16740-73-1

Basic information

• Product Name: 5-Bromo-2-methoxyacetophenone
• Synonyms: Acetophenone,5'-bromo-2'-methoxy- (6CI,8CI);1-(3-Bromo-6-methoxyphenyl)ethanone;1-(5-Bromo-2-methoxyphenyl)ethanone;5'-Bromo-2'-methoxyacetophenone
• CAS NO: 16740-73-1
• Molecular Formula: C₉H₉BrO₂
• Molecular Weight: 229.072
• EINECS: 604-604-1
• Mol File: 16740-73-1.mol

Chemical Properties

• Melting Point: 39 °C
• Boiling Point: 296.6 °C at 760 mmHg
• Flash Point: 133.2 °C
• Appearance: /
• Density: 1.421 g/cm³
• Vapor Pressure: 0.00142mmHg at 25°C
• Refractive Index: 1.541
• CAS DataBase Reference: 5-Bromo-2-methoxyacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-2-methoxyacetophenone(16740-73-1)
• EPA Substance Registry System: 5-Bromo-2-methoxyacetophenone(16740-73-1)

Safety Data

• Hazardous Substances Data: 16740-73-1(Hazardous Substances Data)

Usage

Preparation

Preparation by reaction of methyl iodide with 5-bromo-2-hydroxyacetophenone in the presence of potassium carbonate in refluxing acetone for 3 h (86%).

InChI:InChI=1/C9H9BrO2/c1-6(11)8-5-7(10)3-4-9(8)12-2/h3-5H,1-2H3

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 108-24-7 acetic anhydride 
• 579-74-8 2-Methoxyacetophenone 
• 106-41-2 4-bromo-phenol 
• 1927-95-3 4-bromophenyl acetate 
• 75-36-5 acetyl chloride 
• 7664-93-9 sulfuric acid 
• 874-60-2 4-methyl-benzoyl chloride 
• 14804-32-1 2-ethylanisole 
• 16602-17-8 1-(5-bromo-2-methoxyphenyl)-1-ethanol 
• 1761-61-1 5-bromosalicyclaldehyde 
• 1450-75-5 5-Bromo-2-hydroxyacetophenone 
• 74-88-4 methyl iodide 
• 7446-70-0 aluminium trichloride 

Downstream Products

• 67639-58-1 2-bromo-1-(5-bromo-2-methoxyphenyl)ethan-1-one 
• 216663-81-9 (R)-1-(3'-bromo-6'-methoxyphenyl)-ethanol 
• 915070-51-8 4-(2-methoxy-5-bromo-phenyl)-pyrimidin-2-ylamine 
• 1403758-59-7 4-(4,4'-Dimethoxy-biphenyl-3-yl)-pyrimidin-2-ylamine 
• 1098984-15-6 3-(5-Bromo-2-methoxy-phenyl)-3-oxo-propionic Acid Methyl Ester 
• 218627-14-6 3-[3-[3-[3-[(aminoiminomethyl)amino]phenyl]-1-oxopropenyl]-4-methoxyphenyl]propenoic acid, trifluoroacetate salt 
• 1304704-46-8 3-(2-chloroquinolin-3-yl)-1-(5-bromo-2-methoxyphenyl)prop-2-en-1-one 
• 1619222-60-4 C₁₆H₁₂Br₂O₂ 
• 303111-31-1 2-methoxy-5-bromobenzene carboxamide 
• 16602-17-8 1-(5-bromo-2-methoxyphenyl)-1-ethanol 
• 579-74-8 2-Methoxyacetophenone 
• 31405-60-4 1-(5-hydroxy-2-methoxyphenyl)ethan-1-one 
• 130623-33-5 3-(5-Bromo-2-methoxy-phenyl)-5,6-dihydro-imidazo[2,1-b]thiazole; hydrobromide 
• 130623-10-8 1-(5-Bromo-2-methoxy-phenyl)-2-(4,5-dihydro-1H-imidazol-2-ylsulfanyl)-ethanone; hydrobromide 

Relevant articles and documents

Structural Simplification of a Tetrahydroquinoline-Core Peptidomimetic μ-Opioid Receptor (MOR) Agonist/δ-Opioid Receptor (DOR) Antagonist Produces Improved Metabolic Stability

We have previously reported a series of μ-opioid receptor (MOR) agonist/δ-opioid receptor (DOR) antagonist ligands to serve as potential nonaddictive opioid analgesics. These ligands have been shown to be active in vivo, do not manifest withdrawal syndromes or reward behavior in conditioned-place preference assays in mice, and do not produce dependence. Although these attributes are promising, these analogues exhibit poor metabolic stability in mouse liver microsomes, likely due to the central tetrahydroquinoline scaffold in this series. As such, a structure-activity relationship (SAR) campaign was pursued to improve their metabolic stability. This resulted in a shift from our original bicyclic tetrahydroquinoline core to a monocyclic benzylic-core system. By eliminating one of the rings in this scaffold and exploring the SAR of this new core, two promising analogues were discovered. These analogues (5l and 5m) had potency and efficacy values at MOR better or comparable to morphine, retained their DOR-antagonist properties, and showed a 10-fold improvement in metabolic stability.

