3-BROMO-4-CHLOROTOLUENE Chemical Properties

Boiling point:

112 °C

Density 

1,55 g/cm³

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform, Methanol (Slightly)

form 

liquid

Specific Gravity

1.55

color 

Colourless

InChI

InChI=1S/C7H6BrCl/c1-5-2-3-7(9)6(8)4-5/h2-4H,1H3

InChIKey

UWXPTVKKHVOZLJ-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

57310-39-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,N,Xn

Risk Statements 

22-51/53

Safety Statements 

61

RIDADR 

UN 2811 6.1 / PGIII

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2903998090

3-BROMO-4-CHLOROTOLUENE Usage And Synthesis

Uses

2-Bromo-1-chloro-4-methyl-benzene is a useful synthetic intermediate. It can be used to synthesize N-heterocycle-fused phenanthridines via palladium-catalyzed tandem N-H/C-H arylation of aryl-N-heteroarenes with dihaloarenes. It can also be used to synthesize substituted fluorenes.

Synthesis

General procedure for the synthesis of 4-chloro-3-bromotoluene from 2-bromo-4-methylaniline: tert-butyl nitrite (48 mmol, 6.34 mL) and anhydrous copper(II) chloride (60 mmol, 8.07 g) were mixed at 65 °C in anhydrous acetonitrile (100 mL). 2-Bromo-4-methylaniline (30 mmol) was slowly added under vigorous stirring for 30 min. Subsequently, the reaction mixture was continued to be stirred at 65 °C for 2 hours. After completion of the reaction, the mixture was cooled, poured into 20% hydrochloric acid (400 mL) and extracted with ether (3 x 120 mL). The organic phases were combined, washed with brine (100 mL), dried over anhydrous Na2SO4 and the solvent was subsequently evaporated. The crude product was purified by fast column chromatography.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 22, p. 5568 - 5572

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