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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

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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

Quality Level

100

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK9699
BCCL1807
BCCJ9637
BCCH0686
BCCJ5299

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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
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Synthesis of chiral peptide nucleic acids using Fmoc chemistry
Yun W and Jie-Cheng X
Tetrahedron, 57, 8107-8113 (2001)
Hsuan-Ni Lin et al.
Journal of orthopaedic research : official publication of the Orthopaedic Research Society, 34(11), 1883-1893 (2016-02-27)
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Tetrahedron, 55, 6813-6813 (1999)
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