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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
CAS Number	75-31-0 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	605259
ChEBI	CHEBI:15739 ;
ChEMBL	ChEMBL117080 ;
ChemSpider	6123 ;
ECHA InfoCard	100.000.783
EC Number	200-860-9;
KEGG	C06748 ;
MeSH	2-propylamine
PubChem CID	6363;
RTECS number	NT8400000;
UNII	P8W26T4MTD ;
UN number	1221
CompTox Dashboard (EPA)	DTXSID2025682 ;
	InChI InChI=1S/C3H9N/c1-3(2)4/h3H,4H2,1-2H3 Key: JJWLVOIRVHMVIS-UHFFFAOYSA-N ;
	SMILES CC(C)N;
Properties
Chemical formula	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
Solubility in water	Miscible
log P	0.391
Vapor pressure	63.41 kPa (at 20 °C)
Refractive index (nD)	1.3742
Thermochemistry
Heat capacity (C)	163.85 J K−1 mol−1
Std molar; entropy (S⦵298)	218.32 J K−1 mol−1
Std enthalpy of; formation (ΔfH⦵298)	−113.0–−111.6 kJ mol−1
Std enthalpy of; combustion (ΔcH⦵298)	−2.3540–−2.3550 MJ mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H224, H315, H319, H335
Precautionary statements	P210, P261, P305+P351+P338
Flash point	−18 °C (0 °F; 255 K)
Autoignition; temperature	402 °C (756 °F; 675 K)
Explosive limits	2–10.4%
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	380 mg kg−1 (dermal, rabbit); 550 mg kg−1 (oral, rat);
LC50 (median concentration)	4,000 ppm (rat, 4 hr)
LCLo (lowest published)	7000 ppm (mouse, 40 min)
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 5 ppm (12 mg/m3)
REL (Recommended)	None established
IDLH (Immediate danger)	750 ppm
Related compounds
Related alkanamines	Ethylamine; Propylamine; 1,2-Diaminopropane; 1,3-Diaminopropane; Isobutylamine; tert-Butylamine; n-Butylamine; sec-Butylamine; Putrescine;
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). verify (what is ?) Infobox references

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

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 pK_a of [(CH₃)₂)CHNH₃]⁺ is 10.63.^[4]

Preparation and use

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

^ ^a ^b ^c NIOSH Pocket Guide to Chemical Hazards. "#0360". National Institute for Occupational Safety and Health (NIOSH).
^ ^a ^b "Isopropylamine". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health. 4 December 2014. Retrieved 14 April 2015.
^ ^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)
^ H. K. Hall, Jr. (1957). "Correlation of the Base Strengths of Amines". J. Am. Chem. Soc. 79 (20): 5441–5444. doi:10.1021/ja01577a030.