N-(4-Cyanophenyl)guanidine Chemical Properties

Melting point:

155-162°C

Boiling point:

316.6±44.0 °C(Predicted)

Density 

1.25±0.1 g/cm3(Predicted)

vapor pressure 

0-0Pa at 20-25℃

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO, Methanol

form 

Solid

pka

9.91±0.10(Predicted)

color 

Off-White

InChI

InChI=1S/C8H8N4/c9-5-6-1-3-7(4-2-6)12-8(10)11/h1-4H,(H4,10,11,12)

InChIKey

BTDGLZSKNFJBER-UHFFFAOYSA-N

SMILES

N(C1=CC=C(C#N)C=C1)C(=N)N

LogP

-2.2-0.4 at 20℃ and pH7.1-11

Safety Information

HS Code 

2926.90.4801

N-(4-Cyanophenyl)guanidine Usage And Synthesis

Chemical Properties

Off-White Solid

Uses

An intermediate in the preparation of Etravirine

Synthesis

The general procedure for the synthesis of N-(4-cyanophenyl)guanidine from cyanamide and p-aminobenzonitrile is as follows: P-aminobenzonitrile (100 g), ethanol (500 ml), concentrated nitric acid (36 ml), and a 50% aqueous ammoniacal nitrile solution (54 ml) were mixed and heated to reflux. The reflux reaction was maintained for 16 hours. Upon completion of the reaction, the reaction mixture was cooled to 0 °C, followed by the slow addition of methyl tert-butyl ether (500 mL) at 0 to 5 °C. The mixture was continued to be stirred at 0 to 5 °C for 5 h. The precipitated solid was separated by filtration to give 59 g of guanidine nitrate. Guanidine nitrate (59 g) was dissolved in water (590 mL) and 1M sodium hydroxide solution (325 mL) was added. The precipitated solid was separated by filtration again and dried to give 33 g of 1-(4-cyanophenyl)guanidine.

References

[1] European Journal of Medicinal Chemistry, 2010, vol. 45, # 1, p. 244 - 255
[2] Patent: WO2012/1695, 2012, A1. Location in patent: Page/Page column 10
[3] Patent: US2013/96148, 2013, A1. Location in patent: Paragraph 0085; 0086
[4] Patent: US2015/336900, 2015, A1. Location in patent: Paragraph 0027; 0028