Isopropylamine

Isopropylamine
Names
Preferred IUPAC name
Propan-2-amine
Other names
  • (Propan-2-yl)amine
  • Isopropylamine
  • 2-aminopropane
  • 2-propanamine
  • monoisopropylamine
  • MIPA
Identifiers
75-31-0 YesY
3D model (Jmol) Interactive image
3DMet B01040
605259
ChEBI CHEBI:15739 YesY
ChEMBL ChEMBL117080 YesY
ChemSpider 6123 YesY
ECHA InfoCard 100.000.783
EC Number 200-860-9
KEGG C06748 YesY
MeSH 2-propylamine
PubChem 6363
RTECS number NT8400000
UNII P8W26T4MTD YesY
UN number 1221
Properties
C3H9N
Molar mass 59.11 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)
1.3742
Thermochemistry
163.85 J K−1 mol−1
218.32 J K−1 mol−1
−113.0–−111.6 kJ mol−1
−2.3540–−2.3550 MJ mol−1
Hazards
GHS pictograms
GHS signal word DANGER
H224, H315, H319, H335
P210, P261, P305+351+338
F+ Xi
R-phrases R12, R36/37/38
S-phrases (S2), S16, S26, S29
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):
  • 380 mg kg−1 (dermal, rabbit)
  • 550 mg kg−1 (oral, rat)
4,000 ppm (rat, 4 hr)[1]
7000 ppm (mouse, 40 min)[1]
US health exposure limits (NIOSH):
PEL (Permissible)
 TWA 5 ppm (12 mg/m3)[2]
REL (Recommended)
 None established[2]
IDLH (Immediate danger)
 750 ppm[2]
Related compounds
Related alkanamines
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).
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Infobox references

'Isopropylamine (MIPA) 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]

pKa of protonated form is 10.63[4]

Preparation and use

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

Isopropylamine is a building block for the preparation of many herbicides and pesticides including atrazine.bentazon, Roundup, 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.

Together with isopropyl alcohol it is used in some binary chemical weapons (e.g. M687), as a mixture called OPA which in turn mixed with methylphosphonyl difluoride (known to the military as DF) produces sarin gas.

References

  1. 1 2 "Isopropylamine". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health. 4 December 2014. Retrieved 14 April 2015.
  2. 1 2 3 "NIOSH Pocket Guide to Chemical Hazards #0360". National Institute for Occupational Safety and Health (NIOSH).
  3. 1 2 Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. doi:10.1002/14356007.a02_001
  4. ↑ H. K. Hall (1957) J. Am. Chem. Soc. 79 5441.
  5. ↑ US 4014933, Boettger, Guenther; Hubert Corr & Herwig Hoffmann et al., "Production of Amines from Alcohols", published 1977-03-29.
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