2476-35-9

Basic information

• Product Name: 5-Bromo-2-methoxybenzoic acid
• Synonyms: RARECHEM AL BE 0053;2-METHOXY-5-BROMOBENZOIC ACID;5-BROMO-2-METHOXYBENZOIC ACID;5-BROMO-O-ANISIC ACID;AKOS BBB/391;AKOS BB-8176;AKOS B025214;ASISCHEM Y08619
• CAS NO: 2476-35-9
• Molecular Formula: C₈H₇BrO₃
• Molecular Weight: 231.04
• Product Categories: Benzoic acid;Acids & Esters;Anisoles, Alkyloxy Compounds & Phenylacetates;Bromine Compounds;C8;Carbonyl Compounds;Carboxylic Acids
• Mol File: 2476-35-9.mol

Chemical Properties

• Melting Point: 118-122 °C
• Boiling Point: 334.7 °C at 760 mmHg
• Flash Point: 156.2 °C
• Appearance: /
• Density: 1.625 g/cm³
• Vapor Pressure: 4.97E-05mmHg at 25°C
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.70±0.10(Predicted)
• CAS DataBase Reference: 5-Bromo-2-methoxybenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-2-methoxybenzoic acid(2476-35-9)
• EPA Substance Registry System: 5-Bromo-2-methoxybenzoic acid(2476-35-9)

Safety Data

• Hazard Codes: Xi,T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• HazardClass: IRRITANT
• PackingGroup: Ⅲ
• Hazardous Substances Data: 2476-35-9(Hazardous Substances Data)

Usage

Chemical Properties

off-white powder

Synthesis Reference(s)

Tetrahedron Letters, 34, p. 931, 1993 DOI: 10.1016/S0040-4039(00)77457-0

InChI:InChI=1/C8H7BrO3/c1-12-7-3-2-5(9)4-6(7)8(10)11/h2-4H,1H3,(H,10,11)/p-1

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 60-29-7 diethyl ether 
• 917-54-4 methyllithium 
• 21702-84-1 2,4-dibromoanisole 
• 14804-31-0 2-methyl-4-bromoanisole 
• 579-75-9 2-Methoxybenzoic acid 
• 4068-76-2 5-bromo-2-hydroxy-benzoic acid methyl ester 
• 74-88-4 methyl iodide 
• 124-38-9 carbon dioxide 
• 25016-01-7 5-bromo-2-methoxybenzaldehyde 
• 7664-93-9 sulfuric acid 
• 7726-95-6 bromine 
• 163260-76-2 4-bromo-2-(2-bromo-ethyl)-anisole 
• 861362-94-9 2-bromo-3-(5-bromo-2-methoxy-phenyl)-3-hydroxy-propionic acid 

Downstream Products

• 99-58-1 3-bromo-4-methoxybenzoic acid 
• 773134-60-4 ethyl 5-bromo-2-methoxybenzoate 
• 190248-43-2 C₁₈H₂₆N₂O₇ 
• 106-41-2 4-bromo-phenol 
• 95-56-7 2-hydroxybromobenzene 
• 13130-23-9 3,5-dibromo-2-methoxybenzoic acid 
• 107410-07-1 2-methoxy-5-phenylbenzoic acid 
• 60541-89-1 5-bromo-2-methoxy-3-nitro-benzoic acid 
• 54450-20-3 5-bromo-3(2H)-benzofuranone 
• 123987-22-4 (-)-(S)-5-bromo-N-<(1-ethyl-2-pyrrolidinyl)methyl>-2-methoxybenzamide 
• 63987-24-6 2-methoxy-5-phenoxy-benzoic acid 
• 502924-41-6 1-(5-bromo-2-methoxyphenyl)propan-1-one 
• 1190223-44-9 5-(5-formylfuran-2-yl)-2-methoxybenzoic acid 
• 1416255-21-4 (5-bromo-2-methoxyphenyl)(2-methyl-1-benzofuran-3-yl)methanone 

Relevant articles and documents

Synthesis and antioxidant activities of berberine 9-: O -benzoic acid derivatives

