[ CAS No. 1186026-67-4 ] {[proInfo.proName]}

Name: 1186026-67-4|Trimethyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane|98%
Brand: Ambeed
SKU: A220184
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Quality Control of [ 1186026-67-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1186026-67-4 ]

SDS Specification

Alternatived Products of [ 1186026-67-4 ]

Product Details of [ 1186026-67-4 ]

CAS No. :	1186026-67-4	MDL No. :	MFCD09037796
Formula :	C₁₅H₂₅BO₂Si	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OPGOPAKVZDQUMR-UHFFFAOYSA-N
M.W :	276.25	Pubchem ID :	17999382
Synonyms :

Calculated chemistry of [ 1186026-67-4 ]

Physicochemical Properties

Num. heavy atoms :	19
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.6
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	85.9
TPSA :	18.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-4.64 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	4.71
Log Po/w (WLOGP) :	2.53
Log Po/w (MLOGP) :	2.54
Log Po/w (SILICOS-IT) :	1.6
Consensus Log Po/w :	2.28

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.62
Solubility :	0.0066 mg/ml ; 0.0000239 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.83
Solubility :	0.00412 mg/ml ; 0.0000149 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.26
Solubility :	0.00151 mg/ml ; 0.00000548 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.91

Safety of [ 1186026-67-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1186026-67-4 ]

* 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.

Downstream synthetic route of [ 1186026-67-4 ]

[ 1186026-67-4 ] Synthesis Path-Downstream 1~47

1
[ 76-09-5 ]
C₉H₁₅BSi [ No CAS ]
[ 1186026-67-4 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 5370 - 5373

2
[ 1186026-67-4 ]
[ 100-39-0 ]
[ 93961-29-6 ]
[ 1334531-92-8 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 5370 - 5373

3
[ 1186026-67-4 ]
[ 17889-23-5 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 16449 - 16451,3

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 90 - 100℃;	General procedure: After the bromine compound (1 equivalent) was dissolved in DMF,Bis (pinacolato) diboron (1.1 eq.), Pd (dppf) Cl2 (0.03 mmol)After addition of KOAc (3 eq) And stirred at 90 to 100 C. When the reaction was complete, DMF was removed by distillation and extracted with CH2Cl2 and water.The organic layer was dried over MgSO4 and concentrated. The resulting compound was purified by silicagel column and recrystallized to give product Sub2.

5
[ 1186026-67-4 ]
[ 1443645-32-6 ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 7575 - 7586

6
[ 1186026-67-4 ]
[ 1443645-35-9 ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 7575 - 7586

7
[ 950202-24-1 ]
[ 1186026-67-4 ]
[ 1443645-30-4 ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 7575 - 7586

8
[ 6999-03-7 ]
[ 73183-34-3 ]
[ 1186026-67-4 ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 7575 - 7586

9
[ 1186026-67-4 ]
4,4”-dibromo-4’,5’-dimethyl-o-terphenyl [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 14074 - 14077

10
[ 1186026-67-4 ]
4,4”-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4’,5’-dimethyl-o-terphenyl [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 14074 - 14077

11
[ 1186026-67-4 ]
C₅₆H₄₈ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 14074 - 14077

12
[ 1186026-67-4 ]
[ 24932-48-7 ]
4,4”-bis(trimethylsilyl)-4’,5’-dimethyl-o-terphenyl [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 14074 - 14077

13
[ 61676-62-8 ]
[ 6999-03-7 ]
[ 1186026-67-4 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 14074 - 14077

14
[ 1186026-67-4 ]
[ 1602576-69-1 ]
[ 1602576-73-7 ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 1525 - 1528
Angew. Chem.,2014,vol. 126,p. 1551 - 1554,4

