Isopropylamine

Isopropylamine

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 (Jmol)	Interactive image
3DMet	B01040
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	6363
RTECS number	NT8400000
UNII	P8W26T4MTD Y
UN number	1221
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	59.11 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
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
GHS signal word	DANGER
GHS hazard statements	H224, H315, H319, H335
GHS precautionary statements	P210, P261, P305+351+338
EU classification (DSD)	F+ Xi
R-phrases	R12, R36/37/38
S-phrases	(S2), S16, S26, S29
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)
US health exposure limits (NIOSH):
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).
Y  (what is YN ?)
Infobox references

'Isopropylamine (MIPA) 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.

pK_a of protonated form is 10.63

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

Isopropylamine is a building block for the preparation of many herbicides and pesticides including atrazine, bentazon, Roundup, imazapyr, ametryne, desmetryn, prometryn, pramitol, dipropetryn, propazine, fenamiphos, and iprodione. It is 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.