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Revision as of 04:40, 7 September 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (changes to watched fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report errors or [[user talk← Previous edit Latest revision as of 16:18, 9 February 2024 edit undoTrasheater Midir (talk | contribs)Extended confirmed users3,423 edits →Preparation: Paragraph edited #MiniEdit 
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{{Short description|Organic compound (HCCCCH)}}
{{Chembox {{Chembox
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 443634762 | verifiedrevid = 448883521
| ImageFile = Diacetylene.svg | ImageFile = Diacetylene.svg
| ImageName = Structural formula | ImageName = Structural formula
| ImageFile1 = Diacetylene-3D-vdW-B.png | ImageFile1 = Diacetylene-3D-vdW-B.png
| ImageName1 = Space-filling model | ImageName1 = Space-filling model
| PIN = Buta-1,3-diyne
| IUPACName =
| OtherNames = 1,3-butadiyne, buta-1,3-diyne, biacetylene, butadiyne | OtherNames = 1,3-Butadiyne<br />Biacetylene<br />Butadiyne
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 9603 | ChemSpiderID = 9603
| InChI = 1/C4H2/c1-3-4-2/h1-2H | InChI = 1/C4H2/c1-3-4-2/h1-2H
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| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 460-12-8 | CASNo = 460-12-8
| PubChem = 9997 | EC_number = 207-303-9
| Beilstein = 1236317
⚫ | ChEBI_Ref = {{ebicite|correct|EBI}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 6389J044O5
| PubChem = 9997
⚫ | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 37820 | ChEBI = 37820
| SMILES = C#CC#C | SMILES = C#CC#C
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C = 4 | H = 2 | C=4 | H=2
| Appearance = Gas | Appearance = Gas
| Density = | Density =
| MeltingPtC = -10 | MeltingPtC =
| BoilingPtC = 10 | BoilingPtC = 10
| Solubility = | Solubility =
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| ExternalMSDS = | ExternalSDS =
| MainHazards = Highly flammable | MainHazards = Highly flammable; Peroxide forming
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
| RPhrases = {{R11}} {{R19}} | GHSPictograms = {{GHS01}}{{GHS02}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|}}
| PPhrases = {{P-phrases|}}
}} }}
}} }}


'''Diacetylene''' (also known as '''butadiyne'''), with the formula C<sub>4</sub>H<sub>2</sub>, is a highly ] ] that contains three ]s and two ]s. It is the first in the series of ]s. '''Diacetylene''' (also known as '''butadiyne''') is the ] with the formula C<sub>4</sub>H<sub>2</sub>. It is the simplest compound containing two ]s. It is first in the series of ]s, which are of theoretical but not of practical interest.


==Occurrence== ==Occurrence==
Diacetylene has been identified in the atmosphere of ] and in the ] ] by its characteristic vibrational modes. The molecule is most likely to have formed in Titan's atmosphere by a reaction between ] and the ] C<sub>2</sub>H, which is produced when acetylene undergoes ]. This radical can in turn attack the triple bond in acetylene and react efficiently even at cold temperatures. Diacetylene has also been found on the ].<ref>, March 18, 2010. Retrieved on 2010-03-18.</ref> Diacetylene has been identified in the atmosphere of ] and in the ] ] by its characteristic ]. It is proposed to arise by a reaction between ] and the ] (C<sub>2</sub>H), which is produced when acetylene undergoes ]. 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 ].


==Preparation== ==Preparation==
This compound may be made by the dehydrohalogenation of 1,4-dichloro-2-butyne by potassium hydroxide at low temperature:<ref>{{cite journal | last1 = Verkruijsse | first1 = H. D. | last2 = Brandsma | first2 = L. | title = A Detailed procedure for the preparation of Butadiyne | journal = Synthetic Communications | volume = 21 | pages = 657 | year = 1991 | doi = 10.1080/00397919108020833}}</ref> This compound may be made by the ] of 1,4-dichloro-2-butyne by ] (in alcoholic medium) at ~70°C:<ref>{{cite journal | last1 = Verkruijsse | first1 = H. D. | last2 = Brandsma | first2 = L. | title = A Detailed Procedure for the Preparation of Butadiyne | journal = Synthetic Communications | volume = 21 | page = 657 | year = 1991 | doi = 10.1080/00397919108020833 | issue = 5}}</ref>
: <chem>ClCH2C#CCH2Cl + 2 KOH -> HC#C-C#CH + 2 KCl + 2 H2O</chem>
: ClCH<sub>2</sub>C&equiv;CCH<sub>2</sub>Cl &rarr; HC&equiv;C-C&equiv;CH


The bis(])-protected derivative may be prepared by the ] of (trimethylsilyl)acetylene:<ref>{{OrgSynth | title = 1,4-Bis(trimethylsilyl)buta-1,3-diyne | prep = cv8p0063 | collvol = 8 | collvolpages = 63 | year = 1993 | author = Graham E. Jones, David A. Kendrick, and Andrew B. Holmes}}</ref> The bis(])-protected derivative may be prepared by the ] of (trimethylsilyl)acetylene:<ref>{{cite journal |doi=10.15227/orgsyn.065.0052|title=1,4-Bis(trimethylsilyl)buta-1,3-diyne|journal=Organic Syntheses|year=1987|volume=65|page=52|author1=Graham E. Jones|author2= David A. Kendrick|author3=Andrew B. Holmes}}</ref>
:<chem>2 Me3Si-C#CH -> Me3Si-C#C-C#C-SiMe3</chem>

:2 (tms)C&equiv;CH &rarr; (tms)C&equiv;C-C&equiv;CH


==See also== ==See also==
* ] * ]
* ]
* ]
* ] * ]


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==Further reading== ==Further reading==
* {{cite journal | last1 =Maretina | first1 =Irina A | last2 =Trofimov | first2 =Boris A | title =Diacetylene: a candidate for industrially important reactions | journal =Russian Chemical Reviews | volume =69 | pages =591 | year =2000 | doi =10.1070/RC2000v069n07ABEH000564}} * {{cite journal | last1 =Maretina | first1 =Irina A | last2 =Trofimov | first2 =Boris A | title =Diacetylene: a candidate for industrially important reactions | journal =Russian Chemical Reviews | volume =69 | page =591 | year =2000 | doi =10.1070/RC2000v069n07ABEH000564 | issue =7| s2cid =250889660 }}
{{Molecules detected in outer space}}

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