{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 464216301 | Name = Propargyl alcohol | ImageFile = propargyl alcohol.svg | ImageClass = skin-invert | ImageSize = 200px | ImageName = | ImageFile1 = Propargyl alcohol 3D ball.png | ImageClass1 = bg-transparent | ImageSize1 = | ImageName1 = 3D ball-and-stick structure of propargyl alcohol | PIN = Prop-2-yn-1-ol | OtherNames = propynol, 2-propynol, 2-propyn-1-ol, hydroxymethylacetylene. |Section1={{Chembox Identifiers | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C05986 | InChI = 1/C3H4O/c1-2-3-4/h1,4H,3H2 | InChIKey = TVDSBUOJIPERQY-UHFFFAOYAE | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C3H4O/c1-2-3-4/h1,4H,3H2 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = TVDSBUOJIPERQY-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 107-19-7 | UNII_Ref = {{fdacite|changed|FDA}} | UNII = E920VF499L | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID=21106466 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 28905 | ChEMBL = 1563026 | PubChem = 7859 | EC_number = 203-471-2 | RTECS = UK5075000 | UNNumber = 1986 2929 | SMILES = C#CCO }} |Section2={{Chembox Properties | C=3|H=4|O=1 | Density = 0.9715 g/cm<sup>3</sup> | MeltingPtC = -51 to -48 | BoilingPtC = 114 to 115 | Appearance = Colorless to straw-colored liquid<ref name=PGCH/> | Odor = geranium-like<ref name=PGCH/> | Solubility = miscible<ref name=PGCH/> | VaporPressure = 12 mmHg (20&nbsp;°C)<ref name=PGCH/> }} |Section7={{Chembox Hazards | Hazards_ref = <ref name="GESTIS">{{GESTIS|ZVG=29350 |CAS=107-19-7 |Name=Prop-2-yn-1-ol |Date=11 March 2020 }}</ref> | GHSPictograms = {{GHS flame}} {{GHS skull and crossbones}} {{GHS corrosion}} {{GHS health hazard}} {{GHS environment}} | GHSSignalWord = Danger | HPhrases = {{H-phrases|226|301|310|330|314|373|411}} | 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}} | NFPA-H = 3 | NFPA-R = 3 | NFPA-F = 3 | ExternalSDS = [http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=US&language=en&productNumber=P50803&brand=ALDRICH&PageToGoToURL=http%3A%2F%2Fwww.sigmaaldrich.com%2Fcatalog%2Fproduct%2Faldrich%2Fp50803%3Flang%3Den External SDS] | IDLH = N.D.<ref name=PGCH>{{PGCH|0527}}</ref> | REL = TWA 1 ppm (2 mg/m<sup>3</sup>) [skin]<ref name=PGCH/> | PEL = none<ref name=PGCH/> | FlashPtF = 97 | FlashPt_notes = (open cup)<ref name=PGCH/> }} }}

'''Propargyl alcohol''', or '''2-propyn-1-ol''', is an organic compound with the formula C<sub>3</sub>H<sub>4</sub>O. It is the simplest stable alcohol containing an alkyne 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.

==Reactions and applications== Propargyl alcohol polymerizes with heating or treatment with base. It is used as a corrosion inhibitor, a metal complex solution, a solvent stabilizer and an electroplating brightener additive. It is also used as an intermediate in organic synthesis. Secondary and tertiary substituted propargylic alcohols undergo catalyzed rearrangement reactions to form α,β-unsaturated carbonyl compounds via the Meyer–Schuster rearrangement and others. It can be oxidized to propynal<ref>{{OrgSynth|author= J. C. Sauer |year=1956|title=Propionaldehyde|volume=36|pages=66|collvol=4|collvolpages=813|prep=CV4P0813}}</ref> or propargylic acid.

As an indication of the electronegativity of an sp carbon, propargyl alcohol is significantly more acidic (p''K''<sub>a</sub> = 13.6) compared to its sp<sup>2</sup>-containing analog allyl alcohol (p''K''<sub>a</sub> = 15.5), which is in turn more acidic than the fully saturated (sp<sup>3</sup> carbons only) ''n-''propyl alcohol (p''K''<sub>a</sub> = 16.1).<ref>{{Cite book|last=Anslyn, Eric V., 1960-|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>

== Preparation == Propargyl alcohol is produced by the copper-catalysed addition of formaldehyde to acetylene as a by-product of the industrial synthesis of but-2-yne-1,4-diol.<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 dehydrochlorination of 3-chloro-2-propen-1-ol by NaOH.<ref name="J. Am. Chem. Soc., 1944, 66 (2), pp 285–287">[http://pubs.acs.org/doi/abs/10.1021/ja01230a038] J. Am. Chem. Soc., 1944, 66 (2), pp 285–287</ref>

== Safety == Propargyl alcohol is a flammable liquid, toxic by inhalation, highly toxic by ingestion, toxic by skin absorption, and corrosive.{{citation needed|date=September 2020}}

== See also == * Alkynylation * Allyl alcohol * Propargyl * Propargyl chloride

== References == {{reflist}}

== External links == * [http://nj.gov/health/eoh/rtkweb/documents/fs/1597.pdf Hazardous substance fact sheet for propargyl alcohol] * [https://www.cdc.gov/niosh/npg/npgd0527.html CDC - NIOSH Pocket Guide to Chemical Hazards]

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Category:Alkynols Category:Primary alcohols Category:Propargyl compounds