2'-BROMOACETANILIDE Chemical Properties

Melting point:

96.5-100.5 °C(lit.)

Boiling point:

346.8±25.0 °C(Predicted)

Density 

1.543±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

14.19±0.70(Predicted)

form 

Crystalline Powder

color 

White

BRN 

2086970

CAS DataBase Reference

614-76-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29242990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2'-BROMOACETANILIDE Usage And Synthesis

Uses

2''-Bromoacetanilide is used as a reagent in the preparation of furan-2-ylmethylene thiazolidinediones as novel, potent, and selective inhibitors of phosphoinositide 3-kinase γ.

Synthesis

General procedure for the synthesis of 2'-bromoacetanilide from ethanoic anhydride and o-bromoaniline: o-bromoaniline (22.0 g, 128 mmol), acetic anhydride (13.06 g, 128 mmol) and a catalytic amount of 4-dimethylaminopyridine (DMAP) were dissolved in dichloromethane (100 mL), and stirred at 0 °C. The reaction mixture was slowly warmed to room temperature and stirring was continued overnight. Upon completion of the reaction, the reaction mixture was washed with saturated aqueous sodium bicarbonate solution and subsequently concentrated. The concentrated residue was ground with a solvent mixture of hexane/dichloromethane, the solid product was collected by filtration and rinsed with hexane to give 2'-bromoacetanilide (25.4 g, 92.8% yield). The high performance liquid chromatography (HPLC) retention time (Rt) was 1.523 min.

References

[1] Journal of Medicinal Chemistry, 2003, vol. 46, # 11, p. 2187 - 2196
[2] Organic Letters, 2004, vol. 6, # 19, p. 3293 - 3296
[3] Organic Letters, 2016, vol. 18, # 22, p. 5896 - 5899
[4] Dyes and Pigments, 2018, vol. 159, p. 419 - 428
[5] Patent: US2005/192310, 2005, A1. Location in patent: Page/Page column 20

2'-BROMOACETANILIDE(614-76-6)Related Product Information

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