26118-14-9

Basic information

• Product Name: 2-CHLORO-PHENYL-OXO-ACETIC ACID
• Synonyms: 2-CHLORO-PHENYL-OXO-ACETIC ACID;2-Chloro-.alpha.-oxo-benzeneacetic acid;(2-Chlorophenyl)glyoxylic acid;2-(2-Chlorophenyl)-2-oxoacetic acid;2-Chlorobenzoylformic acid
• CAS NO: 26118-14-9
• Molecular Formula: C₈H₅ClO₃
• Molecular Weight: 184.58
• Mol File: 26118-14-9.mol

Chemical Properties

• Melting Point: 114-117 °C
• Boiling Point: 308.705°C at 760 mmHg
• Flash Point: 140.5°C
• Appearance: /
• Density: 1.447g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.585
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 1.93±0.54(Predicted)
• CAS DataBase Reference: 2-CHLORO-PHENYL-OXO-ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-PHENYL-OXO-ACETIC ACID(26118-14-9)
• EPA Substance Registry System: 2-CHLORO-PHENYL-OXO-ACETIC ACID(26118-14-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 26118-14-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-phenyl-oxo-acetic acid is used as an intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
2-Chloro-phenyl-oxo-acetic acid is used as an intermediate in the synthesis of agrochemicals, particularly for its potential to enhance the effectiveness of pesticides and other agricultural products.
Used in Anticancer Research:
2-Chloro-phenyl-oxo-acetic acid is used as a potential anticancer agent, being studied for its ability to target and inhibit the growth of cancer cells, offering a promising avenue for the development of novel cancer treatments.
Used in Antimicrobial and Anti-Fungal Applications:
2-Chloro-phenyl-oxo-acetic acid is used for its antimicrobial and antifungal properties, making it a valuable component in the development of products to combat microbial infections and fungal growth in various settings, including medical and agricultural applications.

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

Upstream product

• 34966-49-9 methyl 2-chlorobenzoylformate 
• 156276-21-0 rac-methyl 2-chloromandelate 
• 35022-42-5 2-chlorobenzoyl cyanide 
• 2142-68-9 1-(2-chlorophenyl)ethanone 
• 62123-75-5 ethyl 2-(2-chlorophenyl)-2-oxoacetate 
• 694-80-4 2-bromo-1-chlorobenzene 
• 124-38-9 carbon dioxide 
• 89-98-5 2-chloro-benzaldehyde 
• 615-41-8 2-iodochlorobenzene 
• 10421-85-9 (S)-2-chloromandelic acid 
• 10421-85-9 2-chloromandelic acid 

Downstream Products

• 808732-87-8 α-(2-thiophenylethylamino)-o-chlorophenylacetic acid 
• 10421-85-9 (S)-2-chloromandelic acid 
• 1239986-54-9 N-(2-(2-chlorobenzoyl)phenyl)acetamide 
• 1417412-46-4 (2-chlorophenyl)(8-(methoxyimino)-5,6,7,8-tetrahydronaphthalen-1-yl)methanone 
• 1438283-02-3 2-(2-chlorophenyl)-N,N-diethyl-2-oxoacetamide 
• 16619-64-0 1-(2-chlorophenyl)-3-phenyl-2-propyn-1-one 
• 1094749-50-4 (2-chlorophenyl)(1-methyl-1H-indol-3-yl)methanone 
• 1393824-68-4 N-[3-(2-chloro-benzoyl)-2H-chromen-4-yl]acetamide 
• 10421-85-9 (R)-2-chloromandelic acid 
• 959161-44-5 S-t-butyl (2-chlorophenyl)-hydroxythioacetate 

Relevant articles and documents

Hypervalent Iodine(III)-Promoted Radical Oxidative C-H Annulation of Arylamines with α-Keto Acids

A novel catalyst-free radical oxidative C-H annulation reaction of arylamines with α-keto acids toward benzoxazin-2-ones synthesis under mild conditions was developed. This hypervalent iodine(III)-promoted process eliminated the use of a metal catalyst or additive with high levels of functional group tolerance. Hypervalent iodine(III) was both an oxidant and a radical initiator for this reaction. The synthetic utility of this method was confirmed by the synthesis of the natural product cephalandole A.

Visible-Light-Promoted Switchable Synthesis of C-3-Functionalized Quinoxalin-2(1H)-ones

A visible-light-promoted synthesis of quinoxalin-2(1H)-ones has been developed using 9-mesityl-10-methylacridinium perchlorate as an organo-photocatalyst. The atmosphere-controlled method (Ar/air) enabled the selective synthesis of hydroxyl- and acyl-containing quinoxalin-2(1H)-ones under mild reaction conditions without the use of any metal catalysts or toxic reagents. A fluorescent labelling experiment showed that hydroxyl-containing quinoxalin-2(1H)-ones may have utility in various biological applications as potent fluorophores. (Figure presented.).

