Diacetylene
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| Names | |
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| Preferred IUPAC name
Buta-1,3-diyne | |
| Other names
1,3-Butadiyne
Biacetylene Butadiyne | |
| Identifiers | |
3D model (JSmol)
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| 1236317 | |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.006.641 |
| EC Number |
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PubChemCID
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| UNII | |
CompTox Dashboard(EPA)
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| Properties | |
| C4H2 | |
| Molar mass | 50.060g·mol−1 |
| Appearance | Gas |
| Boiling point | 10 °C (50 °F; 283 K) |
| Hazards | |
| Occupational safety and health(OHS/OSH): | |
Main hazards
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Highly flammable; Peroxide forming |
| GHSlabelling: | |
 
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| Danger | |
| Safety data sheet(SDS) | External MSDS |
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).
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Diacetylene(also known asbutadiyne) is theorganic compoundwith the formula C4H2.It is the simplest compound containing twotriple bonds.It is first in the series ofpolyynes,which are of theoretical but not of practical interest.
Occurrence
[edit]Diacetylene has been identified in the atmosphere ofTitanand in theprotoplanetary nebulaCRL 618by its characteristicvibrational spectrum.It is proposed to arise by a reaction betweenacetyleneand theethynyl radical(C2H), which is produced when acetylene undergoesphotolysis.This radical can in turn attack the triple bond in acetylene and react efficiently even at low temperatures. Diacetylene has also been detected on theMoon.
Preparation
[edit]This compound may be made by thedehydrohalogenationof 1,4-dichloro-2-butyne bypotassium hydroxide(in alcoholic medium) at ~70°C:[1]
The bis(trimethylsilyl)-protected derivative may be prepared by theHay couplingof (trimethylsilyl)acetylene:[2]
See also
[edit]References
[edit]- ^Verkruijsse, H. D.; Brandsma, L. (1991). "A Detailed Procedure for the Preparation of Butadiyne".Synthetic Communications.21(5): 657.doi:10.1080/00397919108020833.
- ^Graham E. Jones; David A. Kendrick; Andrew B. Holmes (1987). "1,4-Bis(trimethylsilyl)buta-1,3-diyne".Organic Syntheses.65:52.doi:10.15227/orgsyn.065.0052.
Further reading
[edit]- Maretina, Irina A; Trofimov, Boris A (2000). "Diacetylene: a candidate for industrially important reactions".Russian Chemical Reviews.69(7): 591.doi:10.1070/RC2000v069n07ABEH000564.S2CID250889660.
