| Revision as of 18:23, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 473879124 of page 4-Vinylcyclohexene for the Chem/Drugbox validation project (updated: 'KEGG'). |
Latest revision as of 19:31, 27 August 2024 edit 139.138.157.58 (talk) →ReferencesTag: Visual edit |
| Line 1: |
Line 1: |
|
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
|
|
{{chembox |
|
{{chembox |
|
| Verifiedfields = changed |
|
|Verifiedfields = changed |
|
| Watchedfields = changed |
|
|Watchedfields = changed |
|
| verifiedrevid = 401776856 |
|
|verifiedrevid = 477223538 |
|
| Name = 4-Vinylcyclohexene |
|
|Name = 4-Vinylcyclohexene |
|
| ImageFile_Ref = {{chemboximage|correct|??}} |
|
|ImageFile_Ref = {{chemboximage|correct|??}} |
|
| ImageFile = 4-Vinylcyclohexene.png |
|
|ImageFile = 4-Vinylcyclohexene.svg |
|
| ImageSize = 200px |
|
|ImageSize= 120px |
|
| ImageName = 4-Vinylcyclohexene |
|
|ImageName = 4-Vinylcyclohexene |
|
|
|PIN = 4-Ethenylcyclohex-1-ene |
|
| IUPACName = 4-Vinylcyclohexene |
|
|
| OtherNames = Butadiene dimer, 4-ethenylcyclohexene, 1-vinyl-3-cyclohexene; 4-vinyl-1-cyclohexene |
|
|OtherNames = {{bulletedlist|Butadiene dimer|4-Ethenylcyclohexene|1-Vinyl-3-cyclohexene|4-Vinyl-1-cyclohexene}} |
|
| Section1 = {{Chembox Identifiers |
|
|Section1={{Chembox Identifiers |
|
|
|CASNo = 100-40-3 |
|
| InChI = 1/C8H12/c1-2-8-6-4-3-5-7-8/h2-4,8H,1,5-7H2 |
|
|
|
|CASNo_Ref = {{cascite|correct|CAS}} |
|
| SMILES = C=CC1C\C=C/CC1 |
|
|
|
|ChEBI = 82377 |
|
| InChIKey = BBDKZWKEPDTENS-UHFFFAOYAZ |
|
|
| PubChem = 7499 |
|
|ChEMBL = 1330194 |
|
|
|InChI = 1/C8H12/c1-2-8-6-4-3-5-7-8/h2-4,8H,1,5-7H2 |
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
|
|
|SMILES = C=CC1C\C=C/CC1 |
|
| StdInChI = 1S/C8H12/c1-2-8-6-4-3-5-7-8/h2-4,8H,1,5-7H2 |
|
|
|
|InChIKey = BBDKZWKEPDTENS-UHFFFAOYAZ |
|
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
|
|
|PubChem = 7499 |
|
| StdInChIKey = BBDKZWKEPDTENS-UHFFFAOYSA-N |
|
|
|
|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| CASNo = 100-40-3 |
|
|
|
|StdInChI = 1S/C8H12/c1-2-8-6-4-3-5-7-8/h2-4,8H,1,5-7H2 |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
|
|
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
| RTECS = GW6650000 |
|
|
|
|StdInChIKey = BBDKZWKEPDTENS-UHFFFAOYSA-N |
|
| EINECS = |
|
|
|
|UNII_Ref = {{fdacite|changed|FDA}} |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
|
|
|UNII = 212JQJ15PS |
|
| ChemSpiderID = 7218 |
|
|
|
|RTECS = GW6650000 |
|
| KEGG_Ref = {{keggcite|changed|kegg}} |
|
|
|
|EINECS = 202-848-9 |
|
| KEGG = <!-- blanked - oldvalue: C19310 --> |
|
|
|
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
|
|ChemSpiderID = 7218 |
|
|
|KEGG_Ref = {{keggcite|correct|kegg}} |
|
|
|KEGG = C19310 |
|
}} |
|
}} |
|
| Section2 = {{Chembox Properties |
|
|Section2={{Chembox Properties |
|
|
|C=8|H=12 |
|
| Formula = C<sub>8</sub>H<sub>12</sub> |
|
|
|
|Appearance = Colorless liquid |
|
| MolarMass = 108.181 g/mol |
|
|
|
|Density = 0.8299 g/cm<sup>3</sup> at 20°C |
|
| Appearance = colorless liquid |
|
|
|
|Solubility = 0.05 g/L<ref name="hand"> |
|
| Density = 0.8299 g/cm<sup>3</sup> at 20°C |
|
|
| Solubility = 0.05 g/L<ref name="hand"> |
|
|
{{Cite book |
|
{{Cite book |
|
| last = Lide |
|
|last = Lide |
|
| first = David R. |
|
|first = David R. |
|
|
|year = 1998 |
|
| author-link = |
|
|
|
|title = Handbook of Chemistry and Physics |
|
| last2 = |
|
|
| first2 = |
|
|edition = 87 |
|
|
|location = Boca Raton, Florida |
|
| author2-link = |
|
|
|
|publisher = CRC Press |
|
| publication-date = |
|
|
|
|isbn = 0-8493-0594-2 |
|
| date = |
|
|
| year = 1998 |
|
|pages = 8–111 |
|
| title = Handbook of Chemistry and Physics |
|
|
| edition = 87 |
|
|
| volume = |
|
|
| series = |
|
|
| publication-place = Boca Raton, FL |
|
|
| place = |
|
|
| publisher = CRC Press |
|
|
| id = |
|
|
| isbn = 0-8493-0594-2 |
