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Propargyl alcohol

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Propargyl alcohol
3D ball-and-stick structure of propargyl alcohol
Names
Preferred IUPAC name Prop-2-yn-1-ol
Other names propynol, 2-propynol, 2-propyn-1-ol, hydroxymethylacetylene.
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.157 Edit this at Wikidata
EC Number
  • 203-471-2
KEGG
PubChem CID
RTECS number
  • UK5075000
UNII
UN number 1986 2929
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H4O/c1-2-3-4/h1,4H,3H2Key: TVDSBUOJIPERQY-UHFFFAOYSA-N
  • InChI=1/C3H4O/c1-2-3-4/h1,4H,3H2Key: TVDSBUOJIPERQY-UHFFFAOYAE
SMILES
  • C#CCO
Properties
Chemical formula C3H4O
Molar mass 56.064 g·mol
Appearance Colorless to straw-colored liquid
Odor geranium-like
Density 0.9715 g/cm
Melting point −51 to −48 °C (−60 to −54 °F; 222 to 225 K)
Boiling point 114 to 115 °C (237 to 239 °F; 387 to 388 K)
Solubility in water miscible
Vapor pressure 12 mmHg (20 °C)
Hazards
GHS labelling:
Pictograms GHS02: Flammable GHS06: Toxic GHS05: Corrosive GHS08: Health hazard GHS09: Environmental hazard
Signal word Danger
Hazard statements H226, H301, H310, H314, H330, H373, H411
Precautionary statements P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P312, P321, P322, P330, P361, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxideSpecial hazards (white): no code
3 3 3
Flash point 36 °C; 97 °F; 309 K (open cup)
NIOSH (US health exposure limits):
PEL (Permissible) none
REL (Recommended) TWA 1 ppm (2 mg/m)
IDLH (Immediate danger) N.D.
Safety data sheet (SDS) External SDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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. 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 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 sp-containing analog allyl alcohol (pKa = 15.5), which is in turn more acidic than the fully saturated (sp carbons only) n-propyl alcohol (pKa = 16.1).

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. It can also be prepared by dehydrochlorination of 3-chloro-2-propen-1-ol by NaOH.

Safety

Propargyl alcohol is a flammable liquid, toxic by inhalation, highly toxic by ingestion, toxic by skin absorption, and corrosive.

See also

References

  1. ^ NIOSH Pocket Guide to Chemical Hazards. "#0527". National Institute for Occupational Safety and Health (NIOSH).
  2. Record of Prop-2-yn-1-ol in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 11 March 2020.
  3. Merck Index, 11th Edition, 7819
  4. J. C. Sauer (1956). "Propionaldehyde". Organic Syntheses. 36: 66; Collected Volumes, vol. 4, p. 813.
  5. Anslyn, Eric V., 1960- (2006). Modern physical organic chemistry. Dougherty, Dennis A., 1952-. Mill Valley, California: University Science Books. ISBN 1-891389-31-9. OCLC 55600610.{{cite book}}: CS1 maint: multiple names: authors list (link) CS1 maint: numeric names: authors list (link)
  6. Falbe, Jürgen; Bahrmann, Helmut; Lipps, Wolfgang; Mayer, Dieter. "Alcohols, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_279. ISBN 978-3527306732..
  7. J. Am. Chem. Soc., 1944, 66 (2), pp 285–287

External links

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