Acetyl cyanide

From Wikipedia, the free encyclopedia
Not to be confused with Acetonitrile.
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 51.9300003051758 mmHg
1.3764
40.86 Å2
Hazards
Safety data sheet External MSDS
GHS labelling:
GHS02: Flammable GHS06: Toxic
Signal word
 Danger
H225, H301, H315, H331, H335, H401, H412
P210, P261, P273, P301+P310, P311
NFPA 704 (fire diamond)
2
3
0
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.
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).
checkY  (what is checkY☒N ?)
Infobox references

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.[5]

Acyl cyanide synthesis.png

References[]

  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 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]
  5. ^ [2]

Further reading[]

Retrieved from ""