Isopropylamine

Isopropylamine
IUPAC name Propan-2-amine
Other names 2-Propylamine 2-Aminopropane
Identifiers
CAS number	75-31-0 Y
PubChem	6363
ChemSpider	6123 Y
UNII	P8W26T4MTD Y
EC number	200-860-9
KEGG	C06748 Y
ChEBI	CHEBI:15739 Y
ChEMBL	CHEMBL117080 Y
RTECS number	NT8400000
Jmol-3D images	Image 1 Image 2
SMILES NC(C)C NC(C)C
InChI InChI=1S/C3H9N/c1-3(2)4/h3H,4H2,1-2H3 Y Key: JJWLVOIRVHMVIS-UHFFFAOYSA-N Y InChI=1/C3H9N/c1-3(2)4/h3H,4H2,1-2H3
Properties[2][3]
Molecular formula	C3H9N
Molar mass	59.110 g/mol
Appearance	colourless liquid, hygroscopic, with odour of ammonia
Density	0.722 g/cm3 (25 ºC)
Melting point	−95.2 ºC
Boiling point	32.4 ºC
Solubility in water	miscible
Acidity (pKa)	10.63[1]
Refractive index (nD)	1.3742 (20 ºC)
Hazards[3][4]
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H224, H319, H335, H315
GHS precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+352, P303+361+353, P304+340, P305+351+338
EU Index	612-007-00-1
EU classification	Extremely flammable (F+) Irritant (Xi)
R-phrases	R12, R36/37/38
S-phrases	(S2), S16, S26, S29
Flash point	−51 °C (−35 ºF) open cup
Autoignition temperature	402 ºC (756 ºF)
Related compounds
Related amines	Ethylamine Propylamine sec-Butylamine
Related compounds	Diisopropylamine
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.

Isopropylamine can be obtained by aminating isopropyl alcohol with ammonia in presence of a nickel/copper or similar catalyst^[5]:

(CH₃)₂CHOH + NH₃ → (CH₃)₂CHNH₂ + H₂O

The main uses of isopropylamine are in glyphosate herbicide formulations (e.g., Roundup or Vantage), 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, as a mixture called OPA which in turn mixed with methylphosphonyl difluoride (known to the military as DF) produces sarin gas.

References

1. ^ Hall, H.K., J. Am. Chem. Soc., 1957, 79, 5441.
2. ^ Weast, Robert C., ed (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, FL: CRC Press. p. C-478. ISBN 0-8493-0462-8. .
3. ^ ^{a b} Isopropylamine, International Chemical Safety Card 0908, Geneva: International Programme on Chemical Safety, April 1997, http://www.inchem.org/documents/icsc/icsc/eics0908.htm .
4. ^ "Isopropylamine", Pocket Guide to Chemical Hazards, U.S. Department of Health and Human Services (NIOSH) Publication No. 2005-149, Washington, DC: Government Printing Office, 2005, ISBN 9780160727511, http://www.cdc.gov/niosh/npg/npgd0360.html .
5. ^ US 4014933, Boettger, Guenther; Hubert Corr & Herwig Hoffmann et al., "Production of Amines from Alcohols", published 1977-03-29 .

External links

• International Chemical Safety Card 0908
• NIOSH Pocket Guide to Chemical Hazards 0360
• Atrazine News - an Atrazine specific news site