53456-09-0

Basic information

• Product Name: 2-bromo-4-methylbenzoyl chloride
• Synonyms: 2-bromo-4-methylbenzoyl chloride
• CAS NO: 53456-09-0
• Molecular Formula: C₈H₆BrClO
• Molecular Weight: 233.5
• Mol File: 53456-09-0.mol

Chemical Properties

• Boiling Point: 277.8±20.0 °C(Predicted)
• Appearance: /
• Density: 1.574±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2-bromo-4-methylbenzoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-bromo-4-methylbenzoyl chloride(53456-09-0)
• EPA Substance Registry System: 2-bromo-4-methylbenzoyl chloride(53456-09-0)

Safety Data

• Hazardous Substances Data: 53456-09-0(Hazardous Substances Data)

Upstream product

• 7697-27-0 2-bromo-4-methylbenzoic acid 

Relevant articles and documents

Modification of 5-methylphenanthridium from benzothiazoles to indoles as potent FtsZ inhibitors: Broadening the antibacterial spectrum toward vancomycin-resistant enterococci

The death caused by pathogenic bacteria has always been a severe threat to mankind. The prevalence of drug resistance among bacteria underscores an urgent goal for new antibacterial agents with novel mode of action. Here we first designed and synthesized a class of benzothiazolyl-5-methylphenanthridium derivatives and evaluated their antibacterial activity. On this basis, we further designed and synthesized another class of novel indolyl-5-methylphenanthridium derivatives by optimizing the benzothiazolyl-5-methylphenanthridium core and evaluated their antibacterial activity targeting the bacterial cell division protein FtsZ. The results showed that the indolyl-5-methylphenanthridium derivatives had greatly improved activity against various drug-resistant bacterial strains including methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococcus (VRE). Among them, compound C5 displayed excellent antibacterial activity against susceptible (MIC = 1 μg/mL), methicillin-resistant and clinical isolated S. aureus (MIC = 2 μg/mL). With low hemolytic activity towards mice red blood cells, C5 exhibited good antibacterial effect in vivo in preliminary pharmacodynamic assay. More importantly, C5 was difficult to induce bacterial resistance. Further mechanism studies proved that C5 could inhibit bacterial cell division by promoting FtsZ polymerization, leading to disorderly polymerization and disordered knots. Therefore, our findings suggest that this class of novel indolyl-5-methylphenanthridium derivatives are promising for future antibacterial agents.

NEUROPROTECTIVE PDI MODULATING SMALL MOLECULES AND METHODS OF USE THEREOF

The present disclosure provides, inter alia, compounds and compositions having the formula (I) as defined herein. Methods of using and making such compounds and compositions are also provided. The present disclosure further provides screening methods, including detectable probes as well as diagnostic methods and methods for monitoring the progress of a disease, such as a neurodegenerative disease.

Palladium-Catalyzed Stereoselective Aza-Wacker-Heck Cyclization: One-Pot Stepwise Strategy toward Tetracyclic Fused Heterocycles

Palladium-catalyzed intramolecular tandem cyclization reactions were conducted for the synthesis of densely cis/cis-fused aza-tetracyclic structures. The process involved a palladium(II)-catalyzed aerobic aza-Wacker reaction, followed by a palladium(0)-catalyzed Heck reaction. The effects of the solvent and benzene substitution pattern on the one-pot, two-step cascade reaction were studied systematically, and a probable mechanism was proposed. Strained pentahydrobenzo[f]cyclopenta[hi]indolizin-6-one and racemic γ-lycorane can also be synthesized rapidly using this palladium-catalyzed aza-Wacker-Heck cyclization reaction.

Design, synthesis and biological evaluation of novel 1-phenyl phenanthridin-6(5H)-one derivatives as anti-tumor agents targeting TOPK

T–lymphokine-activated killer cell–originated protein kinase (TOPK) is a serine-threonine mitogen-activated protein kinase that is highly expressed in many types of human cancer. Due to its important role in cancer progression, TOPK is becoming an attractive target in chemotherapeutic drug design. In this study, a series of 1-phenyl phenanthridin-6(5H)-one derivatives have been identified as a novel chemical class of TOPK inhibitors. Some of them displayed very potent anti-cancer activity with IC50s less than 100 nM, superior than reference compound OTS964. The most potent compound, 9g suppressed the growth of cancer cells by apoptosis and specifically inhibited the activities of TOPK. Oral administration of 9g effectively suppressed tumor growth with TGI >79.7% in colorectal cancer xenograft models, demonstrating superior efficacy compared to OTS964. Pharmacokinetic studies reveal its good oral bioavailability. Our findings therefore show that 9g is a specific inhibitor of TOPK both in vitro and in vivo that may be further developed as a potential therapeutic agent against colorectal cancer.

Copper-Catalyzed Cascade Synthesis of [1,2,4]-Triazoloquinazolinones

An efficient and practical method for the synthesis of 1,2,4-triazolo[5,1- b ]quinazolin-9(3 H)-ones has been developed via the copper-catalyzed domino reactions of readily available substituted N ′-acetyl-2-bromobenzohydrazides with cyanamide. The protocol uses inexpensive CuI as the catalyst, and no other ligand or additive was required. The target products were prepared in good to excellent yields with tolerance of various functional groups.

Synthesis of Substituted Naphthalenes by 1,4-Palladium Migration Involved Annulation with Internal Alkynes

The palladium catalyzed annulation of 1-bromo-2-vinylbenzene derivatives with internal alkynes was realized for the efficient synthesis of substituted naphthalenes. A controllable aryl to vinylic 1,4-palladium migration process is the key for success.

Ni-Catalyzed Alkene Carboacylation via Amide C-N Bond Activation

We report Ni-catalyzed formal carboacylation of o-allylbenzamides with arylboronic acid pinacol esters. The reaction is triggered by oxidative addition of an activated amide C-N bond to a Ni(0) catalyst and proceeds via alkene insertion into a Ni(II)-acyl bond. The exo-selective carboacylation reaction generates 2-benzyl-2,3-dihydro-1H-inden-1-ones in moderate to high yields (46-99%) from a variety of arylboronic acid pinacol esters and substituted o-allylbenzamides. These results show that amides are practical substrates for alkene carboacylation via amide C-N bond activation, and this approach bypasses challenges associated with alkene carboacylation triggered by C-C bond activation.

Preparation method of 1-alkyl-2-phenyl-4-quinolones

Provided is a novel method for synthesizing 1-alkyl-2-phenyl-4-quinolones from 2-halobenzoates. The synthesizing method in the present invention has advantages capable of synthesizing 1-alkyl-2-phenyl-4-quinolones in high yield through a simplified stage in a simple reaction condition by means of 2-halobenzoates as an inexpensive starting material.COPYRIGHT KIPO 2015

Enantioselective synthesis of planar chiral ferrocenes via Pd(0)-catalyzed intramolecular direct C-H bond arylation

A highly efficient synthesis of planar chiral ferrocenes by enantioselective Pd(0)-catalyzed direct C-H arylation from readily available starting materials under mild reaction conditions was developed (up to 99% yield, 99% ee). The products can be easily transformed to the highly efficient planar ferrocene ligands, which have demonstrated high efficiency in Pd-catalyzed asymmetric allylic alkylation and amination reactions.