21971-21-1

Basic information

• Product Name: 2-Chloro-4-methoxybenzoic acid
• Synonyms: 2-CHLORO-4-(METHYLOXY)BENZOIC ACID;2-Chloro-4-metxybenzoic acid;2-Chloro-4-methoxybenzoic acid;2-Chloro-4-Methoxybenzoic acid, 97%+
• CAS NO: 21971-21-1
• Molecular Formula: C₈H₇ClO₃
• Molecular Weight: 186.59
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
• Mol File: 21971-21-1.mol

Chemical Properties

• Melting Point: 210.0 to 214.0 °C
• Boiling Point: 303.039 °C at 760 mmHg
• Flash Point: 137.074 °C
• Appearance: /
• Density: 1.353 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.562
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly, Heated, Sonicated), DMSO (Slightly), Methanol (Slightly, S
• PKA: 3.32±0.25(Predicted)
• CAS DataBase Reference: 2-Chloro-4-methoxybenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-4-methoxybenzoic acid(21971-21-1)
• EPA Substance Registry System: 2-Chloro-4-methoxybenzoic acid(21971-21-1)

Safety Data

• Hazardous Substances Data: 21971-21-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-4-methoxybenzoic acid is used as a reactant for the preparation of benzamidochromenone carboxylic acids. These compounds serve as selective agonists for the orphan G protein-coupled receptor GPR35, which has been linked to various biological processes and therapeutic applications, including inflammation, immune response, and cancer.
The specific application of 2-Chloro-4-methoxybenzoic acid in the pharmaceutical industry is to facilitate the synthesis of benzamidochromenone carboxylic acids, which can potentially be used as therapeutic agents targeting GPR35. This makes it a valuable compound for drug discovery and development, particularly in the areas of inflammation, immune regulation, and oncology.

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

Upstream product

• 54788-38-4 2-chloro-4-methoxy-1-methylbenzene 
• 101080-63-1 2-chloro-4-methoxybenzyl chloride 
• 127-09-3 sodium acetate 
• 4294-95-5 4-methoxyanthranilic acid 
• 41068-36-4 2-chloro-4-methoxyacetophenone 
• 56363-84-9 2-chloro-4-hydroxybenzoic acid 
• 77-78-1 dimethyl sulfate 
• 100-09-4 4-methoxybenzoic acid 
• 2845-89-8 1-chloro-3-methoxy-benzene 
• 33844-21-2 2-nitro-4-methoxybenzoic acid 
• 615-62-3 3-chloro-4-methylphenol 
• 95-74-9 3-chloro-p-toluidine 
• 2252-51-9 2-choro-4-fluorobenzoic acid 
• 124-41-4 sodium methylate 

Downstream Products

• 56363-84-9 2-chloro-4-hydroxybenzoic acid 
• 19218-83-8 5-methoxydiphenylamine-2-carboxylic acid 
• 334018-24-5 (2-chloro-4-methoxyphenyl)methanol 
• 84126-73-8 2-<(2-carboxyphenyl)amino>-4-methoxybenzoic acid 
• 791618-64-9 4-chloro-N-(2-chloro-4-methoxy-benzoyl)-benzenesulfonamide 
• 86611-53-2 9-(4-Methanesulfonylamino-2-methoxy-phenylamino)-6-methoxy-acridine-4-carboxylic acid methylamide; hydrochloride 
• 101080-63-1 2-chloro-4-methoxybenzyl chloride 
• 127817-94-1 N-(4-Hydroxyphenyl)-N-(1,1,1-trifluor-2-propyl)-2-chlor-4-hydroxybenzamid 
• 127817-89-4 N-(4-Methoxyphenyl)-N-(1,1,1-trifluor-2-propyl)-2-chlor-4-methoxybenzamid 
• 849479-54-5 2-(3-fluoro-anilino)-4-methoxybenzoic acid 
• 1463965-23-2 2-chloro-4-methoxy-N-(2-(m-tolyloxy)ethyl)benzamide 
• 37934-89-7 2,6-Dimethyl-4-methoxybenzoic acid 
• 50638-46-5 4-bromo-3-chloroanisole 

Relevant articles and documents

First general, direct, and regioselective synthesis of substituted methoxybenzoic acids by ortho metalation

(Chemical Equation Presented) New general methodology of value in aromatic chemistry based on ortho-metalation sites in o-, m-, and p-anisic acids (1-3) (Scheme 1) is described. The metalation can be selectively directed to either of the ortho positions by varying the base, metalation temperature, and exposure times. Metalation of o-anisic acid (1) with s-BuLi/TMEDA in THF at -78°C occurs exclusively in the position adjacente to the carboxylate. On the other hand, a reversal of regioselectivity is observed with n-BuLi/t-BuOK. With LTMP at 0°C, the two directors of m-anisic acid (2) function in concert to direct introduction of the metal between them while n-BuLi/t-BuOK removes preferentially the proton located ortho to the methoxy and para to the carboxylate (H-4). s-BuLi/TMEDA reacts with p-anisic acid (3) exclusively in the vicinity of the carboxylate. According to these methodologies, routes to very simple methoxybenzoic acids with a variety of functionalities that are not easily accessible by other means have been developed (Table 1).

