| Revision as of 14:32, 5 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 444069654 of page Propargyl_alcohol for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 14:33, 3 January 2024 edit Mazewaxie (talk | contribs)Extended confirmed users, Pending changes reviewers, Rollbackers113,599 editsm formattingTag: AWB |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 444067966 |
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| Watchedfields = changed |
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| Name = Propargyl alcohol |
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| verifiedrevid = 464216301 |
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| ImageFile = propargyl alcohol.svg |
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| Name = Propargyl alcohol |
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| ImageSize = 120px |
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| ImageFile = propargyl alcohol.svg |
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| ImageName = |
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| ImageSize = 200px |
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| IUPACName = 2-Propyn-1-ol |
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| OtherNames = |
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| ImageFile1 = Propargyl alcohol 3D ball.png |
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| Section1 = {{Chembox Identifiers |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| ImageName1 = 3D ball-and-stick structure of propargyl alcohol |
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| PIN = Prop-2-yn-1-ol |
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| OtherNames = propynol, 2-propynol, 2-propyn-1-ol, hydroxymethylacetylene. |
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|Section1={{Chembox Identifiers |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C05986 |
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| KEGG = C05986 |
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| InChI = 1/C3H4O/c1-2-3-4/h1,4H,3H2 |
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| InChI = 1/C3H4O/c1-2-3-4/h1,4H,3H2 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 107-19-7 |
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| CASNo = 107-19-7 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = E920VF499L |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID=21106466 |
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| ChemSpiderID=21106466 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 28905 |
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| ChEBI = 28905 |
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| ChEMBL = 1563026 |
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| PubChem = 7859 |
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| EC_number = 203-471-2 |
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| RTECS = UK5075000 |
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| UNNumber = 1986 2929 |
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| SMILES = C#CCO |
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| SMILES = C#CCO |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=3|H=4|O=1 |
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| C=3|H=4|O=1 |
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| Density = 0.9715 g/cm³ |
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| Density = 0.9715 g/cm<sup>3</sup> |
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| MeltingPtCL = -51 |
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| MeltingPtC = -51 to -48 |
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| BoilingPtC = 114 to 115 |
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| MetlingPtCH = -48 |
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| Appearance = Colorless to straw-colored liquid<ref name=PGCH/> |
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| BoilingPtCL = 114 |
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| Odor = ]-like<ref name=PGCH/> |
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| BoilingPtCH = 115 |
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| Solubility = miscible<ref name=PGCH/> |
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| VaporPressure = 12 mmHg (20 °C)<ref name=PGCH/> |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| Hazards_ref = <ref name="GESTIS">{{GESTIS|ZVG=29350 |CAS=107-19-7 |Name=Prop-2-yn-1-ol |Date=11 March 2020 }}</ref> |
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| NFPA-H = 4 |
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| GHSPictograms = {{GHS flame}} {{GHS skull and crossbones}} {{GHS corrosion}} {{GHS health hazard}} {{GHS environment}} |
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| NFPA-R = 3 |
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| NFPA-F = 3 |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|226|301|310|330|314|373|411}} |
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| ExternalMSDS = }} |
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| PPhrases = {{P-phrases|210|233|240|241|242|243|260|261|264|270|271|273|280|301+310|301+330+331|302+352|303+361+353|304+340|305+351+338|310|311|312|321|322|330|361|363|370+378|391|403+233|403+235|405|501}} |
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| NFPA-H = 3 |
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| NFPA-R = 3 |
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| NFPA-F = 3 |
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| ExternalSDS = |
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| IDLH = N.D.<ref name=PGCH>{{PGCH|0527}}</ref> |
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| REL = TWA 1 ppm (2 mg/m<sup>3</sup>) <ref name=PGCH/> |
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| PEL = none<ref name=PGCH/> |
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| FlashPtF = 97 |
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| FlashPt_notes = (open cup)<ref name=PGCH/> |
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'''Propargyl alcohol''', or '''2-propyn-1-ol''', is an ] with the ] C<sub>3</sub>H<sub>4</sub>O. It is the simplest stable ] containing an ] functional group.<ref>''Merck Index'', 11th Edition, '''7819'''</ref> Propargyl alcohol is a colorless viscous liquid that is miscible with water and most polar organic solvents. |
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==Reactions and applications== |
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Propargyl alcohol polymerizes with heating or treatment with ]. It is used as a corrosion inhibitor, a metal complex solution, a solvent stabilizer and an ] brightener additive. It is also used as an intermediate in ]. ] and ] substituted propargylic alcohols undergo catalyzed rearrangement reactions to form ] via the ] and others. It can be oxidized to ]<ref>{{OrgSynth|author= J. C. Sauer |year=1956|title=Propionaldehyde|volume=36|pages=66|collvol=4|collvolpages=813|prep=CV4P0813}}</ref> or ]. |
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As an indication of the ] of an ], propargyl alcohol is significantly more acidic (p''K''<sub>a</sub> = 13.6) compared to its sp<sup>2</sup>-containing analog ] (p''K''<sub>a</sub> = 15.5), which is in turn more acidic than the fully saturated (sp<sup>3</sup> carbons only) ] (p''K''<sub>a</sub> = 16.1).<ref>{{Cite book|last=Anslyn, Eric V., 1960-|url=https://www.worldcat.org/oclc/55600610|title=Modern physical organic chemistry|date=2006|publisher=University Science Books|others=Dougherty, Dennis A., 1952-|isbn=1-891389-31-9|location=Mill Valley, California|oclc=55600610}}</ref> |
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== Preparation == |
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Propargyl alcohol is produced by the copper-catalysed addition of ] to ] as a by-product of the industrial synthesis of ].<ref name="Ullmann">{{Ullmann | first1 = Jürgen | last1 = Falbe | first2 = Helmut | last2 = Bahrmann | first3 = Wolfgang | last3 = Lipps | first4 = Dieter | last4 = Mayer | title = Alcohols, Aliphatic | doi = 10.1002/14356007.a01_279}}.</ref> It can also be prepared by ] of 3-chloro-2-propen-1-ol by ].<ref name="J. Am. Chem. Soc., 1944, 66 (2), pp 285–287"> J. Am. Chem. Soc., 1944, 66 (2), pp 285–287</ref> |
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== Safety == |
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Propargyl alcohol is a flammable liquid, toxic by inhalation, highly toxic by ingestion, toxic by skin absorption, and corrosive.{{citation needed|date=September 2020}} |
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== See also == |
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* ] |
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* ] |
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* ] |
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* ] |
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== References == |
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{{reflist}} |
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== External links == |
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{{Authority control}} |
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] |
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] |