70135-28-3

Upstream product

• 87829-00-3 4-(hydrazonomethyl)benzonitrile 
• 105-07-7 4-cyanobenzaldehyde 
• 41780-79-4 N'-(4-cyanobenzylidene)-4-methylbenzenesulfonohydrazide 

Downstream Products

• 121829-30-9 4-((1S,4S,5R,6R,7S)-6-Chloro-7-methylsulfanyl-2,3-diaza-bicyclo[3.2.0]hept-2-en-4-yl)-benzonitrile 
• 121829-29-6 4-((1S,4S,5R,6R,7S)-7-Chloro-6-methylsulfanyl-2,3-diaza-bicyclo[3.2.0]hept-2-en-4-yl)-benzonitrile 
• 121829-43-4 4-((1S,4S,5R,6R,7S)-6,7-Bis-methylsulfanyl-2,3-diaza-bicyclo[3.2.0]hept-2-en-4-yl)-benzonitrile 
• 874-89-5 4-Cyanobenzyl alcohol 
• 16473-21-5 1-cyano-4-(fluoromethyl)benzene 
• 88584-52-5 4,4'-(oxydimethylene)dibenzonitrile 
• 4381-02-6 1,2-bis-(4-cyanophenyl)ethane 
• 98446-88-9 4-(2-Hydroxy-2-methyl-propyl)-benzonitrile 
• 98446-86-7 4-isopropoxymethylbenzonitrile 
• 104-85-8 para-methylbenzonitrile 
• 6292-62-2 4,4'-dicyano-stilbene 
• 68861-51-8 bis-(4-cyano-benzylidene)-hydrazine 
• 98446-82-3 4-(cyclohexylmethyl)benzonitrile 
• 98446-76-5 C₁₄H₁₇N 

Relevant academic research and scientific papers

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.

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.

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.

Novel Liquid Crystalline Compounds Containing Bicyclo[3.1.0]hexane Core Units

Additions of ethyl or tert-butyl diazoacetates to 4-substituted cyclopentenes 6 and 17 under dirhodium tetraacetate/tetraoctanoate catalysis led to mixtures of tert-butyl endo,exo- and exo,exo-3-carboxyl(aryl)bicyclo[3.1.0]hexane-6-carboxylates 7 and 18 in yields of 54-90% from which exo,exo-diastereomers were isolated in yields of 39-63%. Diester exo,exo-7 was saponified and converted into diaryl diesters exo,exo-9a, b in overall yields of 42 and 46%, respectively. The esters exo,exo-18 were reduced to the corresponding hydroxymethyl derivatives, these were transformed to the iodomethyl compounds which in turn were coupled with various alkylmagnesium halides, via Li2CuCl4 catalysis, to give 3-aryl-6-alkylbicyclo[3.1.0]hexyl derivatives exo,exo-21 in overall yields of 72-83%. Fluorinated 3-(2-arylethyl)-6-pentylbicyclo[3.1.0]hexane exo,exo-32 could be prepared in five steps from 4-ethoxy-2,3-difluorobenzaldehyde 26a adopting essentially the same synthetic strategy, but in an overall yield of only 8%, and 6-(4-cyanophenyl)-3-pentylbicyclo[3.1.0]hexane exo,exo-38b was obtained by Pd(OAc)2 catalyzed cyclopropanation of 4-pentylcyclopentene 34b with (4-cyanophenyl)diazomethane 36b in 29% yield. A comparison of the liquid crystalline properties of these newly prepared compounds containing a bicyclo[3.1.0]hexane core with those of the known analogous compounds with a cyclohexane fragment shows that as a rule, a bicyclo[3.1.0]hexane moiety decreases the transition temperature, while the dielectric (Δε) and optical (Δn) anisotropies are comparable. However, the bicyclo[3.1.0]hexane unit has a poorer mesogenic potential, Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

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