1-Aminopropan-2-ol

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 ; (R): 2799-16-8 ; (S): 2799-17-9 ;
3D model (JSmol)	(R): Interactive image; (S): Interactive image;
ChEBI	CHEBI:19030 ;
ChEMBL	ChEMBL326602 ;
ChemSpider	3 ; (R): 388968 ; (S): 5641722 ;
ECHA InfoCard	100.001.057
EC Number	201-162-7; (R): 220-532-9; (S): 220-533-4;
KEGG	C05771 ;
PubChem CID	4; (R): 439938; (S): 7311736;
UNII	UE40BY1BZW ;
CompTox Dashboard (EPA)	DTXSID9021764 ;
	InChI InChI=1S/C3H9NO/c1-3(5)2-4/h3,5H,2,4H2,1H3 Key: HXKKHQJGJAFBHI-UHFFFAOYSA-N ; (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 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 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.

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

Synthesis of Hexylcaine is one application.

References

Amino-2-propanol at Sigma-Aldrich
Smith, Michael B. (19 February 2020). March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. ISBN 9781119371809.
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.
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.
"Monoisopropanolamine". Nanjing HBL International. Retrieved 2020-04-28.
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.

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[sigmaaldrich-1] Amino-2-propanol at Sigma-Aldrich

[2] Smith, Michael B. (19 February 2020). March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. 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.