1-Hydroxy-7-azabenzotriazole

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1-Hydroxy-7-azabenzotriazole
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Names
Preferred IUPAC name
3H-[1,2,3]Triazolo[4,5-b]pyridin-3-ol
Identifiers
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3D model (JSmol)
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  • 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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 has a melting point of 213-216 °C.[4]

References

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  1. ^ GHS: Sigma Aldrich 445452
  2. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content."HOAt". Chemical Book. Retrieved January 30, 2019.

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