Fluoral

Last updated
Fluoral
Trifluoroacetaldehyde.png
Names
IUPAC name
Trifluoroethanal
Other names
Trifluoroacetaldehyde
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 200-914-1
  • hydrate:207-006-4
PubChem CID
UNII
  • InChI=1S/C2HF3O/c3-2(4,5)1-6/h1H
    Key: JVTSHOJDBRTPHD-UHFFFAOYSA-N
  • hydrate:InChI=1S/C2H3F3O2/c3-2(4,5)1(6)7/h1,6-7H
    Key: VGJWVEYTYIBXIA-UHFFFAOYSA-N
  • C(=O)C(F)(F)F
  • hydrate:OC(O)C(F)(F)F
Properties
CF3CHO
Molar mass 98.024 g·mol−1
Appearancegas, hydrate is colourless crystals
Melting point 66 °C (hydrate) [1]
Boiling point –18 °C [2]

104 °C (hydrate) [1]

forms hydrate
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Trifluoroacetaldehyde, trifluoroethanal, or fluoral, [2] is a fluorinated derivative of acetaldehyde with the formula CF3CHO. It is a gas at room temperature. Fluoral is used to introduce trifluoromethyl groups into organic compounds. [2] [3] It is highly electrophilic and fluoral forms a hydrate CF3CH(OH)2 upon contact with water like other halogenated acetaldehydes. [4] It is commonly used in form of ethyl hemiacetal (1-ethoxy-2,2,2-trifluoroethanol, CF3CH(OCH2CH3)(OH)) due to the aldehyde's high reactivity, including the tendency to polymerise. [5]

Contents

Synthesis and reactions

Upon storage, fluoral polymerises into a waxy, white solid that is soluble in diethyl ether and acetone but not water and chlorocarbons. Heating of this polymer gives monomeric fluoral. [6] Fluoral can be prepared from trifluoroacetic acid with lithium aluminium hydride in diethyl ether: [4]

CF3COOH + LiAlH4 → CF3CHO[ clarification needed ]

or with concentrated sulfuric acid.[ clarification needed ]

Cathodic reduction of bromotrifluoromethane in dimethylformamide with aluminium as anode gives high yields of fluoral. In this reaction, DMF acts both as the solvent and the formylation agent. [7] Vapour-phase oxidation of trifluoroethanol also gives fluoral. [5]

Photolysis of fluoral gives fluoroform, hexafluoroethane and carbon monoxide, along with some hydrogen. [8]

See also

Related Research Articles

<span class="mw-page-title-main">Ether</span> Organic compounds made of alkyl/aryl groups bound to oxygen (R–O–R)

In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula R−O−R′, where R and R′ represent the alkyl or aryl groups. Ethers can again be classified into two varieties: if the alkyl or aryl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers. A typical example of the first group is the solvent and anaesthetic diethyl ether, commonly referred to simply as "ether". Ethers are common in organic chemistry and even more prevalent in biochemistry, as they are common linkages in carbohydrates and lignin.

<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 CH3CHO, 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">Lithium aluminium hydride</span> Chemical compound

Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula Li[AlH4] or LiAlH4. It is a white solid, discovered by Finholt, Bond and Schlesinger in 1947. This compound is used as a reducing agent in organic synthesis, especially for the reduction of esters, carboxylic acids, and amides. The solid is dangerously reactive toward water, releasing gaseous hydrogen (H2). Some related derivatives have been discussed for hydrogen storage.

In retrosynthetic analysis, a synthon is a hypothetical unit within a target molecule that represents a potential starting reagent in the retroactive synthesis of that target molecule. The term was coined in 1967 by E. J. Corey. He noted in 1988 that the "word synthon has now come to be used to mean synthetic building block rather than retrosynthetic fragmentation structures". It was noted in 1998 that the phrase did not feature very prominently in Corey's 1981 book The Logic of Chemical Synthesis, as it was not included in the index. Because synthons are charged, when placed into a synthesis an uncharged form is found commercially instead of forming and using the potentially very unstable charged synthons.

<span class="mw-page-title-main">Wacker process</span>

The Wacker process or the Hoechst-Wacker process refers to the oxidation of ethylene to acetaldehyde in the presence of palladium(II) chloride and copper(II) chloride as the catalyst. This chemical reaction was one of the first homogeneous catalysis with organopalladium chemistry applied on an industrial scale.

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

Diethyl azodicarboxylate, conventionally abbreviated as DEAD and sometimes as DEADCAT, is an organic compound with the structural formula CH3CH2−O−C(=O)−N=N−C(=O)−O−CH2CH3. Its molecular structure consists of a central azo functional group, RN=NR, flanked by two ethyl ester groups. This orange-red liquid is a valuable reagent but also quite dangerous and explodes upon heating. Therefore, commercial shipment of pure diethyl azodicarboxylate is prohibited in the United States and is carried out either in solution or on polystyrene particles.

Glyoxal is an organic compound with the chemical formula OCHCHO. It is the smallest dialdehyde. It is a crystalline solid, white at low temperatures and yellow near the melting point (15 °C). The liquid is yellow, and the vapor is green.

