Acetic formic anhydride

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Acetic formic anhydride
Formic acetic anhydride skeletal.svg
Acetic-formic-anhydride-3D-balls.png
Names
Preferred IUPAC name
Acetic formic anhydride
Other names
  • Acetyloxymethanone
  • Formyl acetate
  • Formic acetic anhydride
  • ethanoic methanoic anhydride
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C3H4O3/c1-3(5)6-2-4/h2H,1H3 Yes check.svgY
    Key: ORWKVZNEPHTCQE-UHFFFAOYSA-N Yes check.svgY
  • CC(=O)OC=O
Properties
C3H4O3
Molar mass 88.062 g·mol−1
Appearancecolourless liquid
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 ?)

Acetic formic anhydride is an organic compound with the chemical formula C
3
H
4
O
3
, which can be viewed as the mixed anhydride of acetic acid and formic acid. It is used on a laboratory-scale as a formylating agent. [1]

Contents

Preparation

Acetic formic anhydride can be produced by reacting sodium formate with acetyl chloride in anhydrous diethyl ether between 23–27 °C. [2] It can also be prepared by the reaction of acetic anhydride and formic acid at 0 °C.

Properties

While more stable than formic anhydride, acetic formic anhydride is thermally unstable and gradually decomposes above about 60 °C, with the evolution of carbon monoxide. [3] Impurities such as pyridine or residual acid can promote this, resulting in decomposition commencing as low as 0 °C. Crude material has been successfully purified by distillation at ≤30 °C under reduced pressure. [3]

Applications

Acetic formic anhydride is a formylation agent for amines, amino acids, and alcohols. It is also a starting material for other compounds such as formyl fluoride. [2] [1]

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">Ketene</span> Organic compound of the form >C=C=O

In organic chemistry, a ketene is an organic compound of the form RR'C=C=O, where R and R' are two arbitrary monovalent chemical groups. The name may also refer to the specific compound ethenone H2C=C=O, the simplest ketene.

<span class="mw-page-title-main">Formic acid</span> Simplest carboxylic acid (HCOOH)

Formic acid, systematically named methanoic acid, is the simplest carboxylic acid, and has the chemical formula HCOOH and structure H−C(=O)−O−H. It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. Esters, salts and the anion derived from formic acid are called formates. Industrially, formic acid is produced from methanol.

In chemistry, acylation is a broad class of chemical reactions in which an acyl group is added to a substrate. The compound providing the acyl group is called the acylating agent. The substrate to be acylated and the product include the following:

<span class="mw-page-title-main">Acyl halide</span> Oxoacid compound with an –OH group replaced by a halogen

In organic chemistry, an acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.

In chemistry, acetylation is an organic esterification reaction with acetic acid. It introduces an acetyl group into a chemical compound. Such compounds are termed acetate esters or simply acetates. Deacetylation is the opposite reaction, the removal of an acetyl group from a chemical compound.

<span class="mw-page-title-main">Acetic anhydride</span> Organic compound with formula (CH₃CO)₂O

Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis. It is a colorless liquid that smells strongly of acetic acid, which is formed by its reaction with moisture in the air.

<span class="mw-page-title-main">Organic acid anhydride</span> Any chemical compound having two acyl groups bonded to the same oxygen atom

An organic acid anhydride is an acid anhydride that is also an organic compound. An acid anhydride is a compound that has two acyl groups bonded to the same oxygen atom. A common type of organic acid anhydride is a carboxylic anhydride, where the parent acid is a carboxylic acid, the formula of the anhydride being (RC(O))2O. Symmetrical acid anhydrides of this type are named by replacing the word acid in the name of the parent carboxylic acid by the word anhydride. Thus, (CH3CO)2O is called acetic anhydride.Mixed (or unsymmetrical) acid anhydrides, such as acetic formic anhydride (see below), are known, whereby reaction occurs between two different carboxylic acids. Nomenclature of unsymmetrical acid anhydrides list the names of both of the reacted carboxylic acids before the word "anhydride" (for example, the dehydration reaction between benzoic acid and propanoic acid would yield "benzoic propanoic anhydride").

