3-Nitrophenacylbromide Chemical Properties

Melting point:

90-96 °C(lit.)

Boiling point:

288.6±15.0 °C(Predicted)

Density 

1.8033 (rough estimate)

refractive index 

1.6090 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Soluble in methanol.

form 

Crystalline Powder

color 

Beige-orange to yellow-green

BRN 

610594

CAS DataBase Reference

2227-64-7(CAS DataBase Reference)

NIST Chemistry Reference

2-Bromo-3'-nitroacetophenone(2227-64-7)

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:2-Bromo-3'-nitroacetophenone
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Nitrophenacylbromide Usage And Synthesis

Chemical Properties

beige-orange to yellow-green crystalline powder

Uses

2-Bromo-3′-nitroacetophenone may be used in the preparation of 2-bromo-3′-nitroacetophenone. It may be used in the preparation of 2-hydroxy-ethyl-1-[(3-nitro-phenyl)-2-oxoethyl]-piperidinium bromide.

General Description

Debromination of 2-bromo-3′-nitroacetophenone in various solvents has been reported.

Synthesis

The general procedure for the synthesis of 2-bromo-3'-nitroacetophenone from m-nitroacetophenone is as follows: preparation of 2-bromo-1-(3-nitrophenyl)acetophenone (2a-1). Aluminum chloride (0.16 g, 1.20 mmol) was added to a suspension of commercially available 3-nitroacetophenone (4.82 g, 29.19 mmol) in anhydrous ether (25 mL). The reaction mixture was cooled to 0 °C, followed by the slow dropwise addition of bromine (1.50 mL, 29.19 mmol). The reaction mixture was stirred at room temperature for 1 h until complete conversion of the feedstock (monitored by 1H NMR) and the reaction was quenched quickly to avoid dibromide formation. After addition of water (30 mL), the mixture was extracted with ether (3 x 30 mL) and dried over anhydrous magnesium sulfate to afford compound 2a-1 as a yellow-brown solid (5.73 g, 97% yield).1H NMR (CDCl3, 200 MHz): δ 4.50 (s, 2H, H1), 7.73 (t, J = 8.0 Hz, 1H, H7), 8.31 ( ddd, J = 7.8, 1.7, 1.1 Hz, 1H, H8), 8.43 (ddd, J = 8.2, 2.3, 1.1 Hz, 1H, H6), 8.76 (t, J = 1.9 Hz, 1H, H4).13C NMR (CDCl3, 200 MHz): δ 30.4, 123.9, 128.2, 130.4, 134.6, 135.2, 148.6, 189.5. MS-ESI (m/z): [M + H]+ = 244.9.

References

[1] Journal of Medicinal Chemistry, 2016, vol. 59, # 18, p. 8276 - 8292
[2] Patent: WO2017/17004, 2017, A1. Location in patent: Page/Page column 17
[3] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 10, p. 2192 - 2196
[4] Tetrahedron Letters, 2011, vol. 52, # 31, p. 4026 - 4029
[5] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 10, p. 1424 - 1430

3-Nitrophenacylbromide(2227-64-7)Related Product Information

• 2-Bromo-5-nitropyridine
• PIPERACETAZINE (250 MG)
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• 2-Nitroacetophenone
• 3-Nitroacetophenone
• 2-Bromoacetophenone
• 4'-Bromoacetophenone
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• Bromine
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• 4-Nitrobenzyl bromide
• 2-BROMO-4'-HYDROXY-3'-NITROACETOPHENONE
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• 2-BROMO-1-(5-CHLORO-2-METHOXY-4-METHYL-3-NITRO-PHENYL)ETHANONE
• 2-BROMO-1-(4-CHLORO-3-NITROPHENYL)ETHAN-1-ONE