1-Aminopropan-2-ol

1-Aminopropan-2-ol is the organic compound with the formula CH₃CH(OH)CH₂NH₂. It is an amino alcohol. The term isopropanolamine may also refer more generally to the additional homologs diisopropanolamine (DIPA) and triisopropanolamine (TIPA).

1-Aminopropan-2-ol

Names
Preferred IUPAC name 1-Aminopropan-2-ol
Other names 1-Amino-2-propanol Isopropanolamine MIPA; Threamine
Identifiers
Compounds (+/−)-1-Aminopropan-2-ol (R): (−)-1-Aminopropan-2-ol (S): (+)-1-Aminopropan-2-ol
CAS Number	78-96-6 Y (R): 2799-16-8 Y (S): 2799-17-9 Y
3D model (JSmol)	(R): Interactive image (S): Interactive image
ChEBI	CHEBI:19030 Y
ChEMBL	ChEMBL326602 Y
ChemSpider	3 Y (R): 388968 Y (S): 5641722 Y
ECHA InfoCard	100.001.057
EC Number	201-162-7 (R): 220-532-9 (S): 220-533-4
KEGG	C05771 Y
PubChem CID	4 (R): 439938 (S): 7311736
UNII	UE40BY1BZW Y
CompTox Dashboard (EPA)	DTXSID9021764
InChI InChI=1S/C3H9NO/c1-3(5)2-4/h3,5H,2,4H2,1H3 Y Key: HXKKHQJGJAFBHI-UHFFFAOYSA-N Y (R): InChI=1S/C3H9NO/c1-3(5)2-4/h3,5H,2,4H2,1H3/t3-/m1/s1 Key: HXKKHQJGJAFBHI-GSVOUGTGSA-N (S): InChI=1S/C3H9NO/c1-3(5)2-4/h3,5H,2,4H2,1H3/t3-/m0/s1 Key: HXKKHQJGJAFBHI-VKHMYHEASA-N
SMILES OC(C)CN (R): O[C@H](C)CN (S): O[C@@H](C)CN
Properties
Chemical formula	C3H9NO
Molar mass	75.111 g·mol−1
Appearance	liquid
Odor	ammonia-like
Density	0.973 g/mL (18 °C) [1]
Melting point	1.74 °C (35.13 °F; 274.89 K)
Boiling point	159.46 °C (319.03 °F; 432.61 K)
Solubility in water	soluble
Solubility	soluble in alcohol, ether, acetone, benzene, CCl4
Refractive index (nD)	1.4479
Hazards
NFPA 704 (fire diamond)	2 2 0
Flash point	77 °C (171 °F; 350 K)
Autoignition temperature	374 °C (705 °F; 647 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)	4.26 g/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

1-Aminopropan-2-ol is chiral. It can be prepared by the addition of aqueous ammonia to propylene oxide.^[2]

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 by the enzyme Threonine-phosphate decarboxylase.^[3][4]

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, waterborne coatings, personal care products, and in the production of titanium dioxide and polyurethanes.^[5] It is an intermediate in the synthesis of a variety of pharmaceutical drugs.^{[citation needed]}

(R)-1-aminopropan-2-ol is metabolised to aminoacetone by the enzyme (R)-aminopropanol dehydrogenase.^[6]

Synthesis of Hexylcaine is one application.

References

1. Amino-2-propanol at Sigma-Aldrich
2. Smith, Michael B. (19 February 2020). March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. John Wiley & Sons. ISBN 9781119371809.
3. Cheong, Cheom-Gil; Bauer, Cary B.; Brushaber, Kevin R.; Escalante-Semerena, Jorge C.; Rayment, Ivan (2002). "Three-Dimensional Structure of the L-Threonine-O-3-phosphate Decarboxylase (CobD) Enzyme from Salmonella enterica". Biochemistry. 41 (15): 4798–4808. doi:10.1021/bi012111w. PMID 11939774.
4. Warren, Martin J.; Raux, Evelyne; Schubert, Heidi L.; Escalante-Semerena, Jorge C. (2002). "The biosynthesis of adenosylcobalamin (Vitamin B₁₂)". Natural Product Reports. 19 (4): 390–412. doi:10.1039/b108967f. PMID 12195810.
5. "Monoisopropanolamine". Nanjing HBL International. Retrieved 2020-04-28.
6. Turner, JM (1967). "Microbial metabolism of amino ketones. L-1-aminopropan-2-ol dehydrogenase and L-threonine dehydrogenase in Escherichia coli". Biochemical Journal. 104 (1): 112–121. doi:10.1042/bj1040112. PMC 1270551. PMID 5340733.