174913-09-8

Basic information

• Product Name: 2-BROMO-5-CHLOROANISOLE
• Synonyms: 2-BROMO-5-CHLOROANISOLE;2-BROMO-5-CHLOROANISOLE, 98+%;Benzene, 1- bromo- 4- chloro- 2- methoxy-
• CAS NO: 174913-09-8
• Molecular Formula: C₇H₆BrClO
• Molecular Weight: 221.48
• Product Categories: Miscellaneous;Anisoles, Alkyloxy Compounds & Phenylacetates;Bromine Compounds;Chlorine Compounds
• Mol File: 174913-09-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 236.645 °C at 760 mmHg
• Flash Point: 96.92 °C
• Appearance: /
• Density: 1.564 g/cm³
• Vapor Pressure: 0.0719mmHg at 25°C
• Refractive Index: 1.5875
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-BROMO-5-CHLOROANISOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMO-5-CHLOROANISOLE(174913-09-8)
• EPA Substance Registry System: 2-BROMO-5-CHLOROANISOLE(174913-09-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-24/25
• Hazardous Substances Data: 174913-09-8(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid

InChI:InChI=1/C7H6BrClO/c1-10-7-4-5(9)2-3-6(7)8/h2-4H,1H3

Upstream product

• 57479-70-6 2-methoxy-4-chlorobenzoic acid 
• 13659-23-9 2-Bromo-5-chlorophenol 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 

Downstream Products

• 898538-43-7 (5-bromo-2-chloro-6-methoxyphenyl)(4-ethoxyphenyl)methanone 
• 1036955-11-9 (5-bromo-2-chloro-4-methoxyphenyl)(4-ethylphenyl)methanone 
• 1095544-59-4 4-chloro-1-cyclobutyl-2-methoxybenzene 
• 1340334-65-7 2-methoxy-4-(piperidin-1-yl)aniline 

Relevant articles and documents

Transition-metal-free decarboxylative bromination of aromatic carboxylic acids

Methods for the conversion of aliphatic acids to alkyl halides have progressed significantly over the past century, however, the analogous decarboxylative bromination of aromatic acids has remained a longstanding challenge. The development of efficient methods for the synthesis of aryl bromides is of great importance as they are versatile reagents in synthesis and are present in many functional molecules. Herein we report a transition metal-free decarboxylative bromination of aromatic acids. The reaction is applicable to many electron-rich aromatic and heteroaromatic acids which have previously proved poor substrates for Hunsdiecker-type reactions. In addition, our preliminary mechanistic study suggests that radical intermediates are not involved in this reaction, which is in contrast to classical Hunsdiecker-type reactivity. Overall, the process demonstrates a useful method for producing valuable reagents from inexpensive and abundant starting materials.

(1 S)-1,5-anhydro-1-[5-(4-ethoxybenzyl)-2-methoxy-4-methylphenyl]-1-thio- d -glucitol (TS-071) is a potent, selective sodium-dependent glucose cotransporter 2 (SGLT2) inhibitor for type 2 diabetes treatment

Derivatives of a novel scaffold, C-phenyl 1-thio-d-glucitol, were prepared and evaluated for sodium-dependent glucose cotransporter (SGLT) 2 and SGLT1 inhibition activities. Optimization of substituents on the aromatic rings afforded five compounds with potent and selective SGLT2 inhibition activities. The compounds were evaluated for in vitro human metabolic stability, human serum protein binding (SPB), and Caco-2 permeability. Of them, (1S)-1,5-anhydro-1-[5- (4-ethoxybenzyl)-2-methoxy-4-methylphenyl]-1-thio-d-glucitol (3p) exhibited potent SGLT2 inhibition activity (IC50 = 2.26 nM), with 1650-fold selectivity over SGLT1. Compound 3p showed good metabolic stability toward cryo-preserved human hepatic clearance, lower SPB, and moderate Caco-2 permeability. Since 3p should have acceptable human pharmacokinetics (PK) properties, it could be a clinical candidate for treating type 2 diabetes. We observed that compound 3p exhibits a blood glucose lowering effect, excellent urinary glucose excretion properties, and promising PK profiles in animals. Phase II clinical trials of 3p (TS-071) are currently ongoing.