56658-04-9

Basic information

• Product Name: 2-BROMO-5-METHOXYBENZOYL CHLORIDE
• Synonyms: 2-BROMO-5-METHOXYBENZOYL CHLORIDE;2-BROMO-5-METHOXYBENZENE-1-CARBONYL CHLORIDE;BUTTPARK 43\57-16;6-Bromo-m-anisoyl chloride
• CAS NO: 56658-04-9
• Molecular Formula: C₈H₆BrClO₂
• Molecular Weight: 249.49
• Mol File: 56658-04-9.mol

Chemical Properties

• Boiling Point: 110 °C
• Flash Point: 175-177°C/15mm
• Appearance: /
• Density: 1.598 g/cm³
• Vapor Pressure: 0.00121mmHg at 25°C
• Refractive Index: 1.565
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: 2-BROMO-5-METHOXYBENZOYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMO-5-METHOXYBENZOYL CHLORIDE(56658-04-9)
• EPA Substance Registry System: 2-BROMO-5-METHOXYBENZOYL CHLORIDE(56658-04-9)

Safety Data

• Hazard Codes: Xn
• Statements: 34-22
• Safety Statements: 26-36/37/39
• RIDADR: 3265
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 56658-04-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-BROMO-5-METHOXYBENZOYL CHLORIDE is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to introduce benzoyl and methoxy functional groups into organic molecules, contributing to the development of new drugs with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, 2-BROMO-5-METHOXYBENZOYL CHLORIDE serves as a crucial component in the production of agrochemicals, leveraging its reactivity to create compounds with pesticidal or herbicidal activities, thereby enhancing crop protection and yield.
Used in Fine Chemicals Production:
2-BROMO-5-METHOXYBENZOYL CHLORIDE is utilized as a versatile building block in the synthesis of fine chemicals, where its selective modification capabilities are harnessed to produce specialty chemicals for various applications, including fragrances, dyes, and other aromatic compounds.
Used in Dye Synthesis:
2-BROMO-5-METHOXYBENZOYL CHLORIDE is employed as a precursor in the synthesis of dyes, capitalizing on its aromatic structure and functional groups to create dyes with specific color properties and stability for use in various industries such as textiles, plastics, and printing inks.

InChI:InChI=1/C8H6BrClO2/c1-12-5-2-3-7(9)6(4-5)8(10)11/h2-4H,1H3

Upstream product

• 79-37-8 oxalyl dichloride 
• 22921-68-2 2-bromo-5-methoxy-benzoic acid 
• 100-84-5 1-methoxy-3-methyl-benzene 
• 586-38-9 3-Methoxybenzoic acid 

Downstream Products

• 6342-63-8 1-(2-bromo-5-methoxyphenyl)ethanone 
• 1375931-12-6 2-bromo-N,N-diisopropyl-5-methoxylbenzamide 
• 1610725-17-1 2-bromo-N-(4-((tert-butyldimethylsilyl)oxy)phenyl)-5-methoxybenzamide 
• 286439-95-0 2-bromo-N-(4-methoxylphenyl)-5-methoxybenzamide 
• 1181959-90-9 2-bromo-N-(4-methylphenyl)-5-methoxybenzamide 
• 903333-55-1 2-bromo-N-(4-chlorophenyl)-5-methoxybenzamide 
• 685121-21-5 2-bromo-N-(4-fluorophenyl)-5-methoxybenzamide 
• 1610725-18-2 2-bromo-N-(4-((tert-butyldimethylsilyl)oxy)phenyl)-5-methoxy-N-(methoxymethyl)benzamide 
• 1610724-89-4 2-bromo-N-(4-methoxylphenyl)-N-(methoxymethyl)-5-methoxybenzamide 
• 1610724-88-3 2-bromo-N-(4-methylphenyl)-N-(methoxymethyl)-5-methoxybenzamide 
• 1610724-87-2 2-bromo-N-(4-chlorophenyl)-N-(methoxymethyl)-5-methoxybenzamide 
• 1610724-86-1 2-bromo-N-(4-fluorophenyl)-N-(methoxymethyl)-5-methoxybenzamide 
• 1610724-85-0 2-bromo-N-(4-phenyl)-N-(methoxymethyl)-5-methoxybenzamide 
• 1613052-79-1 2,5-bis(2-(diphenylphosphino)5-methoxyphenyl)-1,3,4-oxadiazole 

Relevant articles and documents

Multistep Synthesis and Nematicidal Activity of 2-(8-azabicyclo[3.2.1]octan-3-yl)-3-imino-2,3-dihydro-1H-isoindol-1-One Derivatives

[Figure not available: see fulltext.] Novel 2-(8-azabicyclo[3.2.1]octan-3-yl)-3-imino-2,3-dihydro-1H-isoindol-1-ones derived from 5-HT3 receptor antagonists hexahydroazepinylbenzamides were designed and synthesized through isocyanide insertion reaction. All target compounds were evaluated against pinewood nematodes B. xylophilus and root-knot nematodes M. incognita. Good lethal rate (75%) for 3-(tert-butylimino)-5-chloro-2-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-2,3-dihydro-1H-isoindol-1-one and serious nervous curl effect against pinewood nematodes B. xylophilus for 3-(tert-butylimino)-2-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-2,3-dihydro-1H-isoindol-1-one were observed at 10 mg/l. The inhibition activities of 3-[(4-methoxyphenyl)imino]-2-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-2,3-dihydro-1H-isoindol-1-one against root-knot nematodes M. incognita were 84% at 160 mg/l and 60% at 20 mg/l for in vitro test and test tube test, respectively.

