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Sigma-Aldrich

1-Hydroxy-7-azabenzotriazole solution

~0.6 M in DMF, for peptide synthesis

Synonym(s):

3H-[1,2,3]-Triazolo[4,5-b]pyridin-3-ol, HOAt

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About This Item

Empirical Formula (Hill Notation):
C5H4N4O
CAS Number:
39968-33-7
Molecular Weight:
136.11
Beilstein:
1211115
MDL number:
MFCD00210053
UNSPSC Code:
12352005
PubChem Substance ID:
57650093
NACRES:
NA.22

product name

1-Hydroxy-7-azabenzotriazole solution, ~0.6 M in DMF

form

liquid

reaction suitability

reaction type: Addition Reactions

concentration

~0.6 M in DMF

impurities

<1.0% water

refractive index

n20/D 1.441

density

0.978 g/mL at 20 °C

application(s)

peptide synthesis

SMILES string

On1nnc2cccnc12

InChI

1S/C5H4N4O/c10-9-5-4(7-8-9)2-1-3-6-5/h1-3,10H

InChI key

FPIRBHDGWMWJEP-UHFFFAOYSA-N

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General description

1-Hydroxy-7-azabenzotriazole solution, also known as 3H-[1,2,3]-triazolo[4,5-b]pyridin-3-ol, is a benzotriazolic additive that is commonly used as a coupling reagent for amino acids and peptides. It is also used to minimize epimerization.

Application

1-Hydroxy-7-azabenzotriazole solution is used as a reagent in the solid-phase synthesis of chiral peptide nucleic acids.

Other Notes

Coupling additive for efficient racemization-free coupling in peptide synthesis; segment coupling.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Eye Irrit. 2 - Flam. Liq. 3 - Repr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

136.4 °F - closed cup

Flash Point(C)

58 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Y. Nishiyama et al.
Tetrahedron Letters, 42, 8789-8789 (2001)
L.A. Carpino et al.
The Journal of Organic Chemistry, 60, 3561-3561 (1995)
L.A. Carpino, A. El-Faham
Tetrahedron, 55, 6813-6813 (1999)
Simone Di Micco et al.
Frontiers in chemistry, 8, 628609-628609 (2021-02-02)
The most severe outcome of COVID-19 infection is the development of interstitial pneumonia causing acute lung injury (ALI) and/or acute respiratory distress syndrome (ARDS), both responsible for the infected patients' mortality. ALI and ARDS are characterized by a leakage of
Oxyma-B, an excellent racemization suppressor for peptide synthesis
Yahya JE,et al.
Organic & Biomolecular Chemistry, 12, 8379-8385 (2014)
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