Acetyl cyanide

Last updated
Acetyl cyanide
Acetyl cyanide.png
Names
Preferred IUPAC name
Acetyl cyanide [1]
Systematic IUPAC name
Ethanoyl cyanide
Other names
2-Oxopropanenitrile [1]
Pyruvonitrile
Propanenitrile, 2-oxo-
α-Oxopropionitrile
Oxopropionitrile
Oxypropionitrile
Pyruvic acid nitrile
2-Oxopropionitrile
2-Oxopropiononitrile
Identifiers
3D model (JSmol)
1737633
ChemSpider
ECHA InfoCard 100.010.146 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 211-159-2
PubChem CID
UNII
  • InChI=1S/C3H3NO/c1-3(5)2-4/h1H3 Yes check.svgY
    Key: QLDHWVVRQCGZLE-UHFFFAOYSA-N Yes check.svgY
  • CC(=O)C#N
Properties
C3H3NO
Molar mass 69.063 g·mol−1
AppearanceClear, yellow liquid
Density 0.9745 g/cm3
Boiling point 92.3 °C (198.1 °F; 365.4 K)
Vapor pressure 51.9300003051758 mmHg
1.3764
40.86 Å2
Hazards
Occupational safety and health (OHS/OSH):
Ingestion hazards
Toxic if swallowed
Inhalation hazards
Toxic if inhaled. Causes respiratory tract irritation
Eye hazards
Causes eye irritation
Skin hazards
May be harmful if absorbed through skin. Causes skin irritation.
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-skull.svg
Danger
H225, H301, H315, H331, H335, H401, H412
P210, P261, P273, P301+P310, P311
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
3
0
Flash point 14.44 °C (57.99 °F; 287.59 K)
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Acetyl cyanide is the organic compound with the formula CH3C(O)CN. It is an acyl cyanide. Acetyl cyanide is a colorless liquid. [2]

Contents

Structure

Its structure was determined through the use of electron diffraction intensities and rotational spectroscopy. [3]

Reactions

Two main types of reactions can occur with acetyl cyanide as a reactant; aldol condensation and enolate substitution. Aldol condensation can occur when acetyl cyanide reacts with (Z)-but-2-enal to form (2E,4E)-hexa-2,4-dienoyl cyanide:

Aldol condensation of Acetyl cyanide.png

The photochemical and thermal reactions of acetyl cyanide have been extensively studied. For example, formyl cyanide does not undergo unimolecular decomposition to HCN and CO spontaneously. However, acetyl cyanide, also a member of this family, breaks down through this unimolecular decomposition at 470 °C. This reaction occurs through decarbonylation. This division of the molecule to a ketone and hydrogen cyanide were noted to be under competitive circumstances. This caused a study of the thermal unimolecular reactions that acetyl cyanide undergoes.

The unimolecular decompositions that acetyl cyanide undergo have been confirmed to be less energetically favorable than the molecule undergoing isomerization to acetyl isocyanide. However, through other photolysis experiments have resulted in the formation of a CN radical through acetyl cyanide decomposing into CH3CO + CN or CH3COCN. [4]

Synthesis

Acetyl cyanide is prepared from acetyl chloride and cyanide sources, often in the presence of copper catalysts. [2] Acetyl cyanide is also synthesized at 350 °C from ketene and hydrogen cyanide. [4]

Acyl cyanide synthesis.png

Related Research Articles

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<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.

Hydrogen cyanide is a chemical compound with the formula HCN and structural formula H−C≡N. It is a colorless, extremely poisonous, and flammable liquid that boils slightly above room temperature, at 25.6 °C (78.1 °F). HCN is produced on an industrial scale and is a highly valued precursor to many chemical compounds ranging from polymers to pharmaceuticals. Large-scale applications are for the production of potassium cyanide and adiponitrile, used in mining and plastics, respectively. It is more toxic than solid cyanide compounds due to its volatile nature.

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

Sodium cyanide is a poisonous compound with the formula NaCN. It is a white, water-soluble solid. Cyanide has a high affinity for metals, which leads to the high toxicity of this salt. Its main application, in gold mining, also exploits its high reactivity toward metals. It is a moderately strong base.

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<span class="mw-page-title-main">Aldol condensation</span> Type of chemical reaction

An aldol condensation is a condensation reaction in organic chemistry in which two carbonyl moieties react to form a β-hydroxyaldehyde or β-hydroxyketone, and this is then followed by dehydration to give a conjugated enone.

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.

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

Trimethylsilyl cyanide is the chemical compound with the formula (CH3)3SiCN. This volatile liquid consists of a cyanide group, that is CN, attached to a trimethylsilyl group. The molecule is used in organic synthesis as the equivalent of hydrogen cyanide. It is prepared by the reaction of lithium cyanide and trimethylsilyl chloride:

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The captodative effect is the stabilization of radicals by a synergistic effect of an electron-withdrawing substituent and an electron-donating substituent. The name originates as the electron-withdrawing group (EWG) is sometimes called the "captor" group, whilst the electron-donating group (EDG) is the "dative" substituent. Olefins with this substituent pattern are sometime described as captodative. Radical reactions play an integral role in several chemical reactions and are also important to the field of polymer science.

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

Methyl isocyanide or isocyanomethane is an organic compound and a member of the isocyanide family. This colorless liquid is isomeric and isoelectronic to methyl cyanide (acetonitrile), but its reactivity is very different. In contrast to the faintly sweet, ethereal odor of acetonitrile, the smell of methyl isocyanide, like that of other simple volatile isocyanides, is distinctly penetrating and vile. Methyl isocyanide is mainly used for making 5-membered heterocyclic rings. The C-N distance in methyl isocyanide is very short, 1.158 Å as is characteristic of isocyanides.

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

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References

  1. 1 2 Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 796–797, 903. doi:10.1039/9781849733069-FP001. ISBN   978-0-85404-182-4.
  2. 1 2 Morris, Joel (2001). "Acetyl Cyanide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.ra026. ISBN   0471936235.
  3. Sugié, Masaaki; Kuchitsu, Kozo (1974). "Molecular structure of acetyl cyanide as studied by gas electron diffraction". Journal of Molecular Structure. 20 (3): 437–448. Bibcode:1974JMoSt..20..437S. doi:10.1016/0022-2860(74)85121-5.
  4. 1 2 R. Sumathi; Minh Tho Nguyen (1998). "Theoretical Study on Unimolecular Reactions of Acetyl Cyanide and Acetyl Isocyanide" (PDF). J. Phys. Chem. A. 102 (2): 412–421. doi:10.1021/jp9724582. Archived from the original (PDF) on 17 April 2007. Retrieved 7 March 2022.

Further reading