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
3D model (JSmol)
3DMet
605277
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.367
EC Number
  • 203-702-7
1298
KEGG
MeSH trimethylenediamine
RTECS number
  • TX6825000
UNII
UN number 2922
  • InChI=1S/C3H10N2/c4-2-1-3-5/h1-5H2 checkY
    Key: XFNJVJPLKCPIBV-UHFFFAOYSA-N checkY
  • 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)
-58.1·10−6 cm3/mol
1.458
Hazards
GHS labelling:
GHS02: Flammable GHS05: Corrosive GHS06: Toxic
Danger
H226, H302, H310, H314
P280, P302+P350, P305+P351+P338, P310
NFPA 704 (fire diamond)
NFPA 704 four-colored 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):
  • 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).
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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)

References
  1. Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. doi:10.1002/14356007.a02_001
  2. C. A. Brown and A. Yamashita (1975). "Saline hydrides and superbases in organic reactions. IX. Acetylene zipper. Exceptionally facile contrathermodynamic multipositional isomeriazation of alkynes with potassium 3-aminopropylamide". J. Am. Chem. Soc. 97 (4): 891–892. doi:10.1021/ja00837a034.
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