2785-95-7

Basic information

• Product Name: 3-lithio-1,2-dimethoxybenzene
• Synonyms: 3-lithio-1,2-dimethoxybenzene
• CAS NO: 2785-95-7
• Molecular Weight: 144.099
• Mol File: 2785-95-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3-lithio-1,2-dimethoxybenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 3-lithio-1,2-dimethoxybenzene(2785-95-7)
• EPA Substance Registry System: 3-lithio-1,2-dimethoxybenzene(2785-95-7)

Safety Data

• Hazardous Substances Data: 2785-95-7(Hazardous Substances Data)

Upstream product

• 91-16-7 1,2-dimethoxybenzene 

Downstream Products

• 500300-69-6 1-(2,3-Dimethoxy-phenyl)-cyclohexanol 
• 854716-02-2 2-(2,3-dimethoxy-phenyl)-2-hydroxy-cyclohexanone 
• 139290-71-4 4-(2,3-Dimethoxybenzoyl)-1-piperidinecarboxylic acid 1,1-dimethylethyl ester 
• 243640-28-0 4-(2,3-dimethoxybenzoyl)pyridine 
• 243640-27-9 4-[1-hydroxy-1-(2,3-dimethoxyphenyl)methyl]pyridine 
• 93013-75-3 4-(2,3-dimethoxy-phenyl)-cinnoline 
• 109313-57-7 3-cinnolin-4-yl-pyrocatechol 
• 102555-20-4 3-indol-3-yl-pyrocatechol 
• 82359-73-7 C₂₀H₂₇NO₃ 
• 82359-65-7 (1S,4aR,8aS)-4a-(2,3-Dimethoxy-phenyl)-2-methyl-6-methylene-decahydro-isoquinoline-1-carbaldehyde 
• 82359-74-8 C₂₀H₂₇NO₂ 
• 82359-64-6 4-(4-Bromo-2-methylene-butyl)-4-(2,3-dimethoxy-phenyl)-1-methyl-1,2,3,4-tetrahydro-pyridine 
• 83999-52-4 4a-(2,3-Dimethoxy-phenyl)-2-methyl-6-methylene-2,3,4,4a,5,6,7,8-octahydro-isoquinoline 
• 82359-63-5 4-(2,3-Dimethoxyphenyl)-1,2,3,6-tetrahydro-1-methyl-pyridine 

Relevant articles and documents

Ortho-lithiations reassessed: The advantages of deficiency catalysis in hydrocarbon media

Hydrocarbon media based metalation procedures involving "deficiency catalysis" are described for the ortho-lithiation of anisole (A), p-chloroanisole (p-ClA), o-, m-, p-methylanisoles (o-, m-, p-MA), the three dimethoxybenzenes (DMB's), dimethylaniline (DMA), dimethybenzylamine (DMBA), m-methoxydimethylaniline (m-MeODMA), and tetramethyl-p-phenylenediamine (p-TMPDA). These procedures involve certain mechanistic considerations, which must be fine-tuned to maximize the extent of metalation (EoM). Our working hypothesis is that a controlled deoligomerization of the n-BuLi hexamer found in hydrocarbon media will afford a "sweet spot" of deoligomerization such that a maximally efficient metalation medium can be formed. In many cases, a substoichiometric ratio of equivalent TMEDA to n-BuLi is 0.1-0.2:1.0, but certain substrates suffer multiple sites of metalation under these conditions, so different promoted hydrocarbon media systems incorporating measured equivalents of an ether have been formulated. This paper represents the summary of our successful efforts to render ortho-lithiations safer, greener, and more atom-economical by use of hydrocarbon solvent media. EoM's of 11 of the 12 substrates under these atom-economical conditions range from 87 to 97%.

Nucleophilic photosubstitutions of o-methoxynitrobenzenes

We report a new synthesis of 3-nitroveratrole, based on the directed lithiation of veratrole, and photochemical substitutions of both 3-nitroveratrole and o-nitroanisole with several nucleophiles.Both aromatic substrates undergo photocyanation meta to the nitro group.With hydroxide ion, 3-nitroveratrole reacts meta to the nitro group, but 2-nitroanisole undergoes replacement of either substituent, the proportion of reaction at each site depending upon the OH(-) concentration. 3-Nitroveratrole undergoes an inefficient reaction with butylamine at each methoxy group; this reaction is apparently second order in amine.The reaction between o-nitroanisole and diethylamine results only in photohydrolysis.Keywords: photosubstitution, nucleophilic, 3-nitroveratrole, o-nitroanisole