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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