Isopropylamine

Isopropylamine
Isopropylamine
Identifiers
CAS number 75-31-0 YesY
PubChem 6363
ChemSpider 6123 YesY
UNII P8W26T4MTD YesY
EC number 200-860-9
KEGG C06748 YesY
ChEBI CHEBI:15739 YesY
ChEMBL CHEMBL117080 YesY
RTECS number NT8400000
Jmol-3D images Image 1
Image 2
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 (25 ºC)
Melting point

−95.2 ºC

Boiling point

32.4 ºC

Solubility in water miscible
Acidity (pKa) 10.63[1]
Refractive index (nD) 1.3742 (20 ºC)
Hazards[3][4]
GHS pictograms Flam. Liq. 1Eye Irrit. 2, Skin Irrit. 2, STOT SE3
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 (−35 ºF) open cup
Autoignition
temperature
402 ºC (756 ºF)
Related compounds
Related amines Ethylamine
Propylamine
sec-Butylamine
Related compounds Diisopropylamine
 YesY (verify) (what is: YesY/N?)
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-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.

References

  1. ^ Hall, H.K., J. Am. Chem. Soc., 1957, 79, 5441.
  2. ^ 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. .
  3. ^ 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 .
  4. ^ "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 .
  5. ^ US 4014933, Boettger, Guenther; Hubert Corr & Herwig Hoffmann et al., "Production of Amines from Alcohols", published 1977-03-29 .

External links


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  • isopropylamine — izopropilaminas statusas T sritis chemija formulė (CH₃)₂CHNH₂ atitikmenys: angl. isopropylamine rus. изопропиламин …   Chemijos terminų aiškinamasis žodynas

  • isopropylamine — noun An amine, a hygroscopic colourless flammable liquid with an ammonia odour, with various applications such as in herbicides, plastics, pharmaceuticals, and chemical weapons. Syn: monoisopropylamine …   Wiktionary

  • isopropylamine — /ˌaɪsoʊproʊpəlˈæmin/ (say .uysohprohpuhl ameen) noun a colourless, highly flammable liquid with a pungent ammonia like odour, used in the manufacture of glyphosate herbicides, and in the production of plastics, pesticides, pharmaceuticals, etc …  

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  • C6H17N2O5P — Glyphosate Glyphosate …   Wikipédia en Français

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