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.

1,3-Diaminopropane
Names
Preferred IUPAC name
Propane-1,3-diamine
Other names
  • Propandiamine
  • 1,3-Propylenediamine
  • Trimethylenediamine
  • 3-Aminopropylamine
Identifiers
3D model (JSmol)
3DMet
605277
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.367
EC Number
  • 203-702-7
1298
KEGG
MeSH trimethylenediamine
PubChem CID
RTECS number
  • TX6825000
UNII
UN number 2922
  • InChI=1S/C3H10N2/c4-2-1-3-5/h1-5H2 Y
    Key: XFNJVJPLKCPIBV-UHFFFAOYSA-N Y
SMILES
  • NCCCN
Properties
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:
Danger
H226, H302, H310, H314
P280, P302+P350, P305+P351+P338, P310
NFPA 704 (fire diamond)
3
3
0
Flash point 51 °C (124 °F; 324 K)
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
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.

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

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