77344-70-8

Basic information

• Product Name: 1-(2-bromo-5-methylphenyl)ethanone
• Synonyms: 1-(2-bromo-5-methylphenyl)ethanone
• CAS NO: 77344-70-8
• Molecular Formula: C₉H₉BrO
• Molecular Weight: 213.07116
• Mol File: 77344-70-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 276.6°Cat760mmHg
• Flash Point: 83.6°C
• Appearance: /
• Density: 1.388g/cm³
• Vapor Pressure: 0.00474mmHg at 25°C
• Refractive Index: 1.548
• CAS DataBase Reference: 1-(2-bromo-5-methylphenyl)ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-bromo-5-methylphenyl)ethanone(77344-70-8)
• EPA Substance Registry System: 1-(2-bromo-5-methylphenyl)ethanone(77344-70-8)

Safety Data

• Hazardous Substances Data: 77344-70-8(Hazardous Substances Data)

Usage

Description

1-(2-bromo-5-methylphenyl)ethanone is a chemical compound with the molecular formula C10H11BrO. It is a ketone compound with a bromine atom attached to the benzene ring, along with a methyl group. Its chemical structure and reactivity make it a valuable tool in the field of organic chemistry for creating new molecules and studying their properties.
Used in Pharmaceutical Industry:
1-(2-bromo-5-methylphenyl)ethanone is used as an intermediate in the production of various drugs and pharmaceuticals. Its unique chemical structure allows for the synthesis of a wide range of compounds with potential therapeutic applications.
Used in Organic Synthesis:
1-(2-bromo-5-methylphenyl)ethanone is used as a reagent in the preparation of other organic compounds. Its versatility and reactivity make it a useful building block for the synthesis of complex organic molecules.
Used in Research:
1-(2-bromo-5-methylphenyl)ethanone is used in pharmaceutical research to study the properties and potential applications of newly synthesized compounds. Its unique structure and reactivity provide valuable insights into the behavior of related compounds and contribute to the advancement of organic chemistry.

InChI:InChI=1/C9H9BrO/c1-6-3-4-9(10)8(5-6)7(2)11/h3-5H,1-2H3

Upstream product

• 409110-31-2 2-bromo-5-methylbenzoyl chloride 
• 109572-65-8 BrMgCH(CO₂Et)2 
• 103260-54-4 1-(2-bromo-5-methyl-phenyl)-ethanol 
• 90221-55-9 2-bromo-5-methylbenzaldehyde 
• 6967-82-4 2-bromo-5-methylbenzoic acid 
• 75-16-1 methylmagnesium bromide 
• 676-58-4 methylmagnesium chloride 
• 1048108-06-0 2-bromo-N-methoxy-N,5-dimethylbenzamide 
• 53078-85-6 2-bromo-5-methylaniline 
• 5326-34-1 4-Bromo-3-nitrotoluene 
• 917-64-6 methyl magnesium iodide 
• 42872-83-3 2-bromo-5-methylbenzylnitrile 

Downstream Products

• 17980-09-5 2,9-dimethylphenanthrene 
• 38968-41-1 1-(2-azido-5-methylphenyl)ethan-1-one 
• 1378431-00-5 5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-[{[3-(1-{[(methyloxy)methyl]oxy}ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}(methylsulfonyl)amino]-1-benzofuran-3-carboxamide 
• 1378427-83-8 5-cyclopropyl-2-(4-fluorophenyl)-6-[{[(3S)-1-hydroxy-3-methyl-1,3-dihydro-2,1-benzoxaborol-5-yl]methyl}(methylsulfonyl)amino]-N-methyl-1-benzofuran-3-carboxamide 
• 1378427-84-9 5-cyclopropyl-2-(4-fluorophenyl)-6-[{[(3R)-1-hydroxy-3-methyl-1,3-dihydro-2,1-benzoxaborol-5-yl]methyl}(methylsulfonyl)amino]-N-methyl-1-benzofuran-3-carboxamide 

Relevant articles and documents

Structure-activity relationship studies in substituted sulfamoyl benzamidothiazoles that prolong NF-κB activation

In the face of emerging infectious diseases, there remains an unmet need for vaccine development where adjuvants that enhance immune responses to pathogenic antigens are highly desired. Using high-throughput screens with a cell-based nuclear factor κB (NF-κB) reporter assay, we identified a sulfamoyl benzamidothiazole bearing compound 1 that demonstrated a sustained activation of NF-κB after a primary stimulus with a Toll-like receptor (TLR)-4 agonist, lipopolysaccharide (LPS). Here, we explore systematic structure–activity relationship (SAR) studies on compound 1 that indicated the sites on the scaffold that tolerated modification and yielded more potent compounds compared to 1. The selected analogs enhanced release of immunostimulatory cytokines in the human monocytic cell line THP-1 cells and murine primary dendritic cells. In murine vaccination studies, select compounds were used as co-adjuvants in combination with the Food and Drug Administration approved TLR-4 agonistic adjuvant, monophosphoryl lipid A (MPLA) that showed significant enhancement in antigen-specific antibody titers compared to MPLA alone. Additionally, our SAR studies led to identification of a photoaffinity probe which will aid the target identification and mechanism of action studies in the future.

VACCINE ADJUVANT

Compounds useful as an adjuvant, e.g., formulas (I)-(VI) and uses thereof, for example, with immunogenic moieties or other adjuvants, are provided.

Preparation of isoindolinones via a palladium-catalyzed diamination

A Pd(II)-catalyzed cyclization using oxidative olefin diamination was developed for the preparation of isoindolinones from ortho-olefinic N-methoxybenzamides. Using the optimized reaction conditions, the desired products were obtained in up to 90% yield using NFSI as the oxidant. This reaction provides an efficient and direct access to isoindolinones with amine functionality, an important drug skeleton.