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D204307

Sigma-Aldrich

Diphenylacetic acid

99%

Synonym(s):

α,α-Diphenylacetic acid, α-Phenylbenzeneacetic acid, 2,2-Diphenylacetic acid, Diphenylethanoic acid

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$103.00

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5 G
$22.60
100 G
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About This Item

Linear Formula:
(C6H5)2CHCO2H
CAS Number:
117-34-0
Molecular Weight:
212.24
Beilstein/REAXYS Number:
1910978
EC Number:
204-185-0
MDL number:
MFCD00004251
UNSPSC Code:
12352100
PubChem Substance ID:
24893604
NACRES:
NA.22

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Quality Level

100

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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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.[1][2]
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.[3]
  • 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.[4]

pictograms

Exclamation mark
GHS07

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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Certificates of Analysis (COA)

Lot/Batch Number
STBK2672
STBB9170V
STBG2747V
STBF6654V
STBD6122V

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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
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
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)
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
Alison Rinderspacher et al.
Molecules (Basel, Switzerland), 25(2) (2020-01-16)
A novel generation of indole-2,3-quinodimethanes via the deamination of 1,2,3,4-tetrahydropyrrolo[s3,4-b]indoles is reported.
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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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