2-Amino-1-cyclopentene-1-carbonitrile Chemical Properties

Melting point:

147-148℃

Boiling point:

321.2±42.0 °C(Predicted)

Density 

1.08±0.1 g/cm3(Predicted)

RTECS 

GY5976010

storage temp. 

Amber Vial, -20°C Freezer, Under inert atmosphere

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

6.70±0.20(Predicted)

form 

Solid

color 

Off-white

Water Solubility 

Slightly soluble in water.

Stability:

Light Sensitive

InChI

InChI=1S/C6H8N2/c7-4-5-2-1-3-6(5)8/h1-3,8H2

InChIKey

NSMYBPIHVACKQG-UHFFFAOYSA-N

SMILES

C1(C#N)CCCC=1N

CAS DataBase Reference

2941-23-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HazardClass 

6.1

HS Code 

2926907090

2-Amino-1-cyclopentene-1-carbonitrile Usage And Synthesis

Physical Form

Liquid

Uses

2-Amino-1-cyclopentene-1-carbonitrile s an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.

Uses

2-Amino-1-cyclopentene-1-carbonitrile is a reagent used in the synthesis of tacrine-huperzine A hybrids as acetylcholinesterase inhibitors.

Synthesis

General procedure for the synthesis of 2-amino-1-cyclopentene-1-carbonitrile from hexanedinitrile: hexanedinitrile (5.40 g, 50 mmol) was mixed with powdered potassium tert-butanolate (t-BuOK, 6.72 g, 60 mmol) and the reaction was stirred at room temperature overnight. Upon completion of the reaction, water was added to the reaction mixture, and the precipitated crystalline solid was collected by filtration and purified by recrystallization with methanol (MeOH) to finally obtain the target product 2-amino-1-cyclopentene-1-carbonitrile (4.26 g, 79% yield).

References

[1] Synthetic Communications, 1984, vol. 14, # 10, p. 967 - 972
[2] Tetrahedron Asymmetry, 2011, vol. 22, # 5, p. 506 - 511
[3] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 3, p. 625 - 629
[4] Journal of the American Chemical Society, 1987, vol. 109, p. 1160
[5] Advanced Synthesis and Catalysis, 2015, vol. 357, # 2-3, p. 371 - 376

2-Amino-1-cyclopentene-1-carbonitrile(2941-23-3)Related Product Information

• 1-Methylcyclopentene
• Indene
• Methylene dithiocyanate
• ETHYL 2-CYANOACRYLATE
• Sodium cyanoborohydride
• Ethyl N-cyanoethanimideate
• Glycine
• Methyl cyclopentenolone
• Betaine
• ALTRENOGEST
• 6-AMINO CAPRONITRILE
• 1-CYANOCYCLOPENTENE
• N-(2-Cyano-1-cyclopenten-1-yl)-acetamide
• AMINO ACIDS
• Carbonitrile
• 2-Amino-1-cyclopentene-1-carbonitrile