Phenanthridine Derivative Host Heat Shock Cognate 70 Down-Regulators as Porcine Epidemic Diarrhea Virus Inhibitors

Porcine epidemic diarrhea virus (PEDV) has become increasingly problematic around the world, not only for its hazards to livestock but also due to the possibility that it is a zoonotic disease. Although vaccine therapy has made some progress toward PEDV c

Synthesis of Methoxy-, Methylenedioxy-, Hydroxy-, and Halo-Substituted Benzophenanthridinone Derivatives as DNA Topoisomerase IB (TOP1) and Tyrosyl-DNA Phosphodiesterase 1 (TDP1) Inhibitors and Their Biological Activity for Drug-Resistant Cancer

As a recently discovered DNA repair enzyme, tyrosyl-DNA phosphodiesterase 1 (TDP1) removes topoisomerase IB (TOP1)-mediated DNA protein cross-links. Inhibiting TDP1 can potentiate the cytotoxicity of TOP1 inhibitors and overcome cancer cell resistance to

Ni-Catalyzed Reductive Arylcyanation of Alkenes

We disclose a Ni-catalyzed reductive arylcyanation of alkene using environmentally benign and nontoxic organo cyanating reagent N-cyano-N-phenyl-p-toluenesulfonamide. This reaction provides a new method for the rapid synthesis of cyano-substituted oxindoles and isoquinoline-1,3-diones and features high functional group tolerance. In addition, an enantioselective version was developed for the construction of enantiomerically enriched 3-cyanomethyl oxindole. This method has also been applied to the synthesis of natural alkaloids (+)-esermethole and (+)-physostigmine.

Direct Synthesis of Enamides via Electrophilic Activation of Amides

A novel, one-step N-dehydrogenation of amides to enamides is reported. This reaction employs the unlikely combination of LiHMDS and triflic anhydride, which serves as both the electrophilic activator and the oxidant, and is characterized by its simple setup and broad substrate scope. The synthetic utility of the formed enamides was readily demonstrated in a range of downstream transformations.

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.

Stereoinvertive C–C Bond Formation at the Boron-Bound Stereogenic Centers through Copper-Bipyridine-Catalyzed Intramolecular Coupling of α-Aminobenzylboronic Esters

Enantiospecific intramolecular Suzuki–Miyaura-type coupling with α-(2-halobenzoylamino)benzylboronic esters to give 3-substituted isoindolinones is achieved by using copper catalysts with 2,2′-bipyridine-based achiral ligands. Enantioenriched α-aminobenzylboron reactants bearing a hydrogen atom at the boron-bound stereogenic carbons undergo stereoinvertive coupling in the presence of a 6-phenyl-2,2′-bipyridine ligand with high enantiospecificity. α-Aminobenzylboronates bearing fully substituted boron-bound stereogenic centers also gave the 3,3-disubstituted isoindolinones with stereospecific stereochemical inversion in the presence of simple 2,2′-bipyridine as a ligand.

Enantiotropic Transformation of Carbethoxyhydrazones of Acetophenones

Abstract: Hydrazinecarboxylates have been synthesized by reacting substituted acetophenones with carbethoxyhydrazine. One of product is formed as a mixture of E- and Z-isomers. In the process of measuring the melting point of the resulting hydrazinecarbox

Isoquinolinone derivatives as potent CNS multi-receptor D2/5-HT1A/5-HT2A/5-HT6/5-HT7 agents: Synthesis and pharmacological evaluation

In this study, a series of novel Isoquinolinone derivatives were synthesized as potential multi-target antipsychotics. Among these, compound 13 showed high affinity for dopamine D2 and serotonin 5-HT1A, 5-HT2A, 5-HT6, and 5-HT7 receptors, showed low affinity for off-target receptors (5-HT2C, H1, and α1), and negligible effects on ether-a-gogo-related gene (hERG; i.e., reduced QT interval prolongation). An animal behavioral study revealed that compound 13 reversed APO-induced hyperlocomotion, MK-801-induced hyperactivity, and DOI-induced head twitch. Moreover, compound 13 exhibited a high threshold for acute toxicity, a lack of tendency to induce catalepsy, and did not cause prolactin secretion or weight gain when compared to risperidone. Furthermore, in the forced swim test, tail suspension test, and novel object recognition test, treatment with compound 13 resulted in improvements in depression and cognitive impairment. In addition, compound 13 had a favorable pharmacokinetic profile in rats. Thus, the antipsychotic drug-like effects of compound 13 indicate that it may be useful for developing a novel class of drugs for the treatment of schizophrenia.

Cobalt-Catalyzed Regio- A nd Enantioselective Allylic Alkylation of Malononitriles

Cobalt-catalyzed highly branched- A nd enantioselective allylic alkylation of malononitriles has been developed. Chiral ?,?′-unsaturated malononitriles could be synthesized with >20:1 branched/linear regioselectivity and up to 99% enantiomeric excess from easily accessible racemic allylic carbonates under mild reaction conditions. The electron-rich and sterically less hindered bisoxazolinephosphine ligand is essential to realize the high reactivity in the carbon-carbon bond formation process.