1,3-Diaminopropane

1,3-Diaminopropane
Names
IUPAC name
Propane-1,3-diamine
Other names
  • Propandiamine
  • 1,3-Propylenediamine
  • Trimethylenediamine
Identifiers
109-76-2 YesY
3D model (Jmol) Interactive image
3DMet B00214
Abbreviations TMEDA
605277
ChEBI CHEBI:15725 YesY
ChEMBL ChEMBL174324 YesY
ChemSpider 415 YesY
ECHA InfoCard 100.003.367
EC Number 203-702-7
1298
KEGG C00986 YesY
MeSH trimethylenediamine
PubChem 428
RTECS number TX6825000
UN number 2922
Properties
C3H10N2
Molar mass 74.13 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)
1.458
Hazards
GHS pictograms
GHS signal word DANGER
H226, H302, H310, H314
P280, P302+350, P305+351+338, P310
T C
R-phrases R10, R22, R24, R35
S-phrases S26, S36/37/39, S45
NFPA 704
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., gasoline) Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 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

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]

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)

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". J. Am. Chem. Soc. 97 (4): 891–892. doi:10.1021/ja00837a034.
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