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Isopropylamine (also known as monoisopropyl amine, MIPA, or 2-propylamine) is an organic compound, an amine. It is a hygroscopic colorless liquid with ammonia-like odor. It is miscible with water and flammable. It is a valuable intermediate in chemical industry.[3]
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| Names | |||
|---|---|---|---|
| Preferred IUPAC name
Propan-2-amine | |||
Other names
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| Identifiers | |||
3D model (JSmol) |
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| 605259 | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider | |||
| ECHA InfoCard | 100.000.783 | ||
| EC Number |
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| KEGG | |||
| MeSH | 2-propylamine | ||
PubChem CID |
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| RTECS number |
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| UNII | |||
| UN number | 1221 | ||
CompTox Dashboard (EPA) |
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| Properties | |||
| C3H9N | |||
| Molar mass | 59.112 g·mol−1 | ||
| Appearance | Colourless liquid | ||
| Odor | "Fishy"; ammoniacal | ||
| Density | 688 mg mL−1 | ||
| Melting point | −95.20 °C; −139.36 °F; 177.95 K | ||
| Boiling point | 31 to 35 °C; 88 to 95 °F; 304 to 308 K | ||
| Miscible | |||
| log P | 0.391 | ||
| Vapor pressure | 63.41 kPa (at 20 °C) | ||
Refractive index (nD) |
1.3742 | ||
| Thermochemistry | |||
Heat capacity (C) |
163.85 J K−1 mol−1 | ||
Std molar entropy (S⦵298) |
218.32 J K−1 mol−1 | ||
Std enthalpy of formation (ΔfH⦵298) |
−113.0–−111.6 kJ mol−1 | ||
Std enthalpy of combustion (ΔcH⦵298) |
−2.3540–−2.3550 MJ mol−1 | ||
| Hazards | |||
| GHS labelling: | |||
  | |||
| Danger | |||
| H224, H315, H319, H335 | |||
| P210, P261, P305+P351+P338 | |||
| Flash point | −18 °C (0 °F; 255 K) | ||
| 402 °C (756 °F; 675 K) | |||
| Explosive limits | 2–10.4% | ||
| Lethal dose or concentration (LD, LC): | |||
LD50 (median dose) |
| ||
LC50 (median concentration) |
4,000 ppm (rat, 4 hr)[1] | ||
LCLo (lowest published) |
7000 ppm (mouse, 40 min)[1] | ||
| NIOSH (US health exposure limits): | |||
PEL (Permissible) |
TWA 5 ppm (12 mg/m3)[2] | ||
REL (Recommended) |
None established[2] | ||
IDLH (Immediate danger) |
750 ppm[2] | ||
| Related compounds | |||
Related alkanamines |
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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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Isopropylamine exhibits reactions typical of other simple alkyl amines, i.e. protonation, alkylation, acylation, condensation with carbonyls. Like other simple aliphatic amines, isopropylamine is a weak base: the pKa of [(CH3)2)CHNH3]+ is 10.63.[4]
Isopropylamine can be obtained by reaction of isopropyl alcohol with ammonia in presence of a catalyst:[3]
- (CH3)2CHOH + NH3 → (CH3)2CHNH2 + H2O
Isopropylamine is a building block for the preparation of many herbicides and pesticides including atrazine, bentazon, glyphosate, imazapyr, ametryne, desmetryn, prometryn, pramitol, dipropetryn, propazine, fenamiphos, and iprodione.[3] It is a regulating agent for plastics, an intermediate in organic synthesis of coating materials, plastics, pesticides, rubber chemicals, pharmaceuticals and others, and is an additive in the petroleum industry.
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