54802

1-Hydroxybenzotriazole hydrate

≥97.0% dry basis (T)

• Synonym(s): HOBt Hydrate
• Empirical Formula (Hill Notation): C₆H₅N₃O · xH₂O
• CAS Number: 123333-53-9
• Molecular Weight: 135.12 (anhydrous basis)
• Beilstein/REAXYS Number: 4515
• EC Number: 219-989-7
• UNSPSC Code: 12352000
• PubChem Substance ID: 57651485
• NACRES: NA.22

Properties

• Quality Level: 200
• assay: ≥97.0% dry basis (T)
• form: solid
• composition: water, ~12%
• reaction suitability: reaction type: Addition Reactions
• mp: 155-158 °C (lit.)
• solubility: DMF: 0.1 g/mL, clear
• application(s): peptide synthesis
• SMILES string: [H]O[H].On1nnc2ccccc12
• InChI: 1S/C6H5N3O.H2O/c10-9-6-4-2-1-3-5(6)7-8-9;/h1-4,10H;1H2
• InChI key: PJUPKRYGDFTMTM-UHFFFAOYSA-N

Description

General description

1-Hydroxybenzotriazole is a coupling reagent used to synthesize amides by the condensation reaction between the activated ester/acid and the amino group of protected amino acids. It is also used as a racemization suppressor during peptide synthesis.

Application

1-Hydroxybenzotriazole hydrate can be used as a condensation reagent to prepare:

• Poly-γ-glutamic acid methyl ester from a dimer of γ-glutamic acid.
• Oxadiazoles via cyclo condensation of amidoximes with trifluoroacetic anhydride or benzoic acid derivatives.

Other Notes

Widely used additive to decrease racemization in the carbodiimide peptide coupling; Racemization-free condensation of peptide fragments

Safety Information

• pictograms: GHS02,GHS07
• signalword: Danger
• hcodes: H207 - H319 - H412
• pcodes: P210 - P212 - P230 - P233 - P280 - P370 + P380 + P375 - P501
• Hazard Classifications: Aquatic Chronic 3 - Desen. Expl. 2 - Eye Irrit. 2
• Storage Class: 4.1A - Other explosive hazardous materials
• wgk_germany: WGK 1
• flash_point_f: 314.6 °F
• flash_point_c: 157 °C