K2S2O8activation by glucose at room temperature for the synthesis and functionalization of heterocycles in water

While persulfate activation at room temperature using glucose has primarily been focused on kinetic studies of the sulfate radical anion, the utilization of this protocol in organic synthesis is rarely demonstrated. We reinvestigated selected K2S2O8-mediated known organic reactions that invariably require higher temperatures and an organic solvent. A diverse, mild functionalization and synthesis of heterocycles using the inexpensive oxidant K2S2O8 in water at room temperature is reported, demonstrating the sustainability and broad scope of the method. Unlike traditional methods used for persulfate activation, the current method uses naturally abundant glucose as a K2S2O8 activator, avoiding the use of higher temperature, UV light, transition metals or bases.

Diazotrifluoroethyl Radical: A CF3-Containing Building Block in [3 + 2] Cycloaddition

We present herein a visible-light-induced [3 + 2] cycloaddition of a hypervalent iodine(III) reagent with α-ketoacids for the construction of 5-CF3-1,3,4-oxadiazoles that are of importance in medicinal chemistry. The reaction proceeds smoothly without a photocatalyst, metal, or additive under mild conditions. Different from the well-established trifluorodiazoethane (CF3CHN2), the diazotrifluoroethyl radical [CF3C(·)N2], a trifluoroethylcarbyne (CF3C?:) equivalent and an unusual CF3-containing building block, is involved in the present reaction system.

General Synthesis of Chiral α,α-Diaryl Carboxamides by Enantioselective Palladium-Catalyzed Cross-Coupling

A general synthesis of chiral α,α-diaryl carboxamides is developed by enantioselective cross-coupling between 2-bromo-2-aryl carboxamides and arylboronic acids, leading to a series of chiral α,α-diaryl carboxamides with various electronic properties and functionalities in moderate to excellent enantioselectivities and yields. The employment of a sterically bulky chiral P,P═O ligand L2 is critical for the reactivity and selectivity. This protocol is applied to an efficient asymmetric synthesis of a key intermediate of dopamine receptor agonist SKF 38393.

Novel synthesis method of benzene ring polysubstituted compound based on benzoyl formic acid

The invention relates to a novel synthesis method of a benzene ring polysubstituted compound based on benzoyl formic acid. According to the synthesis method, an acetophenone-based benzene ring polysubstituted compound is used as a raw material, a specific

Aroylation of Electron-Rich Pyrroles under Minisci Reaction Conditions

The development of Minisci acylation on electron-rich pyrroles under silver-free neutral conditions has been reported featuring the regioselective monoacylation of (NH)-free pyrroles. Unlike conventional Minisci conditions, the avoidance of any acid that could result in the polymerization of pyrroles was the key to success. The umpolung reactivity of the nucleophilic acyl radical, generated in situ from arylglyoxylic acid, could help explain the mechanism of product formation with electron-rich pyrroles. Alternatively, the nucleophilic substitution of the acyl radical on the electron-deficient pyrrole radical cation is proposed.

Selective photoredox decarboxylation of α-ketoacids to allylic ketones and 1,4-dicarbonyl compounds dependent on cobaloxime catalysis

A photoredox/cobaloxime co-catalyzed coupling reaction of α-ketoacids and methacrylates to obtain allylic ketones is described. Without the cobaloxime catalyst, 1,4-dicarbonyl compounds are generated. The cobaloxime catalyst enables dehydrogenation to generate the formation of new olefins. The generality, good substrate scope and mild conditions are good features in the photoredox/cobaloxime catalysis protocol, and this method will provide new opportunities for the functionalization of more olefins.

Photoredox Catalysis Enables Decarboxylative Cyclization with Hypervalent Iodine(III) Reagents: Access to 2,5-Disubstituted 1,3,4-Oxadiazoles

A novel approach to 2,5-disubstituted 1,3,4-oxadiazoles derivatives via a decarboxylative cyclization reaction by photoredox catalysis between commercially available α-oxocarboxylic acids and hypervalent iodine(III) reagent is described. This powerful transformation involves the coupling reaction between two different kinds of radical species and the formation of C-N and C-O bonds.

METHOD FOR PRODUCING BENZOYL FORMIC ACID COMPOUND AND PYRIDAZINE COMPOUND

The present invention provides an industrially-advantageous process for preparing a benzoyl formic acid compound, and an efficient process for preparing a pyridazine compound using the same process. Specifically, the present invention provides a process for preparing a compound represented by formula (2), which comprises a step (B): a step of reacting a compound represented by formula (1) with a nitrosyl sulfuric acid in water to produce the compound represented by formula (2).