58814-69-0

Basic information

• Product Name: Benzonitrile, 4,5-dimethoxy-2-methyl-
• CAS NO: 58814-69-0
• Molecular Formula: C10H11NO2
• Molecular Weight: 177.203
• Mol File: 58814-69-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzonitrile, 4,5-dimethoxy-2-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzonitrile, 4,5-dimethoxy-2-methyl-(58814-69-0)
• EPA Substance Registry System: Benzonitrile, 4,5-dimethoxy-2-methyl-(58814-69-0)

Safety Data

• Hazardous Substances Data: 58814-69-0(Hazardous Substances Data)

Upstream product

• 4885-02-3 Dichloromethyl methyl ether 
• 494-99-5 1,2-dimethoxy-4-methylbenzene 
• 41864-45-3 4,5-dimethoxy-2-methylaniline 
• 52806-46-9 1-bromo-4,5-dimethoxy-2-methylbenzene 
• 544-92-3 copper(I) cyanide 

Downstream Products

• 63005-37-8 2-bromomethyl-4,5-dimethoxybenzonitrile 
• 1122570-42-6 2-dibromomethyl-4,5-dimethoxybenzonitrile 
• 577-68-4 m-hemipinic acid 
• 523-02-4 (S)-(-)-norcoralydine 
• 406215-59-6 Toluene-4-sulfonic acid 2-[2-((S)-6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinolin-3-yl)-4,5-dimethoxy-phenyl]-ethyl ester 
• 406215-98-3 (S)-(-)-3-[2-(2-benzyloxyethyl)-4,5-dimethoxyphenyl]-6,7-dimethoxy-3,4-dihydro-2H-isoquinolin-1-one 
• 406215-57-4 (S)-(-)-3-[2-(2-hydroxyethyl)-4,5-dimethoxyphenyl]-6,7-dimethoxy-3,4-dihydro-2H-isoquinolin-1-one 
• 406215-56-3 (S)-(-)-2-[2-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-3-yl)-4,5-dimethoxyphenyl]ethanol 
• 406215-55-2 (S)-(-)-2-[2-(6,7-dimethoxy-3,4-dihydroisoquinolin-3-yl)-4,5-dimethoxyphenyl]ethanol 
• 406215-72-3 2-Methoxy-naphthalene-1-sulfinic acid [(S)-1-[2-(2-benzyloxy-ethyl)-4,5-dimethoxy-phenyl]-2-(2-cyano-4,5-dimethoxy-phenyl)-ethyl]-amide 
• 406215-71-2 4-methyl-benzenesulfinic acid [1-{2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4,5-dimethoxy-phenyl}-2-(2-cyano-4,5-dimethoxy-phenyl)-ethyl]-amide 
• 113533-94-1 1-amino-6,7-dimethoxy-3-(dimethylamino)isoquinoline hydrochloride 

Relevant articles and documents

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.

Asymmetric synthesis of the protoberberine alkaloid (s)-(-)-xylopinine using enantiopure sulfinimines

A concise enantioselective synthesis of (S)-(-)-xylopinine (1) is described involving the addition of the laterally lithiated derivative of o-tolunitrile of 16 to enantiopure sulfinimine (+)-14. Treatment of the resulting cyano sulfinamide adduct (-)-17b with DIBAL-H accomplishes five operations in a single pot and furnishes the cyclic imine (+)-18 in good yield. Reduction and cyclization affords (S)-(-)-1. Alternatively basic hydrolysis of 17b,c gives isoquinolone 21 that is cyclized and reduced to give (S)-(-)-1.