(E)-2-(2-cyclopropylvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: (E)-2-(2-cyclopropylvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 849061-99-0
• Molecular Formula: C11H19 B O2
• Molecular Weight: 194.082
• Hs Code.: 2934999090
• European Community (EC) Number: 641-146-0
• Nikkaji Number: J3.344.102I,J2.898.738B
• Wikidata: Q76511213
• Mol file: 849061-99-0.mol

Synonyms:849061-99-0;(E)-2-Cyclopropylvinylboronic acid pinacol ester;(E)-2-(2-cyclopropylvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-[(E)-2-CYCLOPROPYLETHENYL]-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;(trans)-2-Cyclopropylvinylboronic acid pinacol ester;trans-2-Cyclopropylvinylboronic acid pinacol ester;2-(2-CYCLOPROPYLVINYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;2-(2-cyclopropylethenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;trans-2-Cyclopropylvinylboronic acid pinacol ester,96%;MFCD07369776;SCHEMBL447591;SCHEMBL447592;FCWYPDPDAZGFRJ-BQYQJAHWSA-N;AKOS015893167;GS-5856;1092449-35-8;CS-0145823;EN300-802219;H10376;EN300-1722097;A863908;Z1255379736;(trans)-2-Cyclopropylvinylboronic acid pinacol ester, 96%;2-[(E)-2-cyclopropylvinyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property of (E)-2-(2-cyclopropylvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Vapor Pressure: 0.434mmHg at 25°C
• Refractive Index: n20/D 1.466(lit.)
• Boiling Point: 90-95 °C/3-4 mmHg(lit.)
• Flash Point: 93 °C
• PSA: 18.46000
• Density: 0.937 g/mL at 25 °C(lit.)
• LogP: 2.58400
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 194.1478100
• Heavy Atom Count: 14
• Complexity: 238

Purity/Quality:

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

(E)-2-Cyclopropylvinylboronicacidpinacolester ^*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=CC2CC2
• Isomeric SMILES: B1(OC(C(O1)(C)C)(C)C)/C=C/C2CC2

Technology Process of (E)-2-(2-cyclopropylvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 7 articles about (E)-2-(2-cyclopropylvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 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: 99.0%

Cyclopropylacetylene (6746-94-7) + bis(pinacol)diborane (73183-34-3) → (E)-4,4,5,5-tetramethyl-2-(cyclopropyl-1-ethenyl)-1,3,2-dioxaborolane (849061-99-0)

Guidance literature:

With sodium methylate; copper; In ethanol; at 20 ℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.0c01469

Reference yield: 91.0%

Cyclopropylacetylene (6746-94-7) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → (E)-4,4,5,5-tetramethyl-2-(cyclopropyl-1-ethenyl)-1,3,2-dioxaborolane (849061-99-0)

Guidance literature:

With zirconocene dichloride; triethylamine; at 60 ℃; for 16h; Inert atmosphere;

DOI:10.1021/ol402237w

Reference yield: 63.0%

Cyclopropylacetylene (6746-94-7) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → (E)-4,4,5,5-tetramethyl-2-(cyclopropyl-1-ethenyl)-1,3,2-dioxaborolane (849061-99-0) + 2-(2-cyclopropylethynyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1432491-43-4)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; iron(II) triflate; In toluene; at 100 ℃; for 36h; chemoselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1002/adsc.201800588

upstream raw materials:

Cyclopropylacetylene

2,3-dimethyl-2,3-butane diol

2-[(E)-2-cyclopropylvinyl]-1,3,2-benzodioxaborole

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

Downstream raw materials:

[2-((E)-2-cyclopropylvinyl)-phenyl]phosphonic acid diethyl ester

[5-chloro-2-((E)-2-cyclopropylvinyl)phenyl]phosphonic acid diethyl ester

[2-((E)-2-cyclopropylvinyl)-5-methoxyphenyl]phosphonic acid diethyl ester

trans-2-cyclopropylvinylboronic acid

Refernces

• 1、 Bismuto, Alessandro,Cowley, Michael J.,Thomas, Stephen P.. "Zwitterion-Initiated Hydroboration of Alkynes and Styrene". supporting information. p. 2382 - 2385. Retrieved 2021/01/18.
• 2、 Aelterman, Maude,Jubault, Philippe,Poisson, Thomas,Sayes, Morgane. "Electrochemical Hydroboration of Alkynes". supporting information. p. 8277 - 8282. Retrieved 2021/05/27.