Isopropylamine

Isopropylamine

Skeletal formula of isopropylamine Ball-and-stick model of the isopropylamine molecule
Names
IUPAC name Propan-2-amine
Other names 2-Aminopropane 2-Propylamine 1-Methylethanamine Monoisopropylamine sec-Propylamine
Identifiers
CAS Number	75-31-0 Y
3DMet	B01040
Beilstein Reference	605259
ChEBI	CHEBI:15739 Y
ChEMBL	ChEMBL117080 Y
ChemSpider	6123 Y
EC Number	200-860-9
Jmol 3D model	Interactive image
KEGG	C06748 Y
MeSH	2-propylamine
PubChem	[https://pubchem.ncbi.nlm.nih.gov/compound/6363 Template:Pubchemcit 6363 Template:Pubchemcit]
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
Vapor pressure	{{{value}}}
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

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.

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:

(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.

External links

• International Chemical Safety Card 0908
• Atrazine News - an Atrazine specific news site