56701-20-3

Usage

Stability

Highly stable and non-reactive
The compound is known for its resistance to chemical reactions and decomposition, making it suitable for use in various applications.

Cyclopropane ring structure

Unique and rigid
The compound features a three-membered carbon ring, which contributes to its high degree of rigidity and stability.

Usage in organic synthesis

Commonly used
1-Methyl-2,2-diphenylcyclopropane-1-carbonitrile is frequently used as a building block in the synthesis of various organic compounds.

Pharmaceutical research

Utilized in drug development
The compound is employed in pharmaceutical research for the development of new drugs due to its unique structural and chemical properties.

Chemical transformations

Ability to undergo various reactions
1-Methyl-2,2-diphenylcyclopropane-1-carbonitrile can participate in a range of chemical reactions, making it a versatile building block in synthesis.

Potential applications

New drugs and materials
The compound has potential applications in the development of novel pharmaceuticals and materials, thanks to its distinct properties.

InChI:InChI=1/C17H15N/c1-16(13-18)12-17(16,14-8-4-2-5-9-14)15-10-6-3-7-11-15/h2-11H,12H2,1H3

Upstream product

• 5350-57-2 benzophenone hydrazone 
• 126-98-7 methacrylonitrile 
• 83198-34-9 (S)-(+)-1-bromo-2,2-diphenyl-cyclopropylcarboxylic acid 
• 908093-98-1 diazodiphenylmethane 
• 19481-83-5 1-bromo-2,2-diphenylcyclopropanecarboxylic acid 
• 935853-52-4 (S)-(+)-1-bromo-2,2-diphenyl-cyclopropylcarboxamide 
• 935853-53-5 (S)-(+)-1-bromo-2,2-diphenyl-cyclopropanecarbonitrile 
• 74-88-4 methyl iodide 
• 4545-20-4 benzophenone tosylhydrazone 
• 28098-84-2 1-cyano-2,2-diphenylcyclopropane 
• 86456-50-0 (+/-)-1-methyl-2,2-diphenyl-cyclopropanecarboxylic acid amide 

Relevant academic research and scientific papers

The first enantioenriched metalated nitrile possessing macroscopic configurationat stability

Figure presented Magnesium - bromine exchange on enantiopure cyclopropyl bromonitrile 5 at -100°C for 1 min followed by a D2O quench gives the deuterionitrile in 81% ee (retention); additional trapping experiments establish t1/2(rac) = 11.4 h at -100°C. These experiments provide the first glimpse into the stereochemical aspects of Mg-Br exchange. The intermediate formed is the first metalated nitrile demonstrated to possess macroscopic configurational stability.

Reactions of tosylhydrazones of benzaldehyde and benzophenone with cyanoalkenes in a basic two-phase system

Reaction of tosylhydrazones 1a,b with cyanoalkenes 3a,b, carried out in the presence of concentrated aq. sodium hydroxide in dioxane, afforded either cyanocyclopropanes 5, 9 or pyrazoles 13, 14 and 16, 17. The process takes place via generation of diazocompounds 2a,b from 1a,b their [3+2] cycloaddition to 3a,b with the formation of unstable pyrazolines 4, further fate of which depends on the structure of R1 and R2 substituents.

Electrochemical Oxidation of Benzophenone Hydrazones

The anodic oxidation of benzophenone hydrazones (1) was found to give several products, depending upon the electrolysis conditions employed such as electrode material, temperature, and electrolyte composition.For example, the oxidation using a platinum anode at room temperature in LiClO4-MeCN afforded exclusively benzophenone azines (2), whereas in NaOMe-MeOH benzophenone dimethyl acetals (3) were formed as the main products.On the other hand, the oxidation using a graphite anode in refluxing MeOH containing NaOMe gave diphenylmethyl methyl ethers (4), along with diphenylmethanes (5).When the analogous electrolysis was conducted in the presence of methacrylic acid derivatives, corresponding diphenylcyclopropanes (7) were obtained in relatively high yields.