144649-99-0

Usage

Chemical Properties

off-white crystalline

InChI:InChI=1/C8H6BrNO/c1-11-8-3-2-7(9)4-6(8)5-10/h2-4H,1H3

Upstream product

• 6609-56-9 2-methoxy-benzonitrile 
• 21702-84-1 2,4-dibromoanisole 
• 55305-43-6 N-cyano-N-phenyl-p-toluenesulfonamide 
• 14804-31-0 2-methyl-4-bromoanisole 
• 184970-28-3 4-bromo-2-(bromomethyl)-1-methoxybenzene 
• 67-56-1 methanol 
• 179897-89-3 5-Bromo-2-fluoro-benzonitrile 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 4885-02-3 Dichloromethyl methyl ether 
• 25016-01-7 5-bromo-2-methoxybenzaldehyde 

Downstream Products

• 334015-82-6 t-Butyl N-(5-bromo-2-methoxybenzyl)carbamate 
• 40530-18-5 5-bromo-2-hydroxybenzonitrile 
• 876918-26-2 5-bromo-2-isobutoxy-benzonitrile 
• 1139901-88-4 tert-butyl 2-(3’-cyano-4’-isobutoxyphenyl)-4-methylthiazole-5-carboxylate 
• 144060-53-7 febuxostat 
• 53078-70-9 2-methoxy-5-methylbenzonitrile 
• 166530-78-5 (5-bromo-2-methoxyphenyl)methanamine 
• 93-98-1 N-phenyl benzoyl amide 
• 1372135-20-0 5-(benzofuran-2-ylmethyl)-2-methoxybenzonitrile 
• 1372135-15-3 5-(benzo[b]thiophen-2-ylmethyl)-2-methoxybenzonitrile 
• 1292317-73-7 tert-butyl N-[4-[[4-(3-cyano-4-methoxy-phenyl)pyrimidin-2-yl]amino]phenyl]carbamate 
• 1292317-51-1 5-(2-chloropyrimidin-4-yl)-2-methoxybenzonitrile 
• 1220219-22-6 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile 
• 956125-10-3 2-(5-Bromo-2-methoxy-phenyl)-pyrimidin-4-ol 

Relevant academic research and scientific papers

Mechanistic study on iodine-catalyzed aromatic bromination of aryl ethers by N-Bromosuccinimide

Although iodine-catalyzed reaction has rapid advances in recent years, examples on iodine-catalyzed bromination are rare and the mechanism of these reactions remains unclear. Herein, we reported an I2-catalyzed aromatic bromination of aryl ethers by NBS and presented the details of the mechanistic study including kinetic study and the study of kinetic isotope effects. The study revealed that the reaction was actually catalyzed by IBr formed in the induction period, and the rate-determining step was the HBr-elimination of the Wheland intermediate assisted by IBr.

Facile one-pot transformation of arenes into aromatic nitriles under metal-cyanide-free conditions

Electron-rich arenes bearing methyl or methoxy groups on the aromatic ring were treated with dichloromethyl methyl ether and ZnBr2, and then with molecular iodine and aq. ammonia to give the corresponding aromatic nitriles in good yields. Using this method, febuxostat was efficiently prepared from 4-bromophenol in four steps. The method can be used for the preparation of aromatic nitriles from arenes in one pot under metal-cyanide-free conditions. Various electron-rich arenes could be effectively converted into the corresponding aromatic nitriles in good yields, by treatment with ZnBr2 and dichloromethyl methyl ether, followed by reaction with molecular iodine and aq. ammonia.

A highly efficient electrochemical route for the conversion of aldehydes to nitriles

Using NH4I as the supporting electrolyte as well as the precursor of an I2 promoter and nitrogen source, a highly efficient electrochemical route was developed to convert aldehydes to nitriles with excellent yields under mild reaction conditions. This electrochemical process could effectively avoid the direct use of NH3 gas, molecular iodine, and oxidants.

One-pot transformation of methylarenes into aromatic nitriles with inorganic metal-free reagents

Various methylarenes were transformed into the corresponding aromatic nitriles in good to moderate yields by the treatment with aq. HBr and aq. H 2O2, followed by reaction with molecular iodine and aq. ammonia in a one-pot procedure. The present reaction is a useful, practical, transition-metal-free, and organic-reagent-free method for the preparation of aromatic nitriles from methylarenes. Various methylarenes were treated with aq. HBr and aq. H2O2 under warming conditions and/or irradiation conditions, followed by the reaction with molecular iodine and aq. ammonia, to provide the corresponding aromatic nitriles, in a one-pot procedure. The present reaction was carried out under metal-free and organic-reagent-free conditions. Copyright

Mild and general palladium-catalyzed synthesis of methyl aryl ethers enabled by the use of a palladacycle precatalyst

A general method for the Pd-catalyzed coupling of methanol with (hetero)aryl halides is described. The reactions proceed under mild conditions with a wide range of aryl and heteroaryl halides to give methyl aryl ethers in high yield.

Direct oxidative conversion of methylarenes into aromatic nitriles

A variety of methylarenes were successfully converted into the corresponding aromatic nitriles in good to moderate yields by the treatment with NBS or DBDMH in the presence of a catalytic amount of AIBN or BPO, followed by the reaction with molecular iodine in aq NH3 in a one-pot procedure. The present reaction is a useful and practical transition-metal-free method for the preparation of aromatic nitriles from methylarenes.

A novel and convenient synthesis of benzonitriles: Electrophilic cyanation of aryl and heteroaryl bromides

N-Cyano-N-phenyl-p-methylbenzenesulfonamide has been used as a more benign electrophilic cyanation reagent for the synthesis of various benzonitriles from (hetero)aryl bromides via formation of Grignard reagents. Electronically different and sterically demanding aryl bromides including functionalized substrates and heteroaryl bromides are successfully cyanated in good to excellent yields. The efficiency of the present methodology is shown by the expeditious syntheses of interesting pharmaceutical intermediates. Notably, chemoselective monocyanation of dibromoarenes is also achieved. Copyright

Dual Pharmacophores - PDE4-Muscarinic Antagonistics

The present invention is directed to novel compounds of Formula (I) and pharmaceutically acceptable salts thereof, pharmaceutical compositions and their use as dual chromaphores having inhibitory activity against PDE4 and muscarinic acetylcholine receptors (mAChRs), and thus being useful for treating respiratory diseases.

Dual Pharmacophores - PDE4-Muscarinic Antagonistics

The present invention relates to novel compounds of Formula (I) and their use in the treatment of respiratory diseases, including anti-inflammatory and allergic diseases such as chronic obstructive pulmonary disease (COPD), asthma, rhinitis (e.g. allergic rhinitis), atopic dermatitis or psoriasis.

Dual Pharmacophores - PDE4-Muscarinic Antagonistics

The present invention is directed to novel compounds of Formula (I), pharmaceutical compositions and their use in therapy, for example as inhibitors of phosphodiesterase type IV (PDE4) and as antagonists of muscarinic acetylcholine receptors (mAChRs), in the treatment of/and or prophylaxis of respiratory diseases, including antiinflammatory and/or allergic diseases such as chronic obstructive pulmonary disease (COPD), asthma, rhinitis (e.g. allergic rhinitis), atopic dermatitis or psoriasis.