26164-15-8

Basic information

• Product Name: Benzeneacetic acid, a-ethyl-, methyl ester, (S)-
• CAS NO: 26164-15-8
• Molecular Formula: C11H14O2
• Molecular Weight: 178.231
• Mol File: 26164-15-8.mol
• Article Data: 19

Chemical Properties

• CAS DataBase Reference: Benzeneacetic acid, a-ethyl-, methyl ester, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneacetic acid, a-ethyl-, methyl ester, (S)-(26164-15-8)
• EPA Substance Registry System: Benzeneacetic acid, a-ethyl-, methyl ester, (S)-(26164-15-8)

Safety Data

• Hazardous Substances Data: 26164-15-8(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 20452-67-9 phenylethylketene 
• 50415-85-5 (E)-benzeneacetic acid, α-ethylidene, methyl ester 
• 167476-42-8 1,1-bis(trimethylsilyloxy)-2-phenylbutene 
• 3196-15-4 Methyl 2-bromobutyrate 
• 100-58-3 phenylmagnesium bromide 
• 495-40-9 propiophenone 
• 149-73-5 trimethyl orthoformate 
• 1268613-70-2 C₁₈H₁₇N₃O 
• 1268613-71-3 C₁₂H₁₃N₃O 
• 90-27-7 2-Phenylbutyric acid 
• 2294-71-5 methyl 2-phenylbutanoate 
• 3127-67-1 2-phenyl-but-2-enoic acid 
• 938-79-4 (2R)-2-phenylbutanoic acid 

Downstream Products

• 42307-60-8 (S)-2-methylbutanal 
• 6957-17-1 (S)-4-phenyl-hexan-3-one 
• 40473-35-6 (S)-(+)-2-phenylbutyric acid chloride 
• 4286-15-1 (S)-2-phenylbutyric acid 

Relevant articles and documents

Design of Hemilabile N,N,N-Ligands in Copper-Catalyzed Enantioconvergent Radical Cross-Coupling of Benzyl/Propargyl Halides with Alkenylboronate Esters

The enantioconvergent radical C(sp3)-C(sp2) cross-coupling of alkyl halides with alkenylboronate esters is an appealing tool in the assembly of synthetically valuable enantioenriched alkenes owing to the ready availability, low toxicity, and air/moisture stability of alkenylboronate esters. Here, we report a copper/chiral N,N,N-ligand catalytic system for the enantioconvergent cross-coupling of benzyl/propargyl halides with alkenylboronate esters (>80 examples) with good functional group tolerance. The key to the success is the rational design of hemilabile N,N,N-ligands by mounting steric hindrance at the ortho position of one coordinating quinoline ring. Thus, the newly designed ligand could not only promote the radical cross-coupling process in the tridentate form but also deliver enantiocontrol over highly reactive alkyl radicals in the bidentate form. Facile follow-up transformations highlight its potential utility in the synthesis of various enantioenriched building blocks as well as in the late-stage functionalization for drug discovery.

Enantioselective Copper-Catalyzed Defluoroalkylation Using Arylboronate-Activated Alkyl Grignard Reagents

A copper-catalyzed system has been introduced for the enantioselective defluoroalkylation of linear 1-(trifluoromethyl)alkenes through C-F activation to synthesize various gem-difluoroalkenes as carbonyl mimics. For the first time, arylboronate-activated alkyl Grignard reagents were uncovered in this cross-coupling reaction. Mechanistic studies confirmed that the tetraorganoborate complexes generated in situ were the key reactive species for this transformation.

Stereoselective Ketone Rearrangements with Hypervalent Iodine Reagents

The first stereoselective version of an iodine(III)-mediated rearrangement of arylketones in the presence of orthoesters is described. The reaction products, α-arylated esters, are very useful intermediates in the synthesis of bioactive compounds such as ibuprofen. With chiral lactic acid-based iodine(III) reagents product selectivities of up to 73 % ee have been achieved.