| Revision as of 18:10, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 399319526 of page 4-Chlorophthalic_anhydride for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 13:33, 22 November 2024 edit Marbletan (talk | contribs)Extended confirmed users5,256 editsm →Production |
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{{chembox |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Chembox |
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| Watchedfields = changed |
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| verifiedrevid = 399318274 |
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| verifiedrevid = 477221399 |
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| ImageFile = 4-Chlorophthalic anhydride.png |
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| ImageFile1 = 4-Cyano-4'-pentylbiphenyl.svg |
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| ImageSize = 120px |
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| ImageSize1 = 260px |
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| IUPACName = 5-Chloro-2-benzofuran-1,3-dione |
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| ImageAlt1 = Skeletal formula of 4-cyano-4'-pentylbiphenyl |
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| OtherNames = |
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| ImageFile2 = 5CB-from-xtal-3D-bs-17.png |
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| Section1 = {{Chembox Identifiers |
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| ImageSize2 = 210 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ImageAlt2 = Space-filling model of the 4-cyano-4'-pentylbiphenyl molecule |
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| ChemSpiderID = 60395 |
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| PIN = 4′-Pentyl-4-carbonitrile |
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| InChI = 1/C8H3ClO3/c9-4-1-2-5-6(3-4)8(11)12-7(5)10/h1-3H |
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| OtherNames = 4'-Amyl-4-biphenylcarbonitrile, 4'-Pentyl-4-biphenylcarbonitrile, 4-Amyl-4'-cyanobiphenyl |
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| InChIKey = BTTRMCQEPDPCPA-UHFFFAOYAB |
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|Section1={{Chembox Identifiers |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| SMILES = N#Cc1ccc(cc1)c2ccc(cc2)CCCCC |
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| StdInChI = 1S/C8H3ClO3/c9-4-1-2-5-6(3-4)8(11)12-7(5)10/h1-3H |
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| InChIKey = HHPCNRKYVYWYAU-UHFFFAOYAV |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = BTTRMCQEPDPCPA-UHFFFAOYSA-N |
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| StdInChI = 1S/C18H19N/c1-2-3-4-5-15-6-10-17(11-7-15)18-12-8-16(14-19)9-13-18/h6-13H,2-5H2,1H3 |
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| CASNo = <!-- blanked - oldvalue: 118-45-6 --> |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| PubChem = |
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| StdInChIKey = HHPCNRKYVYWYAU-UHFFFAOYSA-N |
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| SMILES = Clc1ccc2C(=O)OC(=O)c2c1 |
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| CASNo = 40817-08-1 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 2R6RYG3ZGM |
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| PubChem = 92319 |
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| EC_number = 255-093-2 |
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| CASNo_Ref = {{cascite|changed|CAS}} |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 83347 |
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| InChI = 1/C18H19N/c1-2-3-4-5-15-6-10-17(11-7-15)18-12-8-16(14-19)9-13-18/h6-13H,2-5H2,1H3 |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=8|H=3|Cl=1|O=3 |
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| C=18 | H=19 | N=1 |
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| Appearance = |
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| Appearance = Colorless if isotropic or cloudy white if nematic |
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| Density = |
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| Density = 1.022 g/cm<sup>3</sup><ref name="Zannoni"/> |
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| MeltingPtC = 22.5<ref name="Zannoni"/> |
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| MeltingPt = ~99 °C |
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| RefractIndex = n<sub>//</sub> = 1.71, n<sub>⟂</sub> = 1.53<ref name="Zannoni"/> |
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| BoilingPt = |
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| Viscosity = 28 mPa·s<ref name="Zannoni"/> |
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| Solubility = }} |
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| Section3 = {{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| Autoignition = }} |
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|Section7={{Chembox Hazards |
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| ExternalSDS = |
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| NFPA-H = 2 |
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| NFPA-F = 1 |
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| NFPA-R = 0 |
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| NFPA-S = |
