175883-60-0

Usage

Uses

Used in Suzuki Reaction:
3-Chloro-4-methoxyphenylboronic acid is used as a reactant in the Suzuki reaction for the formation of carbon-carbon bonds. The application reason is its ability to form stable arylboronic acids, which are key intermediates in the cross-coupling reaction with organic halides, leading to the synthesis of biaryl compounds.
Used in Iron-Catalyzed Oxidative Coupling:
In the field of organic synthesis, 3-Chloro-4-methoxyphenylboronic acid is used as a reactant for iron-catalyzed oxidative coupling with benzene derivatives through homolytic aromatic substitution. The application reason is its reactivity in promoting the formation of carbon-carbon bonds under mild conditions, which is beneficial for the synthesis of complex organic molecules.
Used in Preparation of Microtubule Inhibitors:
3-Chloro-4-methoxyphenylboronic acid is used as a building block in the preparation of microtubule inhibitors, which have potential as antitumor agents. The application reason is its structural similarity to natural products that target microtubules, making it a valuable component in the development of new anticancer drugs.
Used in Rhodium/Chiral Ligand-Catalyzed Arylation/Dieckmann-Type Annulation:
In the pharmaceutical industry, 3-Chloro-4-methoxyphenylboronic acid is used as a reactant in rhodium/chiral ligand-catalyzed arylation and Dieckmann-type annulation reactions. The application reason is its compatibility with chiral catalysts, which allows for the enantioselective synthesis of complex molecules with potential biological activities.
Used in Copper-Catalyzed Oxidative N-Arylation:
3-Chloro-4-methoxyphenylboronic acid is used as a reactant in copper-catalyzed oxidative N-arylation reactions. The application reason is its ability to participate in the formation of carbon-nitrogen bonds, which are essential for the synthesis of various nitrogen-containing organic compounds with potential applications in pharmaceuticals and materials science.
Used in Suzuki and Stille Palladium-Catalyzed Coupling:
In the field of materials science, 3-Chloro-4-methoxyphenylboronic acid is used as a reactant in Suzuki and Stille palladium-catalyzed coupling reactions. The application reason is its compatibility with palladium catalysts, which enables the formation of carbon-carbon and carbon-heteroatom bonds, leading to the synthesis of conjugated organic materials with potential applications in optoelectronics and energy storage.
Used in Boron-Heck Arylation:
3-Chloro-4-methoxyphenylboronic acid is used as a reactant in boron-Heck arylation reactions. The application reason is its ability to form stable boron complexes, which can participate in the formation of carbon-carbon bonds through palladium-catalyzed reactions, leading to the synthesis of various organic compounds with potential applications in pharmaceuticals and agrochemicals.

InChI:InChI=1/C8H10BClO3/c1-2-13-8-4-3-6(9(11)12)5-7(8)10/h3-5,11-12H,2H2,1H3

Upstream product

• 5419-55-6 Triisopropyl borate 
• 50638-47-6 4-bromo-2-chloro-1-methoxybenzene 
• 766-51-8 2-Chloroanisole 
• 7732-18-5 water 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 64578-16-1 3,3'-dichloro-4,4'-dimethoxy-biphenyl 
• 441287-33-8 3-chloro-4-(3-chloro-4-methoxyphenyl)-2(5H)-furanone 
• 617688-89-8 5-(3-chloro-4-hydroxyphenyl)-3-(4-hydroxyphenyl)-4-methylthiophene-2-carbaldehyde 
• 617688-83-2 3-(3-chloro-4-hydroxyphenyl)-5-(4-hydroxyphenyl)-4-methylthiophene-2-carbaldehyde 
• 617688-86-5 3-(3-chloro-4-hydroxyphenyl)-5-(3-fluoro-4-hydroxyphenyl)-4-methylthiophene-2-carbaldehyde 
• 897360-46-2 2,4-diamino-6-(3-chloro-4-methoxyphenyl)pyrido[3,2-d]pyrimidine 
• 897360-23-5 4-[(N-3-chlorophenylcarbamoyl)piperazin-1-yl]-7-(3-chloro-4-methoxyphenyl)pyrido[3,2-d]pyrimidine 
• 1046158-89-7 2-butyl-3-(3-chloro-4-methoxyphenyl)-4H-pyrido[1,2-a]pyrimidin-4-one 
• 1222470-43-0 (R)-tert-butyl-3-(3-chloro-4-methoxybenzyl)-1-methyl-4-oxopyrrolidine-3-carboxylate 
• 1222470-49-6 (R)-tert-butyl 1-benzyl-3-(3-chloro-4-methoxybenzyl)-4-oxopyrrolidine-3-carboxylate 
• 1354792-92-9 6-chloro-3-(3'-chloro-4'-methoxyphenyl)-4-hydroxycoumarin 
• 1174429-31-2 3-(3-chloro-4-methoxyphenyl)-5-morpholino-7H-thieno[3,2-b]pyran-7-one 
• 1239313-06-4 2-(3'-chloro-4'-methoxybiphenyl-2-yl)benzoxazole 

