60764-00-3

Basic information

• Product Name: α-deuterio(phenyl)acetic acid
• Synonyms: α-deuterio(phenyl)acetic acid
• CAS NO: 60764-00-3
• Molecular Weight: 137.142
• Mol File: 60764-00-3.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: α-deuterio(phenyl)acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: α-deuterio(phenyl)acetic acid(60764-00-3)
• EPA Substance Registry System: α-deuterio(phenyl)acetic acid(60764-00-3)

Safety Data

• Hazardous Substances Data: 60764-00-3(Hazardous Substances Data)

Upstream product

• 124-38-9 carbon dioxide 
• 79449-94-8 (chloromethyl-d)benzene 
• 64101-09-3 2-Deutero-2-diazo-1-oxo-1-phenylethan 
• 18698-97-0 ortho-bromophenylacetic acid 
• 2444-36-2 2'-chloro-benzeneacetic acid 
• 3240-11-7 Phenylacetylene-d1 
• 103-82-2 phenylacetic acid 
• 17097-90-4 2-phenylmalonic acid monoethyl ester 

Downstream Products

• 127399-19-3 (4R,5S)-3-<2'-(1H,2H)-2'-Phenyl-1-oxoethyl>-4-methyl-5-phenyloxazolidine-2-selone 

Relevant articles and documents

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Reducing versus basic properties of 1,2-diaryl-1,2-disodioethanes

The outcome of the reaction between halogenated arylacetic acids and 1,2-diaryl-1,2-disodioethanes strongly depends on the nature of both reaction partners, and it can be rationalized in terms of a competition between reducing and basic properties of the vic-diorganometals, as well as of the ease of the reductive cleavage of the different carbon-halide bonds. As an application of these findings, we developed a particularly mild approach to the synthesis of halogenated and non halogenated α-substituted arylacetic acids.

The dimethyldioxirane-mediated oxidation of phenylethyne

The product pattern found for the dimethyldioxirane-mediated oxidation of phenylethyne strongly depends on the reaction conditions. Dimethyldioxirane generated in situ from caroate (HSO5) and acetone in acetonitrile-water furnishes phenylacetic acid as the main product. With solutions of dimethyldioxirane in acetone, mandelic acid and phenylacetic acid are mainly formed. The relative abundances of the two acids depend on the residual water present in the dimethyldioxirane-acetone solution. Application of thoroughly dried solutions of the reagent effects increased formation of mandelic acid. When phenylethyne is oxidized by dimethyldioxirane transferred into tetrachloromethane, to minimize traces of water even further, oligomeric mandelic acid is obtained. The results are rationalized by the initial formation of phenyloxirene, which is known to equilibrate with phenylformylcarbene and bcnzoylcarbene. Subsequent Wolff rearrangement produces intermediate phenylketene, which can be trapped by water as phenylacetic acid or suffer from further oxidation to the α-lactone of mandelic acid. The α-lactone can either react with water to yield mandelic acid or, under anhydrous conditions, to yield oligomeric mandelic acid. In addition to mandelic acid and phenylacetic acid phenylglyoxylic acid, benzoic acid and benzaldehyde are observed as reaction products. The formation of phenylglyoxylic acid by transfer of two oxygen atoms to the in rear ranged carbon skeleton of phenylethyne followed by oxygen insertion into the aldehydic C-H bond of the intermediately formed phenylglyoxal is discussed. In a second pathway this acid is formed by partial oxidation of mandelic acid. Benzaldehyde and benzoic acid are explained as products of the oxidative degradation of the α-lactone by dimethyldioxirane. Under in situ conditions benzoic acid is also formed by caroate initiated oxidative decarboxylation of phenylglyoxylic acid and/or intermediate phenylglyoxal. The Royal Society of Chemistry 2005.