2-BROMO-4-NITROANILINE Chemical Properties

Melting point:

104°C

Boiling point:

351.8±22.0 °C(Predicted)

Density 

1.7917 (rough estimate)

refractive index 

1.5150 (estimate)

Flash point:

166℃

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

-1.18±0.10(Predicted)

color 

Dark Yellow

Stability:

Hygroscopic

CAS DataBase Reference

13296-94-1(CAS DataBase Reference)

NIST Chemistry Reference

Benzenamine, 2-bromo-4-nitro-(13296-94-1)

EPA Substance Registry System

2-Bromo-4-nitroaniline (13296-94-1)

Safety Information

Hazard Codes 

T,Xi

Risk Statements 

23/24/25-33

Safety Statements 

28-37-45

RTECS 

BW9350000

HazardClass 

IRRITANT

HS Code 

29214200

2-BROMO-4-NITROANILINE Usage And Synthesis

Chemical Properties

Yellow solid

Uses

2-Bromo-4-nitroaniline is used as a reagent in the synthesis of novel tetrahydrothienopyridopyrimidine derivatives which exhibit antibacterial and antifungal activity against a variety of microorganisms in vitro. Also used as a reagent in synthesis of dialkylimidazole inhibitors of Trypanosoma cruzi sterol 14α-demethylase as anti-Chagas disease agents.

Synthesis

Bromine (2.05 mL, 40 mmol) was slowly added dropwise to a solution of 4-nitroaniline (5.0 g, 36 mmol) in acetic acid (150 mL) at room temperature and under argon protection. The reaction mixture was stirred continuously for 2 hours at room temperature. Upon completion of the reaction, the reaction was quenched with dilute aqueous sodium thiosulfate (150 mL) followed by extraction with ethyl acetate (2 x 500 mL). The organic layers were combined and carefully poured into saturated aqueous sodium bicarbonate solution (1 L) and stirred at room temperature for 30 min until the gas release stopped completely. The organic layer was separated, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (petroleum ether/dichloromethane, 3:1) to afford 2-bromo-4-nitroaniline as a yellow solid (6.3 g, 80% yield).1H NMR (400 MHz, CDCl3) δ: 8.39 (1H, d, J = 2.4 Hz), 8.06 (1H, d, J = 2.4 Hz), 6.77 (1H, d, J = 9.2 Hz).

References

[1] Synthesis, 2004, # 17, p. 2809 - 2812
[2] Tetrahedron Letters, 2017, vol. 58, # 48, p. 4559 - 4562
[3] Tetrahedron Letters, 2005, vol. 46, # 51, p. 8959 - 8963
[4] Synthetic Communications, 2010, vol. 40, # 21, p. 3226 - 3232
[5] Journal of the American Chemical Society, 1994, vol. 116, # 26, p. 11797 - 11810

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