Isopropylamine

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]

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 Y
3D model (JSmol)	Interactive image
Beilstein Reference	605259
ChEBI	CHEBI:15739 Y
ChEMBL	ChEMBL117080 Y
ChemSpider	6123 Y
ECHA InfoCard	100.000.783
EC Number	200-860-9
KEGG	C06748 Y
MeSH	2-propylamine
PubChem CID	6363
RTECS number	NT8400000
UNII	P8W26T4MTD Y
UN number	1221
CompTox Dashboard (EPA)	DTXSID2025682
InChI InChI=1S/C3H9N/c1-3(2)4/h3H,4H2,1-2H3 Y Key: JJWLVOIRVHMVIS-UHFFFAOYSA-N Y
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)[1]
LCLo (lowest published)	7000 ppm (mouse, 40 min)[1]
NIOSH (US health exposure limits):
PEL (Permissible)	TWA 5 ppm (12 mg/m3)[2]
REL (Recommended)	None established[2]
IDLH (Immediate danger)	750 ppm[2]
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). Y verify (what is YN ?) Infobox references

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.