15
[ 768-32-1 ]
[ 73183-34-3 ]
[ 1186026-67-4 ]
trimethyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With [(1,5-cyclooctadiene)(OH)iridium(I)]2; 2,2'-bis-[bis-(3,5-dimethyl-phenyl)-phosphanyl]-biphenyl; In tert-butyl methyl ether; at 85℃; for 20h;Glovebox; Inert atmosphere; Sealed tube;Catalytic behavior;	General procedure: A 20-mL glass vessel equipped with J. Young O-ring tap containing a magnetic stirringbar was dried in an oven at 100 C and then introduced into an argon-filled glove box while thevessel was hot. After cooling the vessel to room temperature, strychnine (1a) (502 mg, 1.50mmol), B2pin2 (572 mg, 2.25 mmol, 1.5 equiv), [Ir(cod)OH]2 (14.7 mg, 23.2 mumol, 1.5 mol%),Xyl-BIPHEP (L1) (28.9 mg, 45.5 mumol, 3.0 mol%), and dry THF (1.5 mL) were added to thevessel. The vessel was sealed with O-ring tap and then heated at 85 C for 3 days in an 8-wellreaction block with stirring. After cooling the reaction mixture to 0 C in an ice bath and thenwarming to room temperature, the solvent was removed under reduced pressure. The borylationproducts were obtained by reverse-phase column chromatography (H2O/MeCN = 7:3 to 0:10)(452 mg, 65% yield, 1b/1c = 73:27). The ratio of isomers was determined by 1H NMR analysis(600 MHz, CDCl3). The major product 1b and the minor product 1c were obtained by furtherpurification of the mixture by GPC (1b: 162 mg, 23% yield; 1c: 76.1 mg, 11% yield). A singlecrystal of 1b was obtained by adding Et2O to CHCl3 solution, and the structure of 1b wasconfirmed by x-ray crystallographic analysis. A single crystal of 1c was obtained from CHCl3solution under pentane vapor, and the structure of 1b was confirmed by x-ray crystallographicanalysis.

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 5193 - 5198
[2]Journal of the American Chemical Society,2015,vol. 137,p. 5193 - 5198
[3]Chem,2020,vol. 6,p. 985 - 993

16
[ 768-32-1 ]
[ 73183-34-3 ]
[ 1186026-67-4 ]
trimethyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane [ No CAS ]
[ 383175-93-7 ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 5193 - 5198

17
[ 1186026-67-4 ]
1,4-bis(4''-iodo-2',6'-dimethylbiphenyl)-1,4-dimethoxy-2,3,5,6-tetrakis(4''-tert-butylphenyl)cyclohexa-2,5-diene [ No CAS ]
1,4-bis(4''-trimethylsilyl-2,6-dimethylterphenyl)-1,4-dimethoxy-2,3,5,6-tetrakis(4''-tert-butylphenyl)cyclohexa-2,5-diene [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 10341 - 10346
Angew. Chem.,2015,vol. 127,p. 10482 - 10487,6

18
[ 1186026-67-4 ]
1,4-bis(4'-chloro-3',5'-dimethylphenyl)-1,4-dimethoxy-2,3,5,6-tetrakis(4''-tert-butylphenyl)cyclohexa-2,5-diene [ No CAS ]
1,4-bis(4''-trimethylsilyl-2',6'-dimethylbiphenyl)-1,4-dimethoxy-2,3,5,6-tetrakis(4''-tert-butylphenyl)cyclohexa-2,5-diene [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 10341 - 10346
Angew. Chem.,2015,vol. 127,p. 10482 - 10487,6

19
[ 768-32-1 ]
[ 25015-63-8 ]
[ 1186026-67-4 ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 10336 - 10340

20
[ 1186026-67-4 ]
[ 99-90-1 ]
[ 1228595-71-8 ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 10336 - 10340

21
[ 491-37-2 ]
[ 1186026-67-4 ]
[ 1395931-80-2 ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 14,p. 777 - 784
[2]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 2613 - 2616

22
[ 22515-25-9 ]
[ 73183-34-3 ]
[ 1186026-67-4 ]

Reference： [1]Organic Letters,2016,vol. 18,p. 2966 - 2969

23
[ 17882-12-1 ]
[ 1186026-67-4 ]

Reference： [1]Organic Letters,2016,vol. 18,p. 2966 - 2969

24
[ 1186026-67-4 ]
C₁₆H₁₄BF₂INO₂ [ No CAS ]
C₂₅H₂₇BF₂NO₂Si [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 1409 - 1414

