(E)-tert-Butyldimethyl((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-yl)oxy)silane

Base Information

• Chemical Name: (E)-tert-Butyldimethyl((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-yl)oxy)silane
• CAS No.: 480425-30-7
• Molecular Formula: C16H33BO3Si
• Molecular Weight: 312.333
• Hs Code.: 2934999090
• European Community (EC) Number: 867-499-2
• DSSTox Substance ID: DTXSID20584337
• Nikkaji Number: J1.857.306G,J3.468.731E
• Wikidata: Q82475984
• Mol file: 480425-30-7.mol

Synonyms:480425-30-7;(E)-tert-Butyldimethyl((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-yl)oxy)silane;tert-Butyldimethyl((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-yl)oxy)silane;trans-4-(tert-Butyldimethylsiloxy)-1-buten-1-ylboronic acid pinacol ester;tert-butyl-dimethyl-[(E)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-enoxy]silane;TRANS-4-(T-BUTYLDIMETHYLSILYLOXY)-1-BUTEN-1-YLBORONIC ACID, PINACOL ESTER;(Z)-tert-butyldimethyl((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-yl)oxy)silane;1426333-10-9;tert-butyl(dimethyl){[(3e)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-yl]oxy}silane;TERT-BUTYLDIMETHYL{[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BUT-3-EN-1-YL]OXY}SILANE;TRANS-2-(4-(TERT-BUTYLDIMETHYLSILYLOXY)&;C16H33BO3Si;SCHEMBL379286;SCHEMBL379287;DTXSID20584337;ODTSJDLTXNDTBB-ZRDIBKRKSA-N;MFCD05664265;ZB0295;AKOS016001174;AS-55595;CS-0154943;C15845;EN300-7377021;A871981;Z2315585506;(E)-4-(tert-butyldimethylsiloxy)-1-buten-1ylboronic acid pinacol ester;trans-4-(t-Butyldimethylsilyloxy)-1-buten-1-ylboronic acid,pinacol ester;tert-butyldimethyl{[(3E)-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-yl]oxy}silane;trans-4-(tert-Butyldimethylsiloxy)-1-buten-1-ylboronic acid pinacol ester, 95%;(E)-tert-butyldimethyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-enyloxy)silane

Chemical Property of (E)-tert-Butyldimethyl((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-yl)oxy)silane

Chemical Property:

• Vapor Pressure: 0.00103mmHg at 25°C
• Refractive Index: n20/D 1.4470(lit.)
• Boiling Point: 297-298 °C(lit.)
• Flash Point: >230 °F
• PSA: 27.69000
• Density: 0.888 g/mL at 25 °C(lit.)
• LogP: 4.58590
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 312.2292016
• Heavy Atom Count: 21
• Complexity: 368

Purity/Quality:

97% ^*data from raw suppliers

trans-4-(tert-Butyldimethylsiloxy)-1-buten-1-ylboronic acid pinacol ester 95% ^*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=CCCO[Si](C)(C)C(C)(C)C
• Isomeric SMILES: B1(OC(C(O1)(C)C)(C)C)/C=C/CCO[Si](C)(C)C(C)(C)C
• Uses: trans-4-(tert-Butyldimethylsiloxy)-1-buten-1-ylboronic acid pinacol ester can be used as a substrate:In the catalyst-free Zweifel olefination of alkenyl boronic esters using triorganocerium reagents.In the study of carbosulfenylation reactions of alkenylboronates.To prepare chiral tris(boronates), which are important building blocks for preparing synthetically challenging compounds.

Technology Process of (E)-tert-Butyldimethyl((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-yl)oxy)silane

There total 5 articles about (E)-tert-Butyldimethyl((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-yl)oxy)silane 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: 90.0%

4-(tert-butyldimethylsilyloxy)-1-butyne (78592-82-2) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → tert-butyl(dimethyl){[(3E)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-yl]oxy}silane (480425-30-7)

Guidance literature:

With triethylamine; Schwartz's reagent; at 60 ℃; for 16h;

DOI:10.1016/j.tetlet.2005.10.031

Reference yield: 62.0%

4-(tert-butyldimethylsilyloxy)-1-butyne (78592-82-2) + bis(pinacol)diborane (73183-34-3) → tert-butyl(dimethyl){[(3E)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-yl]oxy}silane (480425-30-7)

Guidance literature:

With water; In toluene; at 80 ℃; for 10h; regioselective reaction; Schlenk technique; Sealed tube;

DOI:10.1021/jacs.1c08088

Reference yield:

4-[(tert-butyldimethylsilyl)oxy]-1-butene (108794-10-1) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → (Z)-tert-butyldimethyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-enyloxy)silane (116376-35-3) + tert-butyldimethyl-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)butoxy]silane (1140737-38-7) + tert-butyl(dimethyl){[(3E)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-yl]oxy}silane (480425-30-7)

Guidance literature:

With norborn-2-ene; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; (S,S)-[2-(4’-isopropyloxazolin-2’-yl)ferrocenyl]diphenylphosphine; In tetrahydrofuran; at 28 ℃; for 9h; Overall yield = 83 %; stereoselective reaction; Inert atmosphere; Glovebox; Sealed tube;

DOI:10.1002/anie.201506328

upstream raw materials:

4-(tert-butyldimethylsilyloxy)-1-butyne

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

bis(pinacol)diborane

4-[(tert-butyldimethylsilyl)oxy]-1-butene

Downstream raw materials:

(E)-5-(4-(tert-butyldimethylsilyloxy)but-1-enyl)-3-(1-methyl-1H-pyrazol-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

3-{4-[(E)-4-(tert-butyl-dimethyl-silanoxy)-but-1-enyl]-benzyl}-2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine

(E)-tert-butyl-(4-(3,4-dichlorophenyl)but-3-enyloxy)dimethylsilane

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