Isopropylamine
| Isopropylamine | |
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Propan-2-amine |
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Other names
2-Propylamine |
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| Identifiers | |
| CAS number | 75-31-0  |
| PubChem | 6363 |
| ChemSpider | 6123 |
| UNII | P8W26T4MTD |
| EC number | 200-860-9 |
| KEGG | C06748 |
| ChEBI | CHEBI:15739 |
| ChEMBL | CHEMBL117080 |
| RTECS number | NT8400000 |
| Jmol-3D images | Image 1 Image 2 |
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| Properties[2][3] | |
| Molecular formula | C3H9N |
| Molar mass | 59.110 g/mol |
| Appearance | colourless liquid, hygroscopic, with odour of ammonia |
| Density | 0.722 g/cm3 (at 25°C) |
| Melting point |
−95.2°C |
| Boiling point |
32.4°C |
| Solubility in water | miscible |
| Acidity (pKa) | 10.63[1] |
| Refractive index (nD) | 1.3742 (20°C) |
| Hazards[3][4] | |
| GHS pictograms |   |
| GHS signal word | DANGER |
| GHS hazard statements | H224, H319, H335, H315 |
| GHS precautionary statements | P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+352, P303+361+353, P304+340, P305+351+338 |
| EU Index | 612-007-00-1 |
| EU classification | Extremely flammable (F+) Irritant (Xi) |
| R-phrases | R12, R36/37/38 |
| S-phrases | (S2), S16, S26, S29 |
| Flash point | −51°C open cup |
| Autoignition temperature |
402°C |
| Related compounds | |
| Related amines | Ethylamine Propylamine sec-Butylamine |
| Related compounds | Diisopropylamine |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Isopropylamine, also called 2-aminopropane, 2-propanamine, monoisopropylamine, and MIPA, is an organic compound, an amine. It is a base, as typical for amines. It is a hygroscopic colorless liquid with ammonia-like odor. Its melting point is −95.2°C and its boiling point is 32.4°C. It is miscible with water. It is extremely flammable, with flash point at −37°C.
Isopropylamine can be obtained by aminating isopropyl alcohol with ammonia in presence of a nickel/copper or similar catalyst[5]:
- (CH3)2CHOH + NH3 → (CH3)2CHNH2 + H2O
The main uses of isopropylamine are in glyphosate herbicide formulations (e.g., Roundup or Vantage), a key component of atrazine (another herbicide), 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.
Together with isopropyl alcohol it is used in some binary chemical weapons, as a mixture called OPA which in turn mixed with methylphosphonyl difluoride (known to the military as DF) produces sarin gas.
[edit] References
- ^ Hall, H.K., J. Am. Chem. Soc., 1957, 79, 5441.
- ^ Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, FL: CRC Press. p. C-478. ISBN 0-8493-0462-8..
- ^ a b Isopropylamine, International Chemical Safety Card 0908, Geneva: International Programme on Chemical Safety, April 1997, http://www.inchem.org/documents/icsc/icsc/eics0908.htm.
- ^ "Isopropylamine", Pocket Guide to Chemical Hazards, U.S. Department of Health and Human Services (NIOSH) Publication No. 2005-149, Washington, DC: Government Printing Office, 2005, ISBN 9780160727511, http://www.cdc.gov/niosh/npg/npgd0360.html.
- ^ US 4014933, Boettger, Guenther; Hubert Corr & Herwig Hoffmann et al., "Production of Amines from Alcohols", published 1977-03-29.
[edit] External links
- International Chemical Safety Card 0908
- NIOSH Pocket Guide to Chemical Hazards 0360
- Atrazine News - an Atrazine specific news site
