Skip to Content
Merck
All Photos(1)

Documents

41996

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

Looking for similar products? Visit Product Comparison Guide

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service