Relevant academic research and scientific papers

Conformational restriction design of thiophene-biphenyl-DAPY HIV-1 non-nucleoside reverse transcriptase inhibitors

Conformational restriction is a promising strategy in the development of DAPY-type non-nucleoside reverse transcriptase inhibitors (NNRTIs). Herein, eighteen thiophene-biphenyl-DAPY derivatives were designed and synthesized as potent HIV-1 NNRTIs in which halogen and methyl groups were introduced to explore the conformationally constrained effects. Molecular docking and dynamic simulation analysis indicated that substituents on different positions of the biphenyl ring induced different dihedral angles and binding conformations, further explaining their anti-viral activities. The 2′-fluoro and 3′-chloro substitutions could form electrostatic or halogen-bonding interactions with adjacent residues of the RT enzyme. The 2′-methyl group contributed to enlarge the dihedral angle of biphenyl ring and was positioned to a space-filling hydrophobic pocket. Notably, compounds 22 and 23 with two methyl groups exhibited potent biological activity against WT HIV-1-infected MT-4 cells (EC50 = 14 and 17 nM, respectively) and RT enzyme (EC50 = 27 and 42 nM, respectively). In particular, 23 exhibited much lower cytotoxicity (CC50 = 264.19 μM) and higher selectivity index (SI = 18,564) than etravirine. Taken together, a rational conformational model for further design of DAPYs is proposed, providing a new guidance for the development of NNRTIs.

Ligand-Based Design of Nondimethylphenyl-Diarylpyrimidines with Improved Metabolic Stability, Safety, and Oral Pharmacokinetic Profiles

A series of nondimethylphenyl-diarylpyrimidines with much lower cytotoxicities than their dimethyl analogues were developed. Compound B13 with a difluorobiphenyl moiety showed the highest antiviral activity against WT, mutant strains, and RT. The hydrochloride form of B13 exhibited an improved water solubility of 5.6 μg/mL compared with ETR (?1 μg/mL), better stability in human and rat liver microsomes, and a great oral bioavailability of 44%, making it promising as a drug candidate. In addition, no apparent toxicity was observed in the acute toxicity assay (2 g/kg) and HE staining.

Regioselective Synthesis of o-Benzenediboronic Acids via Ir-Catalyzed o-C-H Borylation Directed by a Pyrazolylaniline-Modified Boronyl Group

Ir-catalyzed ortho-directed C-H borylation of pyrazolylaniline (PZA)-modified arylboronic acids with bis(pinacolate)diboron afforded o-benzenediboronic acids in which two boronyl groups are differentially modified by pinacol (PIN) and PZA. By using this borylation after nondirected Ir-catalyzed C-H borylation, o-benzenediboronic acids are conveniently synthesized from unfunctionalized arenes. The differentially modified o-benzenediboronic acids undergo selective oxidation and Suzuki-Miyaura cross-coupling at the PZA-modified boronyl groups, affording o-functionalized arylboronic acids selectively.

PHENYLPYRIDINE CARBONYL PIPERAZINE DERIVATIVE

The present invention relates to a compound which is represented by the following general formula and has type 4 phosphodiesterase inhibitory action, and uses and an intermediate compound thereof. (whereinR1, R2: hydrogen, a halogen, a lower alkyl, a lower alkoxy, or the like,R3, R4: hydrogen, a (substituted) lower alkyl, a halogen, or the like,R5: hydrogen, a lower alkyl, a lower alkoxycarbonyl, or the like, andn: 0 or 1).

Substituted terphenyl compounds for the treatment of inflammation

A class of terphenyl compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula II: STR1 wherein each of R2 and R3 is independently selected from hydrido and halo; or wherein R2 and R3 together form --OCH2 O--; wherein each of R6 through R8 is independently selected from hydrido, lower alkyl, halo, lower alkoxy, lower haloalkyl, and lower dialkylamino; or wherein R6 and R7 together form --OCH2 O; and wherein R12 is selected from lower alkylsulfonyl and aminosulfonyl; or a pharmaceutically-acceptable salt thereof.