Discovery of (R)-9-ethyl-1,3,4,10b-tetrahydro-7-trifluoromethylpyrazino[2, 1-a]isoindol-6(2H)-one, a selective, orally active agonist of the 5-HT 2C receptor

Robust pharmaceutical treatment of obesity has been limited by the undesirable side-effect profile of currently marketed therapies. This paper describes the synthesis and optimization of a new class of pyrazinoisoindolone- containing, selective 5-HT2C agonists as antiobesity agents. Key to optimization of the pyrazinoisoindolone core was the identification of the appropriate substitution pattern and functional groups which led to the discovery of (R)-9-ethyl-1,3,4,10b-tetrahydro-7-trifluoromethylpyrazino[2,1-a] isoindol-6(2H)-one (58), a 5-HT2C agonist with > 300-fold functional selectivity over 5-HT2B and > 70-fold functional selectivity over 5-HT2A. Oral dosing of 58 reduced food intake in an acute rat feeding model, which could be completely reversed by a selective 5-HT2C antagonist and caused a reduction in body weight gain in a 4-day rat model.

QUINAZOLINE POTASSIUM CHANNEL INHIBITORS

The present invention relates to compounds having the structure (I) useful as potassium channel inhibitors to treat cardiac arrhythmias, and the like.

Acyl sulfonamide anti-proliferatives: Benzene substituent structure-activity relationships for a novel class of antitumor agents

Two closely related diaryl acylsulfonamides were recently reported as potent antitumor agents against a broad spectrum of human tumor xenografts (colon, lung, breast, ovary, and prostate) in nude mice. Especially intriguing was their activity against colorectal cancer xenografts. In this paper, rapid parallel synthesis along with traditional medicinal chemistry techniques were used to quickly delineate the structure-activity relationships of the substitution patterns in both phenyl rings of the acylsufonamide anti-proliferative scaffold. Although the molecular target of the compounds remains unclear, we determined that the vascular endothelial growth factor-dependent human umbilical vein endothelial cells assay in combination with a soft agar disk diffusion assay allowed for optimization of potency in the series. The pharmacokinetic properties and in vivo activity in an HCT116 xenograft model are reported for representative compounds.

Therapeutic compounds

Compounds of the formula (I) for use as an estrogen receptor-β-selective ligand are described wherein: X is O or S; and R1, R3 R6 are as described in the specification. The use of these compounds in treating Alzheimer's disease, anxiety disorders, depressive disorders, osteoporosis, cardiovascular disease, rheumatoid arthritis and prostate cancer is described; as are processes for making them.

Aqua(sulfato)platinum(II) Complexes with Variable Substituents in the 2-Phenyl Ring. 1. Synthesis and Antitumor and Estrogenic Properties

Erythro- and threo-configurated aqua(sulfato)platinum(II) complexes with variable substituents in the 2-phenyl ring (2-PtSO4 to 9-PtSO4: H, 4-F, 3-OH, 4-OH, 2,6-F2, 2,6-Cl2, 2-F/4-OH, 2-Cl/4-OH) were synthesized and tested for estrogenic and antitumor activities.The ligands were obtained by a three-step reaction.The stilbenes were reacted with a mixture of IN3 and NaN3 to yield the respective 1,2-diazido-1,2-diphenylethanes.The subsequent reduction with LiAlH4 led to the corresponding 1,2-diphenylethylenediamines.The (sulfato)platinum(II) complexes were synthesized by reaction of Ag2SO4 with the diiodo complexes, which had been obtained by coordination of the diamines with K2PtI4.Two complexes, erythro-8-PtSO4 and erythro-9-PtSO4, possess antitumor and estrogenic effects and are therefore of interest for the therapy of breast cancer.

Antiestrogenic N-(4-hydroxyphenyl)-N-(1,1,1-trifluoro-2-propyl)-4-hydroxybenzamides: Influence of hydrophobic groups substituted in the ortho-position of the benzamide-fragment on activity

Experiments are reported here to develop compounds with antiestrogenic and mammary tumor inhibiting properties. Analogues with hydrophobic groups in 2- or 2,6-position of the benzamide-fragment of N-(4-hydroxyphenyl)-N-(1,1,1-trifluoro-2-propyl)-4-hydroxy