Propargyl alcohol, or 2-propyn-1-ol, is an
organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
with the
formula
In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwe ...
C
3H
4O. It is the simplest stable
alcohol
Alcohol may refer to:
Common uses
* Alcohol (chemistry), a class of compounds
* Ethanol, one of several alcohols, commonly known as alcohol in everyday life
** Alcohol (drug), intoxicant found in alcoholic beverages
** Alcoholic beverage, an alco ...
containing an
alkyne
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Acetylene
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Propyne
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1-Butyne
In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and n ...
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
Electroplating, also known as electrochemical deposition or electrodeposition, is a process for producing a metal coating on a solid substrate through the redox, reduction of cations of that metal by means of a direct current, direct electric cur ...
brightener additive. It is also used as an intermediate in
organic synthesis
Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...
.
Secondary and
tertiary
Tertiary (from Latin, meaning 'third' or 'of the third degree/order..') may refer to:
* Tertiary period, an obsolete geologic period spanning from 66 to 2.6 million years ago
* Tertiary (chemistry), a term describing bonding patterns in organic ch ...
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
Electronegativity, symbolized as , is the tendency for an atom of a given chemical element to attract shared electrons (or electron density) when forming a chemical bond. An atom's electronegativity is affected by both its atomic number and the ...
of an
sp carbon, propargyl alcohol is significantly more acidic (p''K''
a = 13.6) compared to its sp
2-containing analog
allyl alcohol (p''K''
a = 15.5), which is in turn more acidic than the fully saturated (sp
3 carbons only)
''n-''propyl alcohol (p''K''
a = 16.1).
Preparation
Propargyl alcohol is produced by the copper-catalysed addition of
formaldehyde
Formaldehyde ( , ) (systematic name methanal) is an organic compound with the chemical formula and structure , more precisely . The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as ...
to
acetylene
Acetylene (Chemical nomenclature, systematic name: ethyne) is a chemical compound with the formula and structure . It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is u ...
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
Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula . It is a white solid ionic compound consisting of sodium cations and hydroxide anions .
Sodium hydroxide is a highly corrosive base and alkali t ...
.
J. Am. Chem. Soc., 1944, 66 (2), pp 285–287
Safety
Propargyl alcohol is a flammable liquid, toxic by inhalation, highly toxic by ingestion, toxic by skin absorption, and corrosive.
See also
*
Alkynylation
*
Allyl alcohol
*
Propargyl
In organic chemistry, the propargyl group is a functional group of 2- propynyl with the structure . It is an alkyl group derived from propyne ().
The term propargylic refers to a saturated position ( ''sp''3-hybridized) on a molecular framework ...
*
Propargyl chloride
References
External links
Hazardous substance fact sheet for propargyl alcohol
{{Authority control
Alkynols
Primary alcohols
Propargyl compounds