Diacetylene

Diacetylene
Names


IUPAC name Buta-1,3-diyne
Other names 1,3-Butadiyne; Biacetylene; Butadiyne
Identifiers
CAS Number	460-12-8^Y
ChEBI	CHEBI:37820^Y
ChemSpider	9603^Y
Jmol interactive 3D	Image
PubChem	9997
InChI InChI=1S/C4H2/c1-3-4-2/h1-2H^Y Key: LLCSWKVOHICRDD-UHFFFAOYSA-N^Y InChI=1/C4H2/c1-3-4-2/h1-2H Key: LLCSWKVOHICRDD-UHFFFAOYAU
SMILES C#CC#C
Properties
Chemical formula	C₄H₂
Molar mass	50.06 g·mol⁻¹
Appearance	Gas
Melting point	−10 °C (14 °F; 263 K)
Boiling point	10 °C (50 °F; 283 K)
Hazards
Main hazards	Highly flammable
Safety data sheet	External MSDS
R-phrases	R11 R19
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is ^YN ?)
Infobox references

Diacetylene (also known as butadiyne), with the formula C₄H₂, is a highly unsaturated hydrocarbon that contains three single bonds and two triple bonds. It is the first in the series of polyynes. The trivial name "diacetylene" refers to the two C-C triple bonds and the possible formation from acetylene (see below). It does not mean that diacetylene is the formal dimer of acetylene, what is rather true for butenyne or cyclobutadiene.

Occurrence

Diacetylene has been identified in the atmosphere of Titan and in the protoplanetary nebula CRL 618 by its characteristic vibrational modes. The molecule is most likely to have formed in Titan's atmosphere 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 found on the Moon.^[1]

Preparation

This compound may be made by the dehydrohalogenation of 1,4-dichloro-2-butyne by potassium hydroxide at low temperature:^[2]

ClCH₂C≡CCH₂Cl → HC≡C-C≡CH

The bis(trimethylsilyl)-protected derivative may be prepared by the Hay coupling of (trimethylsilyl)acetylene:^[3]

2 TMS-C≡CH → TMS-C≡C-C≡C-TMS

References

↑ "The Multiplying Mystery of Moonwater", March 18, 2010. Retrieved on 2010-03-18.
↑ 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, and Andrew B. Holmes (1993). "1,4-Bis(trimethylsilyl)buta-1,3-diyne". Org. Synth. ; Coll. Vol. 8, p. 63

Diatomic	Aluminium monochloride Aluminium monofluoride Aluminium monoxide Argon hydride Carbon monophosphide Carbon monosulfide Carbon monoxide Carborundum Cyanogen radical Diatomic carbon Fluoromethylidynium Hydrogen chloride Hydrogen fluoride Hydrogen (molecular) Hydroxyl radical Iron(II) oxide Magnesium monohydride cation Methylidyne radical Nitric oxide Nitrogen (molecular) Nitrogen monohydride Nitrogen sulfide Oxygen (molecular) Phosphorus monoxide Phosphorus mononitride Potassium chloride Silicon carbide Silicon mononitride Silicon monoxide Silicon monosulfide Sodium chloride Sodium iodide Sulfur monohydride Sulfur monoxide Titanium oxide

Triatomic	Aluminium hydroxide Aluminium isocyanide Amino radical Carbon dioxide Carbonyl sulfide CCP radical Chloronium Diazenylium Dicarbon monoxide Disilicon carbide Ethynyl radical Formyl radical Hydrogen cyanide Hydrogen isocyanide (HCN) Hydrogen isocyanide (HNC) Hydrogen sulfide Hydroperoxyl Iron cyanide Isoformyl Magnesium cyanide Magnesium isocyanide Methylene radical N₂H⁺ Nitrous oxide Nitroxyl Ozone Phosphaethyne Potassium cyanide Protonated molecular hydrogen Sodium cyanide Sodium hydroxide Silicon carbonitride c-Silicon dicarbide Silicon naphthalocyanine Sulfur dioxide Thioformyl Thioxoethenylidene Titanium dioxide Tricarbon Water

Four atoms	Acetylene Ammonia Cyanic acid Cyanoethynyl Cyclopropynylidyne Formaldehyde Fulminic acid HCCN Hydrogen peroxide Hydromagnesium isocyanide Isocyanic acid Isothiocyanic acid Ketenyl Methylene amidogen Methyl radical Propynylidyne Protonated carbon dioxide Protonated hydrogen cyanide Silicon tricarbide Thioformaldehyde Tricarbon monoxide Tricarbon sulfide Thiocyanic acid

Five atoms	Ammonium Ion Butadiynyl Carbodiimide Cyanamide Cyanoacetylene Cyanoformaldehyde Cyanomethyl Cyclopropenylidene Formic acid Isocyanoacetylene Ketene Methane Methoxy radical Methylenimine Propadienylidene Protonated formaldehyde Protonated formaldehyde Silane Silicon-carbide cluster

Six atoms	Acetonitrile Cyanobutadiynyl radical E-Cyanomethanimine Cyclopropenone Diacetylene Ethylene Formamide HC₄N Ketenimine Methanethiol Methanol Methyl isocyanide Pentynylidyne Propynal Protonated cyanoacetylene

Seven atoms	Acetaldehyde Acrylonitrile Cyanodiacetylene Ethylene oxide Hexatriynyl radical Methylacetylene Methylamine Methyl isocyanate Vinyl alcohol

Eight atoms	Acetic acid Aminoacetonitrile Cyanoallene Ethanimine Glycolaldehyde Heptatrienyl radical Hexapentaenylidene Methylcyanoacetylene Methyl formate Propenal

Nine atoms	Acetamide Cyanohexatriyne Cyanotriacetylene Dimethyl ether Ethanol Methyldiacetylene Octatetraynyl radical Propene Propionitrile

Ten atoms or more	Acetone Benzene Buckminsterfullerene (C₆₀ fullerene) ("bucky-ball") C₇₀ fullerene Cyanodecapentayne Cyanopentaacetylene Cyanotetra-acetylene Ethylene glycol Ethyl formate Methyl acetate Methyl-cyano-diacetylene Methyltriacetylene Propanal n-Propyl cyanide Pyrimidine

Deuterated
molecules

Unconfirmed

Book:Chemistry
Category:Astrochemistry
Category:Molecules
Portal:Astrobiology
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Diacetylene

Occurrence

Preparation

See also

References

Further reading