17100-63-9

Basic information

• Product Name: METHYL 4-BROMO-3-METHOXYBENZOATE
• Synonyms: METHYL 4-BROMO-3-METHOXYBENZOATE;4-BROMO-3-METHOXYBENZOIC ACID METHYL ESTER;2-Bromo-5-(methoxycarbonyl)anisole;Methyl 4-broMo-2-hydroxbenzoate;2-Bromo-5-(methoxycarbonyl)anisole, Methyl 4-bromo-m-anisate;Benzoic acid,4-broMo-3-Methoxy-, Methyl ester
• CAS NO: 17100-63-9
• Molecular Formula: C₉H₉BrO₃
• Molecular Weight: 245.07
• Product Categories: blocks;Bromides;Carboxes
• Mol File: 17100-63-9.mol
• Article Data: 26

Chemical Properties

• Melting Point: 58-61
• Boiling Point: 306.008 °C at 760 mmHg
• Flash Point: 138.869 °C
• Appearance: /
• Density: 1.462g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.538
• Storage Temp.: Keep Cold
• CAS DataBase Reference: METHYL 4-BROMO-3-METHOXYBENZOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 4-BROMO-3-METHOXYBENZOATE(17100-63-9)
• EPA Substance Registry System: METHYL 4-BROMO-3-METHOXYBENZOATE(17100-63-9)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 17100-63-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 10, p. 1623, 1969 DOI: 10.1017/S0009838800024678

InChI:InChI=1/C9H9BrO3/c1-12-8-5-6(9(11)13-2)3-4-7(8)10/h3-5H,1-2H3

Upstream product

• 186581-53-3 diazomethane 
• 106291-80-9 methyl 4-bromo-3-hydroxybenzoate 
• 77-78-1 dimethyl sulfate 
• 14348-38-0 4-bromo-3-hydroxybenzoic acid 
• 99-06-9 3-Carboxyphenol 
• 3556-83-0 methyl 4-methyl-3-methoxybenzoate 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 56256-14-5 4-bromo-3-methoxy-benzoic acid 
• 19438-10-9 methyl 3-hydroxybenzoate 

Downstream Products

• 20105-30-0 Bis-(2-methoxy-4-methoxycarbonylphenyl)-aether 
• 2556-05-0 4,5,3'-trimethoxy-3,4'-oxy-di-benzoic acid dimethyl ester 
• 5368-81-0 methyl 3-methoxybenzoate 
• 2288-42-8 3,3'-dimethoxy-4,4'-oxy-di-benzoic acid 
• 872276-14-7 3-methoxy-4,4'-oxy-di-benzoic acid dimethyl ester 
• 859140-23-1 methyl 3-methoxy-4-(pyridin-4-yl)benzoate 
• 792172-61-3 1-[(6-chloro-2-naphthyl)sulfonyl]-4-[3-methoxy-4-(4-pyridyl)benzoyl]piperazine 
• 52045-79-1 C₂₈H₂₆N₄O₈S₂ 
• 2555-96-6 5,6,2'-Trihydroxy-diphenylaether-dialdehyd-(3.4') 
• 2555-97-7 5,6,2'-Trimethoxy-3,4'-bis-<3-hydroxy-propyl>-diphenylaether 
• 2556-09-4 3-(4-formyl-2-methoxyphenoxy)-4,5-dimethoxybenzaldehyde 
• 2555-98-8 3-(4-formyl-2-methoxyphenoxy)-4-hydroxy-5-methoxybenzaldehyde 
• 2555-99-9 3-(4-carboxy-2-methoxyphenoxy)-4-hydroxy-5-methoxybenzoic acid 
• 2556-00-5 6-Hydroxy-5,2'-dimethoxy-diphenylether-dicarbonsaeure-(3,4')-dimethylester 

Relevant articles and documents

TYK2 INHIBITORS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of TYK2, and the treatment of TYK2-mediated disorders.

Elongated and substituted triazine-based tricarboxylic acid linkers for MOFs

New triazine-based tricarboxylic acid linkers were prepared as elongated relatives of triazinetribenzoic acid (TATB). Additionally, functional groups (NO2, NH2, OMe, OH) were introduced for potential post-synthetic modification (PSM) of MOFs. Functionalized tris(4-bromoaryl)triazine "cores" (3a,3b) were obtained by unsymmetric trimerization mixing one equivalent of an acid chloride (OMe or NO2 substituted) with two equivalents of an unsubstituted nitrile. Triple Suzuki coupling of the cores 3 with suitable phenyl- and biphenylboronic acid derivatives provided elongated tricarboxylic acid linkers as carboxylic acids 17 and 20 or their esters 16 and 19. Reduction of the nitro group and cleavage of the methoxy group gave the respective amino and hydroxy-substituted triazine linkers.

Extended structure-activity study of thienopyrimidine-based EGFR inhibitors with evaluation of drug-like properties

Thieno[2,3-d]pyrimidines are attractive derivatives for cancer treatment, among others through regulation of the epidermal growth factor receptor tyrosine kinase (EGFR-TK). In an extended SAR study, 44 new compounds of this class have been evaluated as inhibitors, while simultaneously focussing on ADME properties. Through the application of bioisosters, hybrid structures, solubilizing tails, and a combination approach several successful alterations in terms of activity and physiochemical properties were accomplished. Compounds based on benzylamines were found superior to aniline hybrid structures with respect to activity and ADME profile. Exploration of the former class revealed meta-and para amides as favourable 6-aryl substituents, contributing to an increase in activity and acting as a linker for solubilizing tails. Next, combinations of activity-inducing groups on the same scaffold resulted in new drug candidates. Compounds containing 6-aryls with the (2-(dimethylamino)ethyl)carbamoyl substituent were found equipotent to Erlotinib. Compared to this commercial drug, improved solubility and metabolic stability were observed. However, the thieno[2,3-d]pyrimidines with a solubilizing tail was by Caco-2 experiments found to have permeability issues, making further drug development difficult. Selected compounds were further analysed for toxicity and teratogenicity in zebrafish embryos. Two thienopyrimidines were both found to be less lethal than Erlotinib and to perform as well in terms of teratogenicity. Finally, the most promising thienopyrimidine drug was evaluated in a panel of human cancer cell lines, showing a clear potential for thienopyrimidines as anti-cancer agents.