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{{About|thymolphthalein|other related dyes in the phthalein family|Phthalein dye}}

{{chembox
{{chembox
| Verifiedfields = changed
| Verifiedfields = changed
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 470609780
| verifiedrevid = 470609780
| ImageFile = Thymolphthalein.svg
| ImageFile = Thymolphthalein skeletal.svg
| ImageSize =
| ImageSize =
| IUPACName = 3,3-bis(4-hydroxy-2-methyl-5-propan-2-ylphenyl)-2-benzofuran-1-one
| PIN = 3,3-Bis[4-hydroxy-2-methyl-5-(propan-2-yl)phenyl]-2-benzofuran-1(3''H'')-one
| OtherNames =
| OtherNames =
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LDKDGDIWEUUXSH-UHFFFAOYSA-N
| StdInChIKey = LDKDGDIWEUUXSH-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|changed|??}}
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 125-20-2
| CASNo = 125-20-2
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = YG5I28WSQP
| EINECS = 204-729-7
| EINECS = 204-729-7
| PubChem = 31316
| PubChem = 31316
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}}
}}
|Section2={{Chembox Properties
|Section2={{Chembox Properties
| C =28
| C=28 | H=30 | O=4
| H =30
| O =4
| Appearance = White powder
| Appearance = White powder
| Density =
| Density =
| MeltingPtC = 248 to 252
| MeltingPtC = 248 to 252
| Melting_notes = (decomposes)
| MeltingPt_notes = (decomposes)
| BoilingPt =
| BoilingPt =
| Solubility =
| Solubility =
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| NFPA-F = 0
| NFPA-F = 0
| NFPA-R = 0
| NFPA-R = 0
| NFPA-O =
| NFPA-S =
| Hazards_ref=<ref>{{cite web |title=Thymolphthalein |url=https://pubchem.ncbi.nlm.nih.gov/compound/31316#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref>
| RPhrases = 4, 10
| SPhrases = {{S22}} {{S24/25}}
| GHSPictograms = {{GHS08}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|341|350|361}}
| PPhrases = {{P-phrases|201|202|210|233|240|241|242|243|280|281|303+361+353|308+313|370+378|403+235|405|501}}
| FlashPt =
| FlashPt =
| AutoignitionPt =
| AutoignitionPt =
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}}
}}


'''Thymolphthalein''' is an [[acid]]-[[base (chemistry)|base]] ([[pH]]) [[PH indicator|indicator]]. Its transition range is around [[pH]] 9.3-10.5. Below this pH, it is colorless; above, it is blue. The [[Molar absorptivity|molar extinction coefficient]] for the blue thymolphthalein [[Anion#Ions|dianion]] is 38000 M<sup>−1</sup>cm<sup>−1</sup> at 595&nbsp;nm.<ref>{{cite journal |author=Hahn HH |author2=Cheuk SF |author3=Elfenbein S |author4= Wood WB |title= Studies on the Pathogenesis of Fever: Xix. Localization of Pyrogen in Granulocytes|journal=J. Exp. Med. |volume=131 |issue=4 |pages=701–9 |date=April 1970 |pmid=5430784 |pmc=2138774 |doi= 10.1084/jem.131.4.701|url= http://www.jem.org/cgi/reprint/131/4/701.pdf}}</ref>
'''Thymolphthalein''' is a [[phthalein dye]] used as an [[acid]]–[[base (chemistry)|base]] ([[pH]]) [[PH indicator|indicator]]. Its transition range is around pH 9.3–10.5. Below this pH, it is colorless; above, it is blue. The [[Molar absorptivity|molar extinction coefficient]] for the blue thymolphthalein [[Anion#Ions|dianion]] is 38,000&nbsp;M<sup>−1</sup>&nbsp;cm<sup>−1</sup> at 595&nbsp;nm.<ref>{{cite journal |author=Hahn HH |author2=Cheuk SF |author3=Elfenbein S |author4= Wood WB |title= Studies on the Pathogenesis of Fever: Xix. Localization of Pyrogen in Granulocytes|journal= The Journal of Experimental Medicine|volume=131 |issue=4 |pages=701–9 |date=April 1970 |pmid=5430784 |pmc=2138774 |doi= 10.1084/jem.131.4.701}}</ref>


{{pH_indicator_template|indicator_name=Thymolphthalein |low_pH=9.3 |high_pH=10.5|low_pH_color=|high_pH_color=blue}}
{{pH_indicator_template|indicator_name=Thymolphthalein |low_pH=9.3 |high_pH=10.5|low_pH_color=white|high_pH_color=blue|high_pH_text=white}}

