3-Bromo-2-chlorophenol

Base Information

• Chemical Name: 3-Bromo-2-chlorophenol
• CAS No.: 863870-87-5
• Molecular Formula: C6H4BrClO
• Molecular Weight: 207.454
• Hs Code.: 2908199090
• European Community (EC) Number: 801-910-8
• DSSTox Substance ID: DTXSID20216242
• Nikkaji Number: J801.758A
• Wikidata: Q72453201
• Mol file: 863870-87-5.mol

Synonyms:3-Bromo-2-chlorophenol;863870-87-5;66024-94-0;Phenol, bromochloro-;Phenol,3-bromo-2-chloro-;MFCD08166321;Phenol, 3-bromo-2-chloro-;bromochlorophenol;2-Chloro-3-bromophenol;SCHEMBL263538;DTXSID20216242;DUKKNDLIWRYBCT-UHFFFAOYSA-N;BBL101150;CL8469;STL554946;AKOS005257424;CS-W019088;GS-4395;SY027065;AM20050176;FT-0600096;EN300-119394;J-511852

Chemical Property of 3-Bromo-2-chlorophenol

Chemical Property:

• Vapor Pressure: 0.0176mmHg at 25°C
• Melting Point: 60 °C
• Refractive Index: 1.619
• Boiling Point: 246.1 °C at 760 mmHg
• PKA: 7.53±0.10(Predicted)
• Flash Point: 102.7 °C
• PSA: 20.23000
• Density: 1.788 g/cm³
• LogP: 2.80810
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 205.91341
• Heavy Atom Count: 9
• Complexity: 99.1

Purity/Quality:

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

3-Bromo-2-chlorophenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C(=C1)Br)Cl)O

Technology Process of 3-Bromo-2-chlorophenol

There total 6 articles about 3-Bromo-2-chlorophenol 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: 72.0%

3-Bromophenol (591-20-8) → 3-bromo-4-chlorophenol (13659-24-0) + 5-bromo-2-chlorophenol (183802-98-4) + 3 -bromo-2-chlorophenol (863870-87-5)

Guidance literature:

With N-chloro-succinimide; (R)-[1,1′-binaphthalene]-2,2′-diylbis-(diphenylphosphine sulfide); In chloroform-d1; at 20 ℃; for 2h; regioselective reaction;

DOI:10.1021/acs.orglett.6b02650

Reference yield:

2-monochlorophenol (95-57-8) + diphenyl sulfide (139-66-2) → 3 -bromo-2-chlorophenol (863870-87-5)

Guidance literature:

With hydrogen bromide; bromine; Zinc chloride;

Reference yield:

O-3-bromophenyl N,N-diethylcarbamate (863870-72-8) → 3 -bromo-2-chlorophenol (863870-87-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 92 percent / hexachloroethane / tetrahydrofuran; hexane / -78 - 20 °C

2.1: 82 percent / NaOH / ethanol / Heating

With sodium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; ethanol; hexane;

DOI:10.1021/jo0508402

upstream raw materials:

2-amino-3-bromophenol

3-Bromophenol

O-3-bromophenyl N,N-diethylcarbamate

2-monochlorophenol

Downstream raw materials:

3,4,6-tribromo-2-chloro-phenol

2-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Refernces

• 1、 Maddox, Sean M.,Dinh, Andrew N.,Armenta, Felipe,Um, Joann,Gustafson, Jeffrey L.. "The Catalyst-Controlled Regiodivergent Chlorination of Phenols". supporting information. p. 5476 - 5479. Retrieved 2016/11/17.
• 2、 Sanz, Roberto,Castroviejo, M. Pilar,Fernandez, Yolanda,Fananas, Francisco J.. "A new and efficient synthesis of 4-functionalized benzo[6]furans from 2,3-dihalophenols". . p. 6548 - 6551. Retrieved 2007/10/03.