| Revision as of 08:33, 4 March 2011 editحسن علي البط (talk | contribs)Extended confirmed users, Pending changes reviewers19,940 edits added Category:Phenols using HotCat← Previous edit |
Latest revision as of 18:46, 10 April 2024 edit undoMarbletan (talk | contribs)Extended confirmed users5,415 editsNo edit summary |
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{{Orphan|date=February 2009}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 399713814 |
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| Watchedfields = changed |
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| verifiedrevid = 417051183 |
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| ImageFile = Chlorophenol red.png |
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| ImageFile = Chlorophenol red.png |
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| ImageSize = 200px |
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| ImageSize = 200px |
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| ImageAlt = Skeletal formula of chlorophenol red in cyclic form |
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| IUPACName = 2-chloro-4-oxathiol-3-yl]phenol |
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| ImageFile1 = Chlorophenol red cyclic 3D ball.png |
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| OtherNames = |
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| ImageAlt1 = Ball-and-stick model of the chlorophenol red molecule in cyclic form |
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| Section1 = {{Chembox Identifiers |
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| PIN = 3,3-Bis(3-chloro-4-hydroxyphenyl)-2,1λ<sup>6</sup>-benzoxathiole-1,1(3''H'')-dione |
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| InChI = 1/C9H12N2O.C6H5ClO/c1-11(2)9(12)10-8-6-4-3-5-7-8;7-5-3-1-2-4-6(5)8/h3-7H,1-2H3,(H,10,12);1-4,8H |
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| OtherNames = 3′,3′-Dichlorophenolsulfonaphthalein |
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| InChIKey = NYKAIYWZWWMAME-UHFFFAOYAD |
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|Section1={{Chembox Identifiers |
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| SMILES1 = Oc1ccccc1Cl.CN(C)C(=O)Nc1ccccc1 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| CASNo_Ref = {{cascite|correct|??}} |
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| StdInChI = 1S/C9H12N2O.C6H5ClO/c1-11(2)9(12)10-8-6-4-3-5-7-8;7-5-3-1-2-4-6(5)8/h3-7H,1-2H3,(H,10,12);1-4,8H |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = NYKAIYWZWWMAME-UHFFFAOYSA-N |
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| CASNo = 4430-20-0 |
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| CASNo = 4430-20-0 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem = 20486 |
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| UNII = P3S5KH33EA |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| PubChem = 20486 |
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| ChemSpiderID=21106425 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| SMILES = C1=CC=C2C(=C1)C(OS2(=O)=O)(C3=CC(=C(C=C3)O)Cl)C4=CC(=C(C=C4)O)Cl |
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| ChemSpiderID = 19293 |
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| EINECS = 224-619-2 |
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| SMILES = C1=CC=C2C(=C1)C(OS2(=O)=O)(C3=CC(=C(C=C3)O)Cl)C4=CC(=C(C=C4)O)Cl |
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| InChI = 1/C19H12Cl2O5S/c20-14-9-11(5-7-16(14)22)19(12-6-8-17(23)15(21)10-12)13-3-1-2-4-18(13)27(24,25)26-19/h1-10,22-23H |
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| InChIKey = WWAABJGNHFGXSJ-UHFFFAOYAK |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C19H12Cl2O5S/c20-14-9-11(5-7-16(14)22)19(12-6-8-17(23)15(21)10-12)13-3-1-2-4-18(13)27(24,25)26-19/h1-10,22-23H |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = WWAABJGNHFGXSJ-UHFFFAOYSA-N |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=19|H=12|Cl=2|O=5|S=1 |
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| Formula = C<sub>19</sub>H<sub>12</sub>C<sub>l2</sub>O<sub>5</sub>S |
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| Appearance = |
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| MolarMass = 423.27 g/mol |
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| Appearance = |
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| Density = |
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| Density = |
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| MeltingPtC = 261 |
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| MeltingPt_ref =<ref name=crc>Haynes, p. 3.116</ref> |
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| MeltingPt = |
