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{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 401935395
| Watchedfields = changed
⚫ | ImageFile = BromcresolPurple.png
⚫ | verifiedrevid = 443145525
| ImageSize =
⚫ | ImageFile = Bromocresol purple.svg
| IUPACName = 4,4'-(1,1-Dioxido-3H-2,1-benzoxathiole-3,3-diyl)- bis(2-bromo-6-methylphenol)
| ImageAlt = Skeletal formula of bromocresol purple in cyclic form
⚫ | OtherNames = <nowiki>5',5''-Dibromo-o-cresolsulfonephthalein</nowiki>
| ImageFile1 = Bromocresol purple cyclic 3D ball.png
⚫ | Section1 = {{Chembox Identifiers
| ImageAlt1 = Ball-and-stick model of the bromocresol purple molecule in cyclic form
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| PIN = 3,3-Bis(3-bromo-4-hydroxy-5-methylphenyl)-2,1λ<sup>6</sup>-benzoxathiole-1,1(3''H'')-dione
⚫ | OtherNames = 5′,5′′-Dibromo-''o''-cresolsulfonephthalein<br />Bromcresol purple
⚫ |Section1={{Chembox Identifiers
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7974 | ChemSpiderID = 7974
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 86154
| EC_number = 204-087-8
| UNII = 201C22C3EC
| InChI = 1/C21H16Br2O5S/c1-11-7-13(9-16(22)19(11)24)21(14-8-12(2)20(25)17(23)10-14)15-5-3-4-6-18(15)29(26,27)28-21/h3-10,24-25H,1-2H3 | InChI = 1/C21H16Br2O5S/c1-11-7-13(9-16(22)19(11)24)21(14-8-12(2)20(25)17(23)10-14)15-5-3-4-6-18(15)29(26,27)28-21/h3-10,24-25H,1-2H3
| InChIKey = ABIUHPWEYMSGSR-UHFFFAOYAH | InChIKey = ABIUHPWEYMSGSR-UHFFFAOYAH
⚫ | InChI2 = 1/C21H17BrO5S/c1-12-9-14(7-8-18(12)23)21(15-10-13(2)20(24)17(22)11-15)16-5-3-4-6-19(16)28(25,26)27-21/h3-11,23-24H,1-2H3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C21H16Br2O5S/c1-11-7-13(9-16(22)19(11)24)21(14-8-12(2)20(25)17(23)10-14)15-5-3-4-6-18(15)29(26,27)28-21/h3-10,24-25H,1-2H3 | StdInChI = 1S/C21H16Br2O5S/c1-11-7-13(9-16(22)19(11)24)21(14-8-12(2)20(25)17(23)10-14)15-5-3-4-6-18(15)29(26,27)28-21/h3-10,24-25H,1-2H3
Line 16: Line 25:
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 115-40-2 | CASNo = 115-40-2
| PubChem = 8273 | PubChem = 8273
| SMILES = Brc1c(O)c(cc(c1)C3(OS(=O)(=O)c2ccccc23)c4cc(c(O)c(Br)c4)C)C | SMILES = Brc1c(O)c(cc(c1)C3(OS(=O)(=O)c2ccccc23)c4cc(c(O)c(Br)c4)C)C
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
|C=21|H=16|Br=2|O=5|S=1 | C=21 | H=16 | Br=2 | O=5 | S=1
| Appearance = Purple powder | Appearance = Purple powder
| Density = | Density =
| MeltingPt = 241 - 242 °C (decomposition) | MeltingPtC = 241 to 242
| MeltingPt_notes = (decomposition)
| BoilingPt =
| Solubility = < 0.1 % | BoilingPt =
| Solubility = < 0.1 %
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
| NFPA-H = 1 | NFPA-H = 1
| NFPA-F = 0 | NFPA-F = 0
| NFPA-R = 0 | NFPA-R = 0
| NFPA-O = | NFPA-S =
| RPhrases = {{R36/37/38}} | GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| SPhrases = {{S26}}, {{S36}}
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}
}} }}
}} }}


'''Bromocresol purple''' ('''BCP''') or '''5′,5″-dibromo-''o''-cresolsulfophthalein''', is a ] of the ] family (]s) and a ]. It is colored yellow below pH 5.2, and violet above pH 6.8. In its cyclic ] ester form, it has a ] value of 6.3, and is usually prepared as a 0.04% aqueous solution.<ref name="pubchem">{{cite web |url= https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8273| title = Bromocresol Purple |work= NCBI PubChem |publisher=]}}</ref>
'''Bromocresol Purple (BCP)''' or '''5',5"-dibromo-o-cresolsulfophthalein''', is a ]. The most common solution is 0.04% ].

