Wikipedia

Acetyl cyanide

Not to be confused with Acetonitrile.

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

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
ECHA InfoCard 100.010.146 Edit this at Wikidata
EC Number
  • 211-159-2
UNII
  • InChI=1S/C3H3NO/c1-3(5)2-4/h1H3 checkY
    Key: QLDHWVVRQCGZLE-UHFFFAOYSA-N checkY
  • CC(=O)C#N
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 51.93 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:
GHS02: Flammable GHS06: Toxic
Danger
H225, H301, H315, H331, H335, H401, H412
P210, P261, P273, P301+P310, P311
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 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).
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Structure

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

Reactions

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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:

 

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

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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]

 

References

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  1. ^ a b 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. ^ a b Morris, Joel (2001). "Acetyl Cyanide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.ra026. ISBN 0-471-93623-5.
  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. ^ a b 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. Bibcode:1998JPCA..102..412S. doi:10.1021/jp9724582. Archived from the original (PDF) on 17 April 2007. Retrieved 7 March 2022.

Further reading

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  • Lide, David R., W. M. Haynes, and Thomas J. Bruno, eds. CRC Handbook of Chemistry and Physics. 93rd ed. Boca Raton, FL: CRC, 2012. Web. 17 October 2012.
  • "1737633 | C3H3NO". Chemspider.com. Retrieved 7 March 2022.
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