2-Bromo-2'-nitroacetophenone Chemical Properties

Melting point:

55-57 °C(lit.)

Boiling point:

335.7±17.0 °C(Predicted)

Density 

1.671±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform, Methanol

form 

Crystalline Powder

color 

White to pale yellow

λmax

262nm(EtOH)(lit.)

InChIKey

SGXUUCSRVVSMGK-UHFFFAOYSA-N

CAS DataBase Reference

6851-99-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-27-28-36/37/39-45

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

HazardClass 

8

PackingGroup 

III

HS Code 

29147000

MSDS

• Language:English Provider:SigmaAldrich

2-Bromo-2'-nitroacetophenone Usage And Synthesis

Chemical Properties

White to pale yellow crystalline powder

Uses

2-Bromo-2′-nitroacetophenone, an electroactive derivative-forming reagent, was used as a precolumn reagent for preparing prostaglandin derivatives.

Uses

2-Bromo-2'-nitroacetophenone is used in the novel synthesis of 5-pyridylindolizine derivatives.

Synthesis Reference(s)

Canadian Journal of Chemistry, 61, p. 400, 1983 DOI: 10.1139/v83-072
The Journal of Organic Chemistry, 49, p. 438, 1984 DOI: 10.1021/jo00177a010

Synthesis

Under argon protection, 2'-nitroacetophenone (20 g, 121 mmol) and anhydrous aluminum trichloride (500 mg, 3.75 mmol) were dissolved in anhydrous ether (600 mL), stirred and cooled to 0 °C. Bromine (6.2 mL, 121 mmol) was added slowly dropwise for a controlled time of 1 hour. After the dropwise addition was completed, the reaction mixture was allowed to gradually warm up to room temperature and stirring was continued for 3 hours (the reaction progress was monitored by TLC). After completion of the reaction, the organic layer was washed with water (3 x 200 mL), dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (dichloromethane/petroleum ether, 70:30) to give 31.7 g of yellow solid 2-bromo-1-(2-nitrophenyl)ethanone. The product was recrystallized with methanol to give 26.1 g of pure product in 88% yield. The product was colorless micro-needle-like crystals; TLC Rf value (dichloromethane/petroleum ether, 70:30) was 0.4; 1H NMR (400 MHz, CDCl3) δ: 8.21 (dd, J=8.1, 1.2 Hz, 1H, Ar-H), 7.79 (td, J=7.5, 1.3 Hz, 1H, Ar-H), 7.68 (ddd, J= 8.1, 7.5, 1.6 Hz, 1H, Ar-H), 7.50 (dd, J=7.5, 1.6 Hz, 1H, Ar-H), 4.30 (s, 2H, CH2); 13C NMR (100 MHz, CDCl3) δ: 194.3 (C=O), 145.4 (Ar-C), 134.9 (Ar-C), 134.8 ( Ar-CH), 131.3 (Ar-CH), 129.1 (Ar-CH), 124.5 (Ar-CH), 33.9 (CH2).

References

[1] Journal of Organic Chemistry, 1984, vol. 49, # 3, p. 438 - 442
[2] Arkivoc, 2014, vol. 2014, # 3, p. 256 - 273
[3] Patent: US4812470, 1989, A
[4] European Journal of Organic Chemistry, 2014, vol. 2014, # 35, p. 7865 - 7877
[5] Angewandte Chemie - International Edition, 2016, vol. 55, # 6, p. 2152 - 2156

2-Bromo-2'-nitroacetophenone(6851-99-6)Related Product Information

• 2-Nitroacetophenone
• 3-Nitroacetophenone
• 2',4'-Dichloroacetophenone
• 4-Nitroacetophenone
• 3-Bromoanisole
• 4'-Hydroxyacetophenone
• 2-Bromoacetophenone
• 4'-Methoxyacetophenone
• 4'-Bromoacetophenone
• Acetophenone
• Bromine
• 3-Bromonitrobenzene
• 2-Bromo-4'-nitroacetophenone
• 4'-Bromo-3'-nitroacetophenone, 99+%,4'-bromo-3'-nitroacetophenone,1-(4-bromo-3-nitrophenyl)ethanone,4-BROMO-3-NITROACETOPHENONE,4'-BROMO-3'-NITROACETOPHENONE
• 3-Nitrophenacylbromide
• 2-BROMO-1-(4,5-DIMETHOXY-2-NITRO-PHENYL)ETHANONE
• 3'-Bromo-4'-nitroacetophenone
• 5'-Bromo-2'-nitroacetophenone