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Revision as of 12:22, 22 March 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (changes to watched fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per [[Misplaced Pages:WikiProject Chemicals/Chembox validation|Chem/Drugbox valida← Previous edit Latest revision as of 04:42, 17 November 2023 edit undoCrafterNova (talk | contribs)Extended confirmed users16,641 edits wording fixTags: Mobile edit Mobile web edit Advanced mobile edit 
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{{Chembox {{Chembox
| Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 400325837 | verifiedrevid = 476995490
| ImageFile = Imidazole-1-sulfonyl azide.png | ImageFile = Imidazole-1-sulfonyl azide.png
| ImageAlt = Space-filling model of the imidazole-1-sulfonyl azide molecule
| ImageSize =
| ImageFile1 = Imidazole-1-sulfonyl-azide-3D-spacefill.png
| IUPACName =
| ImageSize1 = 180
| ImageAlt1 = Space-filling model of the imidazole-1-sulfonyl azide molecule
| PIN = 1''H''-Imidazole-1-sulfonyl azide
| OtherNames = | OtherNames =
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| InChI = 1/C3H3N5O2S.ClH/c4-6-7-11(9,10)8-2-1-5-3-8;/h1-3H;1H | InChI = 1/C3H3N5O2S.ClH/c4-6-7-11(9,10)8-2-1-5-3-8;/h1-3H;1H
| InChIKey = XYURSCOGYWBRDR-UHFFFAOYAJ | InChIKey = XYURSCOGYWBRDR-UHFFFAOYAJ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = XYURSCOGYWBRDR-UHFFFAOYSA-N | StdInChIKey = XYURSCOGYWBRDR-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|PubChem}}
| CASNo = 952234-37-6 | CASNo = 952234-37-6
| PubChem = | PubChem = 23583981
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID=21374920 | ChemSpiderID=21374920
| SMILES = Cl.O=S(=O)(N==)n1ccnc1 | SMILES = Cl.O=S(=O)(N==)n1ccnc1
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C = 3 | H = 3 | N = 5 | O = 2 | S = 1 | C=3 | H=3 | N=5 | O=2 | S=1
| Appearance = | Appearance = Colourless Liquid
| Density = | Density =
| MeltingPt = | MeltingPt =
| BoilingPt = | BoilingPt =
| Solubility = | Solubility =
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = Potentially explosive | MainHazards = Potentially explosive, Harmful
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
}} }}
}} }}


'''Imidazole-1-sulfonyl azide''' is an organic ] compound that can be used as an alternative to ]. It is a colorless liquid; it may also be used as a better-handled ] salt. '''Imidazole-1-sulfonyl azide''' is an organic ] compound that can be used as an alternative ] reagent to ]. It is an explosive colorless liquid, but some of its organic-soluble salts can be safely handled and stored as a solid.


==Preparation== ==Preparation==
The hydrochloride salt of this compound is also available commercially, but can degrade to release explosive byproducts.<ref>{{cite web|last=van Delft|first=Floris|title=SX-B1001|url=http://synaffix.biedmeer.nl/Webwinkel-Category-1120834/SX-B1001.html|work=Synaffix|accessdate=30 January 2014}}</ref>
This compound is not readily available commercially. It may be prepared by reacting ] with ] in ], followed by the addition of excess ]. The hydrochloride salt may be obtained by precipitating with an ethanol solution of HCl.<ref name = Goddard-Borger>{{cite journal | author = E. D. Goddard-Borger and R. V. Stick | title = An Efficient, Inexpensive, and Shelf-Stable Diazotransfer Reagent:&nbsp; Imidazole-1-sulfonyl Azide Hydrochloride | journal = ] | volume = 9 | issue = 19 | pages = 3797–3800 | doi = 10.1021/ol701581g | pmid = 17713918 | year = 2007}}</ref>


:] :]