The Pummerer rearrangement is an organic reaction whereby an alkyl sulfoxide rearranges to an α-acyloxy–thioether (monothioacetal-ester) in the presence of acetic anhydride.

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

Trifluoroacetic acid (TFA) is an organofluorine compound with the chemical formula CF3CO2H. It is a structural analogue of acetic acid with all three of the acetyl group's hydrogen atoms replaced by fluorine atoms and is a colorless liquid with a vinegar-like odor.

In chemistry, aminolysis (/am·i·nol·y·sis/) is any chemical reaction in which a molecule is lysed by reacting with ammonia or an amine. The case where the reaction involves ammonia may be more specifically referred to as ammonolysis.

<span class="mw-page-title-main">Lead(IV) acetate</span> Organometallic compound (Pb(C2H3O2)4)

Lead(IV) acetate or lead tetraacetate is an metalorganic compound with chemical formula Pb(C2H3O2)4. It is a colorless solid that is soluble in nonpolar, organic solvents, indicating that it is not a salt. It is degraded by moisture and is typically stored with additional acetic acid. The compound is used in organic synthesis.

Formyl fluoride is the organic compound with the formula HC(O)F.

<span class="mw-page-title-main">Erlenmeyer–Plöchl azlactone and amino-acid synthesis</span>

The Erlenmeyer–Plöchl azlactone and amino acid synthesis, named after Friedrich Gustav Carl Emil Erlenmeyer who partly discovered the reaction, is a series of chemical reactions which transform an N-acyl glycine to various other amino acids via an oxazolone.

<span class="mw-page-title-main">Ethenone</span> Organic compound with the formula H2C=C=O

In organic chemistry, ethenone is the formal name for ketene, an organic compound with formula C2H2O or H2C=C=O. It is the simplest member of the ketene class. It is an important reagent for acetylations.

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

Trifluoroacetic anhydride (TFAA) is the acid anhydride of trifluoroacetic acid. It is the perfluorinated derivative of acetic anhydride.

<span class="mw-page-title-main">Acetic acid</span> Colorless and faint organic acid found in vinegar

Acetic acid, systematically named ethanoic acid, is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH. Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water. It has been used, as a component of vinegar, throughout history from at least the third century BC.

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

Formic anhydride, also called methanoic anhydride, is an organic compound with the chemical formula C
2
H
2
O
3
and a structural formula of (H(C=O)−)2O. It can be viewed as the anhydride of formic acid (HCOOH).

<span class="mw-page-title-main">Acetic oxalic anhydride</span> Chemical compound

Acetic oxalic anhydride is an organic compound with a chemical formula of C
6
H
6
O
6
and a structural formula of (H3C-(C=O)-O-(C=O)-)2. It can be viewed as a mixed anhydride, formally derived from acetic acid (H3C-(C=O)OH) and oxalic acid ((-(C=O)OH)2), in 2:1 molecular ratio, by the loss of two water molecules.

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

Acetyl hypochlorite, also known as chlorine acetate, is a chemical compound with the formula CH3COOCl. It is a photosensitive colorless liquid that is a short lived intermediate in the Hunsdiecker reaction.

References

  1. 1 2 Strazzolini, Paolo; Giumanini, Angelo G.; Cauci, Sabina (1990). "Acetic formic anhydride a review". Tetrahedron. 46 (4): 1081–1118. doi:10.1016/S0040-4020(01)86676-X.
  2. 1 2 Krimen, Lewis I. (1970). "Acetic Formic Anhydride". Organic Syntheses. 50: 1. doi:10.15227/orgsyn.050.0001.
  3. 1 2 Muramatsu, Ichiro; Murakami, Masahiro; Yoneda, Takahiro; Hagitani, Akira (February 1965). "The Formylation of Amino Acids with Acetic Formic Anhydride". Bulletin of the Chemical Society of Japan. 38 (2): 244–246. doi:10.1246/bcsj.38.244. PMID   14263227.