Isopropylamine

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Isopropylamine
Skeletal formula of isopropylamine
Ball-and-stick model of the isopropylamine molecule
Names
IUPAC name
Propan-2-amine[1]
Other names
  • 2-Aminopropane
  • 2-Propylamine
  • 1-Methylethanamine
  • Monoisopropylamine
  • sec-Propylamine
Identifiers
3DMet B01040
605259
75-31-0 YesY
ChEBI CHEBI:15739 YesY
ChEMBL ChEMBL117080 YesY
ChemSpider 6123 YesY
EC number 200-860-9
Jmol-3D images Image
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 722 mg mL−1
Melting point −95.20 °C; −139.36 °F; 177.95 K
Boiling point 31 °C; 88 °F; 304 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
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 −18 °C (0 °F; 255 K)
402 °C (756 °F; 675 K)
Explosive limits 2–10.4%
  • 380 mg kg−1 (dermal, rabbit)
  • 550 mg kg−1 (oral, rat)
4,000 ppm (rat, 4 hr)[2]
US health exposure limits (NIOSH):
TWA 5 ppm (12 mg/m3)[3]
None established[3]
750 ppm[3]
Related compounds
Related alkanamines
Related compounds
2-Methyl-2-nitrosopropane
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 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.

pKa of protonated form is 10.63[4]

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, 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 (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[edit]

  1. ^ "2-propylamine - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification and Related Records. Retrieved 4 May 2012. 
  2. ^ "Isopropylamine". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health. 4 December 2014. Retrieved 14 April 2015. 
  3. ^ a b c "NIOSH Pocket Guide to Chemical Hazards #0360". National Institute for Occupational Safety and Health (NIOSH). 
  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]