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D204307

Sigma-Aldrich

Diphenylacetic acid

99%

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Synonym(s):
α,α-Diphenylacetic acid, α-Phenylbenzeneacetic acid, 2,2-Diphenylacetic acid, Diphenylethanoic acid
Linear Formula:
(C6H5)2CHCO2H
CAS Number:
Molecular Weight:
212.24
Beilstein/REAXYS Number:
1910978
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

99%

form

powder

mp

146-149 °C
147-149 °C (lit.)

SMILES string

OC(=O)C(c1ccccc1)c2ccccc2

InChI

1S/C14H12O2/c15-14(16)13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,13H,(H,15,16)

InChI key

PYHXGXCGESYPCW-UHFFFAOYSA-N

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1 of 4

This Item
338982U2625T81205
Diphenylacetic acid 99%

D204307

Diphenylacetic acid

Phenylacetic acid-α,α-d2 98 atom % D

338982

Phenylacetic acid-α,α-d2

Uric acid ≥99%, crystalline

U2625

Uric acid

Triphenylacetic acid 99%

T81205

Triphenylacetic acid

form

powder

form

solid

form

crystalline

form

-

mp

146-149 °C

mp

76-78 °C (lit.)

mp

>300 °C (lit.)

mp

270-273 °C (lit.)

Application

Diphenylacetic acid can be used as a reagent in the kinetic resolution of racemic 2-hydroxy-γ-butyrolactones and 1-heteroarylalkanols by asymmetric esterification in the presence of pivalic anhydride and chiral acyl-transfer catalyst.
It can also be used as:
  • An additive in the ortho-arylation of 1-phenyl-β-carbolines using various aryl halides in the presence of ruthenium catalyst.
  • A catalyst to synthesize 2-allyl-3-oxazolin-5-one derivatives via Rh-catalyzed coupling reaction of azlactones and alkynes followed by aza-Cope rearrangement.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

383.5 °F - closed cup

flash_point_c

195.3 °C - closed cup

ppe

Eyeshields, Gloves, type N95 (US)


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Subramani Rajkumar et al.
The Journal of organic chemistry, 80(11), 5532-5545 (2015-04-11)
A Ru(II)-catalyzed C-H arylation approach has been developed utilizing β-carboline alkaloids as the directing group. Selective formations of diarylated products from moderate to excellent yields were accomplished. Broad substrate scope with excellent functional group tolerance for C1-phenyl/thienyl/PAHs-β-carbolines was demonstrated. X-ray
Jinqiang Kuang et al.
Angewandte Chemie (International ed. in English), 56(29), 8422-8425 (2017-05-18)
Rhodium-catalyzed regioselective addition of azlactones to internal alkynes combined with aza-Cope rearrangement provides efficient atom economic access to 2-allyl-3-oxazolin-5-one derivatives. Extension to a triple domino process, in which the above process is combined with in situ azlactone formation starting from amino
Kinetic Resolution of Racemic 1-Heteroarylalkanols by Asymmetric Esterification Using Diphenylacetic Acid with Pivalic Anhydride and a Chiral Acyl-transfer Catalyst
Shiina I, et al.
Chemistry Letters (Jpn), 40(2), 147-149 (2011)
Hugh D Glossop et al.
Biomacromolecules, 20(7), 2515-2529 (2019-05-31)
Peptides can serve as versatile therapeutics with a highly modular structure and tunable biophysical properties. In particular, the efficacy of peptide antibiotics against drug-resistant pathogens is of great promise, as few new classes of antibiotics are being developed to overcome
B C Sallustio et al.
The Journal of pharmacology and experimental therapeutics, 251(1), 288-294 (1989-10-01)
Drugs which are cleared predominantly by forming acyl-glucuronides undergo a futile cycle in which plasma drug clearance is a function of the formation, hydrolysis and renal clearance of the glucuronide conjugate. The effect of impaired renal function, induced by uranyl

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