5-Amino-2-chlorobenzonitrile Chemical Properties

Melting point:

115.5°C

Boiling point:

250.67°C (rough estimate)

Density 

1.9802 (rough estimate)

refractive index 

1.6100 (estimate)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

2.15±0.10(Predicted)

Appearance

Light yellow to brown Solid

CAS DataBase Reference

35747-58-1(CAS DataBase Reference)

Safety Information

HS Code 

2926907090

5-Amino-2-chlorobenzonitrile Usage And Synthesis

Uses

5-Amino-2-chlorobenzonitrile is a useful research reagent for organic synthesis and other chemical transformations.

Synthesis

The general procedure for the synthesis of 3-cyano-4-chloroaniline from 2-chloro-5-nitrobenzonitrile was as follows: 2-chloro-5-nitrobenzonitrile (10 g, 54.8 mmol) was heated and refluxed for 1 h in a mixture of isopropanol (125 mL) and concentrated hydrochloric acid (62.5 mL) with stannous chloride dihydrate (56 g, 248.6 mmol). Upon completion of the reaction, the mixture was cooled to room temperature and neutralized with 2N sodium hydroxide solution. Subsequently, the aqueous layer was extracted with dichloromethane, the organic layers were combined and dried with anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure to afford 3-cyano-4-chloroaniline (8 g, 96% yield). The product was analyzed by high performance liquid chromatography (HPLC) under the following purity detection conditions: detection wavelength 210-370 nm; retention time (RT) 7.2 min; mobile phase 10 mM ammonium formate buffer (pH 3.5)/acetonitrile + methanol (gradient elution from 85/15 to 5/95) for 10 min, hold for 4 min; chromatography column Xterra TM RP18 (3.5 μm, 150×4.6 mm); mobile phase 1.5 μm, 2.5 μm, 2.5 μm, 2.5 μm, 2.5 μm, 2.5 μm. m, 150×4.6 mm); the flow rate was 1.2 mL/min.

References

[1] Tetrahedron Letters, 1984, vol. 25, # 8, p. 839 - 842
[2] Patent: US2007/27126, 2007, A1. Location in patent: Page/Page column 16
[3] Patent: US2007/27201, 2007, A1. Location in patent: Page/Page column 23
[4] Patent: US9204645, 2015, B2. Location in patent: Page/Page column 54; 55
[5] Journal of Heterocyclic Chemistry, 1991, vol. 28, # 3, p. 685 - 695

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