Diallylamine

Diallylamine
Names
	IUPAC name N-prop-2-enylprop-2-en-1-amine
Identifiers
CAS Number	124-02-7;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3186706;
ChemSpider	21106561;
ECHA InfoCard	100.004.248
EC Number	204-671-2;
PubChem CID	31279;
RTECS number	UC6650000;
UNII	N18EXB6V6P;
UN number	2359
CompTox Dashboard (EPA)	DTXSID1024918 ;
	InChI InChI=1S/C6H11N/c1-3-5-7-6-4-2/h3-4,7H,1-2,5-6H2 Key: DYUWTXWIYMHBQS-UHFFFAOYSA-N;
	SMILES C=CCNCC=C;
Properties
Chemical formula	C6H11N
Molar mass	97.161 g·mol−1
Appearance	colorless liquid
Density	0.7874 g/cm3
Melting point	−88 °C (−126 °F; 185 K)
Boiling point	111 °C (232 °F; 384 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H302, H311, H314, H315, H319, H335, H412
Precautionary statements	P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P363, P370+P378, P403+P233, P403+P235, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Diallylamine is the organic compound with the formula HN(CH₂CH=CH₂)₂. It is a colorless liquid with an ammonia-like odor. It is multifunctional, featuring a secondary amine and two alkene groups. Diallylamine is used in the production of N,N-diallyldichloroacetamide (dichlormid) and N,N-diallyldimethylammonium chloride.^[2]

Preparation

It is produced commercially by partial hydrogenation of acrylonitrile:^[2]

2 NCCH=CH₂ + 4 H₂ → HN(CH₂CH=CH₂)₂ + NH₃

A laboratory route to diallylamine entails diallylation of calcium cyanamide followed by decyanation of the product.^[3]

Related compounds

References

^ "Diallylamine". pubchem.ncbi.nlm.nih.gov. Retrieved 2 March 2022.
^ ^a ^b Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut (2000). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_001. ISBN 3527306730.
^ E. B. Vliet (1925). "Diallylamine". Organic Syntheses. 5: 43. doi:10.15227/orgsyn.005.0043.

[1] "Diallylamine". pubchem.ncbi.nlm.nih.gov. Retrieved 2 March 2022.

[Ullmann-2] Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut (2000). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_001. ISBN 3527306730.

[3] E. B. Vliet (1925). "Diallylamine". Organic Syntheses. 5: 43. doi:10.15227/orgsyn.005.0043.

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