1,3-Diaminopropane

1,3-Diaminopropane

1,3-Diaminopropane
Skeletal formula of 1,3-diaminopropane
Identifiers
Abbreviations TMEDA
CAS number  YesY
PubChem
ChemSpider  YesY
EC number
UN number 2922
KEGG  YesY
MeSH
ChEBI  YesY
ChEMBL  YesY
RTECS number TX6825000
Beilstein Reference 605277
Gmelin Reference 1298
3DMet
Jmol-3D images Image 1
Properties
Molecular formula C3H10N2
Molar mass 74.12 g mol−1
Appearance Colourless liquid
Odor Fishy, ammoniacal
Density 888 mg 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)
Refractive index (nD) 1.458
Hazards
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
GHS hazard statements H226, H302, H310, H314
GHS precautionary statements P280, P302+350, P305+351+338, P310
EU classification Toxic T Corrosive C
R-phrases R10, R22, R24, R35
S-phrases S26, S36/37/39, S45
Flash point 51 °C (124 °F; 324 K)
Autoignition temperature 350 °C (662 °F; 623 K)
Explosive limits 2.8–15.2%
LD50
  • 177 mg kg−1 (dermal, rabbit)
  • 700 mg kg−1 (oral, rat)
Related compounds
Related alkanamines
Related compounds 2-Methyl-2-nitrosopropane
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY   YesY/N?)

1,3-Diaminopropane, also known as trimethylenediamine, is a simple 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]

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

Safety

Diamines are typically skin irritants.

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 2and superbases in organic reactions. IX. Acetylene zipper. Exceptionally facile contrathermodynamic multipositional isomeriazation of alkynes with potassium 3-aminopropylamide".