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1,3-Diaminopropane

From Wikipedia, the free encyclopedia
1,3-Diaminopropane
Skeletal formula of 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)
605277
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.003.367Edit this at Wikidata
EC Number
  • 203-702-7
1298
KEGG
MeSHtrimethylenediamine
RTECS number
  • TX6825000
UNII
UN number2922
  • InChI=1S/C3H10N2/c4-2-1-3-5/h1-5H2 checkY
    Key: XFNJVJPLKCPIBV-UHFFFAOYSA-N checkY
  • NCCCN
Properties
C3H10N2
Molar mass74.127 g·mol−1
AppearanceColourless liquid
OdorFishy, ammoniacal
Density0.888 g mL−1
Melting point−12.00 °C; 10.40 °F; 261.15 K
Boiling point140.1 °C; 284.1 °F; 413.2 K
logP−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: FlammableGHS05: CorrosiveGHS06: Toxic
Danger
H226,H302,H310,H314
P280,P302+P350,P305+P351+P338,P310
NFPA 704 (fire diamond)
Flash point51 °C (124 °F; 324 K)
350 °C (662 °F; 623 K)
Explosive limits2.8–15.2%
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 theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

1,3-Diaminopropane, also known as trimethylenediamine, is a simplediamine 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 with1,2-diaminopropane. Both are building blocks in the synthesis ofheterocycles, such as those used intextile finishing, andcoordination complexes. It is prepared by the amination ofacrylonitrile followed byhydrogenation of the resultingaminopropionitrile.[1]

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

Known uses of 1,3-diaminopropane are in the synthesis ofpiroxantrone andlosoxantrone.

Safety

[edit]

1,3-Diaminopropane is toxic on skin exposure with anLD50 of 177 mg kg−1 (dermal, rabbit)

References

[edit]
  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.
AMPARTooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor
KARTooltip Kainate receptor
NMDARTooltip N-Methyl-D-aspartate receptor
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