1,3-Dibromo-5-chlorobenzene Chemical Properties

Melting point:

91-94 °C (lit.)

Boiling point:

256 °C

Density 

2.021±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Toluene

form 

powder to crystal

color 

White to Light yellow

InChI

InChI=1S/C6H3Br2Cl/c7-4-1-5(8)3-6(9)2-4/h1-3H

InChIKey

FNKCOUREFBNNHG-UHFFFAOYSA-N

SMILES

C1(Br)=CC(Cl)=CC(Br)=C1

CAS DataBase Reference

14862-52-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

HS Code 

29039990

MSDS

• Language:English Provider:SigmaAldrich

1,3-Dibromo-5-chlorobenzene Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

1,3-Dibromo-5-chlorobenzene is a reactant in the preparation of orally bioavailable 1-(1H-indol-4-yl)-3,5-disubstituted benzene analogs as antimitotic agents.

Synthesis

General procedure for the synthesis of 1,3-dibromo-5-chlorobenzene from 1,3,5-tribromobenzene: 1,3,5-tribromobenzene (9.44 g, 30 mmol) was dissolved in 120 mL of ethyl ether and cooled to -78 °C in a dry ice/acetone bath. Over 10 min, n-butyllithium (13.2 mL of a 2.5 M hexane solution, 33 mmol) was added slowly and dropwise. The reaction mixture was continued to be stirred at -78 °C for 10 min, followed by the addition of hexachloroethane (7.15 g, 30.2 mmol) in batches over 3 min. After addition, the reaction mixture was stirred at -78 °C for 15 minutes, then brought to room temperature and stirred for 3.2 hours. Upon completion of the reaction, the mixture was transferred to a dispensing funnel and partitioned by adding 100 mL of water and 100 mL of ethyl acetate. The aqueous layer was separated and extracted with another 100 mL of ethyl acetate. The organic layers were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the light brown solid product 1,3-dibromo-5-chlorobenzene (7.72 g, 95% yield). The product was characterized by 1H NMR (CDCl3, 300 MHz): δ 7.57 (t, 1H), 7.47 (d, 2H).

References

[1] Patent: EP1208091, 2006, B1. Location in patent: Page/Page column 23
[2] Journal of Medicinal Chemistry, 2006, vol. 49, # 2, p. 727 - 739
[3] Tetrahedron Letters, 1997, vol. 38, # 9, p. 1559 - 1562

1,3-Dibromo-5-chlorobenzene(14862-52-3)Related Product Information

• 2,4-DIBROMOBIPHENYL
• 3,5-Dibromo-4-hydroxybenzaldehyde
• 1,2-Dibromopropane
• 1,2,4-Trichlorobenzene
• Chlorobenzene
• 1,3-Dibromo-5,5-dimethylhydantoin
• 2,2-Bis(bromomethyl)propane-1,3-diol
• 1,2,3-Trichlorobenzene
• Difluorochloromethane
• 4,6-DIBROMO-2,3-DICHLOROANILINE
• 2,6-Dibromo-4-chloroaniline
• 2-CHLORO-4,6-DIBROMOANILINE
• 2,6-DIBROMO-4-CHLORO-3,5-DIMETHYLPHENOL
• 2,6-DIBROMO-4-CHLOROPHENOL
• 2-AMINO-3,5-DIBROMO-6-CHLOROBENZOIC ACID
• 1,4-DIBROMO-2-CHLOROBENZENE,1,4-Dibromo-2-chlorobenzene, 99+%
• 1,3-DIBROMO-2,5-DICHLOROBENZENE
• 3,5-DIBROMO-1,2-DICHLOROBENZENE