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Revision as of 13:19, 1 September 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (changes to watched fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProject_Chemica← Previous edit Latest revision as of 17:51, 18 October 2024 edit undoCitation bot (talk | contribs)Bots5,425,093 edits Add: authors 1-1. Removed URL that duplicated identifier. Removed parameters. Some additions/deletions were parameter name changes. | Use this bot. Report bugs. | Suggested by Spinixster | Category:Chemicals using indexlabels | #UCB_Category 219/831 
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{{chembox {{chembox
| Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 446185036 | verifiedrevid = 448846752
| Name = Hydroxybenzotriazole | Name = Hydroxybenzotriazole
| ImageFile = HOBT.png | ImageFile = HOBT.png
| ImageSize = 150px | ImageSize = 150px
| ImageName = Hydroxybenzotriazole | ImageAlt = Hydroxybenzotriazole
| ImageFile1 = Hydroxybenzotriazole-3D-spacefill.png
⚫ | IUPACName = 1-Hydroxybenzotriazole
| ImageSize1 = 150
| OtherNames = ''N''-Hydroxybenzotriazole<br />HOBt
| ImageAlt1 = Space-filling model of the hydroxybenzotriazole molecule
⚫ | Section1 = {{Chembox Identifiers
| PIN = 1''H''-1,2,3-Benzotriazol-1-ol
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | OtherNames = ''N''-Hydroxybenzotriazole<br />HOBt
⚫ |Section1={{Chembox Identifiers
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 68282 | ChemSpiderID = 68282
| InChI = 1/C6H5N3O/c10-9-6-4-2-1-3-5(6)7-8-9/h1-4,10H | InChI = 1/C6H5N3O/c10-9-6-4-2-1-3-5(6)7-8-9/h1-4,10H
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H5N3O/c10-9-6-4-2-1-3-5(6)7-8-9/h1-4,10H | StdInChI = 1S/C6H5N3O/c10-9-6-4-2-1-3-5(6)7-8-9/h1-4,10H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = ASOKPJOREAFHNY-UHFFFAOYSA-N | StdInChIKey = ASOKPJOREAFHNY-UHFFFAOYSA-N
<!-- | Cooperative Patent Classification
| C07D 249/18 -->
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 2592-95-2 | CASNo = 2592-95-2
| CASNo2_Ref = {{cascite|correct|CAS}}
| CASOther = <br>123333-53-9 (hydrate)
| CASNo2 = 80029-43-2
⚫ | SMILES = n1nn(O)c2ccccc12
| index2_label= (monohydrate)
| PubChem = 75771
| PubChem2 = 2796029
| EC_number = 219-989-7
| EC_number2 = 602-929-2
| UNII2_Ref = {{fdacite|correct|FDA}}
| UNII2 = S72K7GY45F
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = A2T929DMG4
⚫ | SMILES = n1nn(O)c2ccccc12
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=6|H=5|N=3|O=1 | C =6|H=5|N=3|O=1
| Density = | Density =
| MeltingPt = 156-159 °C (''decomp.'') | MeltingPtC = 156 to 159
| MeltingPt_notes = (decomposes)
| MolarMass = 153.134 g mol^-1 (''hydrate'') | MolarMass = 135.1234 g mol<sup>−1</sup> (''anhydrous'')
}} }}
|Section7={{Chembox Hazards
| GHSPictograms = {{GHS01}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|203}}
| PPhrases = {{P-phrases|210|230|240|250|280|370+380|372|373|401|501}}
}}
}} }}


'''Hydroxybenzotriazole''' (abbreviated HOBt) is an ] that is a derivative of benzotriazole. It is mainly used to suppress racemization and improve the efficiency of ]. It is a white crystalline powder. Commercial HOBt always contains some water (~11.7% wt as the HOBt monohydrate crystal) because anhydrous HOBt is explosive. '''Hydroxybenzotriazole''' (abbreviated HOBt) is an ] that is a derivative of ]. 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.

It is mainly used to suppress the ] of single-] ] molecules and to improve the efficiency of ].


