Diacetylene

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Diacetylene
Diacetylene.svg
Diacetylene-3D-vdW-B.png
Names
Preferred IUPAC name
Buta-1,3-diyne
Other names
1,3-Butadiyne
Biacetylene
Butadiyne
Identifiers
3D model (JSmol)
1236317
ChEBI
ChemSpider
ECHA InfoCard 100.006.641 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-303-9
PubChem CID
UNII
  • InChI=1S/C4H2/c1-3-4-2/h1-2H Yes check.svgY
    Key: LLCSWKVOHICRDD-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C4H2/c1-3-4-2/h1-2H
    Key: LLCSWKVOHICRDD-UHFFFAOYAU
  • C#CC#C
Properties
C4H2
Molar mass 50.060 g·mol−1
AppearanceGas
Boiling point 10 °C (50 °F; 283 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Highly flammable; Peroxide forming
GHS labelling:
GHS-pictogram-explos.svg GHS-pictogram-flamme.svg
Danger
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Diacetylene (also known as butadiyne) is the organic compound with the formula C4H2. It is the simplest compound containing two triple bonds. It is first in the series of polyynes, which are of theoretical but not of practical interest.

Contents

Occurrence

Diacetylene has been identified in the atmosphere of Titan and in the protoplanetary nebula CRL 618 by its characteristic vibrational spectrum. It is proposed to arise by a reaction between acetylene and the ethynyl radical (C2H), which is produced when acetylene undergoes photolysis. This radical can in turn attack the triple bond in acetylene and react efficiently even at low temperatures. Diacetylene has also been detected on the Moon.

Preparation

This compound may be made by the dehydrohalogenation of 1,4-dichloro-2-butyne by potassium hydroxide (in alcoholic medium) at ~70°C: [1]

The bis(trimethylsilyl)-protected derivative may be prepared by the Hay coupling of (trimethylsilyl)acetylene: [2]

See also

Related Research Articles

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<span class="mw-page-title-main">Allyl group</span> Chemical group (–CH₂–CH=CH₂)

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<span class="mw-page-title-main">18-Crown-6</span> Chemical compound

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<span class="mw-page-title-main">Trimethylsilyl chloride</span> Organosilicon compound with the formula (CH3)3SiCl

Trimethylsilyl chloride, also known as chlorotrimethylsilane is an organosilicon compound, with the formula (CH3)3SiCl, often abbreviated Me3SiCl or TMSCl. It is a colourless volatile liquid that is stable in the absence of water. It is widely used in organic chemistry.

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<span class="mw-page-title-main">Trimethylsilylacetylene</span> Chemical compound

Trimethylsilylacetylene is the organosilicon compound with the formula (CH3)3SiC2H. A colorless liquid, "tms acetylene", as it is also called, is used as a source of "HC2" in organic synthesis.

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<i>tert</i>-Butylphosphaacetylene Chemical compound

tert-Butylphosphaacetylene is an organophosphorus compound. Abbreviated t-BuCP, it was the first example of an isolable phosphaalkyne. Prior to its synthesis, the double bond rule had suggested that elements of Period 3 and higher were unable to form double or triple bonds with lighter main group elements because of weak orbital overlap. The synthesis of t-BuCP discredited much of the double bond rule and opened new studies into the formation of unsaturated phosphorus compounds.

<span class="mw-page-title-main">Bis(trimethylsilyl)acetylene</span> Chemical compound

Bis(trimethylsilyl)acetylene (BTMSA) is an organosilicon compound with the formula Me3SiC≡CSiMe3 (Me = methyl). It is a colorless liquid that is soluble in organic solvents. This compound is used as a surrogate for acetylene.

<span class="mw-page-title-main">Metal bis(trimethylsilyl)amides</span>

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<span class="mw-page-title-main">Tris(trimethylsilyl)amine</span> Chemical compound

Tris(trimethylsilyl)amine is the simplest tris(trialkylsilyl)amine which are having the general formula (R3Si)3N, in which all three hydrogen atoms of the ammonia are replaced by trimethylsilyl groups (-Si(CH3)3). Tris(trimethylsilyl)amine has been for years in the center of scientific interest as a stable intermediate in chemical nitrogen fixation (i. e. the conversion of atmospheric nitrogen N2 into organic substrates under normal conditions).

<span class="mw-page-title-main">Tris(trimethylsilyl)phosphine</span> Chemical compound

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<span class="mw-page-title-main">Tris(trimethylsilyl)silane</span> Chemical compound

Tris(trimethylsilyl)silane is the organosilicon compound with the formula (Me3Si)3SiH (where Me = CH3). It is a colorless liquid that is classified as a hydrosilane since it contains an Si-H bond. The compound is notable as having a weak Si-H bond, with a bond dissociation energy estimated at 84 kcal/mol. For comparison, the Si-H bond in trimethylsilane is 94 kcal/mol. With such a weak bond, the compound is used as a reagent to deliver hydrogen atoms. The compound has been described as an environmentally benign analogue of tributyltin hydride.

Niobium(III) chloride also known as niobium trichloride is a compound of niobium and chlorine. The binary phase NbCl3 is not well characterized but many adducts are known.

References

  1. Verkruijsse, H. D.; Brandsma, L. (1991). "A Detailed Procedure for the Preparation of Butadiyne". Synthetic Communications. 21 (5): 657. doi:10.1080/00397919108020833.
  2. 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