1,3-Diaminopropane

1,3-Diaminopropane
Names
	IUPAC name Propane-1,3-diamine
	Other names Propandiamine; 1,3-Propylenediamine; Trimethylenediamine;
Identifiers
CAS Number	109-76-2 ;
3D model (JSmol)	Interactive image;
3DMet	B00214;
Abbreviations	TMEDA
Beilstein Reference	605277
ChEBI	CHEBI:15725 ;
ChEMBL	ChEMBL174324 ;
ChemSpider	415 ;
ECHA InfoCard	100.003.367
EC Number	203-702-7;
Gmelin Reference	1298
KEGG	C00986 ;
MeSH	trimethylenediamine
PubChem CID	428;
RTECS number	TX6825000;
UN number	2922
CompTox Dashboard (EPA)	DTXSID1021906 ;
	InChI InChI=1S/C3H10N2/c4-2-1-3-5/h1-5H2 Key: XFNJVJPLKCPIBV-UHFFFAOYSA-N ;
	SMILES NCCCN;
Properties
Chemical formula	C3H10N2
Molar mass	74.127 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 labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H302, H310, H314
Precautionary statements	P280, P302+P350, P305+P351+P338, P310
NFPA 704 (fire diamond)	3 3 0
Flash point	51 °C (124 °F; 324 K)
Autoignition; temperature	350 °C (662 °F; 623 K)
Explosive limits	2.8–15.2%
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	177 mg kg−1 (dermal, rabbit); 700 mg kg−1 (oral, rat);
Related compounds
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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]

Safety

Diamines are typically skin irritants.

References

^ 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
^ 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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[Ullmann-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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