3438-16-2

Basic information

• Product Name: 5-Chloro-2-methoxybenzoic acid
• Synonyms: 2-Carboxy-4-chloroanisole;5-Chloro-N-(2-phenylethyl)-2-MethoxybenzaMide;Glyburide IMP;RARECHEM AL BO 0576;2-METHOXY-5-CHLOROBENZOIC ACID;5-CHLORO-2-METHOXYBENZOIC ACID;5-CHLORO-2-ANISIC ACID;5-CHLORO-O-ANISIC ACID
• CAS NO: 3438-16-2
• Molecular Formula: C₈H₇ClO₃
• Molecular Weight: 186.59
• EINECS: 222-343-7
• Product Categories: API Intermediate;FINE Chemical & INTERMEDIATES;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Organic acids;(intermediate of glibenclamide);Miscellaneous;Acids & Esters;Anisoles, Alkyloxy Compounds & Phenylacetates;Chlorine Compounds
• Mol File: 3438-16-2.mol

Chemical Properties

• Melting Point: 98-100 °C(lit.)
• Boiling Point: 150-152C
• Flash Point: 140.9 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 1,259g/cm
• Vapor Pressure: 0.000276mmHg at 25°C
• Refractive Index: 1,544-1546
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform, Methanol
• PKA: 3.72±0.10(Predicted)
• CAS DataBase Reference: 5-Chloro-2-methoxybenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloro-2-methoxybenzoic acid(3438-16-2)
• EPA Substance Registry System: 5-Chloro-2-methoxybenzoic acid(3438-16-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36
• WGK Germany: 3
• Hazardous Substances Data: 3438-16-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
5-Chloro-2-methoxybenzoic acid is used as a precursor in the synthesis of 5-chloro-2-methoxybenzoates of La(III), Ga(III), and Lu(III). These synthesized compounds have potential applications in various fields, such as pharmaceuticals, materials science, and catalysis.
Used in Coordination Chemistry:
In coordination chemistry, 5-chloro-2-methoxybenzoic acid is used as a ligand to form complexes with metal ions such as Mn2+, Co2+, Ni2+, Cu2+, and Zn2+. These complexes have been investigated for their potential applications in areas like magnetism, optics, and electronics.

InChI:InChI=1/C8H7ClO3/c1-12-7-3-2-5(9)4-6(7)8(10)11/h2-4H,1H3,(H,10,11)/p-1

Upstream product

• 109-72-8 n-butyllithium 
• 60-29-7 diethyl ether 
• 623-12-1 4-chloromethoxybenzene 
• 60633-25-2 2-bromo-4-chloroanisole 
• 579-75-9 2-Methoxybenzoic acid 
• 124-38-9 carbon dioxide 
• 201230-82-2 carbon monoxide 
• 553-82-2 1,3-dichloro-4-methoxybenzene 
• 321-14-2 5-chloro-2-hydroxybenzoic acid 
• 74-88-4 methyl iodide 
• 1450-74-4 5-chloro-2-hydroxyacetophenone 
• 95-48-7 ortho-cresol 
• 1570-64-5 2-methyl-4-chlorophenol 
• 74-96-4 ethyl bromide 

Downstream Products

• 126645-56-5 N-(4-Benzyl-morpholin-2-ylmethyl)-5-chloro-2-methoxy-benzamide 
• 85002-44-4 5-<4-(5-chloro-2-methoxybenzoylamino)benzyl>thiazolidine-2,4-dione 
• 29568-33-0 2-methoxy-5-chlorobenzoyl chloride 
• 25921-68-0 5-chloro-N-[4-(3-cyclohexyl-2-imino-imidazolidine-1-sulfonyl)-phenethyl]-2-methoxy-benzamide 
• 7035-11-2 4-chloro-2-chloromethyl-1-methoxy-benzene 
• 1083177-70-1 (Z)-5-chloro-N-(6,7-dihydro-1H-pyrano[4,3-d]thiazol-2(4H)-ylidene)-2-methoxybenzamide 
• 1083082-43-2 N-[(2Z)-3-butyl-4,6-dihydrofuro[3,4-d][1,3]thiazol-2(3H)-ylidene]-5-chloro-2-methoxybenzamide 
• 1065641-23-7 N-[(2Z)-3-butyl-7-oxo-6,7-dihydro-4H-pyrano[3,4-d][1,3]thiazol-2(3H)-ylidene]-5-chloro-2-methoxybenzamide 
• 104029-20-1 ethyl 3-(5-chloro-2-methoxyphenyl)-3-oxopropanoate 
• 1260168-75-9 ethyl 5-(5-chloro-2-methoxyphenyl)-1H-pyrazole-4-carboxylate 
• 1260168-73-7 ethyl 2-(5-chloro-2-methoxybenzoyl)-3-(dimethylamino)acrylate 
• 1260168-77-1 ethyl 3-(5-chloro-2-methoxyphenyl)-1-methyl-1H-pyrazole-4-carboxylate 
• 1260168-79-3 ethyl 5-(5-chloro-2-methoxyphenyl)-1-methyl-1H-pyrazole-4-carboxylate 
• 1260168-85-1 C₁₂H₁₁ClN₂O₃ 

