1,2-Diaminopropane

1,2-Diaminopropane

Names
Preferred IUPAC name 1,2-Propanediamine
Systematic IUPAC name Propane-1,2-diamine
Identifiers
CAS Number	78-90-0 N
3D model (Jmol)	Interactive image
Beilstein Reference	605274
ChEBI	CHEBI:30630 Y
ChemSpider	13849260 Y 394801 R N 557530 S N
ECHA InfoCard	100.001.051
EC Number	201-155-9
Gmelin Reference	25709
MeSH	1,2-diaminopropane
PubChem CID	6567 447820 R 642322 S
RTECS number	TX6650000
UN number	2258
InChI InChI=1S/C3H10N2/c1-3(5)2-4/h3H,2,4-5H2,1H3 Y Key: dAOHJOMMDDJHIJH-UHFFFAOYSA-N N
SMILES CC(N)CN
Properties
Chemical formula	C3H10N2
Molar mass	74.13 g·mol−1
Appearance	Colourless liquid
Odor	Fishy, ammoniacal
Density	870 mg mL−1
Melting point	−37.1 °C; −34.9 °F; 236.0 K
Boiling point	119.6 °C; 247.2 °F; 392.7 K
Vapor pressure	1.9 Pa (at 20 °C)
Magnetic susceptibility (χ)	-58.1·10−6 cm3/mol
Refractive index (nD)	1.446
Thermochemistry
Specific heat capacity (C)	205.64 J K−1 mol−1
Std molar entropy (So298)	247.27 J K−1 mol−1
Std enthalpy of formation (ΔfHo298)	−98.2–−97.4 kJ mol−1
Std enthalpy of combustion (ΔcHo298)	−2.5122–−2.5116 MJ mol−1
Hazards
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H226, H302, H312, H314
GHS precautionary statements	P280, P305+351+338, P310
EU classification (DSD)	C
R-phrases	R10, R21/22, R35
S-phrases	S26, S37/39, S45
Flash point	34 °C (93 °F; 307 K)
Autoignition temperature	360 °C (680 °F; 633 K)
Explosive limits	1.9–11.1%
Lethal dose or concentration (LD, LC):
LD50 (median dose)	434 mg kg−1(dermal, rabbit) 2.23 g kg−1(oral, rat)
Related compounds
Related alkanamines	Ethylamine Ethylenediamine Propylamine Isopropylamine 1,3-Diaminopropane Isobutylamine tert-Butylamine n-Butylamine sec-Butylamine Putrescine
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).
N  (what is YN ?)
Infobox references

1,2-Diaminopropane (1,2-propanediamine) is a diamine commonly used as a bidentate ligand in coordination chemistry. Pn is the simplest chiral diamine. The molecules exists as a colorless liquid at room temperature.

Industrially, this compound is synthesized by the ammonolysis of 1,2-dichloropropane: This preparation allows for the use of waste chloro-organic compounds to form useful amines using inexpensive and readily available ammonia:

The racemic mixture of this chiral compound may be separated into enantiomers by conversion into the diastereomeric tartaric acid ammonium salt. After purification of the diastereomer, the diamine can be regenerated by treatment of the ammonium salt with sodium hydroxide. Alternate reagents for chiral resolution include N-p-toluenesulfonylaspartic acid, N-benzenesulfonylaspartic acid, or N-benzoylglutamic acid.

1,2-Diaminopropane can be converted to N,N′-disalicylidene-1,2-propanediamine, a useful salen-type ligand that is abbreviated salpn. The synthesis is achieved by a condensation reaction of the diamine with salicylaldehyde:

Salpn is used as a fuel additive as a metal deactivator in motor oils. Trace metals degrade the fuels by catalyzing oxidation processes that lead to gums and solids. Metal deactivators like salpn form stable complexes with the metals, suppressing their catalytic activity. While salpn forms stable chelate complexes with many metals including copper, iron, chromium, and nickel, it is the coordination with copper that makes it a popular choice as a fuel additive. Copper has the highest catalytic activity in fuel, and salpn forms a highly stable square-planar complex with the metal. This complex is especially stable because salpn is a tetra-dentate ligand with a -2 charge (after deprotonation of the two phenolic groups).

The use of salpn is preferred over the use of ethylenediamine (producing salen), possibly because the propane derivatives has higher solubility.