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ChemicalBook--->CAS DataBase List--->110301-23-0

110301-23-0

110301-23-0 Structure

110301-23-0 Structure
IdentificationBack Directory
[Name]

4-Amino-3,5-difluorobenzonitrile
[CAS]

110301-23-0
[Synonyms]

4-Cyano-2,6-difluoroaniline
4-Amino-3,5-difluorobenzonitrile
Benzonitrile, 4-amino-3,5-difluoro-
[EINECS(EC#)]

670-347-6
[Molecular Formula]

C7H4F2N2
[MDL Number]

MFCD03407467
[MOL File]

110301-23-0.mol
[Molecular Weight]

154.12
Chemical PropertiesBack Directory
[Melting point ]

110-111℃
[Boiling point ]

235.5±40.0 °C(Predicted)
[density ]

1.36±0.1 g/cm3(Predicted)
[storage temp. ]

Keep in dark place,Inert atmosphere,Room temperature
[form ]

solid
[pka]

-1.07±0.10(Predicted)
[color ]

Grey to purple
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302+H312+H332-H315-H319-H335
[Precautionary statements ]

P260-P301+P312-P280
[HS Code ]

2926907090
Hazard InformationBack Directory
[Uses]

4-Amino-3,5-difluorobenzonitrile can be used to prepare tricyclic AKR1C3 dependent KARS inhibitors to treat diseases and disorders mediated by an AKR1C3 dependent KARS inhibitor.
[Synthesis]

2,6-DIFLUORO-4-IODOANILINE

141743-49-9

Copper(I) Cyanide

544-92-3

4-Amino-3,5-difluorobenzonitrile

110301-23-0

General procedure for the synthesis of 4-amino-3,5-difluorobenzonitrile from 2,6-difluoro-4-iodoaniline and cuprous cyanide: a mixture of 2,6-difluoro-4-iodoaniline and cuprous cyanide in N,N-dimethylformamide (DMF) was heated and refluxed for 48 hours. Upon completion of the reaction, the mixture was filtered through a diatomaceous earth pad to remove insoluble impurities. The filtrate was transferred to a partition funnel and partitioned by adding dichloromethane and water. The extraction of the aqueous phase was repeated twice with dichloromethane. All organic phases were combined and washed with saturated brine and subsequently dried over anhydrous sodium sulfate. The desiccant was removed by filtration and the filtrate was concentrated under reduced pressure to give the crude product. The crude product was purified by column chromatography using hexane/ethyl acetate (4:1, v/v) as eluent, resulting in the target product 4-amino-3,5-difluorobenzonitrile (1.03 g, 66% yield) in yellow solid form. The product was characterized by 1H NMR (300 MHz, CDCl3): δ 7.15 (dd, 2H, J = 2.4, 6.0 Hz), 4.28 (br s, 2H).

[References]

[1] Patent: WO2006/98554, 2006, A1. Location in patent: Page/Page column 78
Spectrum DetailBack Directory
[Spectrum Detail]

4-Amino-3,5-difluorobenzonitrile(110301-23-0)1HNMR
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