Crotyl alcohol

Last updated
Crotyl alcohol [1]
Crotonyl alcohol.svg
Names
Preferred IUPAC name
(2E)-But-2-en-1-ol
Other names
(E)-But-2-en-1-ol
Crotyl alcohol
Crotonyl alcohol
2-Butenol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.025.533 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-996-8
PubChem CID
UNII
UN number 2614
  • InChI=1S/C4H8O/c1-2-3-4-5/h2-3,5H,4H2,1H3/b3-2+ Yes check.svgY
    Key: WCASXYBKJHWFMY-NSCUHMNNSA-N Yes check.svgY
  • InChI=1/C4H8O/c1-2-3-4-5/h2-3,5H,4H2,1H3/b3-2+
    Key: WCASXYBKJHWFMY-NSCUHMNNBR
  • C\C=C\CO
Properties
C4H8O
Molar mass 72.10 g/mol
Density 0.8454 g/cm3
Melting point < 25 °C (77 °F; 298 K)
Boiling point 121.2 °C (250.2 °F; 394.3 K)
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
Warning
H226, H302, H312, H315, H319
P210, P233, P240, P241, P242, P243, P264, P270, P280, P301+P312, P302+P352, P303+P361+P353, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P370+P378, P403+P235, P501
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 ?)
Infobox references

Crotyl alcohol, or crotonyl alcohol, is an unsaturated alcohol. It is a colourless liquid that is moderately soluble in water and miscible with most organic solvents. Two isomers of this alcohol exist, cis and trans.

It can be synthesized by the hydrogenation of crotonaldehyde. The compound is of little commercial interest. [2]

See also

Related Research Articles

Alcohol (chemistry) Type of organic compound

In chemistry, alcohol is an organic compound that carries at least one hydroxyl functional group (−OH) bound to a saturated carbon atom. The term alcohol originally referred to the primary alcohol ethanol (ethyl alcohol), which is used as a drug and is the main alcohol present in alcoholic drinks. An important class of alcohols, of which methanol and ethanol are the simplest members, includes all compounds for which the general formula is CnH2n+1OH. Simple monoalcohols that are the subject of this article include primary (RCH2OH), secondary (R2CHOH) and tertiary (R3COH) alcohols.

Ethanol Organic chemical compound

Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic chemical compound. It is a simple alcohol with the chemical formula C2H6O. Its formula can be also written as CH
3
CH
2
OH or C
2
H
5
OH (an ethyl group linked to a hydroxyl group), and is often abbreviated as EtOH. Ethanol is a volatile, flammable, colorless liquid with a characteristic wine-like odor and pungent taste. It is a psychoactive drug, recreational drug, and the active ingredient in alcoholic drinks.

Ethanal (common name acetaldehyde) is an organic chemical compound with the formula CH3CHO, sometimes abbreviated by chemists as MeCHO (Me = methyl). 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.

Allyl group

An allyl group is a substituent with the structural formula H2C=CH−CH2R, where R is the rest of the molecule. It consists of a methylene bridge (−CH2−) attached to a vinyl group (−CH=CH2). The name is derived from the Latin word 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.

Butyraldehyde Chemical compound

Butyraldehyde, also known as butanal, is an organic compound with the formula CH3(CH2)2CHO. This compound is the aldehyde derivative of butane. It is a colourless flammable liquid with an unpleasant smell. It is miscible with most organic solvents.

Crotonic acid Chemical compound

Crotonic acid ((2E)-but-2-enoic acid) is a short-chain unsaturated carboxylic acid, described by the formula CH3CH=CHCO2H. It is called crotonic acid because it was erroneously thought to be a saponification product of croton oil. It crystallizes as colorless needles from hot water. The cis-isomer of crotonic acid is called isocrotonic acid. Crotonic acid is soluble in water and many organic solvents. Its odor is similar to butyric acid.

This is the list of extremely hazardous substances defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act. The list can be found as an appendix to 40 C.F.R. 355. Updates as of 2006 can be seen on the Federal Register, 71 FR 47121.

1-Butanol Chemical compound

1-Butanol, also known as butan-1-ol or n-butanol, is a primary alcohol with the chemical formula C4H9OH and a linear structure. Isomers of 1-butanol are isobutanol, butan-2-ol and tert-butanol. The unmodified term butanol usually refers to the straight chain isomer.

