Propargyl alcohol

Propargyl alcohol
Names
	IUPAC name Prop-2-yn-1-ol
	Other names propynol, 2-propynol, 2-propyn-1-ol, prop-2-yn-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
Odor	geranium-like
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
Vapor pressure	12 mmHg (20 °C)
Hazards
Safety data sheet	External SDS
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H226, H301, H310, H330, H314, H373, H411
GHS precautionary statements	P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P301+310, P301+330+331, P302+352, P303+361+353, P304+340, P305+351+338, P310, P311, P312, P321, P322, P330
NFPA 704 (fire diamond)	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/m3) [skin]
IDLH (Immediate danger)	N.D.
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

^ ^a ^b ^c ^d ^e ^f ^g ^h 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, 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.
^ 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..
^ [1] 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

[PGCH-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h 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, 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.

[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] [1] J. Am. Chem. Soc., 1944, 66 (2), pp 285–287

[1]

[2]

[3]

[4]

[5]

[6]

[7]

Names


IUPAC name Prop-2-yn-1-ol
Other names propynol, 2-propynol, 2-propyn-1-ol, prop-2-yn-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]
Safety data sheet	External SDS
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H226, H301, H310, H330, H314, H373, H411
GHS precautionary statements	P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P301+310, P301+330+331, P302+352, P303+361+353, P304+340, P305+351+338, P310, P311, P312, P321, P322, P330
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]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).