54802

Sigma-Aldrich

1-Hydroxybenzotriazole hydrate

≥97.0% (T)

Synonym(s):
HOBt Hydrate
Empirical Formula (Hill Notation):
C6H5N3O · xH2O
CAS Number:
Molecular Weight:
135.12 (anhydrous basis)
Beilstein/REAXYS Number:
4515
EC Number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥97.0% (T)

reaction suitability

reaction type: Addition Reactions

application(s)

peptide synthesis: suitable

impurities

~12% water

mp

155-158 °C (lit.)

solubility

DMF: 0.1 g/mL, clear

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

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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

Pictograms

FlameExclamation mark

Signal Word

Danger

Hazard Statements

Supp Hazards

EUH044

RIDADR

UN3474 - class 4.1 - PG 1 - 1-Hydroxybenzotriazole, monohydrate

WGK Germany

nwg

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Synthesis of 3, 5-disubstituted 1, 2, 4-oxadiazoles and their behavior of liquid crystallines
Guo J, et al.
Tetrahedron Letters, 55(9), 1557-1560 (2014)
T. Miyazawa et al.
Tetrahedron Letters, 25, 771-771 (1984)
Chemical synthesis of poly-?-glutamic acid by polycondensation of ?-glutamic acid dimer: Synthesis and reaction of poly-?-glutamic acid methyl ester
Sanda F, et al.
Journal of Polymer Science Part A: Polymer Chemistry, 39(5), 732-741 (2001)
Oxyma-B, an excellent racemization suppressor for peptide synthesis
Jad YE, et al.
Organic & Biomolecular Chemistry, 12(42), 8379-8385 (2014)
[A new method for synthesis of peptides: activation of the carboxyl group with dicyclohexylcarbodiimide using 1-hydroxybenzotriazoles as additives].
W König et al.
Chemische Berichte, 103(3), 788-798 (1970-01-01)

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