2-Bromo-4-nitroanisole Chemical Properties

Melting point:

104-106 °C (lit.)

Boiling point:

306.3±22.0 °C(Predicted)

Density 

1.640±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

color 

White to Brown

BRN 

2556372

CAS DataBase Reference

5197-28-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2909309090

MSDS

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

2-Bromo-4-nitroanisole Usage And Synthesis

Uses

2-Bromo-4-nitroanisole is mainly used as an organic synthetic raw material or intermediate compound. It can be used to prepare 3-Bromo-4-methoxyaniline and its derivatives.

Synthesis

The general procedure for the synthesis of 2-bromo-4-nitroanisole from 4-nitroanisole was as follows: 1-methoxy-3,5-dimethylbenzene (100 mg, 0.73 mmol), N-bromosuccinimide (NBS, 260 mg, 1.46 mmol), and a stainless steel ball (5 mm in diameter) were placed in a 10 mL stainless steel grinding jar. The ball milling reaction was carried out and the reaction process was monitored by thin layer chromatography (TLC) and proton nuclear magnetic resonance (1H NMR). Upon completion of the reaction, the reaction mixture was transferred to 30 mL of ethyl acetate and cooled at 0°C. The filtrate containing the product and the spent succinimide precipitate were separated by filtration through filter paper. The filtrate was concentrated under vacuum to give 250 mg (yield: 85%) of 2-bromo-4-nitroanisole as a colorless powder. To assess the efficiency of the large-scale synthesis, another monobromination reaction was carried out with 1.3 g of 1-methoxy-3,5-dimethylbenzene for 1 h. The product was isolated in 87% yield. During the reaction, the ball milling equipment was suspended and a small amount of sample was removed from the reaction tank for TLC and 1H NMR analysis, after which the reaction was continued, and the time of this operation was not included in the total reaction time.

References

[1] Tetrahedron Letters, 2015, vol. 55, # 13, p. 2154 - 2156
[2] Tetrahedron Letters, 2014, vol. 55, # 13, p. 2154 - 2156
[3] Applied Catalysis A: General, 2010, vol. 384, # 1-2, p. 18 - 26
[4] International Journal of Chemical Kinetics, 2016, vol. 48, # 2, p. 98 - 105
[5] Journal of the Indian Chemical Society, 1983, vol. 60, p. 953 - 957

2-Bromo-4-nitroanisole(5197-28-4)Related Product Information

• EOSIN B
• EOSIN B
• 2-Bromo-4-nitroanisole
• 2-BROMO-4-NITRO(TRIFLUOROMETHOXY)BENZENE
• 2-BROMO-6-FLUORO-4-NITROANISOLE
• 2-BROMO-5-NITROANISOLE
• 4-BROMO-2-NITROANISOLE
• 2-Bromo-3-nitroanisole 99%,2-BROMO-3-NITROANISOLE
• 4-BROMO-3-NITROANISOLE
• 3-BROMO-5-NITROANISOLE
• 4-Nitroanisole
• 2-BROMO-1-(4-FLUOROPHENOXY)-4-NITROBENZENE
• 1,3-DIBROMO-2-METHOXY-5-NITROBENZENE
• 3-Bromo-2-nitroanisole
• 3-BROMO-4-NITROANISOLE
• 4-(2-BROMO-4-NITROPHENOXY)BENZENECARBONITRILE
• 3-(2-BROMO-4-NITROPHENOXY)PYRIDO[1,2-A]INDOLE-10-CARBONITRILE
• N-(3-BROMO-2,6-DIMETHOXY-5-NITROBENZOYL)-N'-(2,3,4,5,6-PENTAFLUOROPHENYL)UREA