4'-Fluoro-3'-nitroacetophenone Chemical Properties

Melting point:

47-51 °C

Boiling point:

118-120°C 0,8mm

Density 

1.336±0.06 g/cm3(Predicted)

Flash point:

118-120°C/0.8mm

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

Crystalline Powder

color 

Light yellow

BRN 

2211976

InChIKey

PTCNZDJJIOLIKQ-UHFFFAOYSA-N

CAS DataBase Reference

400-93-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29143990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:ALFA

4'-Fluoro-3'-nitroacetophenone Usage And Synthesis

Chemical Properties

light yellow crystalline powder

Uses

4''-?Fluoro-?3''-?nitroacetophenone is used as reactant/reagent in preparation of substituted furans via copper-catalyzed radical addition of acetophenones to alkynes.

Synthesis

General procedure for the synthesis of 4-fluoro-3-nitroacetophenone from 4-fluoroacetophenone: 1-(4-fluorophenyl)ethanone (1.10 g, 7.97 mmol) was dissolved in concentrated H2SO4 (5 mL) under stirring conditions. Subsequently, a mixed acid consisting of concentrated HCl and concentrated H2SO4 (2 mL) was slowly added. HNO3 (1.50 mL) was added slowly and dropwise at -15°C. The reaction mixture was continued to be stirred at -15 °C for 80 min, after which it was poured into ice-cold H2O (120 mL) and extracted with EtOAc (2 × 100 mL). The organic layers were combined and washed sequentially with H2O (100 mL) and brine (100 mL), and the organic layer was separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 100-200 mesh, 40% EtOAc in hexane solution) to afford 4-fluoro-3-nitroacetophenone (0.80 g, 55%) as an off-white solid.1H NMR (400 MHz, CDCl3) δ 2.64 (s, 3H), 7.39 (t, J=9.30 Hz, 1H), 8.20- 8.26 (m, 1H), 8.57-8.66 (m, 1H).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 10, p. 1725 - 1728
[2] Patent: WO2017/89453, 2017, A1. Location in patent: Page/Page column 55
[3] Patent: WO2007/103260, 2007, A1. Location in patent: Page/Page column 63-64
[4] Archiv der Pharmazie (Weinheim, Germany), 1957, vol. 290, p. 587,595
[5] Archiv der Pharmazie, 1963, vol. 296, p. 324 - 336

4'-Fluoro-3'-nitroacetophenone(400-93-1)Related Product Information

• 4-Fluoronitrobenzene
• Acetophenone
• 2-Nitroacetophenone
• 3-Nitroacetophenone
• 4-Fluoroacetophenone
• 4'-(Trifluoromethyl)acetophenone
• 4'-Hydroxyacetophenone
• 4-Nitroacetophenone
• 4'-Methylacetophenone
• 2-Bromoacetophenone
• Nitrobenzene
• Fluorine
• 4'-CHLORO-4-FLUORO-3-NITROBENZOPHENONE
• 4'-Fluoro-3'-nitroacetophenone
• 2-FLUORO-5-NITROACETOPHENONE
• 2',4'-DICHLORO-5'-FLUORO-3'-NITROACETOPHENONE
• BENZENEPROPANENITRILE, 2,4-DIFLUORO-5-NITRO-B-OXO-
• 2-bromo-1-(4-fluoro-3-nitrophenyl)ethanone