Formyl fluoride is the organic compound

Organic compound

An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 with the formula FC(O)H.

Preparation

FC(O)H was first reported in the 1934. Among the many preparations, a typical one involves the reaction of sodium formate

Sodium formate

Sodium formate, HCOONa, is the sodium salt of formic acid, HCOOH. It usually appears as a white deliquescent powder.-Uses:Sodium formate is used in several fabric dyeing and printing processes...

 with benzoyl fluoride (generated in situ from KHF₂

Potassium bifluoride

Potassium bifluoride is the inorganic compound with the formula KHF2. This colourless salt consists of the potassium cation and the bifluoride anion. The salt is used in etchant for glass...

 and benzoyl chloride

Benzoyl chloride

Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound with the formula C6H5COCl. It is a colourless, fuming liquid with an irritating odour...

):

NaOC(O)H + C₆H₅C(O)F → FC(O)H + C₆H₅CO₂Na

Reactions

HC(O)F decomposes autocatalytically

Autocatalysis

A single chemical reaction is said to have undergone autocatalysis, or be autocatalytic, if the reaction product itself is the catalyst for that reaction....

 near room temperature to carbon monoxide

Carbon monoxide

Carbon monoxide , also called carbonous oxide, is a colorless, odorless, and tasteless gas that is slightly lighter than air. It is highly toxic to humans and animals in higher quantities, although it is also produced in normal animal metabolism in low quantities, and is thought to have some normal...

 and hydrogen fluoride

Hydrogen fluoride

Hydrogen fluoride is a chemical compound with the formula HF. This colorless gas is the principal industrial source of fluorine, often in the aqueous form as hydrofluoric acid, and thus is the precursor to many important compounds including pharmaceuticals and polymers . HF is widely used in the...

:

HC(O)F → HF + CO

Because of the compound’s sensitivity, reactions are conducted at low temperatures and samples are often stored over anhydrous

Anhydrous

As a general term, a substance is said to be anhydrous if it contains no water. The way of achieving the anhydrous form differs from one substance to another...

 alkali metal

Alkali metal

The alkali metals are a series of chemical elements in the periodic table. In the modern IUPAC nomenclature, the alkali metals comprise the group 1 elements, along with hydrogen. The alkali metals are lithium , sodium , potassium , rubidium , caesium , and francium...

 fluorides, e.g. potassium fluoride

Potassium fluoride

Potassium fluoride is the chemical compound with the formula KF. After hydrogen fluoride, KF is the primary source of the fluoride ion for applications in manufacturing and in chemistry. It is an alkali metal halide and occurs naturally as the rare mineral carobbiite...

 which absorbs HF.

Benzene

Benzene

Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....

 (and other arene

Arene

Arene or Arênê or Arène may refer to:*an aromatic hydrocarbon*Arene , a genus of marine snails in the family Areneidae*Arene , the wife of Aphareus and mother of Idas and Lynceus in Greek mythology...

s) react with formyl fluoride in the presence of boron trifluoride

Boron trifluoride

Boron trifluoride is the chemical compound with the formula BF3. This pungent colourless toxic gas forms white fumes in moist air. It is a useful Lewis acid and a versatile building block for other boron compounds.-Structure and bonding:...

 to give benzaldehyde

Benzaldehyde

Benzaldehyde is an organic compound consisting of a benzene ring with a formyl substituent. It is the simplest aromatic aldehyde and one of the most industrially useful. This colorless liquid has a characteristic pleasant almond-like odor...

. In a related reaction, formyl chloride is implicated in Gattermann-Koch

Gattermann-Koch reaction

The Gattermann–Koch reaction, named after the German chemists Ludwig Gattermann and Julius Arnold Koch, in organic chemistry refers to a Friedel–Crafts acylation reaction in which carbon monoxide and hydrochloric acid are used in situ with Friedel–Crafts catalyst, namely AlCl3 to produce a...

 formylation reaction. The reaction of formyl fluoride/BF₃ with perdeuteriobenzene (C₆D

Deuterium

Deuterium, also called heavy hydrogen, is one of two stable isotopes of hydrogen. It has a natural abundance in Earth's oceans of about one atom in of hydrogen . Deuterium accounts for approximately 0.0156% of all naturally occurring hydrogen in Earth's oceans, while the most common isotope ...

₆) exhibits a kinetic isotope effect

Kinetic isotope effect

The kinetic isotope effect is the ratio of reaction rates of two different isotopically labeled molecules in a chemical reaction. It is also called "isotope fractionation," although this term is somewhat broader in meaning...

 of 2.68, similar to the isotope effect observed in Friedel-Crafts acetylation

Acetylation

Acetylation describes a reaction that introduces an acetyl functional group into a chemical compound...

 of benzene. Formylation of benzene with a mixture of CO and hexafluoroantinomic acid however, exhibits no isotope effect (C₆H₆ and C₆D₆ react at the same rate), indicating that this reaction involves a more reactive formylating agent, possibly CHO⁺.

Formyl fluoride undergoes the reactions expected of an acyl halide: alcohol

Alcohol

In chemistry, an alcohol is an organic compound in which the hydroxy functional group is bound to a carbon atom. In particular, this carbon center should be saturated, having single bonds to three other atoms....

s and carboxylic acids are converted to formate ester

Ester

Esters are chemical compounds derived by reacting an oxoacid with a hydroxyl compound such as an alcohol or phenol. Esters are usually derived from an inorganic acid or organic acid in which at least one -OH group is replaced by an -O-alkyl group, and most commonly from carboxylic acids and...

s and mixed acid anhydrides, respectively.