3260-89-7

Basic information

• Product Name: 2-chloro-6-methoxybenzoic acid
• Synonyms: 6-Chloro-o-anisic acid (COOH=1);2-Methoxy-6-chlorobenzoic acid
• CAS NO: 3260-89-7
• Molecular Formula: C₈H₇ClO₃
• Molecular Weight: 186.6
• EINECS: 221-863-1
• Mol File: 3260-89-7.mol
• Article Data: 9

Chemical Properties

• Melting Point: 141 °C
• Boiling Point: 304.6 °C at 760 mmHg
• Flash Point: 138 °C
• Appearance: /
• Density: 1.352 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 2.87±0.10(Predicted)
• CAS DataBase Reference: 2-chloro-6-methoxybenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloro-6-methoxybenzoic acid(3260-89-7)
• EPA Substance Registry System: 2-chloro-6-methoxybenzoic acid(3260-89-7)

Safety Data

• Hazardous Substances Data: 3260-89-7(Hazardous Substances Data)

Usage

General Description

2-chloro-6-methoxybenzoic acid is a chemical compound that is classified as a benzoic acid derivative. It is composed of a benzene ring with a carboxylic acid functional group and a chlorine atom at the 2 position and a methoxy group at the 6 position. 2-chloro-6-methoxybenzoic acid is commonly used in the pharmaceutical and agrochemical industries for the synthesis of various medications and pesticides. It acts as an intermediate in the production of a wide range of organic compounds and can also be utilized as a building block in organic synthesis. Additionally, 2-chloro-6-methoxybenzoic acid exhibits potential biological activities and has been studied for its anti-inflammatory and antioxidant properties.

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

Upstream product

• 936479-46-8 methyl 6-chloro-2-methoxybenzoate 
• 108-98-5 thiophenol 
• 53600-33-2 6-methoxyanthranilic acid 
• 18362-30-6 2-chloro-6-hydroxybenzaldehyde 
• 87-60-5 3-chloro-2-methylbenzenamine 
• 3260-87-5 3-chloro-o-cresol 
• 172217-11-7 ethyl 2-amino-6-chlorobenzoate 
• 112270-06-1 ethyl 2-chloro-6-hydroxybenzoate 
• 172217-16-2 ethyl 2-chloro-6-nitrobenzoate 
• 579-75-9 2-Methoxybenzoic acid 
• 172217-12-8 ethyl 6-chloro-2-methoxybenzoate 
• 29866-54-4 2-chloro-6-methoxybenzaldehyde 
• 6575-10-6 2-Chlor-6-methoxybenzoesaeurenitril 
• 124-38-9 carbon dioxide 

Downstream Products

• 1198420-31-3 ethyl [4-({[2-chloro-6-(methyloxy)phenyl]carbonyl}amino)phenyl]acetate 
• 1198420-35-7 ethyl (4-{[(2-chloro-6-{[(3-chloro-phenyl)methyl]oxy}phenyl)carbonyl]amino}phenyl)acetate 
• 1198420-36-8 (4-{[(2-chloro-6-{[(3-chloro-phenyl)methyl]oxy}phenyl)carbonyl]amino}phenyl)acetic acid 
• 1198420-33-5 ethyl {4-[({2-chloro-6-[(phenylmethyl)oxy]phenyl}carbonyl)amino]phenyl}acetate 
• 1198420-34-6 {4-[({2-chloro-6-[(phenylmethyl)oxy]phenyl}carbonyl)amino]phenyl}acetic acid 
• 1198420-32-4 ethyl (4-{[(2-chloro-6-hydroxyphenyl)carbonyl]amino}phenyl)acetate 
• 1038726-89-4 2-chloro-6-methoxyphenylmethanol 
• 1239586-29-8 6-methoxy-2-(3,5-dimethoxyphenylamino)benzoic acid 
• 902152-88-9 4-([4-(2-chloro-6-methoxy-benzoylamino)-1H-pyrazole-3-carbonyl]-amino)-piperidine-1-carboxylic acid tert-butyl ester 
• 343969-32-4 (2-Chlor-6-methoxyphenyl)phenylketon 
• 81374-99-4 (2-Chlor-6-hydroxyphenyl)phenylketon 
• 112649-95-3 1,7-Dihydroxy-9-acridon 
• 65582-55-0 1,7-Dihydroxy-10-methyl-9-acridon 
• 172217-13-9 ethyl 6-chloro-2-methoxycarbanilate 

Relevant articles and documents

Theoretical and experimental study on the reactivity of methyl dichlorobenzoates with sulfur-centered nucleophiles by electron transfer reactions

Reactions of methyl 2,5-dichlorobenzoate or methyl 3,6-dichloro-2- methoxybenzoate with sulfur-centered nucleophiles gave mono- and disubstitution products, respectively through SRN1 mechanism in liquid ammonia. Products obtained could be potential herbicides less toxic to the environment. Theoretical studies explained the reactivity observed considering geometries, and spin densities of radical anions and potential energy surfaces for the dissociation of the radical anions formed.

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).

Directed ortho-metalation of unprotected benzoic acids. Methodology and regioselective synthesis of useful contiguously 3- and 6-substituted 2-methoxybenzoic acid building blocks

By treatment with s-BuLi/TMEDA at -78 °C, unprotected 2-methoxybenzoic acid is deprotonated exclusively in the position ortho to the carboxylate. A reversal of regioselectivity is observed when the acid is treated with n-BuLi/t-BuOK. These results are of general utility for the one-pot preparation of a variety of very simple 3- and 6-substituted 2-methoxybenzoic acids that are not easily accessible by conventional means. The potential usefulness of the method is demonstrated by the expedient synthesis of lunularic acid.