Chemistry:Acetyl cyanide

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Acetyl cyanide
Acetyl cyanide
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
EC Number
  • 211-159-2
UNII
Properties
C3H3NO
Molar mass 69.063 g·mol−1
Appearance Clear, 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
Hazards
Safety data sheet External MSDS
GHS pictograms GHS02: Flammable GHS06: Toxic
GHS Signal word Danger
HH225Script error: No such module "Preview warning".Category:GHS errors, H301, H315, H331, H335, H401, H412
PP210Script error: No such module "Preview warning".Category:GHS errors, P261, P273, P301+310, P311
Ingestion hazard Toxic if swallowed
Inhalation hazard Toxic if inhaled. Causes respiratory tract irritation
Eye hazard Causes eye irritation
Skin hazard May be harmful if absorbed through skin. Causes skin irritation.
NFPA 704 (fire diamond)
Flammability code 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. gasolineHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
3
2
0
Flash point 14.44 °C (57.99 °F; 287.59 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Tracking categories (test):

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

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

References

  1. ↑ 1.0 1.1 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. ↑ 2.0 2.1 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. doi:10.1016/0022-2860(74)85121-5. Bibcode: 1974JMoSt..20..437S. 
  4. ↑ 4.0 4.1 R. Sumathi; Minh Tho Nguyen (1998). "Theoretical Study on Unimolecular Reactions of Acetyl Cyanide and Acetyl Isocyanide". J. Phys. Chem. A 102 (2): 412–421. doi:10.1021/jp9724582. http://www.quantchem.kuleuven.ac.be/minh/Articles/JPCA/jp9724582.pdf. Retrieved 7 March 2022. 

Further reading



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