2-(Bromomethyl)-3-phenyloxirane

Base Information

• Chemical Name: 2-(Bromomethyl)-3-phenyloxirane
• CAS No.: 60633-79-6
• Molecular Formula: C9H9BrO
• Molecular Weight: 213.074
• DSSTox Substance ID: DTXSID30546582
• Nikkaji Number: J1.015.639D
• Mol file: 60633-79-6.mol

Synonyms:2-(Bromomethyl)-3-phenyloxirane;rac-(2R,3S)-2-(bromomethyl)-3-phenyloxirane, trans;60633-79-6;24193-22-4;SCHEMBL3604580;DTXSID30546582

Chemical Property of 2-(Bromomethyl)-3-phenyloxirane

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 211.98368
• Heavy Atom Count: 11
• Complexity: 132

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2C(O2)CBr

Technology Process of 2-(Bromomethyl)-3-phenyloxirane

There total 11 articles about 2-(Bromomethyl)-3-phenyloxirane 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: 88.6%

Cinnamyl bromide (4392-24-9) → (+/-)-(2S,3R)-2-(bromomethyl)-3-phenyloxirane (24193-22-4,60633-79-6)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 12h;

Reference yield: 81.0%

trans-2,3-epoxy-3-phenylpropan-1-ol (40641-81-4) → (+/-)-(2S,3R)-2-(bromomethyl)-3-phenyloxirane (24193-22-4,60633-79-6)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.orglett.7b01381

Reference yield: 68.0%

3-bromo-1-phenyl-1-propenyl bromide (4392-24-9) → 1-bromo-3-phenyl-2-epoxypropane (60633-79-6)

Guidance literature:

With tert.-butylhydroperoxide; In water; acetonitrile; at 82 ℃; for 18h; Sealed tube;

DOI:10.3762/BJOC.17.46

upstream raw materials:

Cinnamyl bromide

(2RS,3SR)-3-bromo-3-phenyl-1,2-epoxypropane

(+/-)-threo-2-[bromo(phenyl)methyl]-oxirane

3-bromo-1-phenyl-1-propenyl bromide

Downstream raw materials:

trimethyl phosphite

benzyl vinyl ether

(Z)-Propiophenone enolate

3-phenyl-2-propanol

Refernces

• 1、 Zhang, Hao,Ma, Shiqiang,Yuan, Ziyun,Chen, Peng,Xie, Xingang,Wang, Xiaolei,She, Xuegong. "Palladium-Promoted Neutral 1,4-Brook Rearrangement/Intramolecular Allylic Cyclization Cascade Reaction: A Strategy for the Construction of Vinyl Cyclobutanols". . p. 3478 - 3481. Retrieved 2017/07/15.
• 2、 Greszler, Stephen N.,Reichard, Holly A.,Micalizio, Glenn C.. "Asymmetric synthesis of dihydroindanes by convergent alkoxide-directed metallacycle-mediated bond formation". supporting information; scheme or table. p. 2766 - 2774. Retrieved 2012/03/22.