3-AMINO-4-CHLOROBENZONITRILE Chemical Properties

Melting point:

87-91 °C

Boiling point:

292.0±20.0 °C(Predicted)

Density 

1.33±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

0.85±0.10(Predicted)

color 

Light yellow to Yellow to Orange

CAS DataBase Reference

53312-79-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38-43

Safety Statements 

26-36/37

RIDADR 

3439

WGK Germany 

3

Hazard Note 

Harmful

HazardClass 

6.1

PackingGroup 

III

HS Code 

2926907090

MSDS

• Language:English Provider:SigmaAldrich

3-AMINO-4-CHLOROBENZONITRILE Usage And Synthesis

Application

3-Amino-4-chlorobenzonitrile is a pharmaceutical intermediate. Literature reports that 3-amino-4-chlorobenzonitrile can be used to prepare 2-amino-4-cyano-3',4'-difluoro-1,1'-biphenyl. Fluorinated benzidines are an important class of intermediates widely used in the industrial production of pesticides, pharmaceuticals and other fields.

Synthesis Reference(s)

Tetrahedron Letters, 36, p. 9305, 1995 DOI: 10.1016/0040-4039(95)02003-8

Synthesis

General procedure for the synthesis of 3-amino-4-chlorobenzonitrile from 4-chloro-3-nitrobenzonitrile: Example 1: Preparation of N-(1-(5-cyano-2-(3,5-dichlorophenoxy)benzenesulfonyl)piperidin-4-yl)-3-fluorobenzenesulfonamide (25) 1. Commercially available 4-chloro-3-nitrobenzonitrile was dissolved in tetrahydrofuran (THF) with solvent dosage of 4 times the volume of the raw material. 2. Sodium hydrosulfide (3 equiv.) was added to the reaction system and the reaction mixture was stirred at 45 °C overnight. 3. The progress of the reaction was monitored using thin layer chromatography (TLC) with the unfolding agent being a hexane solution of 25% ethyl acetate to confirm the completion of the reaction. 4. Upon completion of the reaction, the THF solvent was removed by rotary evaporator under reduced pressure to precipitate the product. 5. The white solid product was collected by vacuum filtration and washed with water to remove impurities. 6. 6. The product was placed in a vacuum oven and dried under mild heating conditions to obtain the target compound in 97.0% yield.

References

[1] Patent: US2011/230487, 2011, A1. Location in patent: Page/Page column 35
[2] Synlett, 2010, # 20, p. 3019 - 3022
[3] Patent: US2012/196824, 2012, A1
[4] Recueil des Travaux Chimiques des Pays-Bas, 1947, vol. 66, p. 369
[5] Chem.Abstr., 1948, vol. 42, p. 148

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