4-Bromo-2-chlorophenol

4-Bromo-2-chlorophenol Property

Melting point:

47-49 °C (lit.)

Boiling point:

232-235 °C (lit.)

Density 

1.6170

refractive index 

1.5859

Flash point:

>230 °F

storage temp. 

Inert atmosphere,Room Temperature

Water Solubility 

Practically insoluble in water

form 

Low Melting Mass or Crystalline Needles, Powder and Chunks

pka

7.92±0.18(Predicted)

color 

White to off-white

BRN 

2042867

InChIKey

VIBJPUXLAKVICD-UHFFFAOYSA-N

CAS DataBase Reference

3964-56-5(CAS DataBase Reference)

NIST Chemistry Reference

Phenol, 4-bromo-2-chloro-(3964-56-5)

EPA Substance Registry System

Phenol, 4-bromo-2-chloro- (3964-56-5)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-24/25

RIDADR 

UN 3077 9/PG 3

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29081990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

4-Bromo-2-chlorophenol Chemical Properties,Usage,Production

Chemical Properties

white to off-white low melting mass or crystalline

Uses

4-Bromo-2-chlorophenol was used as reagent during the synthesis of 7-arylbenzo
[b][1,4]oxazin derivatives.

Definition

ChEBI: A halophenol that is phenol in which the hydrogens at positions 2 and 4 have been replaced by chlorine and bromine, respectively.

General Description

4-Bromo-2-chlorophenol is biologically inactive metabolite of profenofos, an organophosphorus pesticide. It undergoes enzyme-catalyzed copolymerization with phenols catalyzed by extracellular laccase of the fungus Rhizoctonia praticola.

Synthesis

GENERAL METHODS: REACTION CONDITIONS: Thiourea (5.1 mol%, 2 mg, 0.026 mmol) was added to an acetonitrile solution (10 mL) containing N-bromosuccinimide (NBS, 1.15 eq, 104.4 mg, 0.587 mmol). 2-Chlorophenol (56.3 mg, 0.51 mmol) was immediately added to the resulting stirred solution and stirred for 10 min at room temperature. The reaction was quenched by the addition of 10% Na2S2O3 aqueous solution (10 mL) and extracted with ethyl acetate (70 mL). The organic phase was washed sequentially with 10% Na2S2O3 aqueous solution (2 × 10 mL), deionized water (3 × 15 mL), and saturated saline (2 × 10 mL). The organic phase was dried with anhydrous Na2SO4 and concentrated under reduced pressure to remove the solvent. The products were separated and purified by centrifugal thin layer chromatography (silica gel 60GF254 plate, 2 mm thickness, unfolding agent 5% dichloromethane/hexane). The products obtained are known compounds and their structures were confirmed by GC-MS, IR, 1H NMR and 13C NMR, and the spectral data were in agreement with those reported in the literature.

References

[1] Tetrahedron, 2017, vol. 73, # 46, p. 6564 - 6572
[2] Dalton Transactions, 2013, vol. 42, # 33, p. 11926 - 11940
[3] Journal of Organic Chemistry, 1997, vol. 62, p. 4504 - 4506
[4] Journal of Organic Chemistry, 1997, vol. 62, p. 4504 - 4506
[5] Tetrahedron, 2007, vol. 63, # 23, p. 4959 - 4967