264882-03-3

Basic information

• Product Name: methyl 2-(3-bromophenyl)-2-diazoacetate
• Synonyms: methyl 2-(3-bromophenyl)-2-diazoacetate
• CAS NO: 264882-03-3
• Molecular Weight: 255.071
• Mol File: 264882-03-3.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: methyl 2-(3-bromophenyl)-2-diazoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-(3-bromophenyl)-2-diazoacetate(264882-03-3)
• EPA Substance Registry System: methyl 2-(3-bromophenyl)-2-diazoacetate(264882-03-3)

Safety Data

• Hazardous Substances Data: 264882-03-3(Hazardous Substances Data)

Upstream product

• 1878-67-7 3-Bromophenylacetic acid 
• 150529-73-0 methyl 2-(3-bromophenyl)acetatee 
• 941-55-9 4-toluenesulfonyl azide 

Downstream Products

• 264882-11-3 methyl (R)-α-cyclohexyl-3-bromophenylacetate 
• 1154051-25-8 C₂₆H₂₄BrNO₅ 
• 63096-34-4 methyl 2-(3-bromophenyl)-2-hydroxyacetate 
• 1152170-60-9 methyl 2-(3-bromophenyl)-2-hydroxyacetate 

Relevant articles and documents

B(C6F5)3-catalyzed O-H insertion reactions of diazoalkanes with phosphinic acids

A highly efficient base-, metal-, and oxidant-free catalytic O-H insertion reaction of diazoalkanes and phosphinic acids in the presence of B(C6F5)3has been developed. This powerful methodology provides a green approach towards the synthesis of a broad spectrum of α-phosphoryloxy carbonyl compounds with good to excellent yields (up to 99% yield). The protocol features the advantages of operational simplicity, high atom economy, practicality, easy scalability and environmental friendliness.

Blue LED-Mediated N-H Insertion of Indoles into Aryldiazoesters at Room Temperature in Batch and Flow: Reaction Kinetics, Density Functional Theory, and Mechanistic Study

Mild blue light-mediated N-H insertion of indole and its derivatives into aryldiazoesters has been reported in a batch and flow strategy to afford the corresponding N-alkylated product in moderate-to-excellent yield. Detailed high-performance liquid chromatography-based reaction kinetics measurements, control experiments, and kinetic isotope effect reveal that 3-substituted indoles with electron-withdrawing groups such as -CN and -CHO facilitated the product formation, whereas the electron-donating group retarded the process. The neutral indole performed in between them. Furthermore, Hammett plot and density functional theory-based transition-state optimization studies showed substantial correlation of the electronic nature of the substituents at the C3 position of indoles with the rate of the N-H insertion reaction. The strategy was utilized to synthesize a key intermediate for the natural product (-)-psychotrimine.

Blue LED Induced Manganese (I) Catalysed Direct C2?H Activation of Pyrroles with Aryl Diazoesters

Herein, we have reported a blue LED mediated manganese pentacarbonyl bromide catalysed incorporation of carbene moieties from aryl diazoesters onto 1H-pyrroles via their selective C2?H activation. A manganese metal-carbene has been identified as the active catalyst to facilitate the reaction. Eighteen mono substituted pyrrole derivatives were isolated in good to excellent yields (67→82%) and the disubstituted products were also formed in minor quantities (5 to 8%). HPLC based kinetics study enabled optimization of the reaction. Control experiments, FT-IR, NMR and GC-MS based characterization elucidated the putative reaction mechanism. (Figure presented.).