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| Section3 = {{Chembox Hazards |
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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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{{pH indicator |
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| indicator_name =Chlorophenol red |
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| low_pH=5.4 |
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| high_pH=6.8 |
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| low_pH_color=yellow |
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| high_pH_color=#8800FF |
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| high_pH_text=white |
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'''Chlorophenol red''' is an indicator dye that changes color from yellow to violet in the pH range 5.4 to 6.8.<ref>Haynes, p. 8.88</ref> The ] of a substance is determined by taking the negative logarithm of the Hydronium ion concentration and the indictor changes color due to the dissociation of H<sup>+</sup> ions.<ref>{{Cite web|date=2013-10-02|title=pH Indicators|url=https://chem.libretexts.org/Bookshelves/Physical_and_Theoretical_Chemistry_Textbook_Maps/Supplemental_Modules_(Physical_and_Theoretical_Chemistry)/Acids_and_Bases/Acid_and_Base_Indicators/PH_Indicators|access-date=2021-03-14|website=Chemistry LibreTexts|language=en}}</ref> The ] is at 572 nm.<ref>{{Cite web | url = https://www.sigmaaldrich.com/catalog/product/aldrich/199524 | title = Chlorophenol Red }}</ref> |
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'''Chlorophenol red''' is an indicator dye that changes color from yellow to violet in the pH range 4.8 to 6.7. The ] is at 572 nm. |
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== Properties and uses == |
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The dissociation mechanism of chlorophenol red is similar to that of phenolphthalein meaning it can be used as a color indicator. The dissociation of ] and hydrogen atoms creates the dissociate scheme of chlorophenol red to change color from yellow to red.<ref>{{Cite journal|last=Hanai|first=Toshihiko|date=2016|title=Quantitative Evaluation of Dissociation Mechanisms in Phenolphthalein and the Related Compounds.|url=https://www.researchgate.net/publication/301942181|journal=Journal of Computer Chemistry|volume=15|pages=13–21|doi=10.2477/jccj.2015-0055 |doi-access=free}}</ref> The pH properties of chlorophenol red are used to selectively determine the amount of chlorine dioxide in drinking water. Chlorophenol red selectively reacts with 0.1–1.9 mg/L chlorine dioxide at pH 7.<ref>{{Cite journal|last1=Sweetin|first1=Deborah L.|last2=Sullivan|first2=Elizabeth|last3=Gordon|first3=Gilbert|date=1996-01-01|title=The use of chlorophenol red for the selective determination of chlorine dioxide in drinking water|journal=Talanta|volume=43|issue=1|pages=103–108|doi=10.1016/0039-9140(95)01721-6|pmid=18966469}}</ref> The electrochemical properties of Chlorophenol red allows it to be a chromogenic label and can undergo oxidation creating several phenolic intermediates. The bacterial hydrolysis of a chlorophenol red labelled substrate produces chlorine retaining intermediates on electrodes.<ref>{{Cite journal|last1=Casimero|first1=Charnete|last2=Bigham|first2=Teri|last3=McGlynn|first3=Ruairi J.|last4=Dooley|first4=James S. G.|last5=Ternan|first5=Nigel G.|last6=Snelling|first6=William J.|last7=Critchley|first7=Megan E.|last8=Zinkel|first8=Cameron L.|last9=Smith|first9=Robert B.|last10=Sabogal-Paz|first10=Lyda P.|last11=Davis|first11=James|date=2019-12-01|title=Electroanalytical properties of chlorophenol red at disposable carbon electrodes: Implications for ''Escherichia coli'' detection|journal=Bioelectrochemistry|volume=130|pages=107321|doi=10.1016/j.bioelechem.2019.06.006|pmid=31306878|s2cid=196813601 |url=https://clok.uclan.ac.uk/29045/1/29045%201-s2.0-S1567539419303445-main.pdf }}</ref> |
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==References== |
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==References== |
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{{reflist}} |
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{{Unreferenced|date=September 2007}} |
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<references/> |
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==Cited sources== |
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*{{cite book |ref=Haynes| editor= Haynes, William M. | date = 2016| title = ] | edition = 97th | publisher = ] | isbn = 9781498754293}} |
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{{organic-compound-stub}} |
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