54802

Sigma-Aldrich

1-Hydroxybenzotriazole hydrate

≥97.0% (T)

Sinónimos:
HOBt Hydrate
Empirical Formula (Hill Notation):
C6H5N3O · xH2O
Número de CAS:
Peso molecular:
135.12 (anhydrous basis)
Beilstein/REAXYS Number:
4515
Número de EC:
ID de la sustancia en PubChem:
NACRES:
NA.22

Nivel de calidad

200

ensayo

≥97.0% (T)

reaction suitability

reaction type: Addition Reactions

aplicaciones

peptide synthesis: suitable

impurezas

~12% water

mp

155-158 °C (lit.)

solubilidad

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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Descripción general

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.

Aplicación

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.

Otras notas

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

pictogramas

FlameExclamation mark

Palabra de señalización

Danger

Frases de peligro

hazcat

2 - Aquatic Chronic 3 - Eye Irrit. 2

Riesgos supl.

EUH044

storage_class_code

4.1A - Other explosive hazardous materials

WGK Alemania

nwg

Punto de inflamabilidad F

Not applicable

Punto de inflamabilidad C

Not applicable

Certificado de Análisis

Certificado de origen

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)
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)
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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