81324-61-0

Basic information

• Product Name: 3-BROMO-4-METHOXY-BENZOYL CHLORIDE
• Synonyms: 3-BROMO-4-METHOXY-BENZOYL CHLORIDE
• CAS NO: 81324-61-0
• Molecular Formula: C₈H₆BrClO₂
• Molecular Weight: 249.49
• Mol File: 81324-61-0.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 316.8±27.0 °C(Predicted)
• Appearance: /
• Density: 1.598±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 3-BROMO-4-METHOXY-BENZOYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-4-METHOXY-BENZOYL CHLORIDE(81324-61-0)
• EPA Substance Registry System: 3-BROMO-4-METHOXY-BENZOYL CHLORIDE(81324-61-0)

Safety Data

• Hazardous Substances Data: 81324-61-0(Hazardous Substances Data)

Usage

Description

3-Bromo-4-methoxy-benzoyl chloride is an organic chemical compound characterized by the presence of a bromo and methoxy group attached to a benzoyl chloride moiety. It is a versatile intermediate in the synthesis of various pharmaceutical compounds and has potential applications in the development of new drugs.

Uses

Used in Pharmaceutical Industry:
3-Bromo-4-methoxy-benzoyl chloride is used as an intermediate in the synthesis of (3-Bromo-4-hydroxyphenyl)(2-ethyl-3-benzofuranyl)-methanone (B685230), which is an impurity of benzbromarone (B185200). 3-BROMO-4-METHOXY-BENZOYL CHLORIDE is currently being investigated as a potent human uric acid (U829200) transporter I inhibitor, indicating its potential role in the development of treatments for hyperuricemia and related conditions.
Additionally, 3-Bromo-4-methoxy-benzoyl chloride can be utilized in the synthesis of other pharmaceutical compounds, making it a valuable building block in the medicinal chemistry field. Its unique structure allows for further functionalization and modification, enabling the creation of new drug candidates with improved therapeutic properties.

Upstream product

• 100-09-4 4-methoxybenzoic acid 
• 35450-37-4 methyl 3-bromo-4-methoxybenzoate 
• 99-58-1 3-bromo-4-methoxybenzoic acid 

Downstream Products

• 193964-26-0 2-(4-methoxyphenyl)benzo[b]thiophen-3-yl 3-bromo-4-methoxyphenyl ketone 
• 216968-27-3 N-(6-Methyl-5,6,7,8-tetrahydro[1,6]naphthyridin-3-yl)-3-bromo-4-methoxybenzamide, monohydrochloride 
• 1156807-51-0 (3-bromo-4-methoxyphenyl)(furan-2-yl)methanone 
• 1310849-26-3 (3-bromo-4-hydroxyphenyl)(furan-2-yl)methanone 
• 200956-55-4 3-bromo-4-methoxybenzamide 
• 75570-60-4 N-methyl-N-[2-(N',N'-dimethylamino)cyclohexyl]-3-bromo-4-hydroxybenzamide 
• 1182834-13-4 3-bromo-N,4-dimethoxy-N-methylbenzamide 

Relevant articles and documents

Structure-Activity Relationship of Phenylpyrazolones against Trypanosoma cruzi

Chagas disease is a neglected parasitic disease caused by the parasitic protozoan Trypanosoma cruzi and currently affects around 8 million people. Previously, 2-isopropyl-5-(4-methoxy-3-(pyridin-3-yl)phenyl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one (NPD-0227) was discovered to be a sub-micromolar inhibitor (pIC50=6.4) of T. cruzi. So far, SAR investigations of this scaffold have focused on the alkoxy substituent, the pyrazolone nitrogen substituent and the aromatic substituent of the core phenylpyrazolone. In this study, modifications of the phenyldihydropyrazolone scaffold are described. Variations were introduced by installing different substituents on the phenyl core, modifying the geminal dimethyl and installing various bio-isosteres of the dihydropyrazolone group. The anti T. cruzi activity of NPD-0227 could not be surpassed as the most potent compounds show pIC50 values of around 6.3. However, valuable additional SAR data for this interesting scaffold was obtained, and the data suggest that a scaffold hop is feasible as the pyrazolone moiety can be replaced by a oxazole or oxadiazole with minimal loss of activity.

Identification of Phenylpyrazolone Dimers as a New Class of Anti-Trypanosoma cruzi Agents

Chagas disease is becoming a worldwide problem; it is currently estimated that over six million people are infected. The two drugs in current use, benznidazole and nifurtimox, require long treatment regimens, show limited efficacy in the chronic phase of infection, and are known to cause adverse effects. Phenotypic screening of an in-house library led to the identification of 2,2′-methylenebis(5-(4-bromophenyl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one), a phenyldihydropyrazolone dimer, which shows an in vitro pIC50 value of 5.4 against Trypanosoma cruzi. Initial optimization was done by varying substituents of the phenyl ring, after which attempts were made to replace the phenyl ring. Finally, the linker between the dimer units was varied, ultimately leading to 2,2′-methylenebis(5-(3-bromo-4-methoxyphenyl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one (NPD-0228) as the most potent analogue. NPD-0228 has an in vitro pIC50 value of 6.4 against intracellular amastigotes of T. cruzi and no apparent toxicity against the human MRC-5 cell line and murine cardiac cells.

Synthesis and antibacterial activities of cadiolides A, B and C and analogues

The one-pot multicomponent synthesis of natural butenolides named cadiolides A, B, C and analogues has been realized. The antibacterial structure activity relationship shows that the presence of phenolic hydroxyl groups and the number and position of bromine atoms on the different aromatic rings are important features for antibacterial activity, besides it was demonstrated the tolerance of both benzene and furan ring at position 3 of the butenolide nucleus. Furthermore, none of the most relevant antibacterial compounds showed any cytotoxicity in freshly isolated human neutrophils.