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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/REAXYS Number:
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.

signalword

Danger

Hazard Classifications

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

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

136.4 °F - closed cup

flash_point_c

58 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Júlia García-Pindado et al.
Biopolymers, 109(10), e23112-e23112 (2018-03-13)
While revisiting biologically active natural peptides, the importance of the tryptophan residue became clear. In this article, the incorporation of this amino acid, brominated at different positions of the indole ring, into cyclic peptides was successfully achieved. These products demonstrated
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
L.A. Carpino, A. El-Faham
Tetrahedron, 55, 6813-6813 (1999)
Synthesis of chiral peptide nucleic acids using Fmoc chemistry
Yun W and Jie-Cheng X
Tetrahedron, 57, 8107-8113 (2001)
Y. Nishiyama et al.
Tetrahedron Letters, 42, 8789-8789 (2001)
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