E-2-Chloromethylvinylboronic acid pinacol ester

Base Information

• Chemical Name: E-2-Chloromethylvinylboronic acid pinacol ester
• CAS No.: 873077-21-5
• Molecular Formula: C9H16BClO2
• Molecular Weight: 202.489
• Hs Code.: 2934999090
• Mol file: 873077-21-5.mol

Synonyms:

Chemical Property of E-2-Chloromethylvinylboronic acid pinacol ester

Chemical Property:

• Refractive Index: n20/D 1.4603
• Boiling Point: 57-62?°C/0.3-0.4?mmHg
• Flash Point: 100?°C
• PSA: 18.46000
• Density: 1.028?g/mL?at 25?°C
• LogP: 2.41280

Purity/Quality:

99% ^*data from raw suppliers

trans-2-Chloromethylvinylboronic acid pinacol ester 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of E-2-Chloromethylvinylboronic acid pinacol ester

There total 1 articles about E-2-Chloromethylvinylboronic 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: 75.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + Pinene (80-56-8,177698-18-9,25766-18-1) + dimethylsulfide borane complex (13292-87-0) + 2-propynyl chloride (624-65-7) → 2-chloromethylvinylboronic acid pinacol ester (873077-21-5)

Guidance literature:

With acetaldehyde; In tetrahydrofuran; under N2; pinene is added dropwise to the borane-complex in THF at 0°C, stirred for 1 h, then for 2 h at r. t., cooled to -35°C, the alkyne is added dropwise, stirred for 1.5 h, then 5 h at r. t., MeCHO is added at 0°C; refluxed for 12 h, evapd. in vac. at r. t., then the diol in THF is added, stirred for 3 h at r. t., distd.;

DOI:10.1080/00397919308012607

Reference yield: 64.0%

2-chloromethylvinylboronic acid pinacol ester (873077-21-5) + dimethyl 2-(3-phenylprop-2-yn-1-yl)malonate (346621-58-7) → (E)-dimethyl 2-(3-phenylprop-2-ynyl)-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl)malonate (1263271-91-5)

Guidance literature:

dimethyl 2-(3-phenylprop-2-yn-1-yl)malonate; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

2-chloromethylvinylboronic acid pinacol ester; In tetrahydrofuran; for 15h; Inert atmosphere;

DOI:10.1016/j.tetlet.2010.11.051

Reference yield:

2-chloromethylvinylboronic acid pinacol ester (873077-21-5) + 1-(2-(1-benzyl-5-methyl-1H-pyrazol-4-yl)-2-oxoethyl)-5-bromopyridin-2(1H)-one + N,N-dimethylammonium chloride (506-59-2) → (E)-1-(2-(1-benzyl-5-methyl-1H-pyrazol-4-yl)-2-oxoethyl)-5-(3-(dimethylamino)prop-1-en-1-yl)pyridin-2(1H)-one

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In 1,4-dioxane; water; at 160 ℃; for 0.5h; Sealed tube; Microwave irradiation;

upstream raw materials:

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

Pinene

dimethylsulfide borane complex

2-propynyl chloride

Downstream raw materials:

(E)-dimethyl 2-(3-phenylprop-2-ynyl)-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl)malonate

Refernces