N-(4-fluoro-3-nitrophenyl)acetamide

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N-(4-fluoro-3-nitrophenyl)acetamide Basic information
Product Name:N-(4-fluoro-3-nitrophenyl)acetamide
Synonyms:N-(4-fluoro-3-nitrophenyl)acetamide;N-(3-Nitro-4-fluorophenyl)acetamide;N-(4-fluoro-3-nitro-phenyl)ethanamide;N-(4-Fluoro-3-nitrophenyl)acetamide, 5-(Acetylamino)-2-fluoronitrobenzene, 5-Acetamido-2-fluoronitrobenzene;4'-Fluoro-3'-nitroacetanilide 98%;Acetamide,N-(4-fluoro-3-nitrophenyl)-;4-Fluoro-3-nitrophenylacetamide
CAS:351-32-6
MF:C8H7FN2O3
MW:198.15
EINECS:206-510-1
Product Categories:
Mol File:351-32-6.mol
N-(4-fluoro-3-nitrophenyl)acetamide Structure
N-(4-fluoro-3-nitrophenyl)acetamide Chemical Properties
Melting point 138.5 °C
Boiling point 385.9±32.0 °C(Predicted)
density 1.429±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
form solid
pka13.18±0.70(Predicted)
color Yellow-brown
EPA Substance Registry SystemAcetamide, N-(4-fluoro-3-nitrophenyl)- (351-32-6)
Safety Information
TSCA TSCA listed
HS Code 2924297099
MSDS Information
N-(4-fluoro-3-nitrophenyl)acetamide Usage And Synthesis
Synthesis
4-Fluoro-3-nitroaniline

364-76-1

Acetyl chloride

75-36-5

N-(4-fluoro-3-nitrophenyl)acetamide

351-32-6

Step B. 4-Fluoro-3-nitroaniline (5.0 g, 32.0 mmol) and triethylamine (TEA, 6.7 mL, 48.0 mmol) were dissolved in 50 mL of dichloromethane (DCM) at 0 °C. Subsequently, acetyl chloride (2.75 mL, 38.4 mmol) was slowly added dropwise, and after completion of the dropwise addition the reaction mixture was warmed to room temperature and stirred overnight. Upon completion of the reaction, the organic layer was washed sequentially with 5% aqueous potassium bisulfate (KHSO4), saturated aqueous sodium bicarbonate (NaHCO3) and brine, and then dried over anhydrous magnesium sulfate (MgSO4). By concentrating the organic phase and crystallizing from DCM, 5.3 g of N-(4-fluoro-3-nitrophenyl)acetamide was obtained in 84% yield. The structure of the product was confirmed by 1H NMR (400 MHz, chloroform-D): δ 2.04 (s, 3H), 7.51 (dd, J = 11.23,9.08 Hz, 1H), 7.80 (dd, J = 9.08,4.00,2.93 Hz, 1H), 8.47 (dd, J = 7.03,2.73 Hz, 1H), 10.38 (s 1H).

References[1] Patent: WO2005/72741, 2005, A1. Location in patent: Page/Page column 26
[2] Patent: WO2006/33630, 2006, A1. Location in patent: Page/Page column 34; 35
[3] Patent: WO2005/30733, 2005, A1. Location in patent: Page/Page column 67; 140
[4] Patent: WO2006/33629, 2006, A1. Location in patent: Page/Page column 17
[5] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 20, p. 5545 - 5549
N-(4-fluoro-3-nitrophenyl)acetamide Preparation Products And Raw materials
Raw materials4-Fluoro-3-nitroaniline-->Acetyl chloride-->Acetic anhydride-->Triethylamine-->Dichloromethane
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