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54802

Sigma-Aldrich

1-Hydroxybenzotriazole hydrate

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

Synonym(s):

HOBt Hydrate

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10 G
CN¥323.81
250 G
CN¥4,118.56

CN¥323.81

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10 G
CN¥323.81
250 G
CN¥4,118.56

About This Item

Empirical Formula (Hill Notation):
C6H5N3O · xH2O
CAS Number:
123333-53-9
Molecular Weight:
135.12 (anhydrous basis)
Beilstein:
4515
EC Number:
219-989-7
MDL number:
MFCD00065690
UNSPSC Code:
12352000
PubChem Substance ID:
57651485
NACRES:
NA.22

CN¥323.81

Please contact Customer Service for Availability
Request a Bulk Order

Product Name

1-Hydroxybenzotriazole hydrate, ≥97.0% dry basis (T)

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

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1-Hydroxybenzotriazole hydrate ≥97.0% dry basis (T)

54802

1-Hydroxybenzotriazole hydrate

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

157260

1-Hydroxybenzotriazole hydrate

2-Hydroxybenzothiazole 98%

407607

2-Hydroxybenzothiazole

1-Hydroxybenzotriazole hydrate wetted with not less than 20 wt. % water, 97% dry basis

711489

1-Hydroxybenzotriazole hydrate

assay

≥97.0% dry basis (T)

assay

98% dry basis

assay

98%

assay

97% dry basis

mp

155-158 °C (lit.)

mp

155-158 °C (lit.)

mp

137-140 °C (lit.)

mp

155-158 °C (lit.)

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

solubility

DMF: 0.1 g/mL, clear

solubility

-

solubility

-

solubility

DMF: 0.1 g/mL, clear

composition

water, ~12%

composition

-

composition

-

composition

Water content, ~20%

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.[1] It is also used as a racemization suppressor during peptide synthesis.[2]

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.[2]
  • Oxadiazoles via cyclo condensation of amidoximes with trifluoroacetic anhydride or benzoic acid derivatives.[3]

Other Notes

Widely used additive to decrease racemization in the carbodiimide peptide coupling;[4] Racemization-free condensation of peptide fragments[5][6]

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H207,H319,H412

Hazard Classifications

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

Storage Class Code

4.1A - Other explosive hazardous materials

WGK

WGK 1

Flash Point(F)

314.6 °F

Flash Point(C)

157 °C

  • Specification Sheet

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    Certificates of Analysis (COA)

    Lot/Batch Number
    BCCM8370
    BCCM2597
    BCCL5669
    BCCK1495
    BCCF3867

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    S. Ishizuka et al.
    Pept. Sci., 37, 39-39 (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)
    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)
    View All Related Papers

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