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.

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.

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

The invention relates to the technical field of medicines, and designs and synthesizes a novel A cyclotrimethoxy 4'-hydroxyflavone compound and an A cyclotrimethoxone-substituted salicylate compound. The figure 1 is a general formula of the A cyclotrimethoxone-substituted salicylate compound, wherein in the formula, R1, R2 and R3 are equal to OCH3 or R2, R3 and R4 are equal to OCH3; R5- is equal to OCH3, CH3, F, Cl, Br, I or the like. The novel A cyclotrimethoxy 4'-hydroxyflavone compound and the A cyclotrimethoxone-substituted salicylate compound can have an obvious inhibiting effect on MGC-803 (human gastric carcinoma cells), HepG2 (human hepatoma carcinoma cells), MCF-7 (human breast cancer cells) and hopefully become anti-tumor drugs. The invention discloses a preparation method of the novel A cyclotrimethoxy 4'-hydroxyflavone compound and the A cyclotrimethoxone-substituted salicylate compound.

Design, synthesis and biological evaluation of flavonoid salicylate derivatives as potential anti-tumor agents

A series of flavonoid salicylate derivatives containing trimethoxybenzene and a series of chrysin salicylate derivatives were synthesized for use as anti-tumor agents, and evaluated for antiproliferative activity using three human tumor cells: MCF-7 (breast carcinoma cells), HepG2 (liver carcinoma cells), MGC-803 (gastric carcinoma cells) and the mice tumor cells MFC (forestomach carcinoma cells). A substituent group of a suitable size and the trimethoxybenzene had a certain influence on the bioactivity of the flavonoid salicylate derivatives. Compound 2 and its salicylate derivatives 7a-7g containing the trimethoxybenzene exhibited more antiproliferative activity. Among them, compound 7g displayed the most potent antiproliferative activity against MGC-803 cells and MFC cells with the concentration causing 50% inhibition of cell growth (IC50) values of 11.05 ± 1.58 μM and 13.73 ± 2.04 μM, respectively. The flow cytometry results showed that compound 7g caused the cell cycle to be arrested in the G0/G1 phase and induced apoptosis of MFC cells in a dose-dependent manner. Furthermore, compound 7g showed good anti-tumor activity in vivo. These results suggested that compound 7g could be a new, potent anti-tumor candidate which should be optimized and evaluated further.

Synthesis technology of glibenclamide intermediate 5-chloro-2-methoxyben zoic acid

The invention provides a synthesis technology of a glibenclamide intermediate 5-chloro-2-methoxyben zoic acid. 5-chloro salicylic acid serves as raw materials. The synthesis technology is characterized by including the following steps that 300-400 kg of a sodium hydroxide solution with the mass friction being 20-40% and 30 kg of 5-chloro salicylic acid are sequentially added into a reaction tank, 80-100 kg of dimethyl sulfate is added dropwise after the mixture is uniformly stirred, temperature is raised to 30-40 DEG C, a reaction lasts for 3-4 h, heating reflux lasts for 4 h, reacting liquid is cooled to room temperature, acidification is performed through a hydrochloric acid solution with the concentration being 20-30% till pH is equal to 2-4, vacuum filtration is performed, a 5-chloro-methyl-2-methoxybenzoate wet product is obtained and placed in a drying oven, drying is performed at 35 DEG C, and the yield is 80-90%. The synthesis technology of glibenclamide intermediate 5-chloro-2-methoxyben zoic acid has the advantages that the intermediate 5-chloro-2-methoxyben zoic acid is an important intermediate for synthesizing glibenclamide, technological operation is easy, the technology is suitable for industrial production operation, and the product yield is stable.

