264881-99-4

Basic information

• Product Name: methyl 2-(4-bromophenyl)-2-diazoacetate
• Synonyms: methyl 2-(4-bromophenyl)-2-diazoacetate
• CAS NO: 264881-99-4
• Molecular Formula: C9H7BrN2O2
• Molecular Weight: 255.071
• Mol File: 264881-99-4.mol
• Article Data: 55

Chemical Properties

• Melting Point: 68 - 70 °C
• CAS DataBase Reference: methyl 2-(4-bromophenyl)-2-diazoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-(4-bromophenyl)-2-diazoacetate(264881-99-4)
• EPA Substance Registry System: methyl 2-(4-bromophenyl)-2-diazoacetate(264881-99-4)

Safety Data

• Hazardous Substances Data: 264881-99-4(Hazardous Substances Data)

Upstream product

• 941-55-9 4-toluenesulfonyl azide 
• 41841-16-1 (4-bromo-phenyl)-acetic acid methyl ester 
• 1878-68-8 2-(4-bromophenyl)-acetic acid 

Downstream Products

• 334022-35-4 methyl (αR)-[(2S)-4-(triisopropylsilyloxy)-1,2-dihydro-naphthalen-2-yl]-(4-bromo-phenyl)acetate 

Relevant articles and documents

Highly Selective Ring Expansion of Bicyclo[3.1.0]hexenes

A Ru-carbene-promoted ring expansion of bicyclo[3.1.0]hexenes with terminal alkynes is reported. The reaction delivers seven-membered carbocycles starting from readily available starting materials and was found to be highly regioselective. The resulting seven-membered ring products contain both conjugated diene and cyclopropane substructures that could be selectively reacted in subsequent transformations.

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.

Visible Light-Promoted Sulfoxonium Ylides Synthesis from Aryl Diazoacetates and Sulfoxides

A visible light-promoted reaction of donor/acceptor diazoalkanes with sulfoxides towards the synthesis of synthetically useful sulfoxonium ylides was reported. The reaction occurred under sole visible light irradiation without the need of any transition-metals or additives, affording the corresponding sulfoxonium ylides in moderate to good yields. The success of late-stage modification of natural isolates or drug candidates, scale-up reaction and transformation of sulfoxonium ylides to other useful molecules further rendered the approach valuable.

B(C6F5)3-Catalyzed site-selective N1-alkylation of benzotriazoles with diazoalkanes

Alkylation of benzotriazoles is synthetically challenging, often leading to mixtures of N1 and N2 alkylation. Herein, metal-free catalytic site-selective N1-alkylation of benzotriazoles with diazoalkanes is described in the presence of 10 mol% of B(C6F5)3. These reactions provide N1-alkylated benzotriazoles in good to excellent yields and this protocol is successfully adapted to gram-scale syntheses as well as a derivative with antimicrobial activity.