ChemicalBook Product Catalog Chemical Reagents Organic reagents Aromatic alcohol 2-Bromo-4-chlorophenol

2-Bromo-4-chlorophenol

Product Name2-Bromo-4-chlorophenol
CAS695-96-5
MFC6H4BrClO
MW207.45
EINECS211-785-6
MOL File695-96-5.mol

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
form	powder to lump to clear liquid
pka	7.98±0.18(Predicted)
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
Storage Class	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

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

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

17005-59-3

695-96-5

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

Preparation Products And Raw materials

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