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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.057 Edit this at Wikidata
EC Number
  • 201-162-7
  • (R): 220-532-9
  • (S): 220-533-4
KEGG
UNII
  • InChI=1S/C3H9NO/c1-3(5)2-4/h3,5H,2,4H2,1H3 checkY
    Key: HXKKHQJGJAFBHI-UHFFFAOYSA-N checkY
  • (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
  • OC(C)CN
  • (R): O[C@H](C)CN
  • (S): O[C@@H](C)CN
Properties
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)
soluble
Solubility soluble in alcohol, ether, acetone, benzene, CCl4
1.4479
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
2
0
Flash point 77 °C (171 °F; 350 K)
374 °C (705 °F; 647 K)
Lethal dose or concentration (LD, LC):
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).

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.[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.