89694-46-2

Basic information

• Product Name: 2-Chloro-5-methoxyphenylboronic acid
• Synonyms: 2-CHLORO-5-METHOXYPHENYL BORONIC ACID;(2-CHLORO-5-METHOXY)BENZENEBORONIC ACID;2-Chloro-5-Methoxyphenyl;2-Chloro-5-methoxyphenyl boronic acid ,98%;Boronic acid, B-(2-chloro-5-Methoxyphenyl)-;3-Borono-4-chloroanisole;2-Chloro-5-methoxyphenylboronic Acid (contains varying amounts of Anhydride)
• CAS NO: 89694-46-2
• Molecular Formula: C₇H₈BClO₃
• Molecular Weight: 186.4
• Product Categories: blocks;BoronicAcids;Boronic Acid
• Mol File: 89694-46-2.mol
• Article Data: 2

Chemical Properties

• Melting Point: 106-110
• Boiling Point: 354.8 °C at 760 mmHg
• Flash Point: 168.4 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 1.32 g/cm³
• Vapor Pressure: 1.2E-05mmHg at 25°C
• Refractive Index: 1.544
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 7.81±0.58(Predicted)
• CAS DataBase Reference: 2-Chloro-5-methoxyphenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-5-methoxyphenylboronic acid(89694-46-2)
• EPA Substance Registry System: 2-Chloro-5-methoxyphenylboronic acid(89694-46-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39-37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 89694-46-2(Hazardous Substances Data)

Usage

Chemical Properties

White solid

Uses

2-Chloro-5-methoxyphenylboronic acid

InChI:InChI=1/C7H8BClO3/c1-12-5-2-3-7(9)6(4-5)8(10)11/h2-4,10-11H,1H3

Upstream product

• 10365-98-7 3-methoxyphenylboronic acid 
• 2732-80-1 2-bromo-1-chloro-4-methoxybenzene 

Downstream Products

• 867330-72-1 7-(2-chloro-5-methoxyphenyl)-5-methyl-1,2,4-benzotriazine-3-ylamine 
• 1400704-48-4 (S)-2-({2-[3-(2-chloro-5-hydroxy-phenyl)propylamino]-4,6-dimethyl-pyrimidine-5-carbonyl}amino)-3-[(thiophene-2-carbonyl)amino]propionic acid 
• 1400704-12-2 (S)-2-({2-[3-(2-chloro-5-methoxy-phenyl)propylamino]-4,6-dimethyl-pyrimidine-5-carbonyl}amino)-3-[(thiophene-2-carbonyl)amino]propionic acid methyl ester 
• 1400704-11-1 (S)-2-({2-[3-(2-chloro-5-methoxy-phenyl)prop-2-ynylamino]-4,6-dimethyl-pyrimidine-5-carbonyl}amino)-3-[(thiophene-2-carbonyl)amino]propionic acid methyl ester 
• 2401-25-4 1-chloro-2-iodo-4-methoxybenzene 
• 1239954-94-9 6-(2-chloro-5-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine 

Relevant articles and documents

10-(4-Phenylpiperazine-1-carbonyl)acridin-9(10H)-ones and related compounds: Synthesis, antiproliferative activity and inhibition of tubulin polymerization

As part of our continuing search for potent inhibitors of tubulin polymerization, two novel series of 42 10-(4-phenylpiperazine-1-carbonyl)acridin-9(10H)-ones and N-benzoylated acridones were synthesized on the basis of a retrosynthetic approach. All newly synthesized compounds were tested for antiproliferative activity and interaction with tubulin. Several analogs potently inhibited tumor cell growth. Among the compounds tested, 10-(4-(3-methoxyphenyl)piperazine-1-carbonyl)acridin-9(10H)-one (17c) exhibited excellent growth inhibitory effects on 93 tumor cell lines, with an average GI50 value of 5.4 nM. We were able to show that the strong cytotoxic effects are caused by disruption of tubulin polymerization, as supported by the EBI (N,N'-Ethylenebis(iodoacetamide)) assay and the fact that the most potent inhibitors of cancer cell growth turned out to be the most efficacious tubulin polymerization inhibitors. Potencies were nearly comparable or superior to those of the antimitotic reference compounds. Closely related to this, the most active analogs inhibited cell cycling at the G2/M phase at concentrations down to 30 nM and induced apoptosis in K562 leukemia cells. We believe that our work not only proves the excellent suitability of the acridone scaffold for the design of potent tubulin polymerization inhibitors but also enables synthetic access to further potentially interesting N-acylated acridones.