Allyl cyanide
 |
|
 |
|
| Names | |
|---|---|
|
Systematic IUPAC name
3-Butenenitrile
|
|
| Identifiers | |
|
3D model (Jmol)
|
|
| 605352 | |
| ChemSpider | |
| ECHA InfoCard | 100.003.366 |
| EC Number | 203-701-1 |
|
PubChem CID
|
|
|
|
|
|
| Properties | |
| C4H5N | |
| Molar mass | 67.09 g·mol−1 |
| Appearance | colourless liquid |
| Density | 0.834 g/cm3 |
| Melting point | −87 °C (−125 °F; 186 K) |
| Boiling point | 116 to 121 °C (241 to 250 °F; 389 to 394 K) |
| Hazards | |
| Main hazards | Flammable, poison, irritates skin and eyes |
| Safety data sheet | MSDS |
| GHS pictograms |
 
|
| GHS signal word | Danger |
| H226 H301 H315 H312 H319 H311 | |
| P280 P261 P305+351+338 P301+310 P311 | |
|
EU classification (DSD)
|
|
| R-phrases | R10, R21, R23/25, R36/38, |
| S-phrases | S26, S45, S36/37/39 |
| Ingestion hazard | Toxic if swallowed. |
| Inhalation hazard | May be fatal if inhaled. Causes respiratory tract irritation. |
| Eye hazard | Causes eye irritation. |
| Skin hazard | Causes skin irritation. |
| NFPA 704 | |
| Flash point | 24 °C (75 °F; 297 K) |
| 455 °C (851 °F; 728 K) | |
| Related compounds | |
|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
|
| Infobox references | |
Allyl cyanide is an organic compound with the formula CH2CHCH2CN. Like other small alkyl nitriles, allyl cyanide is soluble in organic solvents. Allyl cyanide occurs naturally as an antifeedant and is used as a cross-linking agent in some polymers. Allyl cyanide was discovered in 1863 by H. Will and W. Koerner in 1863, they found the compound to be present in mustard oil. The first successful synthesis of allyl cyanide was done by A. Claus in 1864. Recent studies show that allyl cyanide may be used as an additive in propylene carbonate-based electrolytes for graphite anodes preventing exfoliation of the anode by film-forming. The underlying mechanism is thought to be a reductive polymerization mechanism.
Allyl cyanide can be prepared by treating allyl bromide with copper(I) cyanide under rigorous heating. This reaction follows a classical SN2 reaction, where the cyanide anion of the copper(I) complex acts as a nucleophile to replace the bromide from the allyl bromide.
Other allyl halides may be used for this reaction including allyl iodide as done by A. Rinne and B. Tollens in 1871 where iodide is a better leaving group than its bromide equivalent and therefore increases the yield.
Another way to gain allyl cyanide is to use rat intestinal microbiota. By adding sinigrin to rat intestinal microbiota and subsequent incubation under anaerobe conditions, this will lead to desulfosinigrin. Further incubation yields allyl cyanide as the major degradation product. More degradation products are isothiocyanate and 1-cyano-2,3-epithiopropane. The exact working principle is not yet understood, but it is suggested that intestinal microbiota may utilize thioglucosidase for this reaction.
Allyl cyanide is produced in cruciferous vegetables by myrosinase, an enzyme which hydrolyses glucosinolates to form nitriles and other products. Myrosinase is activated by l-ascorbic acid (vitamin C) under the influence of the pH, and higher myrosinase activity has been shown in damaged cabbage leaves, while its activity is reduced by cooking the leaves, although the glucosinolates can then be transformed to allyl cyanide by microflora in the intestines. As cruciferous vegetables like cabbage, broccoli, cauliflower and sprouts are part of the human diet, allyl cyanide is normally consumed orally. The normal dose of allyl cyanide contained in a meal is shown to be much lower than the doses used in animal studies. The daily level at which behavioural effects were demonstrated is 500 μg/kg bodyweight, whereas the daily human consumption amounts to 0.12 μg/kg. Although the dose-response relationship is still to be examined, it is therefore thought that allyl cyanide has no potency as a neurotoxicant when consumed in vegetables.
...
Wikipedia