185147-06-2

Usage

Chemical Properties

Off-white crystalline

InChI:InChI=1/C8H6FN/c1-6-7(5-10)3-2-4-8(6)9/h2-4H,1H3

Upstream product

• 443-83-4 2-chloro-6-fluorotoluene 
• 7321-55-3 2,2-dimethylmalononitrile 
• 1422-54-4 1-bromo-3-fluoro-2-methyl-benzene 

Downstream Products

• 887266-95-7 3-fluoro-2-formylbenzonitrile 
• 1376769-20-8 C₁₇H₂₀BrFN₂O₂ 
• 1376769-18-4 C₁₆H₉FN₂O₂ 
• 635723-84-1 2-(bromomethyl)-3-fluorobenzonitrile 
• 1309386-92-2 C₂₆H₂₈FN₅O₄ 
• 1309377-26-1 C₂₆H₂₈FN₅O₄ 
• 1309377-58-9 C₁₄H₈ClFN₄ 
• 1309377-57-8 C₁₈H₂₀ClFN₄O₂ 
• 1309377-56-7 6-amino-3-fluoro-2-methylbenzonitrile 
• 742105-39-1 2-[2-(5-bromo-2-methoxy-phenyl)-ethyl]-3-fluoro-benzonitrile 

Relevant academic research and scientific papers

Transnitrilation from Dimethylmalononitrile to Aryl Grignard and Lithium Reagents: A Practical Method for Aryl Nitrile Synthesis

An electrophilic cyanation of aryl Grignard or lithium reagents, generated in situ from the corresponding aryl bromides or iodides, by a transnitrilation with dimethylmalononitrile (DMMN) was developed. DMMN is a commercially available, bench-stable solid. The transnitrilation with DMMN avoids the use of toxic reagents and transition metals and occurs under mild reaction conditions, even for extremely sterically hindered substrates. The transnitrilation of aryllithium species generated by directed ortho-lithiation enabled a net C-H cyanation. The intermediacy of a Thorpe-type imine adduct in the reaction was supported by isolation of the corresponding ketone from the quenched reaction. Computational studies supported the energetic favorability of retro-Thorpe fragmentation of the imine adduct. (Chemical Equation Presented).

Method for producing aromatic nitriles

PCT No. PCT/EP98/00696 Sec. 371 Date Aug. 17, 1999 Sec. 102(e) Date Aug. 17, 1999 PCT Filed Feb. 9, 1998 PCT Pub. No. WO98/37058 PCT Pub. Date Aug. 27, 1998A process for preparing aromatic nitriles from corresponding chloroaromatics by reaction with cyanides.