Triphenylacetic acid Chemical Properties

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)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163900

MSDS

• Language:English Provider:Triphenylacetic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Triphenylacetic acid Usage And Synthesis

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.

Triphenylacetic acid(595-91-5)Related Product Information

• Folic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• Citric acid
• Nitrilotriacetic acid
• Trifluoroacetic acid
• Triphenylmethyl Chloride
• Hyaluronic acid
• (FORMYLMETHYLENE)TRIPHENYLPHOSPHORANE
• Ethyl trifluoroacetate
• Triphenylphosphine
• Triacetin
• Trifluoroacetic anhydride
• Triphenylmethane
• Ascoric Acid
• N-BOC-IMINO-(TRIPHENYL)PHOSPHORANE
• PROPARGYLTRIPHENYLPHOSPHONIUM BROMIDE
• Triphenylphosphine-3,3',3''-trisulfonic acid trisodium salt
• 2-(TRIMETHYLSILYL)ETHOXYMETHYLTRIPHENYLPHOSPHONIUM CHLORIDE