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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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Latest revision as of 16:18, 9 February 2024

Organic compound (HCCCCH)
Diacetylene
Structural formula
Space-filling model
Names
Preferred IUPAC name Buta-1,3-diyne
Other names 1,3-Butadiyne
Biacetylene
Butadiyne
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 1236317
ChEBI
ChemSpider
ECHA InfoCard 100.006.641 Edit this at Wikidata
EC Number
  • 207-303-9
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H2/c1-3-4-2/h1-2HKey: LLCSWKVOHICRDD-UHFFFAOYSA-N
  • InChI=1/C4H2/c1-3-4-2/h1-2HKey: LLCSWKVOHICRDD-UHFFFAOYAU
SMILES
  • C#CC#C
Properties
Chemical formula C4H2
Molar mass 50.060 g·mol
Appearance Gas
Boiling point 10 °C (50 °F; 283 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards Highly flammable; Peroxide forming
GHS labelling:
Pictograms GHS01: ExplosiveGHS02: Flammable
Signal word Danger
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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.

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:

ClCH 2 C ≡ CCH 2 Cl + 2 KOH ⟶ HC ≡ C − C ≡ CH + 2 KCl + 2 H 2 O {\displaystyle {\ce {ClCH2C#CCH2Cl + 2 KOH -> HC#C-C#CH + 2 KCl + 2 H2O}}}

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

2 Me 3 Si − C ≡ CH ⟶ Me 3 Si − C ≡ C − C ≡ C − SiMe 3 {\displaystyle {\ce {2 Me3Si-C#CH -> Me3Si-C#C-C#C-SiMe3}}}

See also

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

Molecules detected in outer space
Molecules
Diatomic







Triatomic
Four
atoms
Five
atoms
Six
atoms
Seven
atoms
Eight
atoms
Nine
atoms
Ten
atoms
or more
Deuterated
molecules
Unconfirmed
Related
Category: