80866-82-6

Usage

Chemical Properties

white to light yellow crystal powder

InChI:InChI=1/C8H9BrO2/c1-11-8-3-2-7(9)4-6(8)5-10/h2-4,10H,5H2,1H3

Upstream product

• 7017-52-9 4-bromo-2-(chloromethyl)-1-methoxybenzene 
• 25016-01-7 5-bromo-2-methoxybenzaldehyde 
• 2316-64-5 5-bromo-2-hydroxybenzyl alcohol 
• 74-88-4 methyl iodide 
• 612-16-8 (2-methoxyphenyl)methanol 
• 1711-09-7 3-bromobenzoyl chloride 
• 1638287-10-1 5-bromo-2-methoxy-N-(4-methylbenzenesulfonyl)benzenecarboxamide 
• 630050-32-7 3-bromo-N-(4-methylbenzenesulfonyl)benzenecarboxamide 
• 1638291-19-6 5-bromo-2-methoxy-N-methyl-N-(4-methylbenzenesulfonyl)benzenecarboxamide 

Downstream Products

• 7017-52-9 4-bromo-2-(chloromethyl)-1-methoxybenzene 
• 916441-62-8 [2-(5-bromo-2-methoxy-benzyloxymethoxy)-ethyl]-trimethyl-silane 
• 201150-66-5 [(5-bromo-2-methoxyphenyl)methoxy]dimethyl(1,1-dimethylethyl)silane 
• 184970-28-3 4-bromo-2-(bromomethyl)-1-methoxybenzene 
• 7062-40-0 1-(cyanomethyl)-2-methoxy-6-bromobenzene 
• 149488-99-3 2-(2-methoxy-5-bromophenyl)-1-aminoethane 
• 163813-58-9 N-<2-(2-methoxy-5-bromophenyl)ethyl>acetamide 
• 1009303-77-8 [2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanol 
• 1227833-80-8 3-(3-hydroxymethyl-4-methoxyphenyl)pyridine 
• 114303-65-0 2-allyl-4-bromo-1-methoxybenzene 
• 68592-15-4 methylhonokiol 
• 1396506-65-2 di-tert-butyl(3-((tert-butyldimethylsilyloxy)methyl)-4-methoxyphenyl)fluorosilane 
• 1396506-75-4 (5-(di-tert-butylfluorosilyl)-2-methoxyphenyl)methanol 
• 1396506-79-8 5-(di-tert-butylfluorosilyl)-2-methoxybenzaldehyde 

Relevant academic research and scientific papers

Dehydroxymethyl Bromination of Alkoxybenzyl Alcohols by Using a Hypervalent Iodine Reagent and Lithium Bromide

We describe the dehydroxymethylbromination of alkoxybenzyl alcohol by using a hypervalent iodine reagent and lithium bromide in F 3 CCH 2 OH at room temperature. Selective monobromination or dibromination was possible by adjusting the molar ratios of hypervalent iodine reagent and lithium bromide.

Room-temperature ortho-alkoxylation and -halogenation of N-tosylbenzamides by using palladium(II)-catalyzed C-H activation

The N-tosylcarboxamide group can direct the room-temperature palladium-catalyzed C-H alkoxylation and halogenation of substituted arenes in a simple and mild procedure. The room-temperature stoichiometric cyclopalladation of N-tosylbenzamide was first studied, and the ability of the palladacycle to react with oxidants to form C-X and C-O bonds under mild conditions was demonstrated. The reaction conditions were then adapted to promote room-temperature ortho-alkoxylations and ortho-halogenations of N-tosylbenzamides using palladium as catalyst. The scope and limitation of both alkoxylations and halogenations was studied and the subsequent functional transformation of the N-tosylcarboxamide group through nucleophilic additions was evaluated. This methodology offers a simple and mild route to diversely functionalized arenes.

New method of synthesis and biological evaluation of some combretastatin A-4 analogues

A series of novel combretastatin A-4 analogues was synthesized in 36-64% yields by Negishi cross-coupling reaction under mild conditions. The prepared compounds exhibit good cytotoxicity against HBL100 epithelial cell lines (IC50=0.022-10.31 ). Georg Thieme Verlag Stuttgart · New York.

T-Bu2SiF-derivatized D2-receptor ligands: The first SiFA-containing small molecule radiotracers for target-specific PET-imaging