|
|
| doi = |
|
|
| oclc = |
|
|
| pages = 8–111 |
|
|
| url = |
|
|
| accessdate = |
|
|
}}</ref> |
|
}}</ref> |
|
| SolubleOther = soluble in ], ], ] |
|
|SolubleOther = soluble in ], ], ] |
|
| MeltingPt = -108.9°C |
|
|MeltingPtC = -108.9 |
|
| BoilingPt = 128.9°C |
|
|BoilingPtC = 128.9 |
|
| VaporPressure = 2 ] at 25°C |
|
|VaporPressure = 2 ] |
|
|
|RefractIndex = 1.4639 (20 °C) |
|
}} |
|
|
| Section3 = {{Chembox Structure |
|
|
| Coordination = |
|
|
| CrystalStruct = |
|
|
}} |
|
|
| Section7 = {{Chembox Hazards |
|
|
| ExternalMSDS = |
|
|
| EUIndex = Harmful ('''Xn''') |
|
|
| NFPA-H = |
|
|
| NFPA-F = |
|
|
| NFPA-R = |
|
|
| RPhrases = {{R20}} {{R22}} |
|
|
| SPhrases = |
|
|
| FlashPt = 21.2°C<ref name="iarc"> |
|
|
{{cite web |url= http://monographs.iarc.fr/ENG/Monographs/vol60/mono60-13.pdf |title= 4-Vinylcyclohexene |accessdate=2009-04-19 |publisher= IARC|date= }}</ref> |
|
|
| Autoignition = |
|
|
| LD50 = 2563 mg/kg (oral, rat)<ref name="ox"> |
|
|
{{cite web |url= http://msds.chem.ox.ac.uk/VI/4-vinylcyclohexene.html |title= Safety (MSDS) data for 4-vinylcyclohexene |accessdate=2009-04-19 |publisher= Oxford University|date= }}</ref> |
|
|
}} |
|
|
| Section8 = {{Chembox Related |
|
|
| OtherCpds = ]<br/>] |
|
|
}} |
|
|
}} |
|
}} |
|
|
|Section7={{Chembox Hazards |
|
|
|ExternalSDS = |
|
|
|NFPA-H = 0 |
|
|
|NFPA-F =3 |
|
|
|GHSPictograms = {{GHS08}} |
|
|
|GHSSignalWord = Warning |
|
|
|HPhrases = {{H-phrases|351}} |
|
|
|PPhrases = {{P-phrases|201|202|281|308+313|405|501}} |
|
|
|FlashPtC = 21.2 |
|
|
|FlashPt_ref = <ref name="iarc"> |
|
|
{{cite web |url= http://monographs.iarc.fr/ENG/Monographs/vol60/mono60-13.pdf |title= 4-Vinylcyclohexene |access-date=2009-04-19 |publisher= IARC}}</ref> |
|
|
|AutoignitionPtC = 269 |
|
|
|LD50 = 2563 mg/kg (oral, rat)<ref name="ox">{{cite web |url= http://msds.chem.ox.ac.uk/VI/4-vinylcyclohexene.html |title= Safety (MSDS) data for 4-vinylcyclohexene |access-date= 2009-04-19 |publisher= Oxford University |archive-date= 2010-12-31 |archive-url= https://web.archive.org/web/20101231195814/http://msds.chem.ox.ac.uk/VI/4-vinylcyclohexene.html |url-status= dead }}</ref> |
|
|
}} |
|
|
|Section8={{Chembox Related |
|
|
|OtherCompounds = ]<br/>] |
|
|
}} |
|
|
}} |
|
|
|
|
|
'''4-Vinylcyclohexene''' is an ] consisting of a vinyl group attached to the 4-position of the cyclohexene ring. It is a colorless liquid. Although chiral, it is used mainly as the ]. It is a precursor to ].<ref name="thomas">{{Ullmann | first1 = Thomas | last1 = Schiffer | first2 = Georg | last2 = Oenbrink | title = Cyclododecatriene, Cyclooctadiene, and 4-Vinylcyclohexene | doi = 10.1002/14356007.a08_205.pub2}}</ref> |
|
|
|
|
|
==Production== |
|
|
It is produced by ] ] in a ].<ref name="ioc"> |
|
|
{{Cite book |
|
|
| last1 = Wittcoff |
|
|
| first1 = Harold |
|
|
| last2 = Reuben |
|
|
| first2 = B. G. |
|
|
| last3 = Plotkin |
|
|
| first3 = Jeffrey S. |
|
|
| year = 1998 |
|
|
| title = Industrial Organic Chemicals |
|
|
| edition = 2 |
|
|
| publisher = Wiley-Interscience |
|
|
| isbn = 978-0-471-44385-8 |
|
|
| pages = 236–7 |
|
|
| url = https://books.google.com/books?id=4KHzc-nYPNsC&dq=4-vinylcyclohexene+diels-alder&pg=PA236 |
|
|
| access-date = 2009-04-19 |
|
|
}}</ref><ref name="thomas"/> The reaction is conducted at 110 - 425 °C at pressures of 1.3 - 100 MPa in the presence of a ]. A mixture of ] and salts of ] or ] comprises the catalyst. A competing product is ]. |
|
|
|
|
|
:] |
|
|
In North America this is produced by Nippon Chemical Texas Inc. in Pasadena, TX. |
|
|
|
|
|
==Safety== |
|
|
4-Vinylcyclohexene is classified as a ] ("possibly carcinogenic to humans").<ref name="iarc"/> |
|
|
|
|
|
==References== |
|
|
{{reflist}}6. https://nctius.com/op-coproduct-streams/<nowiki/>{{DEFAULTSORT:Vinylcyclohexene, 4-}} |
|
|
] |
|
|
] |
|
|
] |