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1-Hydroxy-7-azabenzotriazole

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"HOAt" redirects here. For other uses, see HOAt (disambiguation).
1-Hydroxy-7-azabenzotriazole
Skeletal formula of HOAt
Space-filling model of the HOAt molecule
Names
Systematic IUPAC name
3-Hydroxytriazolo[4,5-b]pyridine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.122.938 Edit this at Wikidata
UNII
  • InChI=1S/C5H4N4O/c10-9-5-4(7-8-9)2-1-3-6-5/h1-3,10H checkY
    Key: FPIRBHDGWMWJEP-UHFFFAOYSA-N checkY
  • InChI=1/C5H4N4O/c10-9-5-4(7-8-9)2-1-3-6-5/h1-3,10H
    Key: FPIRBHDGWMWJEP-UHFFFAOYAJ
  • n1cccc2nnn(O)c12
Properties
C5H4N4O
Molar mass 136.114 g·mol−1
Density 0.973 g/mL
Melting point 213-216°C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

1-Hydroxy-7-azabenzotriazole (HOAt) is a triazole used as a peptide coupling reagent.[1] It suppresses the loss of chirality.[2]

HOAt has a melting point between 213 and 216 degrees Celsius. [3] As a liquid, it is transparent and without any color.

References

  1. ^ Carpino, Louis A (1993). "1-Hydroxy-7-azabenzotriazole. An efficient peptide coupling additive". Journal of the American Chemical Society. 115 (10): 4397. doi:10.1021/ja00063a082.
  2. ^ Valeur, Eric; Bradley, Mark (2009). "Amide bond formation: beyond the myth of coupling reagents". Chemical Society Reviews. 38: 606–631. doi:10.1039/b701677h. PMID 19169468.
  3. ^ "HOAt". Chemical Book. Retrieved January 30, 2019.


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