4506-45-0

Usage

Uses

Used in Pharmaceutical Industry:
5-Chloro-2-formyl-benzoic acid is used as an intermediate compound for the synthesis of various pharmaceutical products. Its derivatives may be used in the development or synthesis of other products, contributing to the creation of new drugs and medications.
Used in Cosmetics Industry:
5-Chloro-2-formyl-benzoic acid is used as a key component in the formulation of certain cosmetic products. Its derivatives may be employed to enhance the properties of cosmetics, such as improving stability, effectiveness, or providing specific benefits to the skin.
Used in Agriculture Industry:
5-Chloro-2-formyl-benzoic acid is used as a starting material for the production of agrochemicals, such as pesticides and herbicides. Its derivatives may be utilized to develop new and more effective agricultural products, helping to improve crop yields and protect plants from pests and diseases.

InChI:InChI=1/C8H5ClO3/c9-6-2-1-5(4-10)7(3-6)8(11)12/h1-4H,(H,11,12)

Upstream product

• 21739-93-5 2-bromo-5-chlorobenzoic acid 
• 68-12-2 N,N-dimethyl-formamide 
• 19641-29-3 6-chlorophthalide 
• 57319-65-0 6-aminophthalide 
• 87-41-2 2-benzofuran-1(3H)-one 
• 40125-48-2 3-bromo-6-chloro-2-benzofuran-1-(3H)-one 
• 41634-28-0 4-chlorobenzocyclobutene-1,2-dione 
• 610-93-5 6-nitrophthalide 

Downstream Products

• 33886-49-6 6-chloro-2-phenylisoindolin-1-one 
• 871502-89-5 5-chloro-2-bis(5-methyl-2-furyl)methylbenzoic acid 
• 1033595-99-1 6-chloro-3-(5-methylfuran-2-yl)-2-benzofuran-1⁽³⁾-one 
• 1496538-32-9 C₁₄H₉ClN₂O₂ 
• 893768-41-7 C₁₅H₁₀ClNO₄ 
• 1352835-12-1 2-((3-(1-carbamoyl-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylamino)methyl)-5-chlorobenzoic acid 
• 1352836-52-2 5-chloro-2-((3-(4-(methoxycarbonyl)-7-(2-methoxyethoxy)-5H-pyridazino[4,5-b]indol-1-yl)-2-methylphenylamino)methyl)benzoic acid 
• 1352835-72-3 2-((3-(1-carbamoyl-7-((2-(trimethylsilyl)ethoxy)carbonylamino)-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylamino)methyl)-5-chlorobenzoic acid 
• 1352835-62-1 2-((3-(7-(3-tert-butyldimethylsilyloxypyrrolidin-1-yl)-1-carbamoyl-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylamino)methyl)-5-chlorobenzoic acid 
• 1352835-47-2 2-(3-(1-carbamoyl-7-(cyanomethyl)-9H-pyrido[3,4-b]indole-4-yl)-2-methylphenylaminomethyl)-5-chlorobenzoic acid 
• 1203589-45-0 methyl 5-chloro-2-formylbenzoate 
• 1240500-31-5 N-(4-methylphenyl)-7-chloro-1-oxo-1H-isothiochromene-3-carboxamide 
• 1240500-27-9 5-chloro-2-[(4-oxo-2-thioxo-1,3-thiazolidin-5-ylidene)methyl]benzoic acid 
• 640286-54-0 5-chloro-2(2-methoxyvinyl)-benzoic acid 

Relevant academic research and scientific papers

Synthesis of 3-Benzylphthalide Derivatives by Using a TDAE Strategy

A one-pot synthesis of new 3-benzylphthalide derivatives was developed by using a strategy based on tetrakis(dimethylamino)ethylene (TDAE). The reactions in the presence of TDAE of substituted benzyl chlorides with methyl 2-formylbenzoate or of substitute

Synthesis of chiral isoindolinones via asymmetric propargylation/lactamization cascade

A Zn-mediated propargylation/lactamization cascade reaction with chiral 2-formylbenzoate derived N-tert-butanesulfinyl imines was realized, which provided a practical and efficient method for the synthesis of chiral isoindolinones. High diastereoselectivities (up to 97:3 dr) and good reaction yields were observed for most examined cases.

Enantioselective addition of arylboronic acids to methyl 2-formylbenzoates by using a ruthenium/Me-BIPAM catalyst for synthesis of chiral 3-aryl-isobenzofuranones

Ruthenium/Me-BIPAM-catalyzed asymmetric addition of arylboronic acids to methyl 2-formylbenzoates afforded chiral 3-aryl-isobenzofuranones. [RuCl2(p-cymene)]2/Me-BIPAM and RuCl2(PPh3)3/Me-BIPAM catalyst systems tolerate a variety of functional groups and give high yields with high enantioselectivities.

