Benzenemethanol, alpha-(bromomethyl)-, 1-acetate, (alphaR)-

Base Information

• Chemical Name: Benzenemethanol, alpha-(bromomethyl)-, 1-acetate, (alphaR)-
• CAS No.: 73908-24-4
• Molecular Formula: C₁₀H₁₁BrO₂
• Molecular Weight: 243.1
• DSSTox Substance ID: DTXSID901223460
• Mol file: 73908-24-4.mol

Synonyms:Benzenemethanol, alpha-(bromomethyl)-, 1-acetate, (alphaR)-;DTXSID901223460;73908-24-4

Chemical Property of Benzenemethanol, alpha-(bromomethyl)-, 1-acetate, (alphaR)-

Chemical Property:

• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 241.99424
• Heavy Atom Count: 13
• Complexity: 164

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)OC(CBr)C1=CC=CC=C1
• Isomeric SMILES: CC(=O)O[C@@H](CBr)C1=CC=CC=C1

Technology Process of Benzenemethanol, alpha-(bromomethyl)-, 1-acetate, (alphaR)-

There total 6 articles about Benzenemethanol, alpha-(bromomethyl)-, 1-acetate, (alphaR)- 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: 86.0%

acetic anhydride (108-24-7) + (R)-2-bromo-1-phenylethanol (73908-23-3) → (-)-(R)-2-bromo-1-phenyl-1-acetoxyethane (73908-24-4)

Guidance literature:

In pyridine; for 10h; Ambient temperature;

DOI:10.1021/jo01304a044

Reference yield:

(RS)-1-bromo-2-acetoxy-2-(phenyl)ethane (5837-69-4) → (S)-2-bromo-1-phenylethanol (2425-28-7,73908-23-3,74497-33-9,76155-80-1) + (-)-(R)-2-bromo-1-phenyl-1-acetoxyethane (73908-24-4)

Guidance literature:

With Candida antarctica lipase B; In aq. phosphate buffer; at 45 ℃; for 16h; pH=7; enantioselective reaction; Enzymatic reaction;

DOI:10.1016/j.mcat.2020.110819

Reference yield:

vinyl acetate (108-05-4,9003-20-7) + 2-Bromo-1-phenylethanol (2425-28-7) → (S)-2-bromo-1-phenylethanol (2425-28-7,73908-23-3,74497-33-9,76155-80-1) + (R)-2-bromo-1-phenylethanol (73908-23-3) + (-)-(R)-2-bromo-1-phenyl-1-acetoxyethane (73908-24-4) + (S)-1-bromo-2-acetoxy-2-(phenyl)ethane

Guidance literature:

With Burkholderia cepacia lipase; In toluene; at 32 ℃; for 24h; optical yield given as %ee; enantioselective reaction; Resolution of racemate; Enzymatic reaction;

DOI:10.1016/j.molcatb.2010.03.002

upstream raw materials:

acetic anhydride

(R)-2-bromo-1-phenylethanol

α-bromoacetophenone

vinyl acetate