175883-60-0

Basic information

• Product Name: 3-CHLORO-4-METHOXYPHENYLBORONIC ACID
• Synonyms: AKOS BRN-0653;3-CHLORO-4-METHOXYPHENYLBORONIC ACID;3-CHLORO-4-METHOXYBENZENEBORONIC ACID;B-(3-Chloro-4-methoxyphenyl)boronic acid;4-Borono-2-chloroanisole;(3-chloro-4-Methoxyphenyl)boranediol;3-Chloro-4-methoxyphenylboronic Acid (contains varying amounts of Anhydride)
• CAS NO: 175883-60-0
• Molecular Formula: C₇H₈BClO₃
• Molecular Weight: 186.4
• Product Categories: blocks;BoronicAcids;Boronic acid;Aryl;Boronic Acids;Boronic Acids and Derivatives;Boronic Acids
• Mol File: 175883-60-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 238-242 °C(lit.)
• Boiling Point: 344.8 °C at 760 mmHg
• Flash Point: 162.3 °C
• Appearance: /
• Density: 1.32
• Vapor Pressure: 1.26E-05mmHg at 25°C
• Refractive Index: 1.537
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: soluble in Methanol
• PKA: 7.93±0.10(Predicted)
• CAS DataBase Reference: 3-CHLORO-4-METHOXYPHENYLBORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-4-METHOXYPHENYLBORONIC ACID(175883-60-0)
• EPA Substance Registry System: 3-CHLORO-4-METHOXYPHENYLBORONIC ACID(175883-60-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-60-37
• WGK Germany: 3
• HazardClass: IRRITANT, KEEP COLD
• Hazardous Substances Data: 175883-60-0(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 175883-60-0 differently. You can refer to the following data:
1. suzuki reaction
2. Reactant for:Iron-catalyzed oxidative coupling with benzene derivatives through homolytic aromatic substitutionPreparation of microtubule inhibitors as potential antitumorsRhodium/chiral ligand-catalyzed arylation/Dieckmann-type annulationCopper-catalyzed oxidative N-arylationSuzuki and Stille palladium-catalyzed couplingBoron-Heck arylation

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

• 401942-59-4 3-bromo-4-(3-chloro-4-methoxyphenyl)-2(5H)-furanone 
• 64578-16-1 3,3'-dichloro-4,4'-dimethoxy-biphenyl 
• 441287-33-8 3-chloro-4-(3-chloro-4-methoxyphenyl)-2(5H)-furanone 
• 1352545-25-5 5-(3-chloro-4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)-1H-tetrazole 

Relevant articles and documents

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.

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.

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.