==Reactions== ==Reactions==
Like ], this compound generally converts primary amines or ammonium salts to azides.<ref name = Goddard-Borger/> This reaction is effectively the reverse of the ]. Similarly, it is able to transfer the ] group (=N<sub>2</sub>) when catalyzed by copper(II), nickel(II), zinc(II), and cobalt(II) salts.<ref name = Goddard-Borger/> Like ], this compound generally converts primary amines or ammonium salts to azides when catalyzed by copper(II), nickel(II), zinc(II), and cobalt(II) salts.<ref name = Goddard-Borger>{{cite journal | author = E. D. Goddard-Borger and R. V. Stick | title = An Efficient, Inexpensive, and Shelf-Stable Diazotransfer Reagent:&nbsp; Imidazole-1-sulfonyl Azide Hydrochloride | journal = ] | volume = 9 | issue = 19 | pages = 3797–3800 | doi = 10.1021/ol701581g | pmid = 17713918 | year = 2007}}<br>
{{cite journal | author = E. D. Goddard-Borger and R. V. Stick | title = An Efficient, Inexpensive, and Shelf-Stable Diazotransfer Reagent:&nbsp; Imidazole-1-sulfonyl Azide Hydrochloride | journal = ] | volume = 13 | issue = 9 | pages = 2514 | doi = 10.1021/ol2007555 | year = 2011 | url = https://figshare.com/articles/journal_contribution/2986117 | department = Addition/Correction}}</ref> This reaction is effectively the reverse of the ]. Similarly, it is able to transfer the ] group (=N<sub>2</sub>) under basic conditions.<ref name = Goddard-Borger/>


==Safety== ==Safety==
As with all organic azides, this compound is potentially explosive both in use and in preparation. The hydrochloride salt was initially reported to be insensitive to impact, vigorous grinding, and prolonged heating at 80&nbsp;°C, although heating above 150&nbsp;°C resulted in violent decomposition. Further reported impact studies indicated otherwise, showing the sensitivity to be similar to ].<ref name=":0" /> Subsequent reports noted that the hydrochloride salt is ], and upon prolonged storage was hydrolyzed to produce ], which made the material sensitive.<ref name = Goddard-Borger/><ref name=":0">{{cite journal | doi = 10.1021/jo202264r | journal = J. Org. Chem. | title = Sensitivities of Some Imidazole-1-sulfonyl Azide Salts | year = 2012 | last1 = Fischer | first1 = Niko | last2 = Goddard-Borger | first2 = Ethan D. | last3 = Greiner | first3 = Robert | last4 = Klapötke | first4 = Thomas M. | last5 = Skelton | first5 = Brian W. | last6 = Stierstorfer | first6 = Jörg | volume = 77 | issue = 4 | pages = 1760–1764| pmid = 22283437 }}</ref> Synthesis of the HCl salt has led to a significant explosion, with expected explosive byproducts of ] or hydrazoic acid being present.<ref>{{Cite journal|last1=Goddard-Borger|first1=Ethan D.|last2=Stick|first2=Robert V.|date=2011-03-29|title=An Efficient, Inexpensive, and Shelf-Stable Diazotransfer Reagent: Imidazole-1-sulfonyl Azide Hydrochloride|journal=Organic Letters|language=EN|volume=13|issue=9|pages=2514|doi=10.1021/ol2007555|url=https://figshare.com/articles/journal_contribution/2986117 }}</ref>
As with all organic azides, this compound is potentially explosive. Impact tests, vigorous grinding, and prolonged heating at 80 °C of the hydrochloride salt did not result in any explosive reaction, though heating above 150 °C resulted in violent decomposition.<ref name = Goddard-Borger/>

Recent studies have shown the hydrogen sulfate salt to be significantly less hazardous to handle with decomposition temperature of 131&nbsp;°C, insensitivity to impact, and low electrostatic discharge and friction sensitivities.<ref name=":0" /> Further improvements have led to its synthesis with increased safety, making the hydrogen sulfate salt a relatively safe diazo-transfer reagent to both synthesize and handle.<ref>{{Cite journal|last1=Potter|first1=Garrett T.|last2=Jayson|first2=Gordon C.|last3=Miller|first3=Gavin J.|last4=Gardiner|first4=John M.|date=2016-03-29|title=An Updated Synthesis of the Diazo-Transfer Reagent Imidazole-1-sulfonyl Azide Hydrogen Sulfate|journal=The Journal of Organic Chemistry|language=EN|doi=10.1021/acs.joc.6b00177|volume=81|issue=8|pages=3443–3446|pmid=26998999|url=https://www.research.manchester.ac.uk/portal/files/33083992/JOC_note_jo_2016_00177a.pdf|doi-access=free}}</ref>


==References== ==References==
<references/> <references/>


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