Thymolphthalein is also known to have use as a [[laxative]]<ref>{{cite journal | last1 = Hubacher | first1 = MH | last2 = Doernberg | first2 = S | last3 = Horner | first3 = A | year = 1953 | title = Laxatives: chemical structure and potency of phthaleins and hydroxyanthraquinones | journal = Journal of the American Pharmaceutical Association | volume = 42 | issue = 1| pages = 23–30 | pmid = 13034620 | doi = 10.1002/jps.3030420108 }}</ref> and for [[disappearing ink]].<ref>{{Cite web|url=https://www.chymist.com/Disappearing%20Ink.pdf|title=Disappearing Ink|last=Katz|first=David A.|date=1982|website=www.chymist.com|access-date=August 14, 2017}}</ref>


==Preparation==
==Preparation==
Thymolphthalein can be synthesized from [[thymol]] and [[phthalic anhydride]] by [[Friedel-Crafts alkylation]]:
Thymolphthalein can be synthesized from [[thymol]] and [[phthalic anhydride]].
:[[File:ThymolphthaleinSynthesis.png|400px]]{{clear left}}
:[[File:ThymolphthaleinSynthesis.png|400px]]{{clear left}}

==See also==
*[[Phenolphthalein]]


==References==
==References==
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[[Category:PH indicators]]
[[Category:PH indicators]]
[[Category:Triarylmethane dyes]]
[[Category:Triarylmethane dyes]]
[[Category:Cresols]]
[[Category:Phthalides]]
[[Category:Lactones]]
[[Category:Phenols]]
[[Category:Isobenzofurans]]
[[Category:Isopropyl compounds]]

{{organic-compound-stub}}

Latest revision as of 02:40, 3 August 2023

This article is about thymolphthalein. For other related dyes in the phthalein family, see Phthalein dye.
Thymolphthalein
Names
Preferred IUPAC name
3,3-Bis[4-hydroxy-2-methyl-5-(propan-2-yl)phenyl]-2-benzofuran-1(3H)-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.004.300 Edit this at Wikidata
EC Number
  • 204-729-7
UNII
  • InChI=1S/C28H30O4/c1-15(2)20-13-23(17(5)11-25(20)29)28(22-10-8-7-9-19(22)27(31)32-28)24-14-21(16(3)4)26(30)12-18(24)6/h7-16,29-30H,1-6H3 checkY
    Key: LDKDGDIWEUUXSH-UHFFFAOYSA-N checkY
  • InChI=1/C28H30O4/c1-15(2)20-13-23(17(5)11-25(20)29)28(22-10-8-7-9-19(22)27(31)32-28)24-14-21(16(3)4)26(30)12-18(24)6/h7-16,29-30H,1-6H3
    Key: LDKDGDIWEUUXSH-UHFFFAOYAV
  • O=C1OC(c2ccccc12)(c3cc(c(O)cc3C)C(C)C)c4cc(c(O)cc4C)C(C)C
Properties
C28H30O4
Molar mass 430.544 g·mol−1
Appearance White powder
Melting point 248 to 252 °C (478 to 486 °F; 521 to 525 K) (decomposes)
Hazards[1]
GHS labelling:
GHS08: Health hazard
Warning
H341, H350, H361
P201, P202, P210, P233, P240, P241, P242, P243, P280, P281, P303+P361+P353, P308+P313, P370+P378, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
0
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Thymolphthalein is a phthalein dye used as an acid–base (pH) indicator. Its transition range is around pH 9.3–10.5. Below this pH, it is colorless; above, it is blue. The molar extinction coefficient for the blue thymolphthalein dianion is 38,000 M−1 cm−1 at 595 nm.[2]

Thymolphthalein (pH indicator)
below pH 9.3 above pH 10.5
9.3 ⇌ 10.5

Thymolphthalein is also known to have use as a laxative[3] and for disappearing ink.[4]

Preparation[edit]

Thymolphthalein can be synthesized from thymol and phthalic anhydride.

See also[edit]

References[edit]

  1. ^ "Thymolphthalein". pubchem.ncbi.nlm.nih.gov.
  2. ^ Hahn HH; Cheuk SF; Elfenbein S; Wood WB (April 1970). "Studies on the Pathogenesis of Fever: Xix. Localization of Pyrogen in Granulocytes". The Journal of Experimental Medicine. 131 (4): 701–9. doi:10.1084/jem.131.4.701. PMC 2138774. PMID 5430784.
  3. ^ Hubacher, MH; Doernberg, S; Horner, A (1953). "Laxatives: chemical structure and potency of phthaleins and hydroxyanthraquinones". Journal of the American Pharmaceutical Association. 42 (1): 23–30. doi:10.1002/jps.3030420108. PMID 13034620.
  4. ^ Katz, David A. (1982). "Disappearing Ink" (PDF). www.chymist.com. Retrieved August 14, 2017.
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