25
[ 67-56-1 ]
[ 74-85-1 ]
[ 1186026-67-4 ]
[ 1082066-32-7 ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 12386 - 12389

26
[ 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

27
bis[4-(trimethylsilyl)phenyl] sulfoxide [ No CAS ]
[ 73183-34-3 ]
[ 1186026-67-4 ]

Yield	Reaction Conditions	Operation in experiment
81%	With chloro(2-dicyclohexylphosphino-2?,6?-dimethoxy-1,1?-biphenyl)(2?-amino-1,1?-biphenyl-2-yl) palladium(II); lithium hexamethyldisilazane; In tetrahydrofuran; at 80℃; for 20h;Schlenk technique; Inert atmosphere;	General procedure: A Schlenk tube was charged with diphenyl sulfoxide (1a) (41 mg, 0.20mmol), SPhos Pd G2 (7.2 mg, 0.010 mmol), B 2 pin 2 (0.20 g, 0.80 mmol),and LiN(SiMe 3 ) 2 (0.20 g, 1.2 mmol). THF (0.80 mL) was added to thetube and the resulting mixture was stirred at 80 C for 20 h. After thereaction was complete, saturated aqueous NH 4 Cl (2 mL) was addedand the resulting biphasic mixture was extracted with Et 2 O (5 × 5mL). The combined organic layer was dried over Na 2 SO 4 , passedthrough a pad of silica gel, and concentrated under reduced pressure.The residue was purified by preparative TLC (hexane/EtOAc = 10:1) toprovide (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (2a)(54 mg, 0.26 mmol, 66%) as a colorless oil. All the resonances in the 1 Hand 13 C NMR spectra were consistent with the reported data. 12a

Reference： [1]Synthesis,2017,vol. 49,p. 4769 - 4774

28
[ 1186026-67-4 ]
4,4′-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1′-biphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With tetrakis(acetonitrile)palladium(II) bis(tetrafluoroborate); o-tetrachloroquinone; In chloroform; 1,2-dichloro-ethane; at 60℃; for 10h;Inert atmosphere;	General procedure: To a screw-capped glass tube containing a magnetic stirrer bar were addedaryltrimethylsilane 1 (0.30 mmol, 1.0 equiv), Pd(CH3CN)4(BF4)2 (3.3 mg, 0.075 mmol, 2.5mol%), CHCl3 (1.5 mL) or CHCl3/1,2-dichloroethane (1:4, 1.5 mL) and o-chloranil (55.9 mg, 0.225 mmol, 0.75 equiv) under a stream of nitrogen. After stirring at 60 C for 10 hours, thereaction mixture was cooled to room temperature, and then passed through a short pad of silicagel (eluent: CHCl3). After the organic solvent was removed under reduced pressure, the residuewas purified by flash column chromatography on silica gel to yield biaryl 2. The reactions wereconducted in 0.50 mmol scale for 1a in 2.5 mL of CHCl3, 0.30 mmol scale for 1b-1t in 1.5 mLof the indicated solvent, and 0.20 mmol scale for 1w in the indicated solvent, respectively.

Reference： [1]Chemistry Letters,2017,vol. 46,p. 1701 - 1704

29
[ 1176888-27-9 ]
[ 1186026-67-4 ]
C₃₄H₃₈Si₂ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 1216 - 1222

30
[ 1186026-67-4 ]
C₅₈H₅₆Br₂O₂Si₂ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 1216 - 1222

31
[ 1186026-67-4 ]
C₅₆H₅₂Br₂O₂Si₂ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 1216 - 1222

32
[ 1186026-67-4 ]
C₁₅H₃₁BO₂Si [ No CAS ]
C₁₅H₃₁BO₂Si [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 8297 - 8300
Angew. Chem.,2018,vol. 130,p. 8429 - 8432,4

33
[ 4805-22-5 ]
[ 1186026-67-4 ]
5-bromo-5′-[4-(trimehylsilyl)phenyl]-2,2′-bithiophene [ No CAS ]