Bromobenzene-2,3-oxide

Base Information

• Chemical Name: Bromobenzene-2,3-oxide
• CAS No.: 71942-12-6
• Molecular Formula: C₆H₅BrO
• Molecular Weight: 173.009
• DSSTox Substance ID: DTXSID90992647
• Nikkaji Number: J2.790.485H
• Wikidata: Q27116164
• Mol file: 71942-12-6.mol

Synonyms:bromobenzene 2,3-oxide;bromobenzene-2,3-epoxide

Chemical Property of Bromobenzene-2,3-oxide

Chemical Property:

• Vapor Pressure: 0.121mmHg at 25°C
• Boiling Point: 226.6°C at 760 mmHg
• Flash Point: 89.6°C
• PSA: 12.53000
• Density: 1.817g/cm³
• LogP: 1.60240
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 171.95238
• Heavy Atom Count: 8
• Complexity: 171

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2C(O2)C(=C1)Br

Technology Process of Bromobenzene-2,3-oxide

There total 5 articles about Bromobenzene-2,3-oxide 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:

(1aS,5aS)-3,5-dibromo-1a,2,3,5a-tetrahydro-1-benzoxirene → 2-bromo-1a,5a-dihydro-1-benzoxirene (71942-12-6)

Guidance literature:

With sodium methylate; In diethyl ether; at 20 ℃; for 1h;

DOI:10.1039/c3ob40166a

Reference yield:

cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohex-3-ene (174817-06-2) → 2-bromo-1a,5a-dihydro-1-benzoxirene (71942-12-6)

Guidance literature:

Multi-step reaction with 4 steps

1: acetonitrile / 2.5 h / 0 - 20 °C

2: sodium methylate / diethyl ether / 20 °C

3: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / chloroform; tetrachloromethane / 1.5 h / Inert atmosphere; Reflux

4: sodium methylate / diethyl ether / 1 h / 20 °C

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); sodium methylate; In tetrachloromethane; diethyl ether; chloroform; acetonitrile;

DOI:10.1039/c3ob40166a

Reference yield:

(+)-(1S,2R)-1-acetoxy-2,3-dibromocyclohex-3-ene (176166-10-2) → 2-bromo-1a,5a-dihydro-1-benzoxirene (71942-12-6)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium methylate / diethyl ether / 20 °C

2: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / chloroform; tetrachloromethane / 1.5 h / Inert atmosphere; Reflux

3: sodium methylate / diethyl ether / 1 h / 20 °C

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); sodium methylate; In tetrachloromethane; diethyl ether; chloroform;

DOI:10.1039/c3ob40166a

upstream raw materials:

cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohex-3-ene

(+)-(1S,2R)-1-acetoxy-2,3-dibromocyclohex-3-ene

cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene

Refernces