3-Hydroxybutanal

Last updated
3-Hydroxybutanal
3-hydroxybutanal.png
Names
Preferred IUPAC name
3-Hydroxybutanal [1]
Other names
  • Acetaldol
  • 3-Hydroxybutyraldehyde
  • beta-Hydroxybutyraldehyde
  • β-Hydroxybutyraldehyde
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.210 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-530-2
MeSH 3-hydroxybutanal
PubChem CID
UNII
  • InChI=1S/C4H8O2/c1-4(6)2-3-5/h3-4,6H,2H2,1H3 Yes check.svgY
    Key: HSJKGGMUJITCBW-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C4H8O2/c1-4(6)2-3-5/h3-4,6H,2H2,1H3
    Key: HSJKGGMUJITCBW-UHFFFAOYAI
  • CC(O)CC=O
Properties
C4H8O2
Molar mass 88.106 g·mol−1
Appearancecolorless liquid
Density 0.98 g/mL
Boiling point 162 °C (324 °F; 435 K)
Related compounds
Related aldehydes
Glycolaldehyde

Lactaldehyde

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

In organic chemistry, 3-hydroxybutanal (acetaldol, aldol) is an organic compound with the formula CH3CH(OH)CH2CHO and the structure H3C−CH(OH)−CH2CH=O . It is classified as an aldol (R−CH(OH)−CHR'−C(=O)−R") and the word "aldol" can refer specifically to 3-hydroxybutanal. It is formally the product of the dimerization of acetaldehyde (CH3CHO). A thick colorless or pale-yellow liquid, it is a versatile and valuable intermediate with diverse impacts. [2] The compound is chiral although this aspect is not often exploited.

Contents

Production

Acetaldehyde dimerizes upon treatment with aqueous sodium hydroxide: [2]

2 CH3CHO → CH3CH(OH)CH2CHO + H2O

This is the prototypical aldol reaction.

Reactions and uses

Dehydration of 3-hydroxybutanal gives crotonaldehyde. Distillation of 3-hydroxybutanal is sufficiently forcing to effect this conversion: [2]

CH3CH(OH)CH2CHO → CH3CH=CHCHO + H2O

Hydrogenation of 3-hydroxybutanal gives 1,3-butanediol:

CH3CH(OH)CH2CHO + H2 → CH3CH(OH)CH2CH2OH

This diol is a precursor to 1,3-butadiene, precursor to diverse polymers.

Polymerization of 3-hydroxybutanal is also spontaneous, but can be stopped with the addition of water.

Aldol has been used in making perfumes and in ore flotation. [3]

Former or niche uses

It was formerly used in medicine as a hypnotic and sedative. [4]

See also

Related Research Articles

<span class="mw-page-title-main">Carboxylic acid</span> Organic compound containing a –C(=O)OH group

In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group attached to an R-group. The general formula of a carboxylic acid is often written as R−COOH or R−CO2H, sometimes as R−C(O)OH with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.

<span class="mw-page-title-main">Aldehyde</span> Organic compound containing the functional group R−CH=O

In organic chemistry, an aldehyde is an organic compound containing a functional group with the structure R−CH=O. The functional group itself can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are a common motif in many chemicals important in technology and biology.

Acetaldehyde (IUPAC systematic name ethanal) is an organic chemical compound with the formula CH3 CHO, sometimes abbreviated as MeCHO. It is a colorless liquid or gas, boiling near room temperature. It is one of the most important aldehydes, occurring widely in nature and being produced on a large scale in industry. Acetaldehyde occurs naturally in coffee, bread, and ripe fruit, and is produced by plants. It is also produced by the partial oxidation of ethanol by the liver enzyme alcohol dehydrogenase and is a contributing cause of hangover after alcohol consumption. Pathways of exposure include air, water, land, or groundwater, as well as drink and smoke. Consumption of disulfiram inhibits acetaldehyde dehydrogenase, the enzyme responsible for the metabolism of acetaldehyde, thereby causing it to build up in the body.

In chemistry, a hydration reaction is a chemical reaction in which a substance combines with water. In organic chemistry, water is added to an unsaturated substrate, which is usually an alkene or an alkyne. This type of reaction is employed industrially to produce ethanol, isopropanol, and butan-2-ol.

<span class="mw-page-title-main">Ethylene oxide</span> Cyclic compound (C2H4O)

Ethylene oxide is an organic compound with the formula C2H4O. It is a cyclic ether and the simplest epoxide: a three-membered ring consisting of one oxygen atom and two carbon atoms. Ethylene oxide is a colorless and flammable gas with a faintly sweet odor. Because it is a strained ring, ethylene oxide easily participates in a number of addition reactions that result in ring-opening. Ethylene oxide is isomeric with acetaldehyde and with vinyl alcohol. Ethylene oxide is industrially produced by oxidation of ethylene in the presence of a silver catalyst.

<span class="mw-page-title-main">Aldol</span> Organic compound of the form R–CH(OH)–CHR–C(=O)–R

In organic chemistry, an aldol is a structure consisting of a hydroxy group (-OH) two carbons away from either an aldehyde or a ketone. The name combines the suffix 'ol' from the alcohol and the prefix depending on the carbonyl group, either 'ald' for an aldehyde, or 'ket' for a ketone, in which case it referred to as a 'ketol'. An aldol may also use the term β-hydroxy aldehyde. The term "aldol" may refer to 3-hydroxybutanal.

A diol is a chemical compound containing two hydroxyl groups. An aliphatic diol is also called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified. They are used as protecting groups of carbonyl groups, making them essential in synthesis of organic chemistry.

