65864-99-5

Basic information

• Product Name: Benzene, 1-(diazomethyl)-3-methoxy-
• CAS NO: 65864-99-5
• Molecular Formula: C8H8N2O
• Molecular Weight: 148.164
• Mol File: 65864-99-5.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Benzene, 1-(diazomethyl)-3-methoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-(diazomethyl)-3-methoxy-(65864-99-5)
• EPA Substance Registry System: Benzene, 1-(diazomethyl)-3-methoxy-(65864-99-5)

Safety Data

• Hazardous Substances Data: 65864-99-5(Hazardous Substances Data)

Upstream product

• 591-31-1 3-methoxy-benzaldehyde 
• 108087-83-8 [(3-methoxyphenyl)methylidene]hydrazine 
• 19350-71-1 N'-(3-methoxybenzylidene)-4-methylbenzenesulfonohydrazide 

Downstream Products

• 1263474-96-9 3'-(3-methoxyphenyl)-1,3,3-trimethylspiro[bicyclo[2.2.1]heptane-2,2'-thiirane] 
• 1278594-27-6 (S)-2-(3-methoxyphenyl)cyclooctanone 

Relevant articles and documents

Continuous Flow Synthesis and Purification of Aryldiazomethanes through Hydrazone Fragmentation

Electron-rich diazo compounds, such as aryldiazomethanes, are powerful reagents for the synthesis of complex structures, but the risks associated with their toxicity and instability often limit their use. Flow chemistry techniques make these issues avoidable, as the hazardous intermediate can be used as it is produced, avoiding accumulation and handling. Unfortunately, the produced stream is often contaminated with other reagents and by-products, making it incompatible with many applications, especially in catalysis. Herein is reported a metal-free continuous flow method for the production of aryldiazomethane solutions in a non-coordinating solvent from easily prepared, bench-stable sulfonylhydrazones. All by-products are removed by an in-line aqueous wash, leaving a clean, base-free diazo stream. Three successful sensitive metal-catalyzed transformations demonstrated the value of the method.

Iterative reactions of transient boronic acids enable sequential C-C bond formation

The ability to form multiple carbon-carbon bonds in a controlled sequence and thus rapidly build molecular complexity in an iterative fashion is an important goal in modern chemical synthesis. In recent times, transition-metal-catalysed coupling reactions

Cyclopropanation using flow-generated diazo compounds

We have devised a room temperature process for the cyclopropanation of electron-poor olefins using unstabilised diazo compounds, generated under continuous flow conditions. This protocol was applied to a wide range of different diazo species to generate f