1,3-Diaminopropane

1,3-Diaminopropane, also known as trimethylenediamine, is a simple diamine with the formula (CH2)3(NH2)2. 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
Names
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
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 pictograms
GHS Signal word Danger
GHS hazard statements
 H226, H302, H310, H314
P280, P302+350, P305+351+338, P310
NFPA 704 (fire diamond)
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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).
Y verify (what is YN ?)
Infobox references

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

Known uses of 1,3-diaminopropane is 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)

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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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