758692-47-6

Basic information

• Product Name: Ethyl 2-(4-bromophenyl)-2-diazoacetate
• Synonyms: ETHYL 2-(4-BROMOPHENYL)-2-DIAZOACETATE;4-Bromo-alpha-diazobenzeneacetic acid ethyl ester
• CAS NO: 758692-47-6
• Molecular Formula: C₁₀H₉BrN₂O₂
• Molecular Weight: 269.09
• Mol File: 758692-47-6.mol
• Article Data: 41

Chemical Properties

• Melting Point: 54 °C
• Appearance: /
• CAS DataBase Reference: Ethyl 2-(4-bromophenyl)-2-diazoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 2-(4-bromophenyl)-2-diazoacetate(758692-47-6)
• EPA Substance Registry System: Ethyl 2-(4-bromophenyl)-2-diazoacetate(758692-47-6)

Safety Data

• Hazardous Substances Data: 758692-47-6(Hazardous Substances Data)

Usage

General Description

Ethyl 2-(4-bromophenyl)-2-diazoacetate, also known as ethyl 2-(4-bromophenyl)-2-diazoacetoacetate, is a chemical compound that belongs to the diazoacetate family. It is commonly used as a reagent in organic synthesis, specifically in the diazo transfer reactions to generate carbenes. Carbenes are highly reactive intermediates that are important in the formation of new carbon-carbon and carbon-heteroatom bonds in organic chemistry. The 4-bromophenyl group in this compound makes it useful for the functionalization of aromatic rings, and its diazoacetate moiety provides a convenient entry to a wide range of versatile chemical transformations. Due to its reactivity and potential hazards associated with diazo compounds, it should be handled with caution under appropriate safety protocols.

InChI:InChI=1/C10H9BrN2O2/c1-2-15-10(14)9(13-12)7-3-5-8(11)6-4-7/h3-6H,2H2,1H3

Upstream product

• 14062-25-0 Ethyl 4-bromophenylacetate 
• 623-73-4 diazoacetic acid ethyl ester 
• 589-87-7 1,4-bromoiodobenzene 
• 2009-97-4 ethyl 2-diazo-3-oxobutanoate 
• 37859-24-8 2-(4-bromophenyl)acetyl chloride 
• 1878-68-8 2-(4-bromophenyl)-acetic acid 
• 108-86-1 bromobenzene 
• 20201-26-7 ethyl 4-bromophenylglyoxylate 
• 2158-14-7 4-acetamidobenzenesulfonyl azide 

Downstream Products

• 1398180-76-1 ethyl 2-(4-bromophenyl)-3,3,3-trifluoropropanoate 
• 1427218-41-4 ethyl 1-(4-bromophenyl)-3-oxoisoindoline-1-carboxylate 
• 1448726-18-8 ethyl 2-(4-bromophenyl)-3-(4-methoxyphenyl)-3-methylbutanoate 
• 1448726-21-3 ethyl 2-(4-bromophenyl)-3-methyl-3-phenylbutanoate 
• 1448726-17-7 ethyl 2-(4-bromophenyl)-3-methyl-3-(4-methylphenyl)butanoate 
• 1609003-55-5 ethyl 2-(4-bromophenyl)-2-(4-hydroxyphenyl)acetate 
• 1609003-83-9 ethyl 2-(4-bromophenyl)-2-(2-hydroxy-5-methylphenyl)acetate 
• 1609003-85-1 3-(4-bromophenyl)-5-methylbenzofuran-2(3H)-one 
• 1644247-68-6 ethyl 2-(4-bromophenyl)-2-(phenylsulfanyl)acetate 
• 1454928-62-1 ethyl 2-acetoxy-2-(4-bromophenyl)acetate 
• 20201-26-7 ethyl 4-bromophenylglyoxylate 

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By using a charcoal supported nano Cu0catalyst (Cu/C), a highly efficient oxidation of α-diazo esters to α-ketoesters with molecular oxygen as the sole oxidant has been developed. In the presence of the Cu/C catalyst, 2-aryl-α-diazo esters with both electron-donating and electron-withdrawing groups can be oxidized to the corresponding α-ketoesters efficiently. Furthermore, this Cu/C catalyst can catalyse the reaction of aryl α-diazo ester with water to form aryl ketoester, 2-aryl-2-hydroxyl acetate ester and 2-aryl acetate ester. In this case, water is split by α-diazo ester, and the diazo group is displaced by the oxygen or hydrogen atom in water. Mechanistic investigation showed that the reaction of α-diazo ester with oxygen proceeds through a radical pathway. In the presence of 2,2,6,6-tetramethyl piperidine nitrogen oxide, the reaction of α-diazo ester with oxygen is dramatically inhibited. Furthermore, the reaction of α-diazo ester with water is investigated by an isotopic tracer method, and GCMS detection showed that a disproportionation reaction occurred between α-diazo ester and water.