Hydroxybenzotriazole
Page Template:Chembox/styles.css has no content.
Template:Chembox IndexlistTemplate:Chembox CompToxTemplate:Chembox GHS (set)Template:Chembox Datapage check| Lua error in package.lua at line 80: module 'Module:InfoboxImage/data' not found. | |
| Lua error in package.lua at line 80: module 'Module:InfoboxImage/data' not found. | |
| Names | |
|---|---|
| Preferred IUPAC name
1H-1,2,3-Benzotriazol-1-ol | |
| Other names
N-Hydroxybenzotriazole
HOBt | |
| Identifiers | |
Page Template:Plainlist/styles.css has no content.
| |
3D model (JSmol)
|
Page Template:Plainlist/styles.css has no content. |
| ChemSpider | Page Template:Plainlist/styles.css has no content. |
| EC Number | Page Template:Plainlist/styles.css has no content. |
PubChem CID
|
Page Template:Plainlist/styles.css has no content. |
| RTECS number | Page Template:Plainlist/styles.css has no content. |
| UNII | Page Template:Plainlist/styles.css has no content.
|
| |
| Properties | |
| C6H5N3O | |
| Molar mass | 135.1234 g mol−1 (anhydrous) |
| Melting point | 156 to 159 °C (313 to 318 °F; 429 to 432 K) (decomposes) |
| Hazards | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Template:Chembox Footer/trackingTemplate:Short description
Hydroxybenzotriazole (abbreviated HOBt) is an organic compound with the formula Page Module:Chem2/styles.css has no content.C6H4N3OH. It is a derivative of benzotriazole. It is a white crystalline powder, which as a commercial product contains some water (~11.7% wt as the HOBt monohydrate crystal). Anhydrous HOBt is explosive.[1] It is mainly used to suppress the racemization and to improve the efficiency of peptide synthesis.[2]
Use in peptide synthesis
Automated peptide synthesis involves the condensation of the amino group of protected amino acids with the activated ester. HOBt is used to produce such activated esters which react with amines at ambient temperature to give amides.[3]
HOBt is also used for the synthesis of amides from carboxylic acids aside from amino acids. These substrates may not be convertible to the acyl chlorides.[4]
Safety
Due to reclassification as UN0508, a class 1.3C explosive, hydroxybenzotriazole and its monohydrate crystal are no longer allowed to be transported by sea or air as per 49CFR (USDOT hazardous materials regulations). However, UNECE draft proposal ECE/TRANS/WP.15/AC.1/HAR/2009/1 has been circulated to UN delegates and, if implemented, would amend current regulations thus allowing for the monohydrate crystal to be shipped under the less-stringent code of UN3474 as a class 4.1 desensitized explosive. HOBt was demonstrated to not exhibit dermal corrosion or irritation but did exhibit eye irritation.[5] The sensitization potential of HOBt was shown to be low (non-sensitizing at 1% in LLNA testing according to OECD 429[6]).
References
- ^ Page Module:Citation/CS1/styles.css has no content.Jones, Ron. "Explosive properties of HOBT". UK Chemical Reaction Hazards Forum. Archived from the original on 2016-12-29. Retrieved 2026-02-01.
- ^ Page Module:Citation/CS1/styles.css has no content.El-Faham, Ayman; Albericio, Fernando (2011). "Peptide Coupling Reagents, More than a Letter Soup". Chemical Reviews. 111 (11): 6557–6602. doi:10.1021/cr100048w. PMID 21866984.
- ^ Page Module:Citation/CS1/styles.css has no content.W. König, R. Geiger (1970). "Eine neue Methode zur Synthese von Peptiden: Aktivierung der Carboxylgruppe mit Dicyclohexylcarbodiimid unter Zusatz von 1-Hydroxy-benzotriazolen". Chem. Ber. 103 (3): 788–798. doi:10.1002/cber.19701030319. PMID 5436656.
- ^ Page Module:Citation/CS1/styles.css has no content.Myers, Andrew G.; Yang, Bryant H.; Chen, Hou (2000). "Transformation of Pseudoephedrine Amides Into Highly Enantiomerically Enriched Aldehydes, Alcohols, and Ketones". Organic Syntheses. Vol. 77. p. 29. doi:10.1002/0471264180.os077.04. ISBN 0471264229.
- ^ Page Module:Citation/CS1/styles.css has no content.Graham, Jessica C.; Trejo-Martin, Alejandra; Chilton, Martyn L.; Kostal, Jakub; Bercu, Joel; Beutner, Gregory L.; Bruen, Uma S.; Dolan, David G.; Gomez, Stephen; Hillegass, Jedd; Nicolette, John; Schmitz, Matthew (2022-06-20). "An Evaluation of the Occupational Health Hazards of Peptide Couplers". Chemical Research in Toxicology. 35 (6): 1011–1022. doi:10.1021/acs.chemrestox.2c00031. ISSN 0893-228X. PMC 9214767. PMID 35532537.
- ^ Page Module:Citation/CS1/styles.css has no content.OECD (2010). Test No. 429: Skin Sensitisation: Local Lymph Node Assay. Paris: Organisation for Economic Co-operation and Development.