Conformations, equilibrium thermodynamics and rotational barriers of secondary thiobenzanilides

The article deals with conformational behaviour of 2-methoxy-2′-hydroxythiobenzanilides. The CS-NH group of these compounds preferentially adopts the Z-conformation. Entropy favours the Z-conformer over the E-conformer, whereas enthalpy slightly favours the E-conformer over the Z-conformer. The rotational barrier about the CS-NH bond was determined to be (81.5±0.4) kJ/mol. No significant rotational barrier was found on the Ar-CS and Ar-NH bonds. All experimental outcomes are compared with the results of quantum-chemical calculations.

Copper-catalyzed formal c-h carboxylation of aromatic compounds with carbon dioxide through arylaluminum intermediates

The C-H bond carboxylation of various aromatic compounds with CO2 was achieved by the deprotonative alumination with a mixed alkyl amido lithium aluminate compound iBu3Al(TMP)Li followed by the NHC-copper-catalyzed carboxylation of the resulting arylaluminum species, which afforded the corresponding carboxylation products in high yield and high selectivity. In addition to benzene derivatives, heteroarenes such as benzofuran, benzothiophene, and indole derivatives are also suitable substrates. Functional groups such as Cl, Br, I, vinyl, amide, and CN could survive the reaction conditions. Some key reaction intermediates such as the copper aryl and isobutyl complexes and their carboxylation products were isolated and structurally characterized by X-ray crystallographic analyses, thus offering important information on the reaction mechanism.

Cobalt-catalyzed methoxycarbonylation of substituted dichlorobenzenes as an example of a facile radical anion nucleophilic substitution in chloroarenes

A thorough mechanistic study on cobalt-catalysed direct methoxycarbonylation reactions of chlorobenzenes in the presence of methyl oxirane on a wide range of substrates, including poly-and monochloro derivatives with multiple substituents, is reported. The results demonstrate that the reaction is potentially useful as it proceeds under very mild conditions (t = 62 °C, PCO = 1 bar) and converts aryl chlorides to far more valuable products (especially ortho-substituted benzoic acids and esters) in high yields. This transformation also offers another opportunity for the utilization of environmentally harmful polychlorinated benzenes and biphenyls (PCBs). This study is the first to discover an unexpected universal positive ortho-effect: the proximity of any substituent (including Me, Ph, and MeO groups and halogen atoms) to the reaction centre accelerates the methoxycarbonylation in chlorobenzenes. The effect of the ortho-substituents is discussed in detail and explained in terms of a radical anion reaction mechanism. The advantages of the methoxycarbonylation as a model for the mechanistic study of radical anion reactions are also illustrated.

COMPOUNDS USEFUL FOR THE TREATMENT OF METABOLIC DISORDERS AND SYNTHESIS OF THE SAME

The present invention provides compounds of Formula (I): wherein variables X, Y, Z and R1 are as described herein. Some of the compounds described herein are glutamate dehydrogenase activators. The invention is also directed to pharmaceutical compositions comprising these compounds, uses of these compounds and compositions in the treatment of metabolic disorders as well as synthesis of the compounds.

In vitro affinities of various halogenated benzamide derivatives as potential radioligands for non-invasive quantification of D2-like dopamine receptors

Benzamide derivatives as radiotracers have played an important role in diagnosing malfunction in dopaminergic neurotransmission. A variety of halogenated and two unsubstituted benzamide derivatives were synthesised and their in vitro affinities to dopaminergic, serotonergic and adrenergic receptors and their lipophilicities were determined. As references IBZM (3), raclopride (4) and FLB457 (5) were tested as well. The two iodinated compounds NAE (27) and NADE (28) displayed Ki values of 0.68 and 14 nM for the D2 receptor. The well-established radiotracers FP (1) and DMFP (2) showed affinities in the same range as did the brominated compounds NABrE (29) and NABrDE (30). The log D7.4 values of 2.91 for NAE (27) and of 2.81 for NADE (28) are in the range of those found for IBZM (3), FP (1) and DMFP (2). These facts allow to expect good properties for the two iodinated compounds NAE (27) and NADE (28) regarding in vivo imaging with SPECT.