==Use in peptide synthesis== ==Use in peptide synthesis==
]
Automated ] involves the condensation of the amino group of protected ]s with the activated ester. HOBt is used to produce such activated esters. These esters are insoluble (like the ] esters) and react with amines at ambient temperature to give amides.<ref>{{cite journal | author = W. König, R. Geiger | title = Eine neue Methode zur Synthese von Peptiden: Aktivierung der Carboxylgruppe mit Dicyclohexylcarbodiimid unter Zusatz von 1-Hydroxy-benzotriazolen | journal = ] | year = 1970 | volume = 103 | pages = 788–798 | doi = 10.1002/cber.19701030319}}</ref>.<br/> Automated ] involves the condensation of the amino group of protected ]s with the activated ester. HOBt is used to produce such ]s. These esters are insoluble (like the ] esters) and react with amines at ambient temperature to give amides.<ref>{{cite journal | author = W. König, R. Geiger | title = Eine neue Methode zur Synthese von Peptiden: Aktivierung der Carboxylgruppe mit Dicyclohexylcarbodiimid unter Zusatz von 1-Hydroxy-benzotriazolen | journal = ] | year = 1970 | volume = 103 | pages = 788–798 | doi = 10.1002/cber.19701030319 | issue = 3| pmid = 5436656 }}</ref>


HOBt is also used for the synthesis of amides from ]s aside from amino acids. These substrates may not be convertable to the ]s.<ref>Andrew G. Myers, Bryant H. Yang, and Hou Chen TRANSFORMATION OF PSEUDOEPHEDRINE AMIDES INTO HIGHLY ENANTIOMERICALLY ENRICHED ALDEHYDES, ALCOHOLS, AND KETONES Organic Syntheses, Vol. 77, p. 29 (2000); Coll. Vol. 10, p.509 (2004).</ref> For instance amide derivatives of ] ] have been prepared in this way.<ref>{{cite journal|last=Łowicki|first=Daniel|coauthors=A. Huczyński, M. Ratajczak-Sitarz, A. Katrusiak, J. Stefańska, B. Brzezinski, F. Bartl|title=Structural and antimicrobial studies of a new N-phenylamide of monensin A complex with sodium chloride|journal=]|year=2009|volume=923|issue=1-3|pages=53-59|doi=10.1016/j.molstruc.2009.01.056}}</ref> HOBt is also used for the synthesis of amides from ]s aside from amino acids. These substrates may not be convertible to the ]s.<ref>{{cite book |first1=Andrew G. |last1=Myers |first2=Bryant H. |last2=Yang |first3=Hou |last3=Chen |chapter=Transformation of Pseudoephedrine Amides Into Highly Enantiomerically Enriched Aldehydes, Alcohols, and Ketones |title=Organic Syntheses |volume=77 |page=29 |date=2000 |doi=10.1002/0471264180.os077.04 |isbn=0471264229}}</ref> For instance amide derivatives of ] ] have been prepared in this way.<ref>{{cite journal|last=Łowicki|first=Daniel|author2=A. Huczyński |author3=M. Ratajczak-Sitarz |author4=A. Katrusiak |author5=J. Stefańska |author6=B. Brzezinski |author7=F. Bartl |title=Structural and antimicrobial studies of a new N-phenylamide of monensin A complex with sodium chloride|journal=]|year=2009|volume=923|issue=1–3|pages=53–59|doi=10.1016/j.molstruc.2009.01.056|bibcode=2009JMoSt.923...53L}}</ref>

]

Together with ], HOBt is also used for bleaching pulps. The method is still on the experimental stage and have yet not been commercialized.


==Safety== ==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 (] ] regulations). However, ] 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. Due to reclassification as ], a class 1.3C explosive, hydroxybenzotriazole and its monohydrate crystal are no longer allowed to be transported by sea or air as per 49CFR (] ] regulations). However, ] 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 ] as a class 4.1 desensitized explosive. HOBt was demonstrated to not exhibit dermal corrosion or irritation but did exhibit eye irritation.<ref>{{Cite journal |last1=Graham |first1=Jessica C. |last2=Trejo-Martin |first2=Alejandra |last3=Chilton |first3=Martyn L. |last4=Kostal |first4=Jakub |last5=Bercu |first5=Joel |last6=Beutner |first6=Gregory L. |last7=Bruen |first7=Uma S. |last8=Dolan |first8=David G. |last9=Gomez |first9=Stephen |last10=Hillegass |first10=Jedd |last11=Nicolette |first11=John |last12=Schmitz |first12=Matthew |date=2022-06-20 |title=An Evaluation of the Occupational Health Hazards of Peptide Couplers |journal=Chemical Research in Toxicology |language=en |volume=35 |issue=6 |pages=1011–1022 |doi=10.1021/acs.chemrestox.2c00031 |issn=0893-228X |pmc=9214767 |pmid=35532537}}</ref> The ] of HOBt was shown to be low (non-sensitizing at 1% in ] testing according to ]<ref>{{Cite book |last=OECD |url=https://www.oecd-ilibrary.org/environment/test-no-429-skin-sensitisation_9789264071100-en |title=Test No. 429: Skin Sensitisation: Local Lymph Node Assay |date=2010 |publisher=Organisation for Economic Co-operation and Development |location=Paris |language=en}}</ref>).


==References== ==References==
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