73900-14-8

Basic information

• Product Name: 1-bromo-4-(diazomethyl)benzene
• Synonyms: 1-bromo-4-(diazomethyl)benzene
• CAS NO: 73900-14-8
• Molecular Weight: 197.034
• Mol File: 73900-14-8.mol

Chemical Properties

• CAS DataBase Reference: 1-bromo-4-(diazomethyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-bromo-4-(diazomethyl)benzene(73900-14-8)
• EPA Substance Registry System: 1-bromo-4-(diazomethyl)benzene(73900-14-8)

Safety Data

• Hazardous Substances Data: 73900-14-8(Hazardous Substances Data)

Upstream product

• 1122-91-4 4-bromo-benzaldehyde 
• 57477-93-7 hydrazone of p-bromobenzaldehyde 
• 19350-68-6 p-bromobenzaldehyde tosylhydrazone 

Downstream Products

• 1007090-51-8 N-(4-bromophenyl)-2-methyl-2-phenylaziridine 
• 40155-54-2 ethyl 4-(4-bromophenyl)-2,4-dioxobutanoate 
• 1064075-16-6 C₁₂H₁₂BrNO₃ 

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.

Adiabatic process of higher electronically excited states: luminescence from an excited state biradical generated by irradiation of benzophenone-substituted cyclopropanes

Adiabatic photochemical reactions of cyclopropanes possessing a benzophenone moiety (trans- and cis-5), which generate a luminescent excited biradical 16??*, were studied. Various photochemical and spectroscopic techniques were used for this purpose. Excitation (350 nm, n,π* band) of 5 at 77?K affords the lowest excited state 15* that undergoes intersystem crossing to form 35*, which deactivates through phosphorescence. In contrast, 295-nm excitation (π,π* band) of 5 affords the higher electronically excited state 15**, which undergoes adiabatic C–C bond cleavage reaction to form the excited biradical 16??* that luminesces at 630?nm. The results suggest that 5 follows 2 photoreaction modes depending on the excitation wavelength, a finding that disobeys Kasha's rule.

Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow-Generated Diazo Compounds and Propargylated Amines

We report herein the asymmetric coupling of flow-generated unstabilized diazo compounds and propargylated amine derivatives, using a new pyridinebis(imidazoline) ligand, a copper catalyst and base. The reaction proceeds rapidly, generating chiral allenes in 10–20 minutes with high enantioselectivity (89–98 % de/ee), moderate yields and a wide functional group tolerance.

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

SMALL MOLECULE LFA-1 INHIBITORS

The present invention relates to novel compounds which are capable of inhibiting the interaction of LFA-1 with its counter ligands.

A Versatile Room-Temperature Route to Di- and Trisubstituted Allenes Using Flow-Generated Diazo Compounds

A copper-catalyzed coupling reaction between flow-generated unstabilized diazo compounds and terminal alkynes provides di- and trisubstituted allenes. This extremely mild and rapid transformation is highly tolerant of several functional groups. Well tolerated: A mild copper-catalyzed coupling reaction between unstabilized diazo compounds (generated in flow) and terminal alkynes is reported. The method provides di- and trisubstituted allenes with high functional-group tolerance.

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

THE SYNTHESIS OF ARYL DIAZOMETHANES

A convenient and rapid method for preparing aryldiazomethanes from the related tosylhydrazones employing phase transfer catalysis with hydrocarbon solvents in good to excellent yields has been developed.

Regioselectivity in the Addition of Singlet and Triplet Carbenes to 1,1-Dimethylallene. A Probe for Carbene Multiplicity

Singlet carbenes add preferentially to the more substituted bond of 1,1-dimethylallene (1), to give methylenecyclopropanes 3 as the major product.In contrast, many triplet carbenes add with differing regioselectivity, giving the thermodynamically preferre