Isopropylamine

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Isopropylamine
Skeletal formula of isopropylamine Ball and stick model of isopropylamine
Identifiers
CAS number 75-31-0 YesY
PubChem 6363
ChemSpider 6123 YesY
UNII P8W26T4MTD YesY
EC number 200-860-9
UN number 1221
KEGG C06748 YesY
MeSH 2-propylamine
ChEBI CHEBI:15739 YesY
ChEMBL CHEMBL117080 YesY
RTECS number NT8400000
Beilstein Reference 605259
3DMet B01040
Jmol-3D images Image 1
Properties
Molecular formula 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 to 35 °C; 88 to 95 °F; 304 to 308 K
Solubility in water Miscible
log P 0.391
Vapor pressure 63.41 kPa (at 20 °C)
Refractive index (nD) 1.3742
Thermochemistry
Specific
heat capacity
C
163.85 J K−1 mol−1
Std molar
entropy
So298
218.32 J K−1 mol−1
Std enthalpy of
formation
ΔfHo298
−113.0–−111.6 kJ mol−1
Std enthalpy of
combustion
ΔcHo298
−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
GHS hazard statements H224, H315, H319, H335
GHS precautionary statements 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)
Explosive limits 2–10.4%
LD50
  • 380 mg kg−1 (dermal, rabbit)
  • 550 mg kg−1 (oral, rat)
Related compounds
Related alkanamines
Related compounds 2-Methyl-2-nitrosopropane
Except where noted otherwise, data are 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[2]

Isopropylamine can be obtained by aminating isopropyl alcohol with ammonia in presence of a nickel/copper or similar catalyst:[3]

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

External links[edit]