₂₄Si [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 6425 - 6429
Angew. Chem.,2019,vol. 131,p. 6491 - 6495,5

70
[ 321-75-5 ]
[ 17865-11-1 ]
2-fluoro-1-phenyl-2-(4-(trimethylsilyl)phenyl)ethan-1-one [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 6844 - 6849

71
[ 201230-82-2 ]
(4,4,4-trifluoro-3-iodobutyl)benzene [ No CAS ]
[ 17865-11-1 ]
C₂₀H₂₃F₃OSi [ No CAS ]

Reference： [1]ACS Catalysis,2020,vol. 10,p. 36 - 42

72
[ 4789-06-4 ]
[ 17865-11-1 ]
(4-trimethylsilylphenyl)(1-oxido-2-pyridinyl)methanone [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 9790 - 9794

73
C₁₃H₈BiClF₃NOS [ No CAS ]
[ 17865-11-1 ]
C₂₂H₂₁BiF₃NOSSi [ No CAS ]

Reference： [1]Science,2020,vol. 367,p. 313 - 317

74
N-(2,6-diisopropylphenyl)-N-(pyridine-2-yl)benzamide [ No CAS ]
[ 17865-11-1 ]
C₂₇H₃₄N₂OSi [ No CAS ]

Reference： [1]ACS Catalysis,2020,vol. 10,p. 3398 - 3403

75
[ 1708-29-8 ]
[ 17865-11-1 ]
C₁₃H₂₀OSi [ No CAS ]

Reference： [1]ACS Catalysis,2020,vol. 10,p. 2958 - 2963

76
[ 1708-29-8 ]
[ 17865-11-1 ]
C₁₃H₂₀OSi [ No CAS ]

Reference： [1]ACS Catalysis,2020,vol. 10,p. 2958 - 2963

77
[ 1708-29-8 ]
[ 17865-11-1 ]
C₁₃H₁₈OSi [ No CAS ]

Reference： [1]ACS Catalysis,2020,vol. 10,p. 2958 - 2963

78
C₁₇H₉FINO [ No CAS ]
[ 17865-11-1 ]
C₂₆H₂₂FNOSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 100℃;Inert atmosphere;	Intermediate 7 (4.2 g, 10.8 mmol), <strong>[17865-11-1](4-(trimethylsilyl)phenyl)boronic acid</strong> (2.3 g, 11.88 mmol), Pd(PPh3)4 (0.6 g, 0.5 mmol), potassium carbonate (2.2 g, 16.2 mmol), dioxane (200 mL) and water (60 mL) were added to a 500 mL round-bottomed flask. N2 replacement three times and N2 protection, stirred at 100 C. for overnight. After the reaction cooled, extracted with EA and washed with brine, the combined organic layers dried with anhydrous magnesium sulfate, then concentrated the crude product was purified by column chromatography, eluting with PE:EA=10:1 to 5:2 (v/v) to obtain intermediate 11 as a white solid (2.6 g, 59% yield).

Reference： [1]Patent: US2020/91442,2020,A1 .Location in patent: Paragraph 0183-0185

79
[ 181820-18-8 ]
[ 17865-11-1 ]
2,2,2-trifluoro-1-(4-(trimethylsilyl)phenyl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With tris-(dibenzylideneacetone)dipalladium(0); copper(I) thiophene-2-carboxylate; trifuran-2-yl-phosphane; In tetrahydrofuran; at 30℃; for 18h;Sealed tube; Inert atmosphere;	General procedure: To a 25 mL sealed tube was added substrates 1 (0.2 mmol, 1 equiv), Pd2dba3·CHCl3 (2.3 mg, 1 mol%), CuTC (57 mg, 0.3 mmol), TFP (1.4 mg, 3 mol%), 2d (74.4 mg, 0.4 mmol) and THF (2 mL). The reaction vessel was purged with nitrogen three times. Then the reaction mixture was stirred at 30 C for 18 h. Upon completion, EtOAc was added to dilute the mixture and washed with NH3·H2O and saturated NaCl (aq). The organic fraction was dried over anhydrous Na2SO4, evaporated and the residue purified by a silica gel packed flash chromatography column, using ethyl acetate/hexane as the eluent.

Reference： [1]Tetrahedron Letters,2020

80
[ 17865-11-1 ]
[ 192637-90-4 ]
[ 413598-24-0 ]

Yield	Reaction Conditions	Operation in experiment
71%	With tris-(dibenzylideneacetone)dipalladium(0); copper(I) thiophene-2-carboxylate; trifuran-2-yl-phosphane; In tetrahydrofuran; at 30℃; for 18h;Sealed tube; Inert atmosphere;	General procedure: To a 25 mL sealed tube was added substrates 1 (0.2 mmol, 1 equiv), Pd2dba3 (2.3 mg, 1 mol%), CuTC (76.0 mg, 0.4 mmol), TFP (1.4 mg, 3 mol%), 4 (67.2 mg, 0.4 mmol) and THF (2 mL). The reaction vessel was purged with nitrogen three times. Then the reaction mixture was stirred at 30 C for 18 h. Upon completion, EtOAc was added to dilute the mixture and washed with NH3·H2O and saturated NaCl (aq). The organic fraction was dried over anhydrous Na2SO4, evaporated and the residue purified by a silica gel packed flash chromatography column, using ethyl acetate/hexane as the eluent.

