Isopropylamine

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Isopropylamine
Skeletal formula of isopropylamine
Ball-and-stick model of the isopropylamine molecule
Names
Preferred IUPAC name
Propan-2-amine
Other names
  • (Propan-2-yl)amine
  • Isopropylamine
  • 2-aminopropane
  • 2-propanamine
  • monoisopropylamine
  • MIPA
Identifiers
3D model (Jmol)
3DMet B01040
605259
ChEBI
ChemSpider
ECHA InfoCard 100.000.783
EC Number 200-860-9
KEGG
MeSH 2-propylamine
RTECS number NT8400000
UNII
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 The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H224, H315, H319, H335
P210, P261, P305+351+338
Extremely Flammable F+ Irritant 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)[2]
7000 ppm (mouse, 40 min)[2]
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 5 ppm (12 mg/m3)[1]
REL (Recommended)
None established[1]
IDLH (Immediate danger)
750 ppm[1]
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 (monoisopropyl amine, 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] The pKa of protonated form is 10.63[4]

Preparation and use[edit]

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[which?] as DF) produces sarin gas.

References[edit]

  1. ^ a b c "NIOSH Pocket Guide to Chemical Hazards #0360". National Institute for Occupational Safety and Health (NIOSH). 
  2. ^ a b "Isopropylamine". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health. 4 December 2014. Retrieved 14 April 2015. 
  3. ^ a b 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 .

External links[edit]