20469-65-2

Usage

Chemical Properties

Pale yellow crystals

Uses

Different sources of media describe the Uses of 20469-65-2 differently. You can refer to the following data:
1. 1-Bromo-3,5-dimethoxybenzene may be used to synthesize the following:bis-[di-(3,5-dimethoxyphenyl)methylcyclopentadienyl]titanium(IV)dichloride,{η5 - C5H4-CH-[C6H4-(OCH3)2]2)2TiCl2 which can be used as an anti-cancer drug and is obtained via a multistep reaction process5-bromo-benzene-1,3-diol via demethylation with boron tribromide(BBr3)1-bromo-3,5-dimethoxy-2-nitrobenzene via nitration reaction
2. 1-Bromo-3,5-dimethoxybenzene is used as an intermediate in the synthetic preparation of pharmaceutical inhibitors via cross-coupling reactions.

General Description

1-Bromo-3,5-dimethoxybenzene can be synthesized by using 1,3-dimethoxybenzene via iridium-catalyzed arene borylation.

InChI:InChI=1/C8H9BrO2/c1-10-7-3-6(9)4-8(5-7)11-2/h3-5H,1-2H3

Upstream product

• 855400-66-7 3-bromo-5-methoxyphenol 
• 77-78-1 dimethyl sulfate 
• 151-10-0 1,3-Dimethoxybenzene 
• 17213-57-9 3,5-dimethoxybenzoyl chloride 
• 626-39-1 1,3,5-trisbromobenzene 
• 124-41-4 sodium methylate 
• 1132-21-4 3,5-dimethoxybenzoic acid 
• 365564-07-4 3,5-dimethoxyphenylboronic acid pinacol ester 
• 10272-07-8 3.5-dimethoxyaniline 

Downstream Products

• 82994-19-2 3,5-dimethoxyphenyl phenyl ether 
• 106120-04-1 5-bromoresorcinol 
• 17988-28-2 1,3-dimethoxy-5-(trimethylsilyl)benzene 
• 112221-35-9 C₁₆H₁₈O₅ 
• 127973-08-4 1-[1-(3,5-Dimethoxy-phenyl)-cyclohexyl]-1,2,3,6-tetrahydro-pyridine 
• 134591-94-9 N-(3',5'-dimethoxyphenyl)-2,5-dimethyl-N-toluene-p-sulfonylaniline 
• 137744-67-3 N-(4-methoxyphenyl)-4-(3,5-dimethoxyphenyl)-3-butenamide 
• 137744-74-2 N-(4-methoxyphenyl)-4,4-bis(3,5-dimethoxyphenyl)-3-butenamide 
• 82079-96-7 (1S,3aS,4S,7aS)-1-tert-Butoxy-4-<(1R)-1-cyan-2-(3,5-dimethoxyphenyl)ethyl>-5,5-(ethylendioxy)-2,3,3a,4,5,6,7,7a-octahydro-7a-methyl-1H-inden 
• 75019-06-6 (1S,3aS,4S,7aS)-1-tert-Butoxy-4-<(1S)-1-cyan-2-(3,5-dimethoxyphenyl)ethyl>-5,5-(ethylendioxy)-2,3,3a,4,5,6,7,7a-octahydro-7a-methyl-1H-inden 
• 81574-72-3 1-bromo-2-chloro-3,5-dimethoxybenzene 
• 84144-31-0 1,2-bis(3,5-dimethoxyphenyl)ditellane 
• 81574-69-8 2-bromo-4,6-dimethoxybenzaldehyde 
• 160757-57-3 N-acetyl-N-(3',5'-dimethoxyphenyl)-4-cyano-2,5-dimethylaniline 

Relevant academic research and scientific papers

Short-step synthesis of a resveratrol derivative from commercially available1,3-dimethoxybenzene and 4-vinylanisole

An efficient synthesis of tri-O-methylated resveratrol is presented using an advanced Heck reaction promoted by Pd(dba)2 in the presence of P(t-Bu)3.