Although berberine (BBR) shows antioxidant activity, its activity is limited. We synthesized 9-O-benzoic acid berberine derivatives, and their antioxidant activities were screened via ABTS, DPPH, HOSC and FRAP assays. The para-position was modified with halogen elements on the benzoic acid ring, which led to an enhanced antioxidant activity and the substituent on the ortho-position was found to be better than the meta-position. Compounds 8p, 8c, 8d, 8i, 8j, 8l, and especially 8p showed significantly higher antioxidant activities, which could be attributed to the electronic donating groups. All the berberine derivatives possessed proper lipophilicities. In conclusion, compound 8p is a promising antioxidant candidate with remarkable elevated antioxidant activity and moderate lipophilicity.

A convenient and efficient H2SO4-promoted regioselective monobromination of phenol derivatives using N-bromosuccinimide

A convenient, rapid H2SO4-promoted regioselective monobromination reaction with N-bromosuccinimide was developed. The desired para-monobrominated or ortho-monobrominated products of phenol derivatives were obtained in good to excellent yields with high selectivity. Regioselective chlorination and iodination were also achieved in the presence of H2SO4 using N-chlorosuccinimide and N-iodosuccinimide, respectively.

Divergent Synthesis of Natural Benzyl Salicylate and Benzyl Gentisate Glucosides

Herein is reported the first total synthesis of benzyl salicylate and benzyl gentisate glucosides present in various plant species, in particular the Salix genus, such as Populus balsamifera and P. trichocarpa. The method permits the synthesis of several natural phenolic acid derivatives and their glucosides starting from salicylic or gentisic acid. The divergent approach afforded access to three different acetylated glucosides from a common synthetic intermediate. The key step in the total synthesis of naturally occurring glycosides - the selective deacetylation of the sugar moiety - was achieved in the presence of a labile benzyl ester group by employing mild deacetylation conditions. The protocol permitted synthesis of trichocarpine (4 steps, 40% overall yield), isotrichocarpine (3 steps, 51% overall yield), trichoside (6 steps, 40% overall yield), and deoxytrichocarpine (3 steps, 42% overall yield) for the first time (>95% purity). Also, the optimized mild deacetylation conditions allowed synthesis of 2-O-acetylated derivatives of all four glycosides (5-17% overall yield, 90-95% purity), which are rare plant metabolites.

COMPOUNDS AND METHODS OF INHIBITING BACTERIAL CHAPERONIN SYSTEMS

The present disclosure relates to novel compounds and methods of killing or inhibiting the growth of bacteria. In some embodiments, a method of killing or inhibiting the growth of bacteria is provided. The method comprises administering a compound of formula I or a pharmaceutically acceptable salt thereof to bacteria. In some embodiments, a method of killing or inhibiting the growth of bacteria is provided. The method comprises administering an anthelmintic to bacteria.

Design, synthesis, and preliminary biological evaluation of 3′,4′,5′-trimethoxy flavonoid salicylate derivatives as potential anti-tumor agents

According to the pharmacophore combination principle, a set of new 3′,4′,5′-trimethoxy flavonoid salicylate derivatives were designed, synthesized, and evaluated for biological activity. The cytotoxicity evaluation revealed that compound 10v exhibited higher potency than 5-Fu against HCT-116 cells. Preliminary biological activity studies showed that compound 10v could inhibit the colony formation and migration of HCT-116 cells. Besides, the Hoechst 33258 staining assay and flow cytometry revealed that treatment with compound 10v induced the apoptosis of HCT-116 cells in a concentration-dependent manner, while it had no effect on their cell cycle. The WB analysis suggested that HIF-1α, tubulin, HK-2, and PFK might be the potential pharmacophore targets of compound 10v. Tubulin was a potential drug target for compound 10v, which was explained by analyzing the crystal structure of compound 10v complexed with tubulin. These results indicated that compound 10v might be a promising anti-tumor agent candidate, deserving further optimization and evaluation.