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| GHSPictograms = {{GHS07}} |
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| GHSSignalWord = Warning |
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| HPhrases = {{H-phrases|302|312|315|319|332|335}} |
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| PPhrases = {{P-phrases|261|264|270|271|280|301+312|302+352|304+312|304+340|305+351+338|312|321|322|330|332+313|337+313|362|363|403+233|405|501}} |
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}} |
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}} |
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'''4-Cyano-4'-pentylbiphenyl''' is a commonly used nematic ] with the chemical formula C<sub>18</sub>H<sub>19</sub>N. It frequently goes by the common name 5CB. 5CB was first synthesized by ], Ken Harrison, and J.A. Nash at the ] in 1972 and at the time it was the first member of the cyanobiphenyls.<ref name=gray/><ref name=Collings/> The liquid crystal was discovered after Gray's group received a grant from the ] to find a liquid crystal that had liquid crystal phases near room temperature with the specific intention of using them in liquid crystal displays. The molecule is about 20 ] long. The liquid crystal 5CB undergoes a phase transition from a crystalline state to a nematic state at 22.5 °C and it goes from a nematic to an isotropic state at 35.0 °C.<ref name="Zannoni"/> |
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==Production== |
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5CB is produced by modifying biphenyl in a linear manner. First Br<sub>2</sub> is added to the biphenyl to introduce a bromine atom to the end of the moiety. Next ] and C<sub>4</sub>H<sub>9</sub>COCl is added to the sample, followed by the addition of ] and NH<sub>2</sub>NH<sub>2</sub>. By this point the molecule will have a bromine atom on one end of the rigid core and C<sub>5</sub>H<sub>11</sub> on the other end. Finally, introduction of ] and ] results in the removal of the bromine and its replacement with CN, yielding 5CB.<ref name=Collings/> |
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:] |
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== References == |
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{{reflist|refs= |
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<ref name=Collings>{{cite book | last1= Collings | first1= Peter J. | editor1-first= George William | editor1-last= Gray | editor1-link= George William Gray | editor2-first= J. W. | editor2-last= Goodby | editor3-first= A. | editor3-last= Fukuda | last2= Hird | first2= Michael | year= 1997 | title= Introduction to Liquid Crystals: Chemistry and Physics | publisher= Taylor and Francis Ltd. | isbn= 0-7484-0643-3 | url-access= registration | url= https://archive.org/details/introductiontoli0000coll|pages=53, 151–152 }}</ref> |
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<ref name=gray>{{cite journal | last1=Gray | first1=George William | author-link1= George William Gray | last2=Harrison | first2=Ken J. | last3=Nash | first3=J A. | journal=Electronics Letters | volume=9 | number=6 | pages=130–131 | title= New family of nematic liquid crystals for displays | year=1973 | doi=10.1049/el:19730096| bibcode=1973ElL.....9..130G }}</ref> |
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<ref name="Zannoni">{{cite book | last=Zannoni | first=Claudio | title=Liquid crystals and their computer simulations |publisher=Cambridge University Press| publication-place=Cambridge, United Kingdom | date=2022 | isbn=978-1-108-53963-0 | page=15}}</ref> |
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}} |
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== Further reading == |
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*{{cite journal | last1=Gray | first1=George William | author-link1= George William Gray | journal=Liquid Crystals | volume=24 | issue=1 |date=January 1998 | pages=5–14 | title= Reminiscences from a life with liquid crystals | doi=10.1080/026782998207523 }} |
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*{{cite journal | last1=Seo | first1=D. S. | last2=Matsuda | first2=H. | last3=Oh-Ide | first3=T. | last4=Kobayashi | first4= S. | journal=Molecular Crystals and Liquid Crystals | volume=224 | issue=1 | pages=13–31 | title= ''Alignment of Nematic Liquid Crystal(5CB) on the Treated Substrates: Characterization of Orientation Films, Generation of Pretilt Angles, and Surface Anchoring Strength'' | year=1993 | doi=10.1080/10587259308032475 }} |
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*{{cite journal | last1=Vill | first1=Volkmar | journal=Liquid Crystals | volume=24 | issue=1 |date=January 1998 | pages=21–24 | title= Grey levels in the history of liquid crystals | doi=10.1080/026782998207541 }} |
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== External links == |
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* |
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* {{cite web |url=http://mraths.org.uk/?page_id=576 |title=Liquid Crystal Displays (1973-1982) |publisher=Malvern Radar and Technology History Society |year=2016}} |
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{{DEFAULTSORT:Cyano-4'-Pentylbiphenyl, 4-}} |
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] |
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