72410-67-4

Basic information

• Product Name: Benzeneacetic acid, a-diazo-, 1,1-dimethylethyl ester
• CAS NO: 72410-67-4
• Molecular Formula: C12H14N2O2
• Molecular Weight: 218.255
• Mol File: 72410-67-4.mol
• Article Data: 28

Chemical Properties

• CAS DataBase Reference: Benzeneacetic acid, a-diazo-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneacetic acid, a-diazo-, 1,1-dimethylethyl ester(72410-67-4)
• EPA Substance Registry System: Benzeneacetic acid, a-diazo-, 1,1-dimethylethyl ester(72410-67-4)

Safety Data

• Hazardous Substances Data: 72410-67-4(Hazardous Substances Data)

Upstream product

• 16537-09-0 t-butyl phenylacetate 
• 591-50-4 iodobenzene 
• 13298-76-5 tert-butyl 2-diazo-3-oxobutanoate 
• 101-41-7 benzeneacetic acid methyl ester 
• 103-82-2 phenylacetic acid 
• 162222-05-1 t-butyl 3-oxo-2-phenylbutanoate 
• 1694-31-1 tert-butyl acetoacetate 

Downstream Products

• 7332-98-1 tert-butyl phenylglyoxylate 
• 1005415-94-0 2-benzoyloxy-2-formyl-1-phenylcyclopropanecarboxylic acid tert-butyl ester 
• 1426657-66-0 tert-butyl 2-(3-oxocyclohex-1-enyl)-2-phenylacetate 
• 1426658-03-8 tert-butyl 2-(3-oxocyclopent-1-enyl)-2-phenylacetate 
• 1432601-51-8 (S)-tert-butyl 2-(3-oxocyclohex-1-enyl)-2-phenylacetate 

Relevant articles and documents

Synthesis of Functionalized Silsesquioxane Nanomaterials by Rhodium-Catalyzed Carbene Insertion into Si?H Bonds

We report carbene insertion into Si?H bonds of polyhedral oligomeric silsesquioxanes (POSS) for the synthesis of highly functionalized siloxane nanomaterials. Dirhodium(II) carboxylates catalyze insertion of aryl-diazoacetates as carbene precursors to afford POSS structures containing both ester and aryl groups as orthogonal functional handles for further derivatization of POSS materials. Four diverse and structurally varied silsesquioxane core scaffolds with one, three, or eight Si?H bonds were evaluated with diazo reactants to produce a total of 20 new POSS compounds. Novel diazo compounds containing a fluorinated octyl group and boron-dipyrromethene (BODIPY) chromophore demonstrate the use of highly functionalized substrates. Transformations of aryl(ester)-functionalized POSS compounds derived from this method are demonstrated, including ester hydrolysis and Suzuki–Miyaura cross-coupling.

Synthesis of Quinolines via the Metal-free Visible-Light-Mediated Radical Azidation of Cyclopropenes

We report the synthesis of quinolines using cyclopropenes and an azidobenziodazolone (ABZ) hypervalent iodine reagent as an azide radical source under visible-light irradiation. Multisubstituted quinoline products were obtained in 34-81% yield. The reaction was most efficient for 3-trifluoromethylcyclopropenes, affording valuable 4-trifluoromethylquinolines. The transformation probably proceeds through the cyclization of an iminyl radical formed by the addition of the azide radical on the cyclopropene double bond, followed by ring-opening and fragmentation.

Catalytic Asymmetric Darzens-Type Epoxidation of Diazoesters: Highly Enantioselective Synthesis of Trisubstituted Epoxides

Highly enantioselective Darzens-type epoxidation of diazoesters with glyoxal derivatives was accomplished using a chiral boron–Lewis acid catalyst, which facilitated asymmetric synthesis of trisubstituted α,β-epoxy esters. In the presence of a chiral oxazaborolidinium ion catalyst, the reaction proceeded in high yield (up to 99 %) with excellent enantio- and diastereoselectivity (up to >99 % ee and >20:1 dr, respectively). The synthetic potential of this method was illustrated by conversion of the products to various compounds such as epoxy γ-butyrolactone, tertiary β-hydroxy ketone and epoxy diester.