2-Bromo-4-chlorophenol Chemical Properties

Melting point:

31-33 °C (lit.)

Boiling point:

121-123 °C/10 mmHg (lit.)

Density 

1.6027 (rough estimate)

refractive index 

1.5730 (estimate)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

methanol: 0.1 g/mL, clear

pka

7.98±0.18(Predicted)

form 

powder to lump to clear liquid

color 

White or Colorles to Yellow to Orange

BRN 

2042871

InChI

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

InChIKey

ZIYRDJLAJYTELF-UHFFFAOYSA-N

SMILES

C1(O)=CC=C(Cl)C=C1Br

CAS DataBase Reference

695-96-5(CAS DataBase Reference)

NIST Chemistry Reference

Phenol, 2-bromo-4-chloro-(695-96-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-28-36/39-24/25

RIDADR 

UN 2020 6.1/PG 3

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29081000

MSDS

• Language:English Provider:2-Bromo-4-chlorophenol
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Bromo-4-chlorophenol Usage And Synthesis

Chemical Properties

White to slightly beige low melting solid

Uses

2-Bromo-4-chlorophenol is a reactant in the preparation of 3-(2-(2,4-dichlorophenoxy)ethoxy)-6-methyl-2-nitropyridine selective sphingosine-1-phosphate 4 receptor (S1P4-R) agonist.

Application

The main use of 2-bromo-4-chlorophenol in the pesticide field is as a key intermediate in the synthesis of profenofos. Profenofos is a highly effective broad-spectrum organophosphorus insecticide with contact and stomach poison effects, and also possesses some fumigation activity. It is widely used to control various pests on crops such as cotton and vegetables.

Synthesis

The general procedure for the synthesis of 2-bromo-4-chlorophenol from the compound (CAS:17005-59-3) is as follows: in a 10 mL round-bottomed flask with a magnetic stir bar, phenols or olefins (0.1 mmol), carbon tetrabromide (CBr4, 33 mg, 0.1 mmol), anhydrous acetonitrile (CH3CN, 1 mL), and dichloro tris(2,2'-) bipyridine)ruthenium(II) (Ru(bpy)3Cl2, 3.8 mg, 0.005 mmol). The reaction mixture was irradiated at room temperature using a blue LED lamp (1 W) and air was continuously passed until the complete disappearance of the raw material was shown by thin layer chromatography (TLC). After completion of the reaction, the solvent was removed by distillation under reduced pressure. Finally, the residue was purified by fast column chromatography to obtain the target product 2-bromo-4-chlorophenol.

References

[1] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 622 - 627

2-Bromo-4-chlorophenol(695-96-5)Related Product Information

• 2-Bromo-4-chlorophenol
• brotianide
• 2,6-DIBROMO-4-CHLOROPHENOL
• 2,2’-methylenebis(6-bromo-4-chlorophenol
• 2-ACETYL-6-BROMO-4-CHLOROPHENOL
• 7-BROMO-5-CHLORO-8-HYDROXYQUINOLINE
• 3-BROMO-5-CHLORO-2,6-DIMETHOXYBENZAMIDE
• 2-Bromo-4-chloroanisole
• 3-Bromo-5-chlorosalicylaldehyde
• 2,6-DIBROMO-4-CHLORO-3,5-DIMETHYLPHENOL
• 3-BROMO-5-CHLORO-2,6-DIMETHOXYBENZOIC ACID
• 4-BROMO-2-CHLOROPHENOL,4-Bromo-2-chlorophenol,98%
• 4-BROMO-3-CHLOROPHENOL
• 3-Bromo-2-chlorophenol
• 3-Bromo-5-chlorophenol
• 4,4'-(3H-2,1-benzoxathiol-3-ylidene)bis[2-bromo-6-chlorophenol] S,S-dioxide,4,4'-[(3H-2,1-Benzoxathiole 2,2-dioxide)-3-ylidene]bis(2-bromo-6-chlorophenol)
• 5-Bromo-2-chlorophenol, 98+%,5-BROMO-2-CHLOROPHENOL
• 4-Chlorophenol