Propargyl alcohol

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Propargyl alcohol

IUPAC name 2-Propyn-1-ol
Identifiers
CAS number	107-19-7^Y
ChemSpider	21106466^Y
KEGG	C05986^Y
ChEBI	CHEBI:28905^Y
Jmol-3D images	Image 1
SMILES C#CCO
InChI InChI=1S/C3H4O/c1-2-3-4/h1,4H,3H2^Y Key: TVDSBUOJIPERQY-UHFFFAOYSA-N^Y InChI=1/C3H4O/c1-2-3-4/h1,4H,3H2 Key: TVDSBUOJIPERQY-UHFFFAOYAE
Properties
Molecular formula	C₃H₄O
Molar mass	56.06 g mol⁻¹
Density	0.9715 g/cm³
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
Hazards
MSDS	External MSDS
NFPA 704	3 4 3
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Propargyl alcohol, or 2-propyn-1-ol, is an organic compound with the formula HC₂CH₂OH. It is the simplest stable alcohol containing an alkyne functional group.^[1] 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. Propargyl alcohol tautomerizes to an enone (α,β-unsaturated ketone). An enal is an α,β-unsaturated aldehyde. Oxidation gives propionaldehyde.^[2]

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.^[3] It can also be prepared by dehydrochlorination of 3-chloro-2-propen-1-ol by NaOH.^[4]

Safety

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

References

↑ Merck Index, 11th Edition, 7819
↑ J. C. Sauer (1956), "Propionaldehyde", Org. Synth. 36: 66 ; Coll. Vol. 4: 813
↑ Falbe, Jürgen; Bahrmann, Helmut; Lipps, Wolfgang; Mayer, Dieter (2005), "Alcohols, Aliphatic", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a01_279 .
↑ J. Am. Chem. Soc., 1944, 66 (2), pp 285–287

External links

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