2134-48-7

Basic information

• Product Name: 2-Aminopropionitrile
• Synonyms: 2-Aminopropionitrile;2-Aminopropion-Nitrile;2-Aminopropiononitrile;2-azanylpropanenitrile;rac-α-AMinopropionitrile;2-aMinopropanonitrile;DL-α-AMinopropionitrile;α-DL-Alanylnitrile
• CAS NO: 2134-48-7
• Molecular Formula: C₃H₆N₂
• Molecular Weight: 70.09314
• Product Categories: Aliphatics;Amino Acids & Derivatives
• Mol File: 2134-48-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 111.55°C (rough estimate)
• Flash Point: 44.5°C
• Appearance: /
• Density: 0.8379 (rough estimate)
• Refractive Index: 1.4200 (estimate)
• PKA: 5.90±0.29(Predicted)
• CAS DataBase Reference: 2-Aminopropionitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Aminopropionitrile(2134-48-7)
• EPA Substance Registry System: 2-Aminopropionitrile(2134-48-7)

Safety Data

• Hazardous Substances Data: 2134-48-7(Hazardous Substances Data)

Usage

Description

2-Aminopropionitrile, also known as aminoacetonitrile, is an organic compound with the chemical formula CH3CH(NH2)CN. It is a versatile building block in the synthesis of various pharmaceuticals, agrochemicals, and other organic compounds.

Uses

Used in Chiral Alanine Manufacturing:
2-Aminopropionitrile is used as a chiral building block for the production of L-alanine, an essential amino acid, through biotransformation with Rhodococcus bacteria. This process allows for the enantioselective synthesis of L-alanine, which is an important component in the pharmaceutical and food industries.
Used in Peptide Synthesis:
2-Aminopropionitrile is used as a key intermediate in the synthesis of various peptides and peptide-based drugs. Its unique structure allows for the formation of stable peptide bonds and contributes to the overall stability and activity of the final peptide product.
Used in Pesticide Synthesis:
2-Aminopropionitrile is used as a starting material in the synthesis of certain pesticides, particularly those targeting insects and pests. Its reactivity and functional groups make it a suitable candidate for the development of effective and environmentally friendly pesticides.
Used in Chemical Research:
2-Aminopropionitrile is used as a model compound in various chemical research studies, particularly in the fields of asymmetric synthesis, catalysis, and organocatalysis. Its unique properties and reactivity make it an ideal candidate for exploring new synthetic methodologies and reaction mechanisms.

Upstream product

• 2869-25-2 2,2'-iminodipropionitrile 
• 151-50-8 potassium cyanide 
• 75-07-0 acetaldehyde 
• 78-97-7 2-hydroxy-propionitrile 
• 67337-69-3 methyl-5 hydantoine 
• 107-13-1 acrylonitrile 
• 7732-18-5 water 
• 107-16-4 glycolonitrile 

Downstream Products

• 19861-71-3 N-(1-cyanoethyl)acetamide 
• 26355-87-3 N-benzoyl-α-aminopropionitrile 
• 2869-25-2 2,2'-iminodipropionitrile 
• 57768-55-5 meso-bis-(1-cyano-ethyl)-amine 
• 57355-08-5 3,5,6-trimethyl-1,2-dihydropyrazin-2-one 
• 859481-43-9 (5-amino-4-methyl-thiazol-2-yl)-carbamic acid ethyl ester 
• 108981-53-9 3-methyl-5,6-diphenyl-1H-pyrazin-2-one 
• 19838-07-4 3-methylpyrazin-2(1H)-one 
• 32464-52-1 3-methyl-1-oxy-5-phenyl-pyrazin-2-ylamine 
• 78-90-0 1,2-diaminopropan 
• 302-72-7 rac-Ala-OH 
• 51806-96-3 α-(N-γ-DL-Glutamyl)-amino-propionitril 
• 40652-03-7 1--1-cyanoaethan 
• 27394-99-6 N-(α-cyanoethyl)formamide 

Relevant articles and documents

SYSTEMES DE STRECKER ET APPARENTES - XI FORMATION ET STABILITE DE L'α-CARBOXYAMINONITRILE. INTERMEDIAIRE ESSENTIEL DANS LA SYNTHESE DES HYDANTOINES SELON BUCHERER-BERGS

The determination of the structure of the intermediate in the Bucherer-Bergs reaction (the transformation in aqueous solution of an aldehyde into the corresponding amino-acid via the hydantoin) showed that this reaction involved the formation of α-aminonitrile carbamate.The slow formation of the carbonic anhydride from the carbonate buffer limited the formation of that main intermediate which was in equilibrium with the α-aminonitrile.The variation of the stability of the carbamate vs pH is mainly determined by the concentration of CO2 dissolved in the mixture, but also by the equilibrated formation of products formed by the degradation of α-aminonitrile, i.e. the aminodinitrile and the cyanohydrin.

Regioselectivity of the photochemical addition of ammonia, phosphine, and silane to olefinic and acetylenic nitriles

An investigation of the regioselectivity and mechanisms of the photochemical addition of NH3, PH3, and SiH4 to olefinic and acetylenic nitriles is described. The photolysis of NH3 in the presence of acrylonitrile led to the α-addition product 2-aminopropanenitrile (2), propanenitrile, and 2,3-dimethylbutanedinitrile (3). When NH3 was photolyzed in the presence of substituted derivatives (crotononitrile, methacrylonitrile, or 1-cyclohexenecarbonitrile), the α-addition products were still obtained. However, under similar reaction conditions, only the β-addition products, 7 and 8, were obtained from acrylonitrile and PH3, or acrylonitrile and SiH4, respectively. On the other hand, the photolysis of 2-butynenitrile and NH3 gave the β-addition products, (Z)- and (E)-3-aminocrotononitrile (10). The photolysis of these acetylenic nitriles with PH3 or SiH4 also gave the β-adducts (12) and (13). The α-addition of NH3 proceeds by the stepwise addition of H· and ·NH2, respectively, to the α,β-unsaturated nitriles. The β-addition products are formed by a radical chain mechanism initiated by photochemically generated radicals. The radical chain pathway provides an explanation for a number of previously described photochemical additions to olefins and acetylenes. Photochemical processes similar to the addition of ammonia and phosphine to unsaturated organic compounds may have played a role in the evolution of the atmosphere of the primitive Earth, and may even be currently occurring in the atmospheres of other planets.