Isopropylamine
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Names | |||
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Preferred IUPAC name Propan-2-amine | |||
Other names
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Identifiers | |||
CAS Number |
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3D model (JSmol) |
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3DMet |
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Beilstein Reference | 605259 | ||
ChEBI |
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ChEMBL |
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ChemSpider |
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ECHA InfoCard | 100.000.783 ![]() | ||
EC Number |
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KEGG |
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MeSH | 2-propylamine | ||
PubChem CID |
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RTECS number |
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UNII |
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UN number | 1221 | ||
CompTox Dashboard (EPA) |
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InChI
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Properties | |||
Chemical formula | 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: | |||
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Danger | |||
H224, H315, H319, H335 | |||
P210, P261, P305+P351+P338 | |||
Flash point | −18 °C (0 °F; 255 K) | ||
Autoignition temperature | 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) | 4,000 ppm (rat, 4 hr)[2] | ||
LCLo (lowest published) | 7000 ppm (mouse, 40 min)[2] | ||
NIOSH (US health exposure limits): | |||
PEL (Permissible) | TWA 5 ppm (12 mg/m3)[1] | ||
REL (Recommended) | None established[1] | ||
IDLH (Immediate danger) | 750 ppm[1] | ||
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). ![]() ![]() ![]() Infobox references |
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]
Reactions
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]
Preparation and use
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, intermediate in organic synthesis of coating materials, plastics, pesticides, rubber chemicals, pharmaceuticals and others, and as an additive in the petroleum industry.
References
- ^ 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
- International Chemical Safety Card 0908
- NIOSH Pocket Guide to Chemical Hazards. "#0360". National Institute for Occupational Safety and Health (NIOSH).