3-Amino-4-pyrazolecarbonitrile Chemical Properties

Melting point:

172-174 °C(lit.)

Boiling point:

192.71°C (rough estimate)

Density 

1.2722 (rough estimate)

refractive index 

1.7380 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Crystalline Powder

pka

11.58±0.50(Predicted)

color 

Light yellow to brown-orange

BRN 

2647

InChI

InChI=1S/C4H4N4/c5-1-3-2-7-8-4(3)6/h2H,(H3,6,7,8)

InChIKey

FFNKBQRKZRMYCL-UHFFFAOYSA-N

SMILES

N1C=C(C#N)C(N)=N1

CAS DataBase Reference

16617-46-2(CAS DataBase Reference)

NIST Chemistry Reference

5-Amino-4-cyano-pyrazole(16617-46-2)

EPA Substance Registry System

1H-Pyrazole-4-carbonitrile, 3-amino- (16617-46-2)

Safety Information

Hazard Codes 

Xn,T

Risk Statements 

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

Safety Statements 

22-24/25-23-36-26

RIDADR 

3439

WGK Germany 

3

F 

10

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29331990

MSDS

• Language:English Provider:3-Amino-4-pyrazolecarbonitrile
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-Amino-4-pyrazolecarbonitrile Usage And Synthesis

Description

The molecular structure of 3-Amino-4-pyrazolecarbonitrile contains a cyano structure and an active amino unit. Its solubility in water is low, but its solubility in alcoholic organic solvents is high. As an intermediate in organic synthesis and medicinal chemistry, 3-Amino-4-pyrazolecarbonitrile can synthesize drug molecules. For example, it can be used to synthesize the drug molecule zaleplon.

Chemical Properties

Tan Crystalline Solid

Uses

Building block used in the synthesis of a variety of heterocycles.

Uses

3-Amino-4-pyrazolecarbonitrile has been a useful synthetic intermediate.

Application

3-Amino-4-pyrazolecarbonitrile is a pharmaceutical intermediate ingredient used in the preparation of antineoplastic drugs (Ibrutinib) and hypnotics (Zaleplon).

Synthesis

The general procedure for the synthesis of 3-amino-4-cyanopyrazole from ethoxymethylene malononitrile was as follows: hydrazine hydrate (5 g, 0.156 mol) was slowly added dropwise to an ethanol solution containing 2-(ethoxymethylene)malononitrile (8.64 g, 0.070 mol), and the reaction mixture was subsequently heated for 30 min on a steam bath. A white precipitate gradually precipitated during the reaction and the reaction mixture was transferred to a refrigerator and left overnight to complete crystallization. Subsequently, the white solid product was collected by filtration and washed with a small amount of pre-cooled ethanol to finally obtain the target compound 5-amino-1H-pyrazole-4-carbonitrile (1) as white crystals in 86% (3.05 g) yield; the melting point was 168-170 °C (literature value: 169-170 °C) [33].

References

[1] Bioorganic Chemistry, 2018, vol. 79, p. 46 - 59
[2] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 24 - 35
[3] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 12, p. 1161 - 1166
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 16, p. 4736 - 4741
[5] Patent: CN103626776, 2017, B. Location in patent: Paragraph 0091; 0092; 0093

3-Amino-4-pyrazolecarbonitrile(16617-46-2)Related Product Information

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• 5-AMINO-4-CYANO-1-(2-HYDROXYETHYL)PYRAZOLE
• 5-AMINO-1-(4-NITROPHENYL)-1H-PYRAZOLE-4-CARBONITRILE
• 5-AMINO-1-PHENYLPYRAZOLE-4-CARBONITRILE
• 3-(Cyanomethyl)-5-amino-1H-pyrazole-4-carbonitrile
• 3-AMINO-5-(METHYLTHIO)PYRAZOLE-4-CARBONITRILE,3-AMINO-5-(METHYLTHIO)PYRAZOLE-4-CARBONITRILE 97%
• 5-AMINO-1-(4-CHLOROPHENYL)-1H-PYRAZOLE-4-CARBONITRILE
• 5-AMINO-4-CYANO-3-CYANOMETHYL-1-PHENYLPYRAZOLE