Terphenyl: Difference between revisions

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{{chembox

| Verifiedfields = changed

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| Name =''para''-Terphenyl

| Watchedfields = changed

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| Reference =

| verifiedrevid = 392374283

| ImageFile = Para-terphenyl.png

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| Name =''para''-Terphenyl

| ImageSize = 200px

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| Reference =

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| ~~ImageName~~ = ~~Skeletal~~ ~~formula~~ of para-terphenyl

| ~~ImageFile1~~ = Para-terphenyl~~-3D-balls~~.png

| ImageFile = Para-terphenyl.png

| ~~ImageSize1~~ = ~~200px~~

| ImageSize =

| ~~ImageName1~~ = ~~Ball-and-stick~~ ~~model~~ of para-terphenyl

| ImageName = Skeletal formula of para-terphenyl

| ImageFile1 = Para-terphenyl-from-xtal-view-2-3D-bs-17.png

| IUPACName = 1,4-Diphenylbenzene

| ImageSize1 =

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| OtherNames=''p''-Terphenyl; 1,4-Diphenylbenzene; ''para''-Diphenylbenzene; ''p''-Diphenylbenzene; ''para''-Triphenyl; ''p''-Triphenyl

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| ImageName1 = Ball-and-stick model of para-terphenyl

| PIN = 11,21:24,31-Terphenyl<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | page = 345 | doi = 10.1039/9781849733069-00130 | isbn = 978-0-85404-182-4}}</ref>

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| OtherNames = 1,1':4',1<nowiki>''</nowiki>-Terphenyl<ref name=iupac2013/> ''p''-Terphenyl 1,4-Diphenylbenzene ''para''-Diphenylbenzene ''p''-Diphenylbenzene ''para''-Triphenyl ''p''-Triphenyl

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo=92-94-4

| CASNo = 92-94-4

| CASOther= (''para'') 92-06-8 (''meta'') 84-15-1 (''ortho'') 26140-60-3 (unspec.)

| CASNo_Comment = (''para'')

| PubChem=7115

| CASNo2_Ref = {{cascite|correct|CAS}}

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| SMILES=C1=CC=C(C=C1)C2=CC=C(C=C2)C3=CC=CC=C3

| CASNo2 = 92-06-8

| CASNo2_Comment = (''meta'')

| CASNo3_Ref = {{cascite|correct|CAS}}

| CASNo3 = 84-15-1

| CASNo3_Comment = (''ortho'')

| CASNo4_Ref = {{cascite|correct|CAS}}

| CASNo4 = 26140-60-3

| CASNo4_Comment = (unspecified)

| Beilstein = 1908447

| ChEMBL1 = 491582

| ChEBI1 = 52242

| PubChem =7115

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 6848

| ChemSpiderID_Comment = (''para'')

| EC_number1 = 202-205-2

| RTECS1 = WZ6475000

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = GWP218ZY6F

| UNII_Comment = (''para'')

| UNII2_Ref = {{fdacite|correct|FDA}}

| UNII2 = WOI2PSS0KX

| UNII2_Comment = (''meta'')

| UNII3_Ref = {{fdacite|correct|FDA}}

| UNII3 = W5675R7KVW

| UNII3_Comment = (''ortho'')

| UNII4_Ref = {{fdacite|correct|FDA}}

| UNII4 = LFX1C55D2Z

| UNII4_Comment = (unspecified)

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| SMILES =C1=CC=C(C=C1)C2=CC=C(C=C2)C3=CC=CC=C3

| SMILES2 = c1ccc(cc1)c2ccc(cc2)c3ccccc3

| SMILES2_Comment = (''para'')

| InChI = 1/C18H14/c1-3-7-15(8-4-1)17-11-13-18(14-12-17)16-9-5-2-6-10-16/h1-14H

| InChI_Comment = (''para'')

| InChIKey = XJKSTNDFUHDPQJ-UHFFFAOYAJ

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C18H14/c1-3-7-15(8-4-1)17-11-13-18(14-12-17)16-9-5-2-6-10-16/h1-14H

| StdInChI_Comment = (''para'')

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = XJKSTNDFUHDPQJ-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

| C=18|H=14

| C=18 | H=14

| ~~Appearance~~=White powder<ref name=chemicalland21~~>[http:~~/~~/chemicalland21.com/industrialchem/IUH/p-TERPHENYL.htm ''p''-Terphenyl] at chemicalland21.com</ref~~>

| Appearance =White powder<ref name=chemicalland21/>

| Density=

| Density = 1.24 g/cm3

| MeltingPtC = 212 to 214

| ~~MeltingPt~~=~~212-214~~ °C<ref name=chemicalland21/> 212-213 °C<ref name=Sigma>[http://www.sigmaaldrich.com/catalog/~~ProductDetail.do~~?lang=en&~~N4=257389|SIAL&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F~~=~~SPEC~~ ''p''-Terphenyl] at [[Sigma-Aldrich]]</ref>

| MeltingPt_ref = <ref name=chemicalland21/> 212-213 °C<ref name=Sigma>[http://www.sigmaaldrich.com/catalog/product/sial/257389?lang=en&region=US ''p''-Terphenyl] at [[Sigma-Aldrich]]</ref>