<span class="mw-page-title-main">Hydroperoxide</span> Class of chemical compounds

Hydroperoxides or peroxols are compounds of the form ROOH, where R stands for any group, typically organic, which contain the hydroperoxy functional group. Hydroperoxide also refers to the hydroperoxide anion and its salts, and the neutral hydroperoxyl radical (•OOH) consist of an unbond hydroperoxy group. When R is organic, the compounds are called organic hydroperoxides. Such compounds are a subset of organic peroxides, which have the formula ROOR. Organic hydroperoxides can either intentionally or unintentionally initiate explosive polymerisation in materials with unsaturated chemical bonds.

<span class="mw-page-title-main">Grignard reagent</span> Organometallic compounds used in organic synthesis

In organic chemistry, a Grignard reagent or Grignard compound is a chemical compound with the general formula R−Mg−X, where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride Cl−Mg−CH3 and phenylmagnesium bromide (C6H5)−Mg−Br. They are a subclass of the organomagnesium compounds.

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

Aluminium hydride is an inorganic compound with the formula AlH3. Alane and its derivatives are part of a family of common reducing reagents in organic synthesis based around group 13 hydrides. In solution—typically in etherial solvents such tetrahydrofuran or diethyl ether—aluminium hydride forms complexes with Lewis bases, and reacts selectively with particular organic functional groups, and although it is not a reagent of choice, it can react with carbon-carbon multiple bonds. Given its density, and with hydrogen content on the order of 10% by weight, some forms of alane are, as of 2016, active candidates for storing hydrogen and so for power generation in fuel cell applications, including electric vehicles. As of 2006 it was noted that further research was required to identify an efficient, economical way to reverse the process, regenerating alane from spent aluminium product.

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

Phenylmagnesium bromide, with the simplified formula C
6
H
5
MgBr
, is a magnesium-containing organometallic compound. It is commercially available as a solution in diethyl ether or tetrahydrofuran (THF). Phenylmagnesium bromide is a Grignard reagent. It is often used as a synthetic equivalent for the phenyl "Ph" synthon.

In organic chemistry, the Nef reaction is an organic reaction describing the acid hydrolysis of a salt of a primary or secondary nitroalkane to an aldehyde or a ketone and nitrous oxide. The reaction has been the subject of several literature reviews.

<span class="mw-page-title-main">Oxygen compounds</span>

The oxidation state of oxygen is −2 in almost all known compounds of oxygen. The oxidation state −1 is found in a few compounds such as peroxides. Compounds containing oxygen in other oxidation states are very uncommon: −12 (superoxides), −13 (ozonides), 0, +12 (dioxygenyl), +1, and +2.

Alcohol oxidation is a collection of oxidation reactions in organic chemistry that convert alcohols to aldehydes, ketones, carboxylic acids, and esters where the carbon carries a higher oxidation state. The reaction mainly applies to primary and secondary alcohols. Secondary alcohols form ketones, while primary alcohols form aldehydes or carboxylic acids.

Fluorination with aminosulfuranes is a chemical reaction that transforms oxidized organic compounds into organofluorine compounds. Aminosulfuranes selectively exchange hydroxyl groups for fluorine, but are also capable of converting carbonyl groups, halides, silyl ethers, and other functionality into organofluorides.

<span class="mw-page-title-main">Jones oxidation</span> Oxidation of alcohol

The Jones oxidation is an organic reaction for the oxidation of primary and secondary alcohols to carboxylic acids and ketones, respectively. It is named after its discoverer, Sir Ewart Jones. The reaction was an early method for the oxidation of alcohols. Its use has subsided because milder, more selective reagents have been developed, e.g. Collins reagent.

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

Diethyl phosphite is the organophosphorus compound with the formula (C2H5O)2P(O)H. It is a popular reagent for generating other organophosphorus compounds, exploiting the high reactivity of the P-H bond. Diethyl phosphite is a colorless liquid. The molecule is tetrahedral.

References

  1. 1 2 The Radiolysis of Some Organic Halogen Compounds in Aqueous Solutions, R. J. Woods and J. W. T Spinks (1960), Canadian Journal of Chemistry vol.38
  2. 1 2 3 Trifluoroacetaldehyde, Peter Lin (2003), DOI:10.1002/047084289X.RN00213
  3. 2. Aldehydes, Fluorocarbon and Related Chemistry: Volume 2 (2007) Royal Society of Chemistry.
  4. 1 2 Kitazume, T., Yamazaki, T. (2019). Experimental Methods in Organic Fluorine Chemistry
  5. 1 2 Trifluoroacetaldehyde: A useful industrial bulk material for the synthesis of trifluoromethylated amino compounds, Hideyuki Mimura, Kosuke Kawada, Tetsuya Yamashita, Takeshi Sakamoto, Yasuo Kikugawa. Journal of Fluorine Chemistry Volume 131, Issue 4, April 2010, Pages 477-486
  6. Oxidative Nitration of 1,1,1-Trifluoropropane. Trifluoroacetaldehyde, Harold Shechter and Franklin Conrad, in J. Am. Chem. Soc. 1950, 72, 8, 3371–3373
  7. Advances in Electron Transfer Chemistry. (1999)
  8. The photolysis of trifluoroacetaldehyde R. E. Dodd and J. Watson Smith, J. Chem. Soc., 1957, 1465-1473 https://doi.org/10.1039/JR9570001465