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Isopropylamine
Isopropylamine.png
IUPAC name
Other names 2-Propylamine
2-Aminopropane
Identifiers
CAS number 75-31-0 Yes check.svgY
PubChem 6363
EC number 200-860-9
RTECS number NT8400000
SMILES
InChI
ChemSpider ID 6123
Properties[1][2]
Molecular formula C3H9N
Molar mass 59.110 g/mol
Appearance colourless liquid, hygroscopic, with odour of ammonia
Density 0.6891 g/cm3 (20 ºC)
Melting point

−95.2 ºC

Boiling point

32.4 ºC

Solubility in water miscible
Refractive index (nD) 1.3742 (20 ºC)
Hazards[2][3]
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 (−35 ºF) open cup
Autoignition
temperature
402 ºC (756 ºF)
Related compounds
Related amines Ethylamine
Propylamine
sec-Butylamine
Related compounds Diisopropylamine
 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 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[4]:

(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) producing sarin gas.

References

  1. ^ 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  .
  2. ^ a b Isopropylamine, International Chemical Safety Card 0908, Geneva: International Labour Organization, April 1997, http://www.inchem.org/documents/icsc/icsc/eics0908.htm  .
  3. ^ "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  .
  4. ^ Boettger, Guenther; Hubert Corr & Herwig Hoffmann et al., "Production of Amines from Alcohols", US 4014933, published 1977-03-29.

External links

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