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 | |||
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| 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)
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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: | |||
 
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| 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)
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LC50 (median concentration)
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4,000 ppm (rat, 4 hr)[2] | ||
LCLo (lowest published)
|
7000 ppm (mouse, 40 min)[2] | ||
| NIOSH (US health exposure limits): | |||
PEL (Permissible)
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TWA 5 ppm (12 mg/m3)[1] | ||
REL (Recommended)
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None established[1] | ||
IDLH (Immediate danger)
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750 ppm[1] | ||
| Related compounds | |||
Related alkanamines
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Related compounds
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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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Reactions
editIsopropylamine 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]
Preparation and use
editIsopropylamine 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.
References
edit- ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0360". National Institute for Occupational Safety and Health (NIOSH).
- ^ a b "Isopropylamine". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health. 4 December 2014. Retrieved 14 April 2015.
- ^ a b c Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke (2005). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_001.
{{cite book}}: CS1 maint: multiple names: authors list (link) - ^ H. K. Hall, Jr. (1957). "Correlation of the Base Strengths of Amines". J. Am. Chem. Soc. 79 (20): 5441–5444. doi:10.1021/ja01577a030.
External links
edit- International Chemical Safety Card 0908
- NIOSH Pocket Guide to Chemical Hazards. "#0360". National Institute for Occupational Safety and Health (NIOSH).