(E)-3-(tert-Butyldimethylsilyloxy)propene-1-yl-boronic acid pinacol ester

Base Information

• Chemical Name: (E)-3-(tert-Butyldimethylsilyloxy)propene-1-yl-boronic acid pinacol ester
• CAS No.: 114653-19-9
• Molecular Formula: C15H33BO4Si
• Molecular Weight: 298.306
• European Community (EC) Number: 870-803-6
• DSSTox Substance ID: DTXSID30450211
• Nikkaji Number: J1.060.872D,J3.316.735K
• Wikidata: Q82269822
• Mol file: 114653-19-9.mol

Synonyms:114653-19-9;(E)-3-(tert-Butyldimethylsilyloxy)propene-1-yl-boronic acid pinacol ester;(E)-tert-butyldimethyl((3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl)oxy)silane;tert-butyl-dimethyl-[(E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-enoxy]silane;tert-Butyldimethyl((3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl)oxy)silane;1426333-09-6;SCHEMBL2411670;SCHEMBL2411677;DTXSID30450211;LUURLZJMKOVITO-ZHACJKMWSA-N;MFCD15144803;(E)-2-[3-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1-propenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-[(1E)-3-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1-propenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;AS-76295;CS-0154945;EN300-21913471;A1-02594;J-003118;Z2588077002;(E)-3-(tert-Butyldimethylsilyloxy)propene-1-yl-boronic acid pinacol ester, 97%;(E)-tert-butyldimethyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyloxy)silane;2-[(E)-3-(tert-Butyldimethylsiloxy)-1-propenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-[3-(tert-Butyl-dimethyl-silanyloxy)-propenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane;2-[3-(tert-Butyldimethylsilyloxy)-1-propenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;tert-butyl(dimethyl){[(2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-yl]oxy}silane;Tert-butyl(dimethyl){[(E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-yl]oxy}silane;TERT-BUTYLDIMETHYL{[(2E)-3-(TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PROP-2-EN-1-YL]OXY}SILANE

Chemical Property of (E)-3-(tert-Butyldimethylsilyloxy)propene-1-yl-boronic acid pinacol ester

Chemical Property:

• Boiling Point: 297.2±42.0 °C(Predicted)
• Flash Point: >110℃
• PSA: 27.69000
• Density: 0.910 g/mL at 25 °C
• LogP: 4.19580
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 298.2135515
• Heavy Atom Count: 20
• Complexity: 354

Purity/Quality:

98%,99%, ^*data from raw suppliers

(E)-3-(tert-Butyldimethylsilyloxy)propene-1-yl-boronic acid pinacol ester 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C=CCO[Si](C)(C)C(C)(C)C
• Isomeric SMILES: B1(OC(C(O1)(C)C)(C)C)/C=C/CO[Si](C)(C)C(C)(C)C
• Uses: (E)-3-(tert-Butyldimethylsilyloxy)propene-1-yl-boronic acid pinacol ester can be used as a reactant in: Palladium-catalyzed Suzuki-Miyaura coupling reaction. The synthesis of anti-homoallylic alcohols by allylation reaction with aldehydes in the presence of iridium complex-catalyst. The preparation of α-imino aldehydes.

Technology Process of (E)-3-(tert-Butyldimethylsilyloxy)propene-1-yl-boronic acid pinacol ester

There total 7 articles about (E)-3-(tert-Butyldimethylsilyloxy)propene-1-yl-boronic acid pinacol ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

tert-Butyldimethyl(prop-2-ynyloxy)silane (76782-82-6) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → tert-butyl (dimethyl){[(2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-yl]oxy}silane (114653-19-9)

Guidance literature:

With Schwartz's reagent; triethylamine; Inert atmosphere;

DOI:10.1016/j.tetlet.2014.01.092

Reference yield: 46.0%

tert-Butyldimethyl(prop-2-ynyloxy)silane (76782-82-6) + bis(pinacol)diborane (73183-34-3) → tert-butyl (dimethyl){[(2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-yl]oxy}silane (114653-19-9)

Guidance literature:

With water; In toluene; at 80 ℃; regioselective reaction; Schlenk technique; Sealed tube;

DOI:10.1021/jacs.1c08088

Reference yield: 44.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + tert-Butyldimethyl(prop-2-ynyloxy)silane (76782-82-6) → tert-butyl (dimethyl){[(2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-yl]oxy}silane (114653-19-9)

Guidance literature:

tert-Butyldimethyl(prop-2-ynyloxy)silane; With Schwartz's reagent; benzo[1,3,2]dioxaborole; In dichloromethane; at 0 - 20 ℃; for 24h; Schlenk technique; Inert atmosphere;

2,3-dimethyl-2,3-butane diol; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1039/c7ob00211d

upstream raw materials:

tert-Butyldimethyl(prop-2-ynyloxy)silane

bis(pinacol)diborane

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

tert-butyldimethylsilyl chloride

Downstream raw materials:

(E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-ol

Refernces

• 1、 Jing, Hongyu,Li, Jiong,Li, Wen-Hao,Li, Yadong,Wang, Dingsheng,Wang, Yu,Yang, Jiarui,Zhang, Jian,Zhao, Jie. "Creating High Regioselectivity by Electronic Metal-Support Interaction of a Single-Atomic-Site Catalyst". supporting information. p. 15453 - 15461. Retrieved 2021/09/30.
• 2、 -. "SUBSTITUTED 3-PHENYLQUINAZOLIN-4(3H)-ONES AND USES THEREOF". Page/Page column 98; 99. . Retrieved 2019/04/26.