Acetyl cyanide
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| Names | |
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Preferred IUPAC name
Acetyl cyanide
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Systematic IUPAC name
Ethanoyl cyanide
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| Other names
2-Oxopropanenitrile
Pyruvonitrile Propanenitrile 2-oxo- α-Oxopropionitrile Oxopropionitrile Oxypropionitrile Pyruvic acid nitrile 2-Oxopropionitrile 2-Oxopropiononitrile |
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| Identifiers | |
631-57-2 
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| 3D model (Jmol) | Interactive image |
| 1737633 | |
| ChemSpider |
62638
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| ECHA InfoCard | 100.010.146 |
| EC Number | 211-159-2 |
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| Properties | |
| C3H3NO | |
| Molar mass | 69.06 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 |
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Refractive index (nD)
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1.3764 |
| 40.86 Å2 | |
| Hazards | |
| Safety data sheet | External MSDS |
| GHS pictograms |
 
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| GHS signal word | Danger |
| H225 H301 H315 H331 H335 H401 H412 | |
| P210 P261 P273 P301+310 P311 | |
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EU classification (DSD)
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| R-phrases | R11, R23/25, R51/53, R37/38 |
| S-phrases | S45, S61, S36/37 |
| 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 | |
| Flash point | 14.44 °C (57.99 °F; 287.59 K) |
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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 | |
Acetyl cyanide is a chemical compound that contains both a nitrile and a carbonyl functional group. Therefore, the molecule falls into the cyanide group as well due to the presence of the carbon nitrogen triple bond. This molecule is part of the acyl cyanide family.
This compound is also known as pyruvonitrile or 2-oxopropionitrile.
Acetyl cyanide typically exists as a clear, colorless liquid.
The structure of acetyl cyanide was determined through the joint use of electron diffraction intensities and rotational constants. These values helped to determine that the average thermal bond distances are 1.116±0.011 Å, 1.167±0.010 Å, 1.208±0.009 Å, 1.477±0.008 Å and 1.518±0.009 Å. Additionally, the bond angles in the structure 124.6±0.7°, 114.2±0.9°, 179.2±2.2° and 109.2±0.7°. This places the single C-C bond at a larger bond distance than the bonds within the vinylacetylene, acrylonitrile and propynal molecules.
Acetyl cyanide is a highly flammable compound. Therefore, this compound should be kept away from sources of heat, flames, and sparks.
Acetyl cyanide's toxicological properties have not been thoroughly investigated. However, it is known that the molecule is toxic if inhaled and would cause a respiratory tract irritation. Also the chemical may cause skin irritation if absorbed through the skin. The compound's toxic affects would target the peripheral nervous system, central nervous system, and the blood stream.
While this chemical has not been confirmed to be a carcinogen, exposure to this chemical causes irritation to the respiratory system and skin. Additionally, acetyl cyanide is toxic by both inhalation and ingestion. Furthermore, this compound may be toxic to aquatic organisms, possibly causing long-term adverse effects in the aquatic environment.
Due to the flammable properties of this molecule, hazardous decomposition could occur within the molecule under extreme heat, forming chemicals such as carbon oxides and nitrogen oxide. Therefore heat, flame, and sparks should all be kept away from this molecule in order to prevent this decomposition from occurring.
Additionally, this molecule should not interact with strong acids and strong bases to ensure that hazardous reactions are prevented.
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:
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