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| ~~BoilingPt~~=~~389~~ °C<ref name=Sigma/>

| BoilingPtC = 389

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| Solubility=Insoluble<ref name=chemicalland21/>

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| BoilingPt_ref = <ref name=Sigma/>

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| Solubility =Insoluble<ref name=chemicalland21/>

| RefractIndex = 1.65<ref name="Cryos Beta">{{cite web | url = http://www.cryos-beta.kharkov.ua/organic.php | title = Organic molecular single crystals | publisher = cryos-beta.kharkov.ua }}</ref>

}}

|Section3={{Chembox Hazards

| MainHazards =

| MainHazards=Iritant ('''Xi''')

| FlashPtC = 207

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| ~~FlashPt~~=~~207~~ °C<ref name=Sigma/>

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| FlashPt_ref = <ref name=Sigma/>

| Autoignition=

| AutoignitionPt =

| RPhrases = {{R36/37/38}} {{R50/53}}

| ~~SPhrases~~ = {{~~S26~~}} ~~{{S60}}~~ {{~~S61~~}}

| GHSPictograms = {{GHS07}}{{GHS09}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|315|319|335|400}}

| PPhrases = {{P-phrases|261|264|271|273|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|391|403+233|405|501}}

| NFPA-H = 2

| NFPA-F = 1

| NFPA-R = 0

| PEL = C 9 mg/m3 (1 ppm)<ref>{{PGCH|0591}}</ref><ref>{{PGCH|0592}}</ref><ref>{{PGCH|0593}}</ref>

}}

'''Terphenyls''' are a group of closely-related [[~~aromaticity|~~aromatic]] [[hydrocarbons]]. Also known as '''diphenylbenzenes''' or '''triphenyls''', they consist of a central [[benzene]] ring substituted with two [[phenyl group]]s. ~~The~~ three ~~isomers~~ ~~are~~ ''ortho''-terphenyl, ''meta''-terphenyl, and ''para''-terphenyl. Commercial grade terphenyl is generally a mixture of the three ~~isomers~~. This mixture is used in the production of [[polychlorinated terphenyl]]s, which were formerly used as heat storage and transfer agents.<ref name=chemicalland21/>

'''Terphenyls''' are a group of closely related [[aromatic hydrocarbons]]. Also known as '''diphenylbenzenes''' or '''triphenyls''', they consist of a central [[benzene]] ring substituted with two [[phenyl group]]s. There are three [[Arene substitution pattern|substitution pattern]]s: ''ortho''-terphenyl, [[Meta-terphenyl|''meta''-terphenyl]], and ''para''-terphenyl. Commercial grade terphenyl is generally a mixture of the three [[isomer]]s. This mixture is used in the production of [[polychlorinated terphenyl]]s, which were formerly used as heat storage and transfer agents.<ref name=chemicalland21>[http://chemicalland21.com/industrialchem/IUH/p-TERPHENYL.htm ''p''-Terphenyl] at chemicalland21.com</ref>

''p''-Terphenyl is the most common isomer. It is used as a laser dye and a sunscreen ingredient.<ref name=chemicalland21/>

''p''-Terphenyl derivatives are found in various fungi and bacteria. One example is [[atromentin]], a pigment found in some mushrooms. These natural ''p''-terphenyls are better described as diphenylquinones or diphenylhydroquinones. Some m-terphenyl compounds occur in plants.<ref>{{cite journal |doi=10.1021/cr050248c |title=Natural Terphenyls: Developments since 1877 |date=2006 |last1=Liu |first1=Ji-Kai |journal=Chemical Reviews |volume=106 |issue=6 |pages=2209–2223 |pmid=16771447 }}</ref>

File:ortho-terphenyl.png|''ortho''-Terphenyl

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==See also==

* [[~~Diphenyl~~]]

* [[Biphenyl]]

* [[Terpyridine]]

* [[Terthiophene]]

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==External links==

* [http://omlc.ogi.edu/spectra/PhotochemCAD/html/p-terphenyl.html p-Terphenyl] at the Oregon Laser Medical Center

* [https://www.cdc.gov/niosh/npg/npgd0591.html o-Terphenyl], [https://www.cdc.gov/niosh/npg/npgd0592.html m-Terphenyl], [https://www.cdc.gov/niosh/npg/npgd0593.html p-Terphenyl] at Centers for Disease Control and Prevention, National Institute for Occupational Safety and Health

[[Category:Aromatic ~~compounds~~]]

[[Category:Aromatic hydrocarbons]]

[[Category:~~Hydrocarbons~~]]

[[Category:Phenyl compounds]]

[[de:Terphenyle]]

[[nl:Terfenyl]]