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3-Aminopropionitrile
[CAS# 151-18-8]

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Identification
Classification Chemical reagent >> Organic reagent >> Cyanide/nitrile
Name 3-Aminopropionitrile
Synonyms Z2CN
Molecular Structure CAS # 151-18-8, 3-Aminopropionitrile, Z2CN
Molecular Formula C3H6N2
Molecular Weight 70.09
CAS Registry Number 151-18-8
EC Number 205-786-0
SMILES C(CN)C#N
Properties
Density 0.9±0.1 g/cm3, Calc.*, 0.9584 g/mL (Expl.)
Melting point 79-81 ºC (Expl.)
Index of Refraction 1.430, Calc.*, 1.4365-1.4395 (Expl.)
Boiling Point 186.3±13.0 ºC (760 mmHg), Calc.*, 185 ºC (Expl.)
Flash Point 66.5±19.8 ºC, Calc.*
* Calculated using Advanced Chemistry Development (ACD/Labs) Software.
Safety Data
Hazard Symbols symbol symbol symbol   GHS05;GHS07;GHS08 Danger    Details
Hazard Statements H302-H314-H361    Details
Precautionary Statements P203-P260-P264-P270-P280-P301+P317-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P318-P321-P330-P363-P405-P501    Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Acute toxicityAcute Tox.4H302
Reproductive toxicityRepr.2H361
Skin corrosionSkin Corr.1BH314
Serious eye damageEye Dam.1H318
Acute toxicityAcute Tox.3H301
Flammable liquidsFlam. Liq.4H227
SDS Available
up Discovory and Applicatios
3-Aminopropionitrile is a simple organic compound with significant chemical versatility, characterized by the presence of both an amine group (-NH2) and a nitrile group (-C≡N) on a three-carbon backbone. This dual functionality makes it an important intermediate in organic synthesis and industrial chemistry.

The origins of 3-aminopropionitrile trace back to studies in early synthetic organic chemistry, particularly during the exploration of nitrile-based compounds for producing amines and carboxylic acids. It is commonly synthesized by methods such as the addition of ammonia to acrylonitrile or through reductive methods starting from malononitrile derivatives. These processes take advantage of the reactivity of nitriles and the ease of amination under controlled conditions.

In industrial applications, 3-aminopropionitrile serves as a precursor in the synthesis of a wide range of products. One notable use is its role in producing β-alanine, a key building block for pharmaceuticals, agrochemicals, and functional materials. Through hydrolysis under acidic or basic conditions, 3-aminopropionitrile can be converted to β-alanine, an important component in the biosynthesis of coenzyme A and the dipeptide carnosine.

3-Aminopropionitrile has also been utilized in polymer chemistry. It acts as a monomer or a functionalizing agent in the creation of specialty polymers with unique properties, such as increased flexibility or enhanced adhesion. These materials find applications in coatings, adhesives, and advanced composites.

In the field of medicinal chemistry, the compound has been studied for its biological activities. Certain derivatives of 3-aminopropionitrile exhibit inhibitory effects on specific enzymes and have potential as therapeutic agents for conditions involving connective tissue or fibrosis. Additionally, its role as an intermediate allows for the efficient construction of more complex molecules, facilitating drug discovery and development.

Recent research continues to explore the potential of 3-aminopropionitrile in new catalytic systems, green chemistry approaches, and its integration into renewable feedstock processes. These efforts aim to expand its utility while minimizing environmental impact.
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