Design, synthesis and biological evaluation of novel ring-opened cromakalim analogues with relaxant effects on vascular and respiratory smooth muscles and as stimulators of elastin synthesis

Two new series of ring-opened analogues of cromakalim bearing sulfonylurea moieties (series A: with N-unmethylated sulfonylureas, series B: with N-methylated sulfonylureas) were synthesized and tested as relaxants of vascular and respiratory smooth muscle

Synthesis of Spirofurooxindoles via Phenyliodine(III) Bis(trifluoroacetate) (PIFA)-Mediated Cascade Oxidative C?O and C?C Bond Formation

Upon treatment with solely a hypervalent iodine reagent of phenyliodine(III) bis(trifluoroacetate) (PIFA), 3-(2-hydroxyphenyl)-3-oxo-N-phenyl propanamides and a series of its derivatives were conveniently converted to a class of undocumented spirofurooxindoles under mild conditions. Control experiments provided evidence that this spirocyclization process encompassed a cascade oxidative reactions involving the formation of a C?O bond prior to that of C?C bond. (Figure presented.).

LYSYL OXIDASE-LIKE 2 INHIBITORS AND USES THEREOF

Described herein are compounds that are LOXL2 inhibitors, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds in the treatment of conditions, diseases, or disorders associated with LOXL2 activity.

Mechanistic study on iodine-catalyzed aromatic bromination of aryl ethers by N-Bromosuccinimide

Although iodine-catalyzed reaction has rapid advances in recent years, examples on iodine-catalyzed bromination are rare and the mechanism of these reactions remains unclear. Herein, we reported an I2-catalyzed aromatic bromination of aryl ethers by NBS and presented the details of the mechanistic study including kinetic study and the study of kinetic isotope effects. The study revealed that the reaction was actually catalyzed by IBr formed in the induction period, and the rate-determining step was the HBr-elimination of the Wheland intermediate assisted by IBr.

Direct Transformation of Ethylarenes into Primary Aromatic Amides with N -Bromosuccinimide and I2-Aqueous NH3

A variety of ethylarenes were converted into the corresponding primary aromatic amides in good yields via treatment with N-bromosuccinimide in the presence of a catalytic amount of 2,2′-azobis(isobutyronitrile) in a mixture of ethyl acetate and water, acetonitrile and water, or chloroform and water, followed by reaction with molecular iodine and aq NH3 in one pot. It was found that aryl α-bromomethyl ketones and/or aryl methyl ketones were formed at the first reaction step and their iodoform-type reaction occurred at the second reaction step to provide primary aromatic amides. The present reaction is a useful and practical transition-metal-free method for the preparation of primary aromatic amides from ethylarenes. (Chemical Equation Presented).

Iridium-Catalyzed Intramolecular Methoxy C?H Addition to Carbon–Carbon Triple Bonds: Direct Synthesis of 3-Substituted Benzofurans from o-Methoxyphenylalkynes

Catalytic hydroalkylation of an alkyne with methyl ether was accomplished. Intramolecular addition of the C?H bond of a methoxy group in 1-methoxy-2-(arylethynyl)benzenes across a carbon–carbon triple bond took place efficiently either in toluene at 110 °C or in p-xylene at 135 °C in the presence of an iridium catalyst. The initial 5-exo cyclization products underwent double-bond migration during the reaction to give 3-(arylmethyl)benzofurans in high yields.

Pyrrole inhibitors of S-nitrosoglutathione reductase as therapeutic agents

The present invention is directed to inhibitors of S-nitrosoglutathione reductase (GSNOR), pharmaceutical compositions comprising such GSNOR inhibitors, and methods of making and using the same.

Pyrazolyl-Based Carboxamides I

The invention relates to pyrazolyl-based carboxamide compounds useful as ICRAC inhibitors, to pharmaceutical compositions containing these compounds and to these compounds for the use in the treatment and/or prophylaxis of diseases and/or disorders, in particular inflammatory diseases and/or inflammatory disorders.

PYRAZOLYL-BASED CARBOXAMIDES I AS CRAC CHANNEL INHIBITORS

The Invention relates to pyrazolyl-based carboxamide compounds of formula (l) useful as ICRAC inhibitors, to pharmaceutical compositions containing these compounds and to these compounds for the use in the treatment and/or prophylaxis of diseases and/or disorders, in particular inflammatory diseases and/or inflammatory disorders.