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2-Amino-4-fluorobenzonitrile

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2-Amino-4-fluorobenzonitrile Basic information
Uses
Product Name:2-Amino-4-fluorobenzonitrile
Synonyms:4-Fluoroanthranilonitrile, 2-Cyano-5-fluoroaniline;Amino-4-fluorobenzonitrile;2-Amino-4-fluorobenzonitrile;Benzonitrile, 2-amino-4-fluoro-;4-Fluoroanthranilonitrile
CAS:80517-22-2
MF:C7H5FN2
MW:136.13
EINECS:
Product Categories:Phenyls & Phenyl-Het
Mol File:80517-22-2.mol
2-Amino-4-fluorobenzonitrile Structure
2-Amino-4-fluorobenzonitrile Chemical Properties
Melting point 102.2 °C (decomp)
Boiling point 284.7±25.0 °C(Predicted)
density 1.25±0.1 g/cm3(Predicted)
storage temp. Keep in dark place,Inert atmosphere,Room temperature
form crystals
pka0.80±0.10(Predicted)
color Light purple
Safety Information
HazardClass TOXIC
HS Code 2926907090
MSDS Information
2-Amino-4-fluorobenzonitrile Usage And Synthesis
Uses2-Amino-4-fluorobenzonitrile is a useful research chemical for organic synthesis and other chemical processes.
Synthesis
2,4-Difluorobenzonitrile

3939-09-1

2-AMINO-4-FLUOROBENZONITRILE

80517-22-2

4-AMINO-2-FLUOROBENZONITRILE

53312-80-4

Using 2,4-difluorobenzonitrile (2.78 g, 20 mmol) and 3,4,5-trimethoxybenzylamine (3.94 g, 20 mmol) as raw material, the two were mixed and heated at 140 °C for 40 min. After completion of the reaction, the mixture was cooled to room temperature and subsequently dissolved in trifluoroacetic acid (TFA, 20 mL) and stirred at room temperature overnight. Afterwards, the mixture was concentrated using a rotary evaporator and subsequently partitioned between 1N NaOH solution (~100 mL, adjusted to alkaline) and ethyl acetate (100 mL). After separation of the organic layer, the aqueous layer was extracted with additional ethyl acetate (100 mL). All organic layers were combined, washed with brine (50 mL), dried over anhydrous magnesium sulfate (MgSO4) and concentrated to give an oil. Separation of the mixture by column chromatography (eluent: 10% to 40% hexane solution of ethyl acetate) gave two well separated isomeric products. Further concentration gave 4-amino-2-fluorobenzonitrile (1.07 g, 39% yield) as a white solid. The structure of the product was confirmed by LC/MS (m/z = 177.8, corresponding to the determination of [M+H]+ in acetonitrile).

References[1] Patent: US2008/76813, 2008, A1. Location in patent: Page/Page column 28
2-Amino-4-fluorobenzonitrile Preparation Products And Raw materials
Raw materials2,4-Difluorobenzonitrile-->4-Amino-2-fluorobenzonitrile
Preparation Products2,4-Dichloro-7-fluoroquinazoline-->7-Fluoroquinazoline-2,4(1H,3H)-dione
Tag:2-Amino-4-fluorobenzonitrile(80517-22-2) Related Product Information
FIPRONIL-DESULFINYL AMINOACETONITRILE 2-Nitrobenzonitrile 2-Chlorobenzonitrile 2-Amino-4-fluorobenzonitrile 4-Fluoro-2-nitrobenzonitrile Benzonitrile, 2-amino-4,5-difluoro- (9CI) IFLAB-BB F2108-0005 4-FLUORO-2-ISOCYANATOBENZONITRILE 4-FLUORO-2-IMIDAZOL-1-YL-BENZONITRILE