Highly enantioselective synthesis of 2,3-dihydro-1 H-imidazo[2,1-a isoindol-5(9b H)-ones via catalytic asymmetric intramolecular cascade imidization-nucleophilic addition-lactamization

Highly enantioselective catalytic asymmetric intramolecular cascade imidization-nucleophilic addition-lactamization of N1-alkylethane-1,2-diamine with methyl 2-formylbenzoate catalyzed by a chiral phosphoric acid represents the first efficient method for the preparation of medicinally interesting chiral 2,3-dihydro-1H-imidazo[2,1-a]isoindol-5(9bH)-ones with high yields and excellent enantioselectivities. This strategy has been shown to be quite general toward various methyl 2-formylbenzoates.

Synthesis of isothiocoumarin derivatives

A method was developed for the synthesis of 1-oxo-1H-isothiochromenes from 2-benzofuran-1(3H)-one (phthalide). 3-Bromo-6-chloro- and 3,6-dibromo-2- benzofuran-1(3H)-ones were prepared by the bromination of 6-chloro- and 6-bromo-2-benzofuran-1(3H)-ones and were converted by hydrolysis into 5-chloro- or 5-bromo-2-formylbenzoic acids. The condensation of these acids with rhodanine followed by recyclization gave 7-chloro- and 7-bromo-1-oxo-1H-isothiochromene- 3-carboxylic acids.

Synthesis of chiral 3-substituted phthalides by a sequential organocatalytic enantioselective aldol-lactonization reaction. Three-step synthesis of (S)-(-)-3-butylphthalide

(Chemical Equation Presented) The development of efficient methods for the facile construction of important molecular frameworks is an important goal in organic synthesis. Chiral 3-substituted phthalides are widely distributed in a large collection of natural products with broad, potent, and potentially path-pointing biological activities. In this investigation, we have uncovered an unprecedented organocatalytic asymmetric aldol-lactonization reaction of 2-formylbenzoic esters with ketones/aldehydes for convenient construction of the enantioenriched "privileged" scaffold. As a result of the sensitive nature of substrate structures of an organocatalytic enantioselective aldol reaction, after extensive optimization of reaction conditions, catalyst L-prolinamide alcohol IV is identified as the best promoter. Interestingly, it is found that in this reaction, addition of an acid additive PhCO2H can significantly enhance reaction efficiency with use of only as low as 2.5 mol % IV for the process. Moreover, due to the sensitivity of reaction conditions toward a sequential aldol-lactonization process without affecting enantioselectivity and racemization, it is essential to remove the catalyst for the subsequent facile lactonization reaction in the presence of K 2CO3. The aldol-lactonization processes serve as a powerful approach to the preparation of synthetically and biologically important 3-substitued phthalides with a high level of enantioselectivities. A 3-step catalytic asymmetric synthesis of the natural product of 3-butylphthalide is reported.

Furan ring opening - Isocoumarine ring closure: A recyclization reaction of 2-carboxyaryldifurylmethanes

A general method for the synthesis of isocoumarine derivatives has been developed. Bis(5-R-2-furyl)methylbenzoic acids (R = methyl, ethyl) underwent recyclization and subsequent cyclization into tetracyclic isochromene-1-one derivatives under treatment with hydrogen chloride in methanol. It has been shown that intermediate 4-(5-R-furan-2-yl)-3-(3-oxo-3-R-propyl)-isochromene-1- ones can be obtained selectively by varying a concentration of the hydrogen chloride and reaction times. In the case of R = tert-butyl only corresponding 4-[5-(tert-butyl)-2-furyl]-3-(4,4-dimethyl-3-oxopentyl)-1-isochromenones were isolated regardless of the reaction conditions.

Reactions of carbonyl compounds in basic solutions. Part 24. 1 The mechanism of the base-catalysed ring fission of substituted benzocyclobutene-1,2-diones

The rate coefficients for the base-catalysed ring fission of a series of substituted benzocyclobutenediones to give the corresponding 2-formylbenzoic acids have been determined in water at 25.0 and 60.0°C. The effects of 4-substituents and 4,5-di-substituents on the rates have been correlated using a modified Hammett equation to give a reaction constant, ρ, equal to ca. 3.6 at 25.0°C. The activation parameters have been calculated. The effect of solvent composition on the rates has been studied. The kinetic solvent isotope effect, product composition and enrichment in 18O-enriched water have also been studied. All the evidence indicates a mechanistic pathway which proceeds by rapid reversible addition of hydroxide anion to the dione, followed by intramolecular nucleophilic attack on the second carbonyl group and formation of a carbanionic intermediate.