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Sigma-Aldrich

1-Hydroxybenzotriazole hydrate

98% dry basis wetted with not less than 14 wt. % water, for peptide synthesis

Synonym(s):

HOBt Hydrate

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About This Item

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:
24849666
NACRES:
NA.22

product name

1-Hydroxybenzotriazole hydrate, wetted with not less than 14 wt. % water, 98% dry basis

Quality Level

200

assay

98% dry basis

form

solid

quality

synthesis grade

reaction suitability

reaction type: Addition Reactions

mp

155-158 °C (lit.)

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 hydrate is a derivative of benzotriazole primarily used as a coupling reagent in peptide synthesis.

Application

1-Hydroxybenzotriazole hydrate can be used as a reagent:
  • To synthesize β-peptides via microwave-assisted amino acid coupling.
  • In the spot synthesis of glycopeptides.
It can also be used as a deprotection agent for the removal of Fmoc (9-fluorenylmethoxycarbonyl) protecting group.

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pictograms

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GHS02,GHS07

signalword

Danger

Hazard Classifications

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

supp_hazards

EUH044

Storage Class

4.1A - Other explosive hazardous materials

wgk_germany

WGK 1

flash_point_f

314.6 °F

flash_point_c

157 °C

Certificates of Analysis (COA)

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T Katoh et al.
International journal of peptide and protein research, 42(3), 264-269 (1993-09-01)
3-Dimethylphosphinothioyl-2(3H)-oxazolone (MPTO) was synthesized, and its ability to effect racemization-free couplings and cyclization of a peptide and its C-terminal epimer was examined. MPTO showed good reactivity in aprotic polar solvents such as N,N-dimethylformamide (DMF) and N-methylpyrrolidone. In reactivity MPTO resembles
Tetrahedron Letters, 34, 6383-6383 (1993)
Synlett, 733-733 (1993)
Tetrahedron Letters, 35, 3315-3315 (1994)
Akul Y Mehta et al.
Cell chemical biology, 27(9), 1207-1219 (2020-07-02)
Glycan recognition is typically studied using free glycans, but glycopeptide presentations represent more physiological conditions for glycoproteins. To facilitate studies of glycopeptide recognition, we developed Glyco-SPOT synthesis, which enables the parallel production of diverse glycopeptide libraries at microgram scales. The
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