3-BROMO-5-CHLOROTOLUENE

3-BROMO-5-CHLOROTOLUENE Property

Melting point:

25℃

Boiling point:

222.3±20.0℃ (760 Torr)

Density 

1.535±0.06 g/cm3 (20 ºC 760 Torr)

Flash point:

101.5±11.9℃

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform, Ethyl Acetate

form 

Solid

color 

Pale Yellow

InChI

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

InChIKey

YRIKDGJWRMHTJP-UHFFFAOYSA-N

SMILES

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

Safety

Hazard Codes 

Xi,Xn

Risk Statements 

22

Hazard Note 

Irritant

HS Code 

2903998090

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.

P271Use only outdoors or in a well-ventilated area.

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

3-BROMO-5-CHLOROTOLUENE Chemical Properties,Usage,Production

Uses

3-Bromo-5-chlorotoluene is a reagent used in the synthesis of novel benzophenones towards the discovery of potent, next generation HIV nonnucleoside reverse transcriptase inhibitors.

Synthesis

2-Bromo-6-chloro-4-methylaniline (30 mmol) was used as a starting material, which was dissolved in a mixed solution of acetic acid (60 mL), water (25 mL), and concentrated hydrochloric acid (7 mL), and the reaction system was subsequently cooled to 5 °C. A solution of sodium nitrite (48 mmol, 3.31 g) in water (12 mL) was added slowly and dropwise while keeping the temperature below 5 °C. After the dropwise addition, the reaction mixture was continued to be stirred at 5-10 °C for 2 hours. Subsequently, the reaction solution was poured into a 50% hypophosphite solution pre-cooled to 0 °C and stirred for 48 h at room temperature. Upon completion of the reaction, extraction was carried out with dichloromethane (3 x 120 mL). The organic phases were combined, washed with saturated saline (100 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent. Finally, the residue was purified by fast column chromatography to obtain the target product 3-bromo-5-chlorotoluene.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 22, p. 5568 - 5572
[2] Journal of Medicinal Chemistry, 2001, vol. 44, # 12, p. 1866 - 1882
[3] Journal of Medicinal Chemistry, 2001, vol. 44, # 12, p. 1866 - 1882