Crotonaldehyde 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.

Crotyl group

A crotyl group is an organic functional group with the formula RCH2CH=CHCH3. Systematically, it is called a but-2-en-1-yl group and exhibits geometric isomerism, being either cis (Z) or trans (E). There are many simple compounds in which the crotyl group forms base carbon chain: crotyl alcohol, crotonaldehyde, crotonic acid, and crotyl acrylate are examples.

The molecular formula C4H8O may refer to:

Crotylbarbital

Crotylbarbital, also known as crotarbital, is a barbiturate derivative developed by Eli Lilly in the 1930s It has sedative and hypnotic effects, and was used for the treatment of insomnia until it was replaced by newer alternative drugs with less side effects and lower risk of overdose.

<i>trans</i>-2-Methyl-2-butenal Chemical compound

trans-2-Methyl-2-butenal is an organic compound with the formula CH3CH=C(CH3)CHO. This colorless liquid is a building block in organic synthesis. It is an α,β-unsaturated aldehyde related to the better-known crotonaldehyde. The European rabbit, Oryctolagus cuniculus, uses 2-methyl-2-butenal as a pheromone. The rabbit pheromone, trans-2-methyl-2-butenal, was reported to be involved in the communication between species, defined under the class of "interomone."

Diisopinocampheylborane Chemical compound

Diisopinocampheylborane is an organoborane that is useful for asymmetric synthesis. This colourless solid is the precursor to a range of related reagents. The compound was reported in 1961 by Zweifel and Brown in a pioneering demonstration of asymmetric synthesis using boranes. The reagent is mainly used for the synthesis of chiral secondary alcohols.

3-Hydroxybutanal (acetaldol) is an organic compound with the formula CH3CH(OH)CH2CHO. It is classified as an aldol, formally the product of the dimerization of acetaldehyde. A colorless liquid, it is a versatile and valuable intermediate with diverse impacts. The compound is chiral although this aspect is not often exploited.

Neocuproine Chemical compound

Neocuproine is a heterocyclic organic compound and chelating agent. Phenanthroline ligands were first published in the late 19th century, and the derivatives substituted at the 2 and 9 positions are among the most studied of the modified phenanthrolines.

Crotyl chloride is an organochloride with the molecular formula C4H7Cl.

Alcohol (drug) Active ingredient in alcoholic beverages

Alcohol, sometimes referred to by the chemical name ethanol, is a psychoactive drug that is the active ingredient in drinks such as beer, wine, and distilled spirits. It is one of the oldest and most common recreational substances, causing the characteristic effects of alcohol intoxication ("drunkenness"). Among other effects, alcohol produces happiness and euphoria, decreased anxiety, increased sociability, sedation, impairment of cognitive, memory, motor, and sensory function, and generalized depression of central nervous system function. Ethanol is only one of several types of alcohol, but it is the only type of alcohol that is found in alcoholic beverages or commonly used for recreational purposes; other alcohols such as methanol and isopropyl alcohol are significantly more toxic. A mild, brief exposure to isopropanol, being only moderately more toxic than ethanol, is unlikely to cause any serious harm. Methanol, being profoundly more toxic than ethanol, is lethal in quantities as small as 10–15 milliliters.

Methallyl chloride Chemical compound

Methallyl chloride is the organic compound with the formula CH2=C(CH3)CH2Cl. It is a colorless liquid and a lacrymator. Its properties are similar to those of allyl chloride. It is a strong alkylating agent used to install isobutenyl groups.

Alpha-beta unsaturated carbonyl compounds

α,β-Unsaturated carbonyl compounds refers to organic compounds with the general structure (O=CR)−Cα=Cβ-R. Examples would be enones and enals. In these compounds the carbonyl group is conjugated with an alkene. Unlike the case for carbonyls without a flanking alkene group, α,β-unsaturated carbonyl compounds are susceptible to attack by nucleophiles at the β carbon. This pattern of reactivity is called vinylogous. Examples of unsaturated carbonyls are acrolein (propenal), mesityl oxide, acrylic acid, and maleic acid. Unsaturated carbonyls can be prepared in the laboratory in an aldol reaction and in the Perkin reaction.

References

  1. Merck Index , 11th Edition, 2604
  2. 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..