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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
CHF 34.70
50 G
CHF 107.00
250 G
CHF 353.00
6 X 250 G
CHF 1’780.00

CHF 34.70

Estimated to ship on29 March 2025

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10 G
CHF 34.70
50 G
CHF 107.00
250 G
CHF 353.00
6 X 250 G
CHF 1’780.00

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

CHF 34.70

Estimated to ship on29 March 2025

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

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.[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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM2597
BCCL5669
BCCK1495
BCCF3867
BCCF4941

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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)
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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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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