91506-05-7

Basic information

• Product Name: 4-bromo-2-chloro-6-methylanisole
• Synonyms: 4-bromo-2-chloro-6-methylanisole
• CAS NO: 91506-05-7
• Molecular Formula: C₈H₈BrClO
• Molecular Weight: 235.50552
• EINECS: 293-839-9
• Mol File: 91506-05-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 260.6°Cat760mmHg
• Flash Point: 111.4°C
• Appearance: /
• Density: 1.492g/cm³
• Vapor Pressure: 0.0197mmHg at 25°C
• Refractive Index: 1.55
• CAS DataBase Reference: 4-bromo-2-chloro-6-methylanisole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-bromo-2-chloro-6-methylanisole(91506-05-7)
• EPA Substance Registry System: 4-bromo-2-chloro-6-methylanisole(91506-05-7)

Safety Data

• Hazardous Substances Data: 91506-05-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H8BrClO/c1-5-3-6(9)4-7(10)8(5)11-2/h3-4H,1-2H3

Upstream product

• 7530-27-0 4-bromo-2-chloro-6-methyl-phenol 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 87-64-9 2-chloro-6-methylphenol 
• 584-08-7 potassium carbonate 

Downstream Products

• 29093-41-2 2,6-dimethoxy-3-methylcarbazole 

Relevant articles and documents

Treatment of estrogen-dependent diseases: Design, synthesis and profiling of a selective 17β-HSD1 inhibitor with sub-nanomolar IC50for a proof-of-principle study

Current endocrine therapeutics for the estrogen-dependent disease endometriosis often lead to considerable side-effects as they act by reducing estrogen action systemically. A more recent approach takes advantage of the fact that the weak estrogen estrone (E1) which is abundant in the plasma, is activated in the target cell to the highly estrogenic estradiol (E2) by 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1). 17β-HSD1 is overexpressed in endometriosis and thus a promising target for the treatment of this disease, with the prospect of less target-associated side-effects. Potent inhibitors from the class of bicyclic substituted hydroxyphenylmethanones with sulfonamide moiety recently described by us suffered from high molecular weight and low selectivity over 17βHSD2, the physiological adversary of 17β-HSD1. We describe the structural optimizations leading to the discovery of (5-(3,5-dichloro-4-methoxyphenyl)thiophen-2-yl)(2,6-difluoro-3-hydroxyphenyl)methanone 20, which displayed a sub-nanomolar IC50towards 17β-HSD1 as well as high selectivity over the type 2 enzyme, the estrogen receptors α and β and a range of hepatic CYP enzymes. The compound did neither show cellular toxicity, nor PXR activation nor mutagenicity in the AMES II assay. Additional favourable pharmacokinetic properties (rat) make 20 a suitable candidate for proof-of-principle studies using xenotransplanted immunodeficient rats.

A REGIOSPECIFIC SYNTHESIS OF CARBAZOLES VIA CONSECUTIVE PALLADIUM-CATALYZED CROSS-COUPLING AND ARYNE-MEDIATED CYCLIZATION

A regiospecific synthesis of carbazoles has been developed using palladium-catalyzed cross-coupling of N-(tert-butoxycarbonyl)-2-tributylstannylanilines with 2- or 3-bromochlorobenzene followed by aryne-mediated cyclization as the key reactions.The carbazole alkaloids, glycozolinine and glycozolidine, were synthesized using this procedure.

Heteroylidene indolone compounds

Certain substituted 1-phenyl-3-(aminoalkylidene)-2(1H,3H)-indolones are highly potent gabaergic agents, valuable in the treatment of individuals suffering from schizophrenia or reversing the side effects of a previously or concurrently administered neuroleptic agent; or in the treatment of epilepsy. A wider class of substituted 1-phenyl-3-(aminoalkylidene)-2(1H,3H)-indolones, together with 1-phenyl-3-(2-pyrrolidinylidene)-2(1H,3H)-indolones, and homologs thereof, are valuable in the treatment of anxiety.