3-Aminopropionitrile Chemical Properties

Melting point:

<25 °C

Boiling point:

185 °C

Density 

0.9584

refractive index 

1.4365-1.4395

Flash point:

79-81°C/16mm

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

Chloroform, Methanol

form 

Liquid

pka

7.80(at 20℃)

color 

Clear colorless to yellow

Water Solubility 

Soluble in water.

Sensitive 

Air & Moisture Sensitive

Merck 

14,469

BRN 

1698848

InChIKey

AGSPXMVUFBBBMO-UHFFFAOYSA-N

CAS DataBase Reference

151-18-8(CAS DataBase Reference)

EPA Substance Registry System

Propanenitrile, 3-amino- (151-18-8)

Safety Information

Hazard Codes 

Xn,C

Risk Statements 

20/21/22-34-22-63

Safety Statements 

36/37-45-36/37/39-26

RIDADR 

3276

RTECS 

UG0350000

TSCA 

Yes

HazardClass 

8

PackingGroup 

III

HS Code 

29269090

Hazardous Substances Data

151-18-8(Hazardous Substances Data)

MSDS

• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Aminopropionitrile Usage And Synthesis

Chemical Properties

clear colourless to yellow liquid. 3-Aminopropionitrile, [151-18-8], 3-aminopropanenitrile, b-aminopropionitrile, H2N – CH2 – CH2CN, Mr 70.09, bp 185℃ (101.3 kPa), n20D 1.4396, is a colorless liquid which tends to slowly polymerize if stored in the presence of air. 3-Aminopropionitrile is prepared by the reaction of acrylonitrile with ammonia and is mainly used as an intermediate in the manufacture of b-alanine and pantothenic acid [48].

Uses

Production of β-alanine and pantothenic acid.

Uses

3-Aminopropionitrile is used for organic synthesis and as pharmaceutical intermediates. As an intermediate used in the manufacture of beta-alanine and pantothenic acid.

Definition

ChEBI: 3-Aminopropionitrile is an aminopropionitrile carrying an amino group at the beta-position. It has a role as a plant metabolite, an antineoplastic agent, an antirheumatic drug and a collagen cross-linking inhibitor. It is a conjugate base of a beta-ammoniopropionitrile.

Safety Profile

Moderately toxic by intraperitoneal route. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. Nitriles usually have cyanide-like effects. See also CYANIDE. Easily oxidized and unstable. A storage hazard; it polymerizes to an explosive yellow solid. When heated to decomposition it emits toxic fumes of CNand NO,. For fire and explosion hazards see CYANIDE.

Metabolism

3-Aminopropionitrile is the compound present in some Lathyms species (Leguminosae), especially sweet-pea seeds (L. odoratus), causing osteolathyrism in man and animals. Although 3-aminopropionitrile is generally present in the fresh plant as the gama-glutamyl derivative, only the free amine is an effective lathyrogen.
Osteolathyrogens cause skeletal deformations due to interference with the cross-linking between polypeptide chains in the connective tissue components, elastin and collagen. This interference is partly due to inhibition of the synthesis of desmosine and isodesmosine, amino acids which effect the cross-linking in elastin. Cross-linking interference of collagen can be prevented in chicks by feed- ing excess calcium.
It is possible that 3-aminopropionitrile is adegradation product of 3-cyano-alanine, although in many plants the latter compound is converted to asparagine and it has not been detected in Lathyms species.

References

[1] CHAO HAN . Nitrilase-catalyzed hydrolysis of 3-aminopropionitrile at high concentration with a tandem reaction strategy for shifting the reaction to β-alanine formation[J]. Journal of Molecular Catalysis B-enzymatic, 2015, 115: Pages 113-118. DOI:10.1016/j.molcatb.2015.02.007.
[2] C. RICHARD . Rotational spectrum of 3-aminopropionitrile and searches for it in Sagittarius B2(N)[J]. Journal of Molecular Spectroscopy, 2018, 345: Pages 51-59. DOI:10.1016/j.jms.2017.12.003.
[3] MSIEDEEN A A. Conformational Stability of 3-aminopropionitrile: DFT and Ab initio Calculations.[J]. Acta Chimica Slovenica, 2024, 71 2: 244-255. DOI:10.17344/acsi.2023.8486.
[4] A.L.G. ALVES PHD1. Effects of beta-aminopropionitrile fumarate and exercise on equine tendon healing: Gross and histological aspects[J]. Journal of Equine Veterinary Science, 2001, 21 7: Pages 335-340. DOI:10.1016/S0737-0806(01)70076-7.

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