Propargyl alcohol
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 464216301
| Name = Propargyl alcohol
| ImageFile = propargyl alcohol.svg
| ImageSize = 200px
| ImageName =
| ImageFile1 = Propargyl alcohol 3D ball.png
| 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/cm3
| MeltingPtC = -51 to -48
| BoilingPtC = 114 to 115
| Appearance = Colorless to straw-colored liquid
| Odor = geranium-like
| VaporPressure = 12 mmHg (20 °C)
}}
|Section7={{Chembox Hazards
| Hazards_ref = {{GESTIS|ZVG=29350 |CAS=107-19-7 |Name=Prop-2-yn-1-ol |Date=11 March 2020 }}
| 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.{{PGCH|0527}}
| REL = TWA 1 ppm (2 mg/m3) [skin]
| FlashPtF = 97
}}
}}
Propargyl alcohol, or 2-propyn-1-ol, is an organic compound with the formula C3H4O. It is the simplest stable alcohol containing an alkyne functional group.Merck Index, 11th Edition, 7819 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{{OrgSynth|author= J. C. Sauer |year=1956|title=Propionaldehyde|volume=36|pages=66|collvol=4|collvolpages=813|prep=CV4P0813}} or propargylic acid.
As an indication of the electronegativity of an sp carbon, propargyl alcohol is significantly more acidic (pKa = 13.6) compared to its sp2-containing analog allyl alcohol (pKa = 15.5), which is in turn more acidic than the fully saturated (sp3 carbons only) n-propyl alcohol (pKa = 16.1).{{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}}
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.{{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}}. It can also be prepared by dehydrochlorination of 3-chloro-2-propen-1-ol by NaOH.[http://pubs.acs.org/doi/abs/10.1021/ja01230a038] J. Am. Chem. Soc., 1944, 66 (2), pp 285–287
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
References
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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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