13659-24-0

Basic information

• Product Name: 3-BROMO-4-CHLOROPHENOL
• Synonyms: 3-BROMO-4-CHLOROPHENOL;3-Bromo-4-chlorophenol 97%;2-Bromo-1-chloro-4-hydroxybenzene;Phenol, 3-broMo-4-chloro-
• CAS NO: 13659-24-0
• Molecular Formula: C₆H₄BrClO
• Molecular Weight: 207.45
• Product Categories: Aromatic Phenols;Phenol&Thiophenol&Mercaptan;Bromine Compounds;Chlorine Compounds;Phenols
• Mol File: 13659-24-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 57 °C
• Boiling Point: 273.095 °C at 760 mmHg
• Flash Point: 118.964 °C
• Appearance: /
• Density: 1.788g/cm³
• Vapor Pressure: 0.004mmHg at 25°C
• Refractive Index: 1.619
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 8.56±0.18(Predicted)
• CAS DataBase Reference: 3-BROMO-4-CHLOROPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-4-CHLOROPHENOL(13659-24-0)
• EPA Substance Registry System: 3-BROMO-4-CHLOROPHENOL(13659-24-0)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 13659-24-0(Hazardous Substances Data)

Usage

General Description

3-Bromo-4-chlorophenol is a chemical compound with the molecular formula C6H4BrClO. It is a white to light brown crystalline solid, and is soluble in organic solvents such as ethanol and ether. 3-Bromo-4-chlorophenol is primarily used as an intermediate in the synthesis of pharmaceuticals, pesticides, and dyes. It is also used as a raw material for the production of various chemical compounds, and has applications in the fields of medicine and agriculture. 3-Bromo-4-chlorophenol is a halogenated phenol compound, and as such, it may pose environmental and health hazards, and should be handled with care.

InChI:InChI=1/C6H4BrClO/c7-5-3-4(9)1-2-6(5)8/h1-3,9H

Upstream product

• 57383-80-9 2,3-dibromophenol 
• 7446-70-0 aluminium trichloride 
• 50586-69-1 2,3,6-tribromo-4-chloro-phenol 
• 71-43-2 benzene 
• 591-20-8 3-Bromophenol 
• 695-96-5 2-bromo-4-chlorophenol 
• 634603-83-1 3-bromo-4-nitrosophenol 
• 2732-80-1 2-bromo-1-chloro-4-methoxybenzene 

Downstream Products

• 933585-10-5 (3-bromo-4-chlorophenyl) acetate 

Relevant articles and documents

Catalyst-Controlled Regioselective Chlorination of Phenols and Anilines through a Lewis Basic Selenoether Catalyst

We report a highly efficient ortho-selective electrophilic chlorination of phenols utilizing a Lewis basic selenoether catalyst. The selenoether catalyst resulted in comparable selectivities to our previously reported bis-thiourea ortho-selective catalyst, with a catalyst loading as low as 1%. The new catalytic system also allowed us to extend this chemistry to obtain excellent ortho-selectivities for unprotected anilines. The selectivities of this reaction are up to >20:1 ortho/para, while the innate selectivities for phenols and anilines are approximately 1:4 ortho/para. A series of preliminary studies revealed that the substrates require a hydrogen-bonding moiety for selectivity.

The Catalyst-Controlled Regiodivergent Chlorination of Phenols

Different catalysts are demonstrated to overcome or augment a substrate's innate regioselectivity. Nagasawa's bis-thiourea catalyst was found to overcome the innate para-selectivity of electrophilic phenol chlorination, yielding ortho-chlorinated phenols that are not readily obtainable via canonical electrophilic chlorinations. Conversely, a phosphine sulfide derived from 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) was found to enhance the innate para-preference of phenol chlorination.

Copper(I)-Induced Bromo-Hydrogen Exchange of 2,3-Dibromoanilines

The copper(I)-induced bromine-hydrogen exchange reaction of 2,3-dibromoaniline and 5-substituted 2,3-dibromoanilines in the 2-position has been kinetically studied in water-acetic acid-hydrochloric acid medium at 90 deg C.The dehalogenation reaction is of second order, first order in both substrate and Cu+, and may be interpreted as a reductive substitution, composed of two one-electron steps.The 2,3-dibromophenol was only qualitatively investigated, but gave similar results.