Chemistry:1-Hydroxy-7-azabenzotriazole

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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
UNII
Properties
C5H4N4O
Molar mass 136.114 g·mol−1
Density 0.973 g/mL
Melting point 213-216°C
Hazards
GHS pictograms GHS01: Explosive GHS05: Corrosive GHS06: Toxic GHS07: Harmful
GHS Signal word danger
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Tracking categories (test):

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 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". https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3256884.htm.