3,4-Diaminobenzonitrile

3,4-Diaminobenzonitrile Property

Melting point:

144-148 °C

Boiling point:

368.7±27.0 °C(Predicted)

Density 

1.24±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Soluble in dichloromethane, methanol and ethyl acetate.

pka

2.35±0.10(Predicted)

form 

Solid

color 

Pale brown

λmax

316nm(THF)(lit.)

Stability:

Store in freezer at -20°C

InChI

InChI=1S/C7H7N3/c8-4-5-1-2-6(9)7(10)3-5/h1-3H,9-10H2

InChIKey

VWLLPPSBBHDXHK-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

17626-40-3(CAS DataBase Reference)

Safety

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38-20/21/22

Safety Statements 

26-36-36/37

RIDADR 

3276

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29269090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

3,4-Diaminobenzonitrile Chemical Properties,Usage,Production

Chemical Properties

White to light yellow crystal powde

Uses

A synthetic intermediate

Uses

3,4-Diaminobenzonitrile is usually used like?synthetic intermediate.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 36, p. 1746, 1993 DOI: 10.1021/jm00064a008

Synthesis

The general procedure for the synthesis of 3,4-diaminobenzonitrile from 4-amino-3-nitrobenzonitrile was as follows: palladium/carbon catalyst (500 mg, 10% purity) was added to a stirring solution of 4-amino-3-nitrobenzonitrile (2.00 g, 12.3 mmol) in methanol (20 mL). Subsequently, the reaction flask was degassed and filled with hydrogen (using a hydrogen balloon). The reaction mixture was stirred vigorously for 18 hours at 25°C. Upon completion of the reaction, the mixture was degassed under vacuum and backfilled with nitrogen, and this process was repeated three times. Afterwards, the reaction mixture was filtered through a diatomaceous earth pad and the filtrate was concentrated under vacuum to give 3,4-diaminobenzonitrile (1.47 g, 11.04 mmol, 90% yield) as a green oil, which was used directly in the next step of the reaction.

References

[1] Australian Journal of Chemistry, 1994, vol. 47, # 9, p. 1751 - 1770
[2] Journal of Medicinal Chemistry, 1993, vol. 36, # 12, p. 1746 - 1753
[3] Journal of Medicinal Chemistry, 1996, vol. 39, # 4, p. 992 - 998
[4] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 8, p. 2589 - 2596
[5] Patent: WO2018/81167, 2018, A1. Location in patent: Page/Page column 244