Propargyl alcohol

Propargyl alcohol
Names
	Preferred IUPAC name Prop-2-yn-1-ol
	Other names propynol, 2-propynol, 2-propyn-1-ol, hydroxymethylacetylene.
Identifiers
CAS Number	107-19-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28905 ;
ChEMBL	ChEMBL1563026;
ChemSpider	21106466 ;
ECHA InfoCard	100.003.157
EC Number	203-471-2;
KEGG	C05986 ;
PubChem CID	7859;
RTECS number	UK5075000;
UNII	E920VF499L ;
UN number	1986 2929
CompTox Dashboard (EPA)	DTXSID5021883 ;
	InChI InChI=1S/C3H4O/c1-2-3-4/h1,4H,3H2 Key: TVDSBUOJIPERQY-UHFFFAOYSA-N ; InChI=1/C3H4O/c1-2-3-4/h1,4H,3H2 Key: TVDSBUOJIPERQY-UHFFFAOYAE;
	SMILES C#CCO;
Properties
Chemical formula	C3H4O
Molar mass	56.064 g·mol−1
Appearance	Colorless to straw-colored liquid[1]
Odor	geranium-like[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)
Solubility in water	miscible[1]
Vapor pressure	12 mmHg (20 °C)[1]
Hazards[2]
	GHS labelling:
Pictograms
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)	3 3 3
Flash point	36 °C; 97 °F; 309 K (open cup)[1]
	NIOSH (US health exposure limits):
PEL (Permissible)	none[1]
REL (Recommended)	TWA 1 ppm (2 mg/m3) [skin][1]
IDLH (Immediate danger)	N.D.[1]
Safety data sheet (SDS)	External SDS
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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.[3] 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[4] or propargylic acid.

As an indication of the electronegativity of an sp carbon, propargyl alcohol is significantly more acidic (pK_a = 13.6) compared to its sp²-containing analog allyl alcohol (pK_a = 15.5), which is in turn more acidic than the fully saturated (sp³ carbons only) n-propyl alcohol (pK_a = 16.1).[5]

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.[6] It can also be prepared by dehydrochlorination of 3-chloro-2-propen-1-ol by NaOH.[7]

Safety

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

References

NIOSH Pocket Guide to Chemical Hazards. "#0527". National Institute for Occupational Safety and Health (NIOSH).
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.
Merck Index, 11th Edition, 7819
J. C. Sauer (1956). "Propionaldehyde". Organic Syntheses. 36: 66.; Collective Volume, vol. 4, p. 813
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)
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..
J. Am. Chem. Soc., 1944, 66 (2), pp 285–287

External links

[http://nj.gov/health/eoh/rtkweb/documents/fs/1597.pdf Hazardous substance fact sheet for propargyl alcohol
CDC - NIOSH Pocket Guide to Chemical Hazards

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[PGCH-1] NIOSH Pocket Guide to Chemical Hazards. "#0527". National Institute for Occupational Safety and Health (NIOSH).

[GESTIS-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.; Collective Volume, 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)

[Ullmann-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..

[J._Am._Chem._Soc.,_1944,_66_(2),_pp_285–287-7] J. Am. Chem. Soc., 1944, 66 (2), pp 285–287