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

Identification

• Classification: Chemical reagent >> Organic reagent >> Cyanide/nitrile
• Name: 3-Aminopropionitrile
• Synonyms: 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 °C (Expl.)
• Index of Refraction: 1.430, Calc.^*, 1.4365-1.4395 (Expl.)
• Boiling Point: 186.3±13.0 °C (760 mmHg), Calc.^*, 185 °C (Expl.)
• Flash Point: 66.5±19.8 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS08 Danger
• Risk Statements: H302-H314-H361
• Safety 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

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Reproductive toxicity	Repr.	2	H361
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	3	H301
Flammable liquids	Flam. Liq.	4	H227

Discovery and Applications

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.

References

1987. Embryotoxic action of beta-aminopropionitrile during early organogenesis in rats. Archives of toxicology. Supplement. = Archiv fur Toxikologie. Supplement, 10.
DOI: 10.1007/978-3-642-72558-6_19

1969. Lathyrism. World review of nutrition and dietetics, 10.
DOI: 10.1159/000387567