 | |
| 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 |
| EC Number |
|
| 25709 | |
| MeSH | 1,2-diaminopropane |
| RTECS number |
|
| UNII | |
| UN number | 2258 |
| |
| |
| Properties | |
| C3H10N2 | |
| Molar mass | 74.127 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 kPa (at 20 °C) |
| −58.1·10−6 cm3/mol | |
Refractive index (nD) | 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: | |
   | |
| Danger | |
| H226,H302,H312,H314 | |
| P280,P305+P351+P338,P310 | |
| Flash point | 34 °C (93 °F; 307 K) |
| 360 °C (680 °F; 633 K) | |
| Explosive limits | 1.9–11.1% |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) |
|
| 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). | |
1,2-Diaminopropane (propane-1,2-diamine) isorganic compound with the formula CH3CH(NH2)CH2NH2. A colorless liquid, it is the simplest chiraldiamine.
Industrially, this compound is synthesized by theammonolysis of1,2-dichloropropane:[1]
This preparation allows for the use of waste chloro-organic compounds to form useful amines using inexpensive and readily availableammonia.[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 forchiral resolution includeN-p-toluenesulfonylaspartic acid,N-benzenesulfonylaspartic acid, orN-benzoylglutamic acid.[3]
1,2-Diaminopropane is used in the synthesis ofN,N′-disalicylidene-1,2-propanediamine, asalen-typeligand, usually abbreviated as salpn, that is used as ametal deactivating additive inmotor oils.[4]
1,2-Diaminopropane formscoordination complexes similar totris(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 are1,2-diaminocyclohexane and2,3-diaminobutane. The chiral diastereomers of those diamines are C2-symmetric.