Hydroxybiphenylamide GroEL/ES Inhibitors Are Potent Antibacterials against Planktonic and Biofilm Forms of Staphylococcus aureus

We recently reported the identification of a GroEL/ES inhibitor (1, N-(4-(benzo[d]thiazol-2-ylthio)-3-chlorophenyl)-3,5-dibromo-2-hydroxybenzamide) that exhibited in vitro antibacterial effects against Staphylococcus aureus comparable to vancomycin, an antibiotic of last resort. To follow up, we have synthesized 43 compound 1 analogs to determine the most effective functional groups of the scaffold for inhibiting GroEL/ES and killing bacteria. Our results identified that the benzothiazole and hydroxyl groups are important for inhibiting GroEL/ES-mediated folding functions, with the hydroxyl essential for antibacterial effects. Several analogs exhibited >50-fold selectivity indices between antibacterial efficacy and cytotoxicity to human liver and kidney cells in cell culture. We found that MRSA was not able to easily generate acute resistance to lead inhibitors in a gain-of-resistance assay and that lead inhibitors were able to permeate through established S. aureus biofilms and maintain their bactericidal effects.

Transition-metal-free decarboxylative bromination of aromatic carboxylic acids

Methods for the conversion of aliphatic acids to alkyl halides have progressed significantly over the past century, however, the analogous decarboxylative bromination of aromatic acids has remained a longstanding challenge. The development of efficient methods for the synthesis of aryl bromides is of great importance as they are versatile reagents in synthesis and are present in many functional molecules. Herein we report a transition metal-free decarboxylative bromination of aromatic acids. The reaction is applicable to many electron-rich aromatic and heteroaromatic acids which have previously proved poor substrates for Hunsdiecker-type reactions. In addition, our preliminary mechanistic study suggests that radical intermediates are not involved in this reaction, which is in contrast to classical Hunsdiecker-type reactivity. Overall, the process demonstrates a useful method for producing valuable reagents from inexpensive and abundant starting materials.

Transition-Metal-Free Decarboxylative Iodination: New Routes for Decarboxylative Oxidative Cross-Couplings

Constructing products of high synthetic value from inexpensive and abundant starting materials is of great importance. Aryl iodides are essential building blocks for the synthesis of functional molecules, and efficient methods for their synthesis from chemical feedstocks are highly sought after. Here we report a low-cost decarboxylative iodination that occurs simply from readily available benzoic acids and I2. The reaction is scalable and the scope and robustness of the reaction is thoroughly examined. Mechanistic studies suggest that this reaction does not proceed via a radical mechanism, which is in contrast to classical Hunsdiecker-type decarboxylative halogenations. In addition, DFT studies allow comparisons to be made between our procedure and current transition-metal-catalyzed decarboxylations. The utility of this procedure is demonstrated in its application to oxidative cross-couplings of aromatics via decarboxylative/C-H or double decarboxylative activations that use I2 as the terminal oxidant. This strategy allows the preparation of biaryls previously inaccessible via decarboxylative methods and holds other advantages over existing decarboxylative oxidative couplings, as stoichiometric transition metals are avoided.

C- ARYL GLYCOSID DERIVATIVES, PHARMACEUTICAL COMPOSITION, PREPARATION PROCESS AND USES THEREOF

This invention relates to a kind of C-aryl glycoside derivatives, its pharmaceutical compositions, preparation methods, and uses thereof. The preparation method comprises: method 1: in a solvent, deprotecting the acetyl protecting groups of compound 1-f in the presence of a base; method 2: 1) compound 2-g reacts with via Mitsunobu reaction; 2) deprotecting the acetyl protecting groups of compound 2-f obtained from step 1; method 3: 1) compound 2-g reacts with via nucleophilic substitution reaction; 2) deprotecting the acetyl protecting groups of compound 3-f obtained from step 1. The pharmaceutical composition comprises a kind of C-aryl glycoside derivatives; it's pharmaceutically acceptable salts and/or prodrugs thereof and excipient thereof. This invention further relates to a kind of C-aryl glycoside derivatives, it's pharmaceutically acceptable salts or pharmaceutical compositions thereof for the use in preparation of a SGLT inhibitor. The C-aryl glycoside derivatives of this invention provides a new direction for the study of SGLT inhibitors.

A cyclotrimethoxone-substituted salicylate compound and anti-tumor effect thereof

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