The synthesis, radiolabeling and in vitro evaluation of new silicon-fluoride acceptor (SiFA) derivatized D2-receptor ligands is reported. The SiFA-technology simplifies the introduction of fluorine-18 into target specific biomolecules for Positron-Emission-Tomography (PET). However, one of the remaining challenges, especially for small molecules such as receptor-ligands, is the bulkiness of the SiFA-moiety. We therefore synthesized four Fallypride SiFA-conjugates derivatized either directly at the benzoic acid ring system (SiFA-DMFP, SiFA-FP, SiFA-DDMFP) or at the butyl-side chain (SiFA-M-FP) and tested their receptor affinities. We found D2-receptor affinities for all compounds in the nanomolar range (Ki(SiFA-DMFP) = 13.6 nM, Ki(SiFA-FP) = 33.0 nM, Ki(SiFA-DDMFP) = 62.7 nM and Ki(SiFA-M-FP) = 4.21 nM). The radiofluorination showed highest yields when 10 nmol of the precursors were reacted with [18F]fluoride/TBAHCO3 in acetonitrile. After a reversed phased cartridge purification the desired products could be isolated as an injectable solution after only 10 min synthesis time with radiochemical yields (RCY) of more than 40% in the case of SiFA-DMFP resulting in specific activities >41 GBq/μmol (>1,100 Ci/mmol). Furthermore, the radiolabeled products were shown to be stable in the injectable solutions, as well as in human plasma, for at least 90 min.

N-bromosuccinimide: A facile reagent for the oxidation of benzylic alcohols to aldehydes

The oxidation of benzylic alcohols to aldehydes using N-bromosuccinimide (NBS) under ambient conditions without use of a transition-metal catalyst has been described. Copyright Taylor & Francis Group, LLC.

3-[(5-Chloro-2-hydroxyphenyl)methyl]-5-[4-(trifluoromethyl)phenyl]-1,3, 4-oxadiazol-2(3H)-one, BMS-191011: Opener of large-conductance Ca 2+-activated potassium (maxi-K) channels, identification, solubility, and SAR

Compound 8a (BMS-191011), an opener of the cloned large-conductance, Ca2+-activated potassium (maxi-K) channel, demonstrated efficacy in in vivo stroke models, which led to its nomination as a candidate for clinical evaluation. Its maxi-K channel opening properties were consistent with its structural topology, being derived by combining elements from other known maxi-K openers. However, 8a suffered from poor aqueous solubility, which complicated elucidation of SAR during in vitro evaluation. The activity of 8a in in vivo stroke models and studies directed toward improving its solubility are reported herein. Enhanced solubility was achieved by appending heterocycles to the 8a scaffold, and a notable observation was made that inclusion of a simple amino group (anilines 8k and 8l) yielded excellent in vitro maxi-K ion channel opening activity and enhanced brain-to-plasma partitioning compared to the appended heterocycles.

Palladium catalyzed α-arylation of methyl isobutyrate and isobutyronitrile: an efficient synthesis of 2,5-disubstituted benzyl alcohol and amine intermediates

Several 2,5-disubstituted benzyl alcohols containing a functionalized t-butyl moiety were synthesized via palladium catalyzed α-arylation of methyl isobutyrate and butyronitrile on synthetically useful scales. The resulting benzyl alcohols could then be further elaborated to benzyl amines or other desirable intermediates.

ALYKYLENE DERIVATIVE HAVING EDG RECEPTOR ANTAGONISM

PROBLEM TO BE SOLVED: To provide novel compounds having EDG (endothelial differentiation gene) receptor antagonism which are useful as active components of drugs for preventing and/or treating inflammatory diseases or the like. SOLUTION: The compounds are represented by formula (I) (wherein R1 is hydrogen or an alkyl group; R2 is hydrogen present at any substitutable position on ring C or a substituent such as a hydroxy group, a carboxy group, and a nitro group; R3 is hydrogen present at any substitutable position on ring D or a substitutent such as a hydroxy group and an aralkyloxy group; X is an alkylamino group, an amino group or the like; Y is a carboxy group, a sulfo group or a phosphono group; Z is oxygen, sulfur or the like; a ring represented by A is a 5- or 6-membered saturated or unsaturated hydrocarbon ring; and a ring represented by B is a 4- or 7-membered saturated or unsaturated hydrocarbon ring containing one -C=C- as a partial structure shown in the above formula) and include their salts and their esters.

Cationic chalcone antibiotics. Design, synthesis, and mechanism of action

This paper describes how the introduction of "cationic" aliphatic amino groups in the chalcone scaffold results in potent antibacterial compounds. It is shown that the most favorable position for the aliphatic amino group is the 2-position of the B-ring, in particular in combination with a lipophilic substituent in the 5-position of the B-ring. We demonstrate that the compounds act by unselective disruption of cell membranes. Introduction of an additional aliphatic amino group in the á-ring results in compounds that are selective for bacterial membranes combined with a high antibacterial activity against both Gram-positive and -negative pathogens. The most potent compound in this study (78) has an MIC value of 2 μM against methicillin resistant Staphylococus aureus.

Bis(sym-collidine)bromine(I) hexafluorophosphate as oxidant

Primary and secondary alcohols in solution in methylene chloride are oxidised with bis(sym-collidine)bromine(I) hexafluorophosphate in good yields to the carbonyl compounds. For secondary and tertiary alcohols in which one of the substituents is a 4-methoxyphenyl group the oxidation takes place by cleavage of the phenyl-sp3 carbon bond and formation of bromoanisole and carbonyl compounds. (C) 2000 Elsevier Science Ltd.