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3-[2-cyanoethyl(propyl)amino]propanenitrile 
CAS: 1555-59-5
SKU: S3247
3-[2-cyanoethyl(propyl)amino]propanenitrile  | SKU: S3247
synonyms: N,N-Bis(2-cyanoethyl)propylamine; 3,3′-(Propylimino)dipropionitrile; 3,3′-(Propylimino)bispropanenitrile; N-Propyliminodipropionitrile
3-[2-cyanoethyl(propyl)amino]propanenitrile 
3-[(2-Cyanoethyl)(propyl)amino]propanenitrile, also named N,N-bis(2-cyanoethyl)propylamine or 3,3′-(propylimino)dipropionitrile (C9H15N3), is the product of adding two acrylonitrile units to propylamine. It has a molecular weight of 165.24 g/mol and combines a tertiary amine centre with two terminal nitrile groups on 2-cyanoethyl arms. That structure makes it a flexible intermediate. Hydrogenation of both nitrile groups gives N-propyl-bis(3-aminopropyl)amine, a branched triamine used in epoxy curing, polyamide and ligand chemistry, and hydrolysis of the nitriles gives N-propyliminodipropionic acid, a chelating β-amino diacid. The compound is also a convenient model for studying cyanoethylation and the retro-Michael loss of acrylonitrile. Sarchem Labs supplies 3-[(2-cyanoethyl)(propyl)amino]propanenitrile (SKU S3247) for research and intermediate-synthesis customers. The physical constants of the shipped material are reported on the Certificate of Analysis, and a Safety Data Sheet accompanies each lot. Laboratory to bulk quantities can be quoted on request.
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Specifications

Chemical Name or Material3-[(2-Cyanoethyl)(propyl)amino]propanenitrile
Molecular Weight165.24 g/mol
SMILES StringCCCN(CCC#N)CCC#N
CAS Number1555-59-5
Empirical FormulaC9H15N3
InChI1S/C9H15N3/c1-2-7-12(8-3-5-10)9-4-6-11/h2-4,7-9H2,1H3
InChI KeyJMCDHLBINXPPQK-UHFFFAOYSA-N
PubChem CID20432905
Functional GroupsNitrile (two), tertiary amine

Applications

No Application Found
Amino-diacid and chelator building block: acid or base hydrolysis converts the nitriles to carboxylic acids, giving N-propyliminodipropionic acid for chelating agents and surfactant intermediates.
Cyanoethylation chemistry: a model double Michael adduct of a primary amine with acrylonitrile, used to study the formation and base-induced retro-Michael cleavage of cyanoethyl groups.
Ligand and monomer precursor research: the tertiary amine and two nitrile donors can be used as a tridentate ligand scaffold or converted to amine, amide or tetrazole functions.

Product Description

What is 3-[(2-Cyanoethyl)(propyl)amino]propanenitrile?

It is a tertiary amine in which a nitrogen atom carries one n-propyl group and two 2-cyanoethyl groups, –CH2CH2CN. The formula is C9H15N3 and the molecular weight is 165.24 g/mol. Compounds of this type are made by double cyanoethylation of a primary amine with acrylonitrile, a Michael-type addition that is usually run neat or in water or alcohol with mild catalysis.

It is a different compound from 3,3′-iminodipropionitrile (the secondary amine without the propyl group), from 3,3′-(methylimino)dipropionitrile and from 3,3′-[[3-(dimethylamino)propyl]imino]dipropionitrile, which have different formulas and CAS numbers.

Uses of 3-[(2-Cyanoethyl)(propyl)amino]propanenitrile

The compound is bought as a chemical intermediate. The two nitriles can be reduced, hydrolysed or converted to heterocycles, and the tertiary amine gives the product basicity and metal-binding ability. Typical downstream products are polyamines, aminocarboxylic acid chelators and specialty amides.

Buying and Handling Considerations

State the intended use and any purity requirement when you ask for a quote, and review the Certificate of Analysis of the lot, which reports the assay and the physical constants of the shipped material. Store in a tightly closed container in a cool, dry, well-ventilated place away from strong acids, strong bases, strong oxidisers and reducing agents. Organic nitriles can release toxic gases, including hydrogen cyanide, on strong heating, combustion or contact with strong acids, so handle in a fume hood.

Safety Information

  • Hazard Classification: A harmonised GHS classification has not been published for this compound.
  • Handling: Treat it as a toxic organic nitrile and tertiary amine: it may be harmful by ingestion, skin contact and inhalation and may irritate the skin, eyes and airways.
  • PPE: Chemical-resistant gloves, eye and face protection, protective clothing and, if vapour or aerosol may form, a respirator suited to organic vapours

The Safety Data Sheet of the shipped lot governs. Use only in a fume hood, avoid contact with strong acids, and do not release to drains.

Related Products

No related products found.

Downloads

Cert-S3247-SL22510ABEY.pdf

Other Products

FAQs: 3-[2-cyanoethyl(propyl)amino]propanenitrile 

It is used as an intermediate: its two nitrile groups can be hydrogenated to a branched triamine, hydrolysed to an amino-diacid, or converted to other functions, and it serves as a model cyanoethylation product.

Yes. 3-[(2-Cyanoethyl)(propyl)amino]propanenitrile, N,N-bis(2-cyanoethyl)propylamine and 3,3′-(propylimino)dipropionitrile are the same compound, CAS 1555-59-5, formula C9H15N3.

The formula is C9H15N3 and the molecular weight is 165.24 g/mol. The structure is CCCN(CCC#N)CCC#N.

By double cyanoethylation of propylamine with two equivalents of acrylonitrile, a Michael-type addition.

A harmonised GHS classification has not been published. Treat it as a toxic organic nitrile and tertiary amine, work in a fume hood, and rely on the Safety Data Sheet of the lot.

Store it tightly closed in a cool, dry, ventilated place, away from strong acids, bases, oxidisers and reducing agents.

Yes. Every lot of SKU S3247 includes a Certificate of Analysis and Safety Data Sheet, and Sarchem Labs can quote laboratory, pilot and bulk quantities.