Isopropylamine

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Isopropylamine
Skeletal formula of isopropylamine
Skeletal formula of isopropylamine
Ball-and-stick model of the isopropylamine molecule
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 (JSmol)
605259
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.783 Edit this at Wikidata
EC Number
  • 200-860-9
KEGG
MeSH 2-propylamine
RTECS number
  • NT8400000
UNII
UN number 1221
  • InChI=1S/C3H9N/c1-3(2)4/h3H,4H2,1-2H3 checkY
    Key: JJWLVOIRVHMVIS-UHFFFAOYSA-N checkY
  • CC(C)N
Properties
C3H9N
Molar mass 59.112 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 labelling:
GHS02: Flammable GHS07: Exclamation mark
Danger
H224, H315, H319, H335
P210, P261, P305+P351+P338
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]
NIOSH (US health exposure limits):
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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Isopropylamine (also known as monoisopropyl amine, MIPA, or 2-propylamine) 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]

Reactions

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Isopropylamine exhibits reactions typical of other simple alkyl amines, i.e. protonation, alkylation, acylation, condensation with carbonyls. Like other simple aliphatic amines, isopropylamine is a weak base: the pKa of [(CH3)2)CHNH3]+ is 10.63.[4]

Preparation and use

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Isopropylamine can be obtained by reaction of isopropyl alcohol with ammonia in presence of a catalyst:[3]

(CH3)2CHOH + NH3 → (CH3)2CHNH2 + H2O

Isopropylamine is a building block for the preparation of many herbicides and pesticides including atrazine, bentazon, glyphosate, imazapyr, ametryne, desmetryn, prometryn, pramitol, dipropetryn, propazine, fenamiphos, and iprodione.[3] It is a regulating agent for plastics, an intermediate in organic synthesis of coating materials, plastics, pesticides, rubber chemicals, pharmaceuticals and others, and is an additive in the petroleum industry.

References

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  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 c Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke (2005). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_001.{{cite book}}: CS1 maint: multiple names: authors list (link)
  4. ^ H. K. Hall, Jr. (1957). "Correlation of the Base Strengths of Amines". J. Am. Chem. Soc. 79 (20): 5441–5444. doi:10.1021/ja01577a030.
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