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54802

Sigma-Aldrich

1-Hydroxybenzotriazole hydrate

≥97.0% dry basis (T), for peptide synthesis

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

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

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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
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H207,H319,H412

Hazard Classifications

Aquatic Chronic 3 - Desen. Expl. 2 - Eye Irrit. 2

WGK

WGK 1

Flash Point(F)

314.6 °F

Flash Point(C)

157 °C

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’.

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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)
T. Miyazawa et al.
Tetrahedron Letters, 25, 771-771 (1984)
Oxyma-B, an excellent racemization suppressor for peptide synthesis
Jad YE, et al.
Organic & Biomolecular Chemistry, 12(42), 8379-8385 (2014)
S. Ishizuka et al.
Pept. Sci., 37, 39-39 (2001)
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)
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