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1-Aminopropan-2-ol





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(Redirected from 1-Amino-2-propanol)
  

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
  • (R): 2799-16-8 checkY
  • (S): 2799-17-9 checkY

    • 3D model (JSmol)
  • (S): Interactive image
    • ChEBI
    ChEMBL
    ChemSpider
    • 3 checkY
  • (R): 388968 checkY
  • (S): 5641722 checkY
    • ECHA InfoCard 100.001.057 Edit this at Wikidata
    EC Number
    • 201-162-7
  • (R): 220-532-9
  • (S): 220-533-4
    • KEGG

    PubChem CID
  • (R): 439938
  • (S): 7311736
    • UNII

    CompTox Dashboard (EPA)

    • 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

    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)
    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)

    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 ammoniatopropylene oxide.[2]

    Biosynthesis

    edit

    (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

    edit

    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

    edit
    1. ^ Amino-2-propanol at Sigma-Aldrich
  • ^ Smith, Michael B. (19 February 2020). March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. John Wiley & Sons. 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.

    • Retrieved from "https://en.wikipedia.org/w/index.php?title=1-Aminopropan-2-ol&oldid=1216582107"
      



    Last edited on 31 March 2024, at 21:46  





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    ●This page was last edited on 31 March 2024, at 21:46 (UTC).
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