1-Hydroxy-7-azabenzotriazole

1-Hydroxy-7-azabenzotriazole
Names
	Preferred IUPAC name 3H-[1,2,3]Triazolo[4,5-b]pyridin-3-ol
Identifiers
CAS Number	39968-33-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	158005 ;
ECHA InfoCard	100.122.938
PubChem CID	181649;
UNII	TX8XYH09H0 ;
CompTox Dashboard (EPA)	DTXSID0075239 ;
	InChI InChI=1S/C5H4N4O/c10-9-5-4(7-8-9)2-1-3-6-5/h1-3,10H Key: FPIRBHDGWMWJEP-UHFFFAOYSA-N ; InChI=1/C5H4N4O/c10-9-5-4(7-8-9)2-1-3-6-5/h1-3,10H Key: FPIRBHDGWMWJEP-UHFFFAOYAJ;
	SMILES n1cccc2nnn(O)c12;
Properties
Chemical formula	C5H4N4O
Molar mass	136.114 g·mol−1
Density	0.973 g/mL
Melting point	213-216°C
Hazards
	GHS labelling:
Pictograms
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 [77 °F], 100 kPa). verify (what is ?) Infobox references

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

^ GHS: Sigma Aldrich 445452
^ 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.
^ 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.
^ "HOAt". Chemical Book. Retrieved January 30, 2019.

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