1-Hydroxy-7-azabenzotriazole

1-Hydroxy-7-azabenzotriazole (HOAt) is a triazole used as a peptide coupling reagent.[2] It suppresses racemization that can otherwise occur during the reaction.[3]

"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-[1,2,3]Triazolo[4,5-b]pyridin-3-ol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.122.938
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
Hazards
GHS labelling:[1]
GHS01: Explosive GHS05: Corrosive GHS06: Toxic GHS07: Exclamation mark
Danger
H204, H301, H302, H315, H318, H319, H335
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 [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

HOAt has a melting point between 213 and 216 degrees Celsius.[4] 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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