1,3-Diaminopropane

1,3-Diaminopropane, also known as trimethylenediamine, is a simple diamine with the formula H₂N(CH₂)₃NH₂. A colourless liquid with a fishy odor, it is soluble in water and many polar organic solvents. It is isomeric with 1,2-diaminopropane. Both are building blocks in the synthesis of heterocycles, such as those used in textile finishing, and coordination complexes. It is prepared by the amination of acrylonitrile followed by hydrogenation of the resulting aminopropionitrile.^[1]

1,3-Diaminopropane

Skeletal formula of 1,3-diaminopropane
Names
Preferred IUPAC name Propane-1,3-diamine
Other names Propandiamine 1,3-Propylenediamine Trimethylenediamine 3-Aminopropylamine
Identifiers
CAS Number	109-76-2 Y
3D model (JSmol)	Interactive image
Beilstein Reference	605277
ChEBI	CHEBI:15725 Y
ChEMBL	ChEMBL174324 Y
ChemSpider	415 Y
ECHA InfoCard	100.003.367
EC Number	203-702-7
Gmelin Reference	1298
KEGG	C00986 Y
MeSH	trimethylenediamine
PubChem CID	428
RTECS number	TX6825000
UNII	CB3ISL56KG Y
UN number	2922
CompTox Dashboard (EPA)	DTXSID1021906
InChI InChI=1S/C3H10N2/c4-2-1-3-5/h1-5H2 Y Key: XFNJVJPLKCPIBV-UHFFFAOYSA-N Y
SMILES NCCCN
Properties
Chemical formula	C3H10N2
Molar mass	74.127 g·mol−1
Appearance	Colourless liquid
Odor	Fishy, ammoniacal
Density	0.888 g mL−1
Melting point	−12.00 °C; 10.40 °F; 261.15 K
Boiling point	140.1 °C; 284.1 °F; 413.2 K
log P	−1.4
Vapor pressure	<1.1 kPa or 11.5 mm Hg(at 20 °C)
Magnetic susceptibility (χ)	−58.1·10−6 cm3/mol
Refractive index (nD)	1.458
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H302, H310, H314
Precautionary statements	P280, P302+P350, P305+P351+P338, P310
NFPA 704 (fire diamond)	3 3 0
Flash point	51 °C (124 °F; 324 K)
Autoignition temperature	350 °C (662 °F; 623 K)
Explosive limits	2.8–15.2%
Lethal dose or concentration (LD, LC):
LD50 (median dose)	177 mg kg−1 (dermal, rabbit) 700 mg kg−1 (oral, rat)
Related compounds
Related alkanamines	Ethylamine Ethylenediamine Propylamine Isopropylamine 1,2-Diaminopropane Isobutylamine tert-Butylamine n-Butylamine sec-Butylamine Putrescine
Related compounds	2-Methyl-2-nitrosopropane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

The potassium salt was used in the alkyne zipper reaction.^[2]

Known uses of 1,3-diaminopropane are in the synthesis of piroxantrone and losoxantrone.

Safety

1,3-Diaminopropane is toxic on skin exposure with an LD₅₀ of 177 mg kg⁻¹ (dermal, rabbit)