1,2-Diaminopropane

Chemical compound From Wikipedia, the free encyclopedia

1,2-Diaminopropane (propane-1,2-diamine) is organic compound with the formula CH3CH(NH2)CH2NH2. A colorless liquid, it is the simplest chiral diamine.

Quick facts Names, Identifiers ...
1,2-Diaminopropane
Skeletal formula of 1,2-diaminopropane with some implicit hydrogens shown
Skeletal formula of 1,2-diaminopropane with some implicit hydrogens shown
Names
Preferred IUPAC name
Propane-1,2-diamine
Other names
1,2-Propanediamine
Identifiers
3D model (JSmol)
605274
ChEBI
ChemSpider
ECHA InfoCard 100.001.051 Edit this at Wikidata
EC Number
  • 201-155-9
25709
MeSH 1,2-diaminopropane
RTECS number
  • TX6650000
UNII
UN number 2258
  • InChI=1S/C3H10N2/c1-3(5)2-4/h3H,2,4-5H2,1H3 checkY
    Key: dAOHJOMMDDJHIJH-UHFFFAOYSA-N â˜’N
  • CC(N)CN
Properties
C3H10N2
Molar mass 74.127 g·mol−1
Appearance Colourless liquid
Odor Fishy, ammoniacal
Density 870 mg mL−1
Melting point −37.1 Â°C; −34.9 Â°F; 236.0 K
Boiling point 119.6 Â°C; 247.2 Â°F; 392.7 K
Vapor pressure 1.9 kPa (at 20 °C)
−58.1·10−6 cm3/mol
1.446
Thermochemistry
205.64 J K−1 mol−1
Std molar
entropy (S⦵298)
 247.27 J K−1 mol−1
Std enthalpy of
formation (ΔfH⦵298)
 −98.2 – −97.4 kJ mol−1
Std enthalpy of
combustion (ΔcH⦵298)
 −2.5122 – −2.5116 MJ mol−1
Hazards
GHS labelling:
GHS02: Flammable GHS05: Corrosive GHS07: Exclamation mark
Danger
H226, H302, H312, H314
P280, P305+P351+P338, P310
Flash point 34 Â°C (93 Â°F; 307 K)
360 Â°C (680 Â°F; 633 K)
Explosive limits 1.9–11.1%
Lethal dose or concentration (LD, LC):
  • 434 mg kg−1 (dermal, rabbit)
  • 2.23 g 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 Â°C [77 Â°F], 100 kPa).
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Preparation

Industrially, this compound is synthesized by the ammonolysis of 1,2-dichloropropane:[1]

CH3CHClCH2Cl + 4 NH3 → CH3CH(NH2)CH2NH2 + 2 NH4Cl

This preparation allows for the use of waste chloro-organic compounds to form useful amines using inexpensive and readily available ammonia.[1]

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.[2] Alternate reagents for chiral resolution include N-p-toluenesulfonylaspartic acid, N-benzenesulfonylaspartic acid, or N-benzoylglutamic acid.[3]

Uses

1,2-Diaminopropane is used in the synthesis of N,N′-disalicylidene-1,2-propanediamine, a salen-type ligand, usually abbreviated as salpn, that is used as a metal deactivating additive in motor oils.[4]

Related compounds and derivatives

1,2-Diaminopropane forms coordination complexes similar to tris(ethylenediamine)cobalt(III). Owing to the presence of the methyl groups, [Co(pn)3]3+ can exist as 24 stereoisomers.[5]

Two chiral 1,2-diamines are 1,2-diaminocyclohexane and 2,3-diaminobutane. The chiral diastereomers of those diamines are C2-symmetric.

References

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