| Identification | More | [Name]
Triphenylacetic acid | [CAS]
595-91-5 | [Synonyms]
2,2,2-TRIPHENYLACETIC ACID
TIMTEC-BB SBB008604
TRIPHENYLACETIC ACID
TRIPHENYLMETHANE-A-CARBOXYLIC ACID
TRITYLFORMIC ACID
Acetic acid, triphenyl-
alpha-Toluic acid, alpha,alpha-diphenyl-
Benzeneacetic acid, alpha,alpha-diphenyl-
Triphenylaceticacid,99%
Triphenylacetic acid, HPLC 99%
Benzeneacetic acid, a,a-diphenyl-
Triphenylmethanecarboxylic acid
α,α-Diphenylbenzeneacetic acid
a,a-Diphenylbenzeneacetic acid | [EINECS(EC#)]
209-873-4 | [Molecular Formula]
C20H16O2 | [MDL Number]
MFCD00004185 | [Molecular Weight]
288.34 | [MOL File]
595-91-5.mol |
| Chemical Properties | Back Directory | [Appearance]
white to beige fine crystalline powder | [Melting point ]
270-273 °C (lit.) | [Boiling point ]
390.57°C (rough estimate) | [density ]
1.0992 (rough estimate) | [refractive index ]
1.7580 (estimate) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Fine Crystalline Powder | [pka]
pK1:3.96 (25°C) | [color ]
White to beige | [InChI]
InChI=1S/C20H16O2/c21-19(22)20(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H,(H,21,22) | [InChIKey]
DCYGAPKNVCQNOE-UHFFFAOYSA-N | [SMILES]
C(C1C=CC=CC=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C(=O)O | [CAS DataBase Reference]
595-91-5(CAS DataBase Reference) | [NIST Chemistry Reference]
Triphenylacetic acid(595-91-5) |
| Hazard Information | Back Directory | [Chemical Properties]
white to beige fine crystalline powder | [Uses]
2,2,2-Triphenylacetic Acid is used in preparation of Rhodium(II) Tetramethyl-benzenedipropioate complex, other Carboxylate complexes, and their catalytic activity. | [Application]
Triphenylacetic acid could be used to seal dye molecules within MOF-5. Introducing triphenylacetic acid (TPAA) capping groups traps organic dyes such as crystal violet (CV) within the MOF crystals. Surface-bound TPAA groups block the MOF pores, preventing the encapsulated dye from diffusing into the solution. Liberating the TPAA from the surface by protonation can reverse guest trapping, but acidic conditions can also degrade the MOF by extruding the carboxylate struts. In addition, triphenylacetic acid could inhibit microsomal bilirubin UDPglucuronosyltransferase activity in rat liver. This compound competitively inhibits bilirubin UDP-glucuronosyltransferase with respect to bilirubin[2-3].
| [Synthesis Reference(s)]
The Journal of Organic Chemistry, 28, p. 1725, 1963 DOI: 10.1021/jo01041a520 | [Reactivity Profile]
Triphenylacetic acid can be selectively fluorinated in dimethylsulfoxide/ HgF2 solutions under UV-visible illumination[1]. | [References]
[1] Habibi, Mohammed H., and T. E. Mallouk. "Photochemical selective fluorination of organic molecules using mercury (II) fluoride." Journal of Fluorine Chemistry 51.2(1991):291-294.
[2] Yan, J. , et al. "On-demand guest release from MOF-5 sealed with nitrophenylacetic acid photocapping groups. " Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 18.12(2019):2849-2853.
[3] Fournel, S, et al. "Inhibition of bilirubin UDPglucuronosyltransferase activity by triphenylacetic acid and related compounds. " BBA - General Subjects 883.2(1986):190-196.
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