In organic chemistry, a nitrile is any organic compound that has a −C≡N functional group. The name of the compound is composed of a base, which includes the carbon of the −C≡N, suffixed with "nitrile", so for example CH3CH2C≡N is called "propionitrile". The prefix cyano- is used interchangeably with the term nitrile in industrial literature. Nitriles are found in many useful compounds, including methyl cyanoacrylate, used in super glue, and nitrile rubber, a nitrile-containing polymer used in latex-free laboratory and medical gloves. Nitrile rubber is also widely used as automotive and other seals since it is resistant to fuels and oils. Organic compounds containing multiple nitrile groups are known as cyanocarbons.

<span class="mw-page-title-main">Allyl group</span> Chemical group (–CH₂–CH=CH₂)

In organic chemistry, an allyl group is a substituent with the structural formula −CH2−HC=CH2. It consists of a methylene bridge attached to a vinyl group. The name is derived from the scientific name for garlic, Allium sativum. In 1844, Theodor Wertheim isolated an allyl derivative from garlic oil and named it "Schwefelallyl". The term allyl applies to many compounds related to H2C=CH−CH2, some of which are of practical or of everyday importance, for example, allyl chloride.

<span class="mw-page-title-main">Vinyl alcohol</span> Chemical compound

Vinyl alcohol, also called ethenol or ethylenol, is the simplest enol. With the formula CH2CHOH, it is a labile compound that converts to acetaldehyde immediately upon isolation near room temperature. It is not a practical precursor to any compound.

In chemistry, a trimer is a molecule or polyatomic anion formed by combination or association of three molecules or ions of the same substance. In technical jargon, a trimer is a kind of oligomer derived from three identical precursors often in competition with polymerization.

In chemistry, disproportionation, sometimes called dismutation, is a redox reaction in which one compound of intermediate oxidation state converts to two compounds, one of higher and one of lower oxidation states. The reverse of disproportionation, such as when a compound in an intermediate oxidation state is formed from precursors of lower and higher oxidation states, is called comproportionation, also known as synproportionation.

<span class="mw-page-title-main">Benzil</span> Chemical compound

Benzil (i.e. Bz2, systematically known as 1,2-diphenylethane-1,2-dione) is the organic compound with the formula (C6H5CO)2, generally abbreviated (PhCO)2. This yellow solid is one of the most common diketones. Its main use is as a photoinitiator in polymer chemistry.

<span class="mw-page-title-main">Ethylamine</span> Chemical compound

Ethylamine, also known as ethanamine, is an organic compound with the formula CH3CH2NH2. This colourless gas has a strong ammonia-like odor. It condenses just below room temperature to a liquid miscible with virtually all solvents. It is a nucleophilic base, as is typical for amines. Ethylamine is widely used in chemical industry and organic synthesis.

<span class="mw-page-title-main">Crotonaldehyde</span> Chemical compound

Crotonaldehyde is a chemical compound with the formula CH3CH=CHCHO. The compound is usually sold as a mixture of the E- and Z-isomers, which differ with respect to the relative position of the methyl and formyl groups. The E-isomer is more common (data given in Table is for the E-isomer). This lachrymatory liquid is moderately soluble in water and miscible in organic solvents. As an unsaturated aldehyde, crotonaldehyde is a versatile intermediate in organic synthesis. It occurs in a variety of foodstuffs, e.g. soybean oils.

<span class="mw-page-title-main">1,3-Butanediol</span> Chemical compound

1,3-Butanediol is an organic compound with the formula CH3CH(OH)CH2CH2OH. With two alcohol functional groups, the molecule is classified as a diol. The compound is also chiral, but most studies do not distinguish the enantiomers. The compound is a colorless, bittersweet, water-soluble liquid. It is one of four common structural isomers of butanediol. It is used in flavoring.

<span class="mw-page-title-main">Phenylacetaldehyde</span> Chemical compound

Phenylacetaldehyde is an organic compound used in the synthesis of fragrances and polymers. Phenylacetaldehyde is an aldehyde that consists of acetaldehyde bearing a phenyl substituent; the parent member of the phenylacetaldehyde class of compounds. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is an alpha-CH2-containing aldehyde and a member of phenylacetaldehydes.

Ivan Ivanovich Ostromislensky was a Russian organic chemist. He is credited as the pioneer in studying polymerization of synthetic rubber as well as inventor of various industrial technologies for production of synthetic rubber, polymers and pharmaceuticals.

<span class="mw-page-title-main">Vinylphosphonic acid</span> Chemical compound

Vinylphosphonic acid is an organophosphorus compound with the formula C2H3PO3H2. It is a colorless, low-melting solid, although commercial samples are often yellowish viscous liquids. It is used to prepare adhesives. As in other phosphonic acids, the phosphorus center is tetrahedral, being bonded to an organic group (vinyl in this case), two OH groups, and an oxygen.

In organic chemistry, alkynylation is an addition reaction in which a terminal alkyne is added to a carbonyl group to form an α-alkynyl alcohol.

References

  1. "3-hydroxybutanal – Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 13 October 2011.
  2. 1 2 3 Kohlpaintner, Christian; Schulte, Markus; Falbe, Jürgen; Lappe, Peter; Weber, Jürgen (2008). Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_321.pub2. ISBN   978-3527306732.
  3. American Heritage Dictionary, 1973.
  4. Hans Brandenberger, Robert A. A. Maes. (1997). Analytical Toxicology: For Clinical, Forensic, and Pharmaceutical Chemists. New York: de Gruyter.