2-CHLORO-1,4-BENZOQUINONE

2-CHLORO-1,4-BENZOQUINONE Property

Melting point:

52-57 °C

Boiling point:

210℃

Density 

1.40

refractive index 

1.4620 (estimate)

Flash point:

83℃

storage temp. 

Storage temp. 2-8°C

form 

Crystals

color 

Yellow to brown

CAS DataBase Reference

695-99-8(CAS DataBase Reference)

Safety

Hazard Codes 

Xi,Xn,F

Risk Statements 

36/37/38-15-10

Safety Statements 

26-37/39-43-36-7/8

WGK Germany 

3

HS Code 

29147000

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.

2-CHLORO-1,4-BENZOQUINONE Chemical Properties,Usage,Production

Chemical Properties

YELLOW TO BROWN CRYSTALS

Uses

2-Chloro-1,4-benzoquinone may be used in the preparation of chloro derivatives of prenylnaphthohydroquinone.

General Description

2-Chloro-1,4-benzoquinone is a quinone derivative. It is one of the intermediate formed during the degradation of 3,4-dichloroaniline in a dielectric barrier discharge plasma reactor. It is formed during lignin peroxidase catalyzed oxidation of 2-chloro-1,4-dimethoxybenzene. 2-Chloro-1,4-benzoquinone on dechlorination yields 1,2,4-trihydroxybenzene.

Synthesis

GENERAL METHOD: Diacetoxyiodobenzene (5 mmol, 1.61 g) and NaHSO4-H2O (1 mmol, 0.138 g) were stirred in an aqueous acetonitrile solution (5 mL of water and 5 mL of acetonitrile) for 10-15 minutes at room temperature. To this reaction mixture, 2-chlorobenzamide (1 mmol) was added and stirring was continued until the reaction was complete (monitored by TLC). Upon completion of the reaction, the reaction mixture was quenched with ice water and subsequently extracted with chloroform (3 x 10 mL). The chloroform layers were combined, washed with water (3 x 20 mL), dried with anhydrous Na2SO4 and concentrated on a rotary evaporator to give the crude product. The crude product was further purified by silica gel column chromatography using ethyl acetate: hexane (1:9, v/v) as eluent to give pure 2-chloro-1,4-benzoquinone.

References

[1] Organic Letters, 2010, vol. 12, # 20, p. 4644 - 4647
[2] Synthetic Communications, 2014, vol. 44, # 4, p. 468 - 473