1-hydroxybenzotriazole

Also known as hydroxybenzotriazole, N-Hydroxybenzotriazole, HOBt

Hydroxybenzotriazole (abbreviated HOBt) is an organic compound with the formula . It is a derivative of benzotriazole. It is a white crystalline powder, which as a commercial product contains some water (~11.7% wt as the HOBt monohydrate crystal). Anhydrous HOBt is explosive. It is mainly used to suppress the racemization and to improve the efficiency of peptide synthesis.

Chemical data

Formula: C6H5N3O
Molecular weight: 135.12 g/mol
IUPAC name: 1-hydroxybenzotriazole
SMILES: C1=CC=C2C(=C1)N=NN2O
InChIKey: ASOKPJOREAFHNY-UHFFFAOYSA-N
XLogP: 1.2
Polar surface area: 50.9 Å²
H-bond donors: 1
H-bond acceptors: 3
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Subclass of: heterocyclic compound
Mass: 135.043

Show 3 more facts

chemical formula: C₆H₅N₃O
canonical SMILES: C1=CC=C2C(=C1)N=NN2O
Commons category: 1-Hydroxybenzotriazole

Sources (3)

via Wikidata · CC0

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Encyclopedic overview

3 sections

Contents

Use in peptide synthesis
Safety
References

==Use in peptide synthesis== center|500x500px Automated peptide synthesis involves the condensation of the amino group of protected amino acids with the activated ester. HOBt is used to produce such activated esters which react with amines at ambient temperature to give amides.

Excerpted from Wikipedia’s “1-hydroxybenzotriazole” article, available under the CC BY-SA 4.0 licence.