⚫ {{pH_indicator_template|indicator_name=Bromocresol Purple|low_pH=5.2 |high_pH=6.8 |low_pH_color=yellow|high_pH_color=violet}}


==Uses== ==Uses==
]
Besides its primary function as an indicator, Bromocresol Purple is used in medical laboratories to measure ], and as an addition to acid stop baths used in photographic processing as an indicator that the bath has reached neutral pH and needs to be replaced.
⚫ {{pH_indicator_template|indicator_name=Bromocresol purple|low_pH=5.2 |high_pH=6.8 |low_pH_color=yellow|high_pH_color=violet}}
Bromocresol purple is used in medical laboratories to measure ]. Use of BCP in this application may provide some advantage over older methods using ].<ref>{{Cite journal|last1=Bachmann|first1=Lorin M.|last2=Yu|first2=Min|last3=Boyd|first3=James C.|last4=Bruns|first4=David E.|last5=Miller|first5=W. Greg|date=2017-03-01|title=State of Harmonization of 24 Serum Albumin Measurement Procedures and Implications for Medical Decisions|journal=Clinical Chemistry|language=en|volume=63|issue=3|pages=770–779|doi=10.1373/clinchem.2016.262899|issn=0009-9147|pmid=28073902|doi-access=free}}</ref><ref>{{Cite journal|last1=Ito|first1=Shigenori|last2=Yamamoto|first2=Daisuke|date=2010-02-02|title=Mechanism for the color change in bromocresol purple bound to human serum albumin|journal=Clinica Chimica Acta|volume=411|issue=3|pages=294–295|doi=10.1016/j.cca.2009.11.019|pmid=19932090}}</ref> In microbiology, it is used for staining dead cells based on their acidity, and for the isolation and ]ing of ].<ref>{{cite journal |title=Fluorescent staining with bromocresol purple: a rapid method for determining yeast cell dead count developed as an assay of killer toxin activity. |journal=Yeast |pages=1207–1211 |volume=9 |issue=11 |first1=H. |last1=Kurzweilová |first2=K. |last2=Sigler |date=November 1993 |pmid=7509098 |doi=10.1002/yea.320091107|s2cid=44782970 }}</ref><ref>{{cite journal |title=A differential medium for lactic acid-producing bacteria in a mixed culture |journal=Letters in Applied Microbiology |pages=676–681 |first1=H.M. |last1=Lee |first2=Y. |last2=Lee |date=June 2008 |pmid=18444977 |doi=10.1111/j.1472-765X.2008.02371.x |volume=46 |issue=6 |doi-access=free }} {{open access}}</ref>

In ], it can be used as an additive to acid ]s to indicate that the bath has reached neutral pH and needs to be replaced.<ref>{{cite book |url=https://books.google.com/books?id=u67OCwAAQBAJ&pg=PT622 |title=The Darkroom Cookbook |first=Steve |last=Anchell |via=Google Books |year=2016 |edition=4 |publisher=] |isbn=9781317337607}}</ref>

Bromocresol purple milk solids glucose agar is used as a medium used to distinguish ]s from bacteria and other organisms in cases of ] fungus ('']'') infestation in cattle and other animals.<ref>{{cite book|last1=Kane|first1 = J.|last2 = Summerbell|first2 = R.|last3 = Sigler|first3 = L.|last4 = Krajden|first4 = S.|last5 = Land|first5 = G.|title = Laboratory Handbook of Dermatophytes: A Clinical Guide and Laboratory Handbook of Dermatophytes and Other Filamentous Fungi from Skin, Hair, and Nails|year = 1997|publisher = ]|location = Belmont, CA|isbn = 9780898631579}}</ref><ref>{{cite book|last1 = Beneke|first1 = E. S.|last2 = Rogers|first2 = A. L.|edition = illustrated|title = Medical Mycology and Human Mycoses|year = 1996|publisher = ]|location = Belmont, CA|isbn = 9780898631753|pages = 85–90}}</ref>

===pH Indicator===
Similar to ], the structure of bromocresol purple changes with pH. Changing the level of acidity causes a shift in the ] between two different structures that have different colors. In near-neutral or alkaline solution, the chemical has a ] structure that gives the solution a purple color. As the pH decreases, it converts to a ] (cyclic sulfonic ester) that colors the solution yellow. In some microbiology tests, this change is used as an indicator of bacterial growth.<ref>{{cite journal |doi=10.1016/j.ifset.2022.103200 |title=Applications of natural polysaccharide-based pH-sensitive films in food packaging: Current research and future trends |date=2022 |last1=Li |first1=Nan |last2=Zhou |first2=Siyu |last3=Yang |first3=Xingbin |last4=Lin |first4=Dehui |journal=Innovative Food Science & Emerging Technologies |volume=82 }}</ref><ref>{{Cite web |url=https://www.thomassci.com/FetchFile.ashx?id=2807195c-9bfc-46a6-b088-61dd6b1f3e42 |title=Archived copy |access-date=2022-02-15 |archive-date=2022-02-16 |archive-url=https://web.archive.org/web/20220216042922/https://www.thomassci.com/FetchFile.ashx?id=2807195c-9bfc-46a6-b088-61dd6b1f3e42 |url-status=dead }}</ref>

⚫ :]

==See also==
* ]


==References== ==References==
{{reflist|30em}}
* from ]


==External links==
<!-- Metadata: see ] -->
{{Commons category}}
{{InChI|
*
⚫ InChI=1/C21H17BrO5S/c1-12-9-14(7-8-18(12)23)21(15-10-13(2)20(24)17(22)11-15)16-5-3-4-6-19(16)28(25,26)27-21/h3-11,23-24H,1-2H3
}}


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