1-Aminopropan-2-ol is the

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the formula CH₃CH(OH)CH2NH₂. It is an amino alcohol. The term ''isopropanolamine'' may also refer more generally to the additional homologs

diisopropanolamine Diisopropanolamine is a chemical compound with the molecular formula used as an emulsifier, stabilizer, and chemical intermediate. Diisopropanolamine can be prepared by the reaction of isopropanolamine or ammonia with propylene oxide Propylene ...

(DIPA) and

triisopropanolamine Triisopropanolamine is an amine In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen H ...

(TIPA). 1-Aminopropan-2-ol is chiral. It can be prepared by the addition of aqueous

ammonia Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous was ...

to propylene oxide.

Biosynthesis

(''R'')-1-Aminopropan-2-ol is one of the components incorporated in the biosynthesis of cobalamin. The ''O''-phosphate ester is produced from

threonine Threonine (symbol Thr or T) is an amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated −NH form under biological conditions), a carboxyl group (which is in the deprotonated −COO� ...

by the enzyme

Threonine-phosphate decarboxylase The enzyme threonine-phosphate decarboxylase () catalyzes the chemical reaction : L-threonine O-3-phosphate \rightleftharpoons (R)-1-aminopropan-2-yl phosphate + CO2 This enzyme belongs to the family of lyases, specifically the carboxy-lyases, w ...

Applications

The isopropanolamines are used as buffers. They are good solubilizers of oil and fat, so they are used to neutralize fatty acids and sulfonic acid-based surfactants. Racemic 1-aminopropan-2-ol is typically used in

metalworking fluid Cutting fluid is a type of coolant and lubricant designed specifically for metalworking processes, such as machining and stamping. There are various kinds of cutting fluids, which include oils, oil-water emulsions, pastes, gels, aerosols (mists), ...

, waterborne coatings, personal care products, and in the production of

titanium dioxide Titanium dioxide, also known as titanium(IV) oxide or titania , is the inorganic compound with the chemical formula . When used as a pigment, it is called titanium white, Pigment White 6 (PW6), or CI 77891. It is a white solid that is insolubl ...

and polyurethanes. It is an intermediate in the synthesis of a variety of pharmaceutical drugs. (''R'')-1-aminopropan-2-ol is metabolised to

aminoacetone Aminoacetone is the simplest monopeptide with the formula CH3C(O)CH2NH2. Although stable in the gaseous form, once condensed it reacts with itself. The protonated derivative forms stable salts, e.g. aminoacetone hydrochloride ( H3C(O)CH2NH3l)). ...

by the enzyme (''R'')-aminopropanol dehydrogenase. Synthesis of Hexylcaine is one application.

References

{{DEFAULTSORT:Amino-2-propanol, 1- Amines Secondary alcohols Amino alcohols