4-Bromo-3-nitroanisole Chemical Properties

Melting point:

32-34 °C (lit.)

Boiling point:

153-154 °C/13 mmHg (lit.)

Density 

1.8134 (rough estimate)

refractive index 

1.6090 (estimate)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

powder to lump to clear liquid

color 

White or Colorles to Yellow to Orange

BRN 

2446617

InChI

InChI=1S/C7H6BrNO3/c1-12-5-2-3-6(8)7(4-5)9(10)11/h2-4H,1H3

InChIKey

KCOBIBRGPCFIGF-UHFFFAOYSA-N

SMILES

C1(Br)=CC=C(OC)C=C1[N+]([O-])=O

CAS DataBase Reference

5344-78-5(CAS DataBase Reference)

NIST Chemistry Reference

4-Bromo-3-nitroanisole(5344-78-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25

WGK Germany 

3

HS Code 

29093090

MSDS

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

4-Bromo-3-nitroanisole Usage And Synthesis

Chemical Properties

Yellow to dark brown solid

Uses

4-Bromo-3-nitroanisole was used in the synthesis of:

• 4-bromo-5-methoxyaniline
• 2-(4-methoxy-2-nitrophenylsulfanyl)benzoic acid
• 4-(1-diethylamino-4-pentylamino)-3-nitrochlorobenzene

General Description

FT-IR and FT-Raman spectra of 4-bromo-3-nitroanisole have been studied.

Synthesis

The general procedure for the synthesis of 4-bromo-3-nitroanisole from ice-dyed diazo component 1 was as follows: a solution of sodium nitrite (11.8 g) in water (28 mL) was slowly added dropwise to a 40% solution of nitroaniline (125 mmol) in hydrobromic acid (110 g) over a period of 0.5 h. The temperature of the reaction was maintained at 10 °C. The reaction mixture was stirred at 0-10 °C for 40 min and then filtered. Subsequently, the filtrate was added dropwise to a purple solution of copper(I) bromide (209 mmol) in hydrobromic acid (74 mL) at 0 °C over a period of 1 hour. The reaction mixture was gradually warmed to room temperature and held for 30 min, then warmed to 60 °C for 0.5 h. The reaction was finally heated and refluxed for 1 h. The reaction was carried out at a temperature of 0.5 °F to 0.5 °F. After completion of the reaction, the mixture was partitioned between water (2.0 L) and dichloromethane (600 mL) and the aqueous phase was then extracted with dichloromethane (300 mL). All organic layers were combined and washed sequentially with 10% sodium hydroxide solution (200 mL), water (600 mL), 10% hydrochloric acid (300 mL) and water (600 mL). The organic layer was dried over magnesium sulfate and concentrated to give 4-bromo-3-nitroanisole in 83% yield as a yellow oil.

References

[1] Journal of Organic Chemistry, 1989, vol. 54, # 25, p. 5856 - 5866
[2] Journal of Organic Chemistry, 1992, vol. 57, # 24, p. 6380 - 6382
[3] Journal of the American Chemical Society, 1994, vol. 116, # 26, p. 11797 - 11810
[4] Tetrahedron Letters, 2006, vol. 47, # 16, p. 2739 - 2742
[5] Tetrahedron, 2010, vol. 66, # 37, p. 7418 - 7422

4-Bromo-3-nitroanisole(5344-78-5)Related Product Information

• 4-Methyl-3-nitroanisole
• 1-Chloro-3-nitrobenzene
• 4-Nitrobenzoic acid
• 4-Bromoanisole
• 4-Chloro-3-nitroanisole
• Sodium 3-nitrobenzenesulphonate
• 2-Methyl-3-nitroanisole
• 4-Bromo-3-fluoroanisole
• 1,3-Dinitrobenzene
• Bromine
• 2-BROMO-4-NITROANISOLE,2-BROMO-4-NITROANISOLE 95%
• 3-BROMO-5-NITROANISOLE
• 3-Nitroanisole
• Nitrobenzene
• 3-Bromonitrobenzene
• 4-Nitroanisole
• 2-BROMO-5-NITROANISOLE
• Azoic Diazo Component 1