Reference： [1]Tetrahedron Letters,2020

81
[ 78941-93-2 ]
[ 17865-11-1 ]
7-chloro-8-(4-(trimethylsilyl)benzyl)quinoline [ No CAS ]

Reference： [1]Chemistry - A European Journal,2020

82
C₁₉H₁₅S₂⁽¹⁺⁾*CF₃O₃S^(1-) [ No CAS ]
[ 17865-11-1 ]
[ 17964-20-4 ]

Yield	Reaction Conditions	Operation in experiment
96%	With bis(tri-t-butylphosphine)palladium(0); sodium hydrogencarbonate; In dichloromethane; acetone; at 20℃; for 12h;Inert atmosphere; Schlenk technique; Sealed tube;	Under a nitrogen atmosphere, a mono-substituted aromatic hydrocarbon substrate 1a (0.2 mmol), thioanthracene-S-oxide (0.24 mmol) was added to a 25 mL Schlenk tube, and DCM (1.0 mL) was added, followed by stirring at -40C.After slowly dropping Tf2O (0.24 mmol), it was stirred at -40C for 30 minutes, followed by stirring at room temperature for 1 hour.Then, under a nitrogen atmosphere, sodium bicarbonate (0.6 mmol), arylboronic acid substrate 4e (0.3 mmol), bis(tri-tert-butylphosphine) palladium (0.01 mmol), acetone (1.0 mL) was added, and the cap was screwed tightly. At room temperature, the reaction was stirred for 12 hours.After the reaction was completed, a small amount of DCM was added to quench the reaction, the celite was filtered, and the solvent was removed under reduced pressure. The crude product was separated and purified by a preparation plate (hexane) to obtain a white solid 3e (46.0 mg) in 96% yield.

Reference： [1]Chemical Communications,2020,vol. 56,p. 5058 - 5061
[2]Patent: CN111187130,2020,A .Location in patent: Paragraph 0188-0191

83
[ 109-83-1 ]
[ 131543-46-9 ]
[ 17865-11-1 ]
4-methyl-3-(4-(trimethylsilyl)phenyl)morpholin-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%		General procedure: A mixture of a 1,2-aminoalcohol (8.4mmol, 1.2 eq) in EtOH (5.0mL) and water (2.5mL) was treated with an arylboronic acid (7.0mmol, 1.0 eq). The mixture was placed under nitrogen and heated to 60C for 15min, after which aqueous glyoxal (40% solution, 0.95mL, 8.4mmol, 1.2 eq) was added in one portion. Heating was continued at 60C for 24h. The mixture was cooled, the EtOH was evaporated and the residue was diluted with water (5mL) and EtOAc (40mL, with warming to 45C if necessary) to dissolve all solids. The EtOAc was separated, washed twice with water, then with brine, dried (Na2SO4) and concentrated. If the residue was a solid, then it was recrystallized, filtered and dried under vacuum. If the residue was an oil or a glass, it was purified by silica gel chromatography.

Reference： [1]Tetrahedron,2020,vol. 76

84
2,2''-dibromo-6,6''-dinitro-5'-phenyl-1,1':3',1''-terphenyl [ No CAS ]
[ 17865-11-1 ]
(3',6'''-dinitro-5''-phenyl-[1,1':2',1'':3'',1''':2''',1''''-quinquephenyl]-4,4''''-diyl)bis(trimethylsilane) [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2020,vol. 59,p. 8873 - 8879
Angew. Chem.,2020,vol. 132,p. 8958 - 8964,7

85
2-bromo-5'-(2-bromo-6-nitrophenyl)-6-nitro-1,1':3',1'':4'',1'''-quaterphenyl [ No CAS ]
[ 17865-11-1 ]
(5''-([1,1'-biphenyl]-4-yl)-3',6'''-dinitro-[1,1':2',1'':3'',1''':2''',1''''-quinquephenyl]-4,4''''-diyl)bi-s(trimethylsilane) [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2020,vol. 59,p. 8873 - 8879
Angew. Chem.,2020,vol. 132,p. 8958 - 8964,7

86
[ 17865-11-1 ]
[ 19199-46-3 ]
1-morpholino-2-phenyl-3-(4-(trimethylsilyl)phenyl)propan-1-one [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2020,vol. 59,p. 8430 - 8434
Angew. Chem.,2020,vol. 132,p. 8508 - 8512,5

87
[ 17865-11-1 ]
[ 1009-43-4 ]

Reference： [1]Journal of the American Chemical Society,2021,vol. 143,p. 20042 - 20048

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H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 17865-11-1 ] {[proInfo.proName]}

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[ 17865-11-1 ] Synthesis Path-Upstream 1~5

[ 17865-11-1 ] Synthesis Path-Downstream 1~87

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