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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
Preferred IUPAC name 3H-Triazolopyridin-3-ol
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.122.938 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H4N4O/c10-9-5-4(7-8-9)2-1-3-6-5/h1-3,10HKey: FPIRBHDGWMWJEP-UHFFFAOYSA-N
  • InChI=1/C5H4N4O/c10-9-5-4(7-8-9)2-1-3-6-5/h1-3,10HKey: FPIRBHDGWMWJEP-UHFFFAOYAJ
SMILES
  • n1cccc2nnn(O)c12
Properties
Chemical formula C5H4N4O
Molar mass 136.114 g·mol
Density 0.973 g/mL
Melting point 213-216°C
Hazards
GHS labelling:
Pictograms GHS01: Explosive GHS05: Corrosive GHS06: Toxic GHS07: Exclamation mark
Signal word Danger
Hazard statements H204, H301, H302, H315, H318, H319, H335
Precautionary statements P210, P240, P250, P261, P264, P270, P271, P280, P301+P310, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P337+P313, P362, P370+P380, P372, P373, P374, P401, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

1-Hydroxy-7-azabenzotriazole (HOAt) is a triazole used as a peptide coupling reagent. It suppresses racemization that can otherwise occur during the reaction.

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

References

  1. GHS: Sigma Aldrich 445452
  2. Carpino, Louis A (1993). "1-Hydroxy-7-azabenzotriazole. An efficient peptide coupling additive". Journal of the American Chemical Society. 115 (10): 4397–4398. doi:10.1021/ja00063a082.
  3. Valeur, Eric; Bradley, Mark (2009). "Amide bond formation: beyond the myth of coupling reagents". Chemical Society Reviews. 38 (2): 606–631. doi:10.1039/b701677h. PMID 19169468.
  4. "HOAt". Chemical Book. Retrieved January 30, 2019.
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