Isopropylamine

Isopropylamine

Names
IUPAC name Propan-2-amine
Other names 2-Aminopropane 2-Propanamine 2-Propylamine 1-Methylethanamine Monoisopropylamine sec-Propylamine
Identifiers
Jmol-3D images	Image
SMILES CC(C)N
Properties
Chemical formula	C3H9N
Molar mass	59.11 g/mol
Appearance	Colorless hygroscopic liquid
Odor	Fish-like Ammoniacal
Density	0.6891 g/cm3 (at 20 °C)
Melting point	−95.20 °C (−139.36 °F; 177.95 K)
Boiling point	32.4 °C (90.3 °F; 305.5 K)
Solubility in water	Miscible
Solubility	Reacts with acids Miscible with acetone, benzene, chloroform
Vapor pressure	63.41 kPa (at 20 °C)
Acidity (pKa)	10.63
Thermochemistry
Std molar entropy (So298)	218.32 J·K−1·mol−1
Std enthalpy of formation (ΔfHo298)	−113.0–−111.6 kJ·mol−1
Hazards
Safety data sheet	ScienceLab
Flash point	−18 °C (-35 °C by others)
Lethal dose or concentration (LD, LC):
LD50 (Median dose)	380 mg/kg (dermal, rabbit) 550 mg/kg (oral, rat)
LC50 (Median concentration)	4,000 ppm (rat, 4 hr)
Related compounds
Related compounds	Propylamine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Isopropylamine, also known as 2-propanamine or propan-2-amine, is an organic amine compound, mostly used as a solvent. It has the chemical formula C₃H₉N or (CH₃)₂CHNH₂. While "isopropylamine" can be shortened to "IPA", this is not recommended, as IPA more commonly stands for isopropyl alcohol.

Properties

Chemical

Isopropylamine reacts with acids, such as hydrochloric acid to form isopropylamine salts, such as isopropylamine chloride.

Physical

Isopropylamine is a hygroscopic colorless volatile liquid, with a strong fish or ammonia-like odor. It has a low boiling point of only 32.4 °C, while its melting point is −95.2 °C. Isopropylamine is miscible with water, as well as other organic solvents, such as ethanol, diethyl ether. It is also soluble in acetone, benzene, chloroform, but reacts with acidic solvents. It is extremely flammable, with a flash point of -18 °C or −35 °C (according to ESIS) and an autoignition temperature of 402 °C.

Availability

Isopropylamine is sold by various chemical suppliers.

Sciencelab sells 500 ml at $85.55.

Preparation

Isopropylamine can be made by reacting isopropanol with ammonia, in the presence of a copper/cobalt/nickel catalyst.

Projects

• Extract natural compounds
• Make N-methylisopropylamine

Handling

Safety

Isopropylamine has an unpleasant fishy smell, and it poses some toxicity. Skin contact with pure isopropylamine may cause burns. Vapors can severely irritate eyes and lungs.

It is volatile and quite flammable.

Storage

Isopropylamine, if desired as free base, must be stored in closed bottles, in dark and well ventilated places. Scrubbers containing low-volatile acids, like oxalic acid can be used to neutralize escaping isopropylamine vapors.

Isopropylamine salts must be stored in closed bottles, away from moisture and acidic vapors.

Disposal

Isopropylamine can be disposed of by burning it, either pure or mixed with a more volatile solvent. This produces carbon dioxide/monoxide, water vapors and traces of unburnt isopropylamine. The traces will give the smoke a bad smell, so it's recommended you do this in open spaces, away from people, and you should burn small amounts at a time.

Isopropylamine can be destroyed by adding it dropwise in a solution of Fenton's reagent. Since the destruction process will aerosolize a small amount of isopropylamine, this is best done outside. As isopropylamine has a strong and unpleasant smell, do not do this indoors!

Adding an acid to isopropylamine will give off a very fine salt mist.

References

Relevant Sciencemadness threads

• Isopropylamine one pot synthesis
• Isopropylamine and Diisopropylamine from Acetone