Meta halogenation of 1,3-disubstituted arenes via iridium-catalyzed arene borylation

We report the meta halogenation of 1,3-disubstituted arenes to form 3,5-disubstituted aryl bromides and chlorides by using iridium-catalyzed arene borylation chemistry. Iridium-catalyzed borylation of arenes with B2pin2, followed by reaction of the boronic ester with copper(II) bromide or chloride converts arylboronic esters to the corresponding aryl halides. A variety of arenes containing alkoxy, alkyl, halogen, nitrile, ester, amide, and pivaloyl and TIPS-protected alcohols were converted to the corresponding 3,5-disubstituted aryl bromides and chlorides in yields ranging from 46% to 85%. In addition, 2,6-disubstituted and 3-substituted pyridines were converted to the 4-halo and 5-halopyridines, respectively. The utility of this methodology was demonstrated by the formal conversion of nicotine to Altinicline in three steps with an overall yield of 61% using meta bromination of nicotine as the first step. Copyright

Solvolysis of methoxy-substituted diaryliodonium tetrafluoroborates: Attempted generation of a stabilized aryl cation

Solvolyses of monomethoxy- and dimethoxyphenyl(phenyl)iodonium (ArI +Ph) tetrafluoroborates were carried out in methanol and 2,2,2-trifluoroethanol (TFE) at 130°C. The solvolysis products include alkoxide substitution products (ArOR and PhOR) as well as iodoarenes (PhI and ArI). The ratios of ArOR/PhOR range from 8/2 to 4/6. The results are argued against formation of aryl cation. Copyright

Model studies towards liquid crystalline dendrimers with mesogenic repeat units throughout the structure

Model studies towards liquid crystal dendrimers in which the mesogenic units are based on alkoxyalkylbiphenyls and repeat through the structure are described; the parent monomers show smectic mesophases demonstrating the suitability of the motifs.

Grindstone chemistry: (Diacetoxyiodo)benzene-mediated oxidative nuclear halogenation of arenes using NaCl, NaBr or I2

A technique of "Grindstone chemistry" is applied to the solvent-free halogenation of arenes with NaCl, NaBr or I2 using (diacetoxyiodo)benzene as the oxidant. Improved yields and higher purities of the products are observed compared with those from established methods.

Adamantyl cannabinoids: A novel class of cannabinergic ligands

Structure-activity relationship studies have established that the aliphatic side chain plays a pivotal role in determining the cannabinergic potency of tricyclic classical cannabinoids. We have now synthesized a series of analogues in which a variety of a

Estrogen Receptor-beta ligands

A method for treating a disease associated with the estrogen receptor-β, comprising the step of administiering a therapeutically-effective amount of a compound that satifies the equation: KiαA/KiβA>25, optionally having general structure (I).

The photochemistry of 1-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)ethyl ethanoate in alcohol solvents: A search for carbocation rearrangements

The photochemistry of the title compound 1 in methanol and 2,2,2-trifluoroethanol has been examined. In both solvents two ether products were obtained: one (18) resulting from trapping of the carbocation 2 (expected from photosolvolysis of 1), and the other (19) from the carbocation 3 (expected after rearrangement by hydride migration of cation 2). The substituted trans- and cis-stilbene derivatives 20 and 21 were also primary pbotoproducts. Analysis of product yields as a function of time revealed that the ether product 19 was formed by secondary photolysis of the stilbene derivatives, presumably by a pathway involving excited state protonation. Nanosecond laser flash photolysis results demonstrated that substituted trans-stilbene 20 was produced on the same time scale as the laser pulse.

Synthesis of 5-substituted resorcinol derivatives via cross-coupling reactions

Suzuki and Stille cross-coupling reactions were utilized in the synthesis of 5-substituted 1,3-dimethoxybenzerie and 5-substituted resorcinol derivatives. The substituted resorcinol derivatives were obtained in only three steps from inexpensive reagents. 1,3-Dimethoxybenzoic acid and 1-chloro-3,5-dimethoxybenzene were transformed into 1-iodo-, 1-bromo-, 1-trimethyltin-3,5-dimethoxybenzene and 3,5-dimethoxyphenyl boronic acid. 5-Allyl-1,3-dimethoxybenzene and 3,5-dimethoxybiphenyl derivatives were obtained via cross coupling reactions under mild conditions. HI, BBr3 and AlI3 were used to demethylate these dimethoxybenzenes into their resorcinol derivatives.