13420-63-8

Usage

Uses

Used in Pharmaceutical Industry:
2-chloro-6-iodobenzoic acid is used as a synthetic intermediate for the development of new pharmaceutical compounds. Its unique structure allows for further functionalization and modification, making it a valuable starting material for the synthesis of various drug candidates.
Used in Chemical Research:
In the field of chemical research, 2-chloro-6-iodobenzoic acid serves as a key building block for the exploration of novel chemical reactions and the development of innovative synthetic methods. Its reactivity and structural properties make it an attractive candidate for studying new reaction mechanisms and improving existing synthetic routes.
Used in Material Science:
2-chloro-6-iodobenzoic acid can be utilized as a component in the development of new materials with specific properties, such as optoelectronic materials or advanced polymers. Its unique structure can contribute to the desired characteristics of these materials, making it a valuable asset in material science research and development.
Synthesis Method:
The synthesis of 2-chloro-6-iodobenzoic acid involves a C-H activation method developed by Yu and coworkers. This method employs the Yu-Wasa Auxiliary (Aldrich 791806) and I2 as the sole oxidant for ortho-iodination from the corresponding benzoic acid derivative. This innovative approach allows for the efficient and selective synthesis of 2-chloro-6-iodobenzoic acid, making it more accessible for various applications.

Upstream product

• 100960-33-6 2-amino-6-chlorobenzoic acid hydrochloride 
• 118-91-2 ortho-chlorobenzoic acid 
• 2148-56-3 2-chloro-6-aminobenzoic acid 

Downstream Products

• 54921-07-2 2-Chloro-6-(2-hydroxymethyl-phenylsulfanyl)-benzoic acid 
• 125091-44-3 2-Chloro-6-<(2-chlorophenyl)thio>benzoic Acid 
• 141402-18-8 2-chloro-6-<(3-chlorophenyl)thio>benzoic acid 
• 125091-45-4 2-Chloro-6-<(4-chlorophenyl)thio>benzoic Acid 
• 100038-80-0 C₁₃H₈ClIO₂ 
• 14359-48-9 2-Chloro-6-phenylthiobenzoic acid 
• 141402-21-3 6-chloro-1-(p-toluenesulfonamido)-9H-thioxanthen-9-one 
• 141402-20-2 1,8-bis(p-toluenesulfonamido)-9H-thioxanthen-9-one 
• 100038-97-9 2-Chloro-6-(2-methoxycarbonyl-phenylamino)-benzoic acid 
• 364727-83-3 6-chloro-2-[[3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acid 
• 945543-21-5 (2-chloro-6-iodophenyl)methanol 
• 1126425-92-0 2-chloro-6-(4-chloro-1-(triisopropylsilyl)-1H-pyrrol-3-yl)aniline 
• 16386-65-5 4-(3'-chloro-2'-aminophenyl)-3-chloropyrrole 
• 84483-28-3 2-chloro-6-iodoaniline 

Relevant academic research and scientific papers

Ortholithiation of unprotected benzoic acids: Application for novel 2-chloro-6-substituted benzoic acid syntheses

2-Chloro-6-substituted benzoic acids of the type 2a-h were prepared by the tandem metallation sequence from 2-chlorobenzoic acid 1 with the 1:1 complex secbutyllithium/TMEDA in THF at -78°C followed by quenching with electrophiles.

Palladium-Catalyzed, Norbornene-Mediated, ortho-Amination ipso-Amidation: Sequential C-N Bond Formation

A palladium-catalyzed, norbornene-mediated ortho- and ipso-C-N bond-forming Catellani reaction is reported. This reaction proceeds through a sequential intermolecular amination followed by intramolecular cyclization of a tethered amide. The products, ortho-aminated dihydroquinolinones, were generated in moderate to good yields and are present in bioactive molecules. This work highlights the challenge of competing intra- vs intermolecular palladium-catalyzed processes.

Base- and Additive-Free Ir-Catalyzed ortho-Iodination of Benzoic Acids: Scope and Mechanistic Investigations

A protocol for the C-H activation/iodination of benzoic acids catalyzed by a simple iridium complex has been developed. The method described in this paper allows the ortho-selective iodination of a variety of benzoic acids under extraordinarily mild conditions in the absence of any additive or base in 1,1,1,3,3,3-hexafluoroisopropanol as the solvent. The iridium catalyst used tolerates air and moisture, and selectively gives ortho-iodobenzoic acids with high conversions. Mechanistic investigations revealed that an Ir(III)/Ir(V) catalytic cycle operates, and that the unique properties of HFIP enables the C-H iodination using the carboxylic moiety as a directing group.

A simple and efficient two-step synthesis of 1,2,3-triiodoarenes via consecutive C-H iodination/ipso-Iododecarboxylation strategy: A potential application towards Ortho-diiodoarenes by Regioselective metal-iodine exchange reaction

A general, robust, and efficient method for the conversion of benzoic acids to 1,2,3-triiodoarenes and 1,2,3-trihaloarenes via a two-step synthesis is reported. Commercially available benzoic acids were used that can allow the reactions to be performed on multi-gram scales with good-to-excellent yields. This report discloses a practical method for the synthesis of 1,2,3-triiodoarenes and 1,2,3-trihaloarenes that is general in scope, scalable, and easy to workup and purify. A potential application of the target compounds as precursors for novel regioselective metal-iodine exchange reaction of 1,2,3-triiodoarenes was also demonstrated. It provided ortho-diiodoaryl derivatives in a high regioselective fashion that are useful intermediates in synthesis and indeed are hard to synthesize by any other means.

TRIAZOLONE COMPOUNDS AS mPGES-1 INHIBITORS

The present disclosure is directed to compounds of formula (I), and pharmaceutically acceptable salts thereof, as mPGES-1 inhibitors. These compounds are inhibitors of the microsomal prostaglandin E synthase-1 (mPGES-1) enzyme and are therefore useful in the treatment of pain and/or inflammation from a variety of diseases or conditions, such as asthma, osteoarthritis, rheumatoid arthritis, acute or chronic pain and neurodegenerative diseases.

PdII-catalyzed monoselective ortho halogenation of C-H bonds assisted by counter cations: A complementary method to directed ortho lithiation

(Chemical Equation Presented) When the counterion counts: The yield and selectivity of the title transformation of benzoic acid derivatives were improved greatly by using tetraalkyl ammonium salts as additives (see scheme; monoselectivity: 5:1-18:1). These effects are attributed to the influence of counter cations. The halogenated products are versatile intermediates for the construction of substituted aromatic compounds. DMF=N,N-dimethylformamide.

Condensed pyrazole derivatives, process for producing the same and use thereof

Novel pharmaceutical compositions for inhibiting Th2-selective immune response and pharmaceutical compositions for inhibiting cyclooxygenase comprising condensed pyrazole derivatives represented by the general formula (I): or salts thereof.