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Propargyl alcohol

Propargyl alcohol
Propargyl alcohol.svg
Names
IUPAC name
2-Propyn-1-ol
Identifiers
3D model (Jmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.157
KEGG
UNII
Properties
C3H4O
Molar mass 56.06 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)
miscible
Vapor pressure 12 mmHg (20 °C)
Hazards
Safety data sheet External SDS
NFPA 704
Flammability code 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., gasoline) Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 36 °C; 97 °F; 309 K (open cup)
US health exposure limits (NIOSH):
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).
N  (what is YesYN ?)
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. Propargyl alcohol is a colorless viscous liquid that is miscible with water and most polar organic solvents.

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.

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.

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


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