62123-75-5

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 2-CHLOROBENZOYLFORMATE is used as a key intermediate in the synthesis of pharmaceuticals for its ability to facilitate the creation of diverse medicinal compounds, contributing to the development of new treatments and therapies.
Used in Pesticide Production:
In the agricultural sector, ETHYL 2-CHLOROBENZOYLFORMATE is utilized as a component in the production of pesticides, playing a crucial role in the development of effective solutions to protect crops and ensure food security.
Used in Dye Manufacturing:
ETHYL 2-CHLOROBENZOYLFORMATE is employed as a vital constituent in the manufacturing of dyes, where its chemical properties contribute to the creation of a broad spectrum of colors for various applications, including textiles, plastics, and printing inks.
Used in Perfumery:
ETHYL 2-CHLOROBENZOYLFORMATE is used as a component in the perfume industry, capitalizing on its fruity odor to enhance the fragrances of various scented products, such as perfumes, colognes, and other fragranced items.

InChI:InChI=1/C10H9ClO3/c1-2-14-10(13)9(12)7-5-3-4-6-8(7)11/h3-6H,2H2,1H3

Upstream product

• 64-17-5 ethanol 
• 1056775-36-0 1-(bromoethynyl)-2-chlorobenzene 
• 1398179-33-3 o-chlorophenyldiazoacetic acid ethyl ester 
• 694-80-4 2-bromo-1-chlorobenzene 
• 95-92-1 oxalic acid diethyl ester 
• 615-41-8 2-iodochlorobenzene 
• 4755-77-5 Ethyl oxalyl chloride 
• 10421-85-9 2-chloromandelic acid 
• 19112-35-7 ethyl (2-chlorobenzoyl)acetate 
• 40018-25-5 2-Chlorobenzoyl acetonitrile 
• 13511-30-3 ethyl 2-(2-chlorophenyl)-2-hydroxyacetate 
• 609-65-4 o-chlorobenzoyl chloride 
• 3900-89-8 2-Chlorobenzeneboronic acid 
• 623-49-4 ethyl cyanoformate 

Downstream Products

• 85905-76-6 (2-Chloro-phenyl)-triethylsilanyloxy-acetic acid ethyl ester 
• 85905-79-9 (2-Chloro-phenyl)-(dibutyl-ethyl-silanyloxy)-acetic acid ethyl ester 
• 85905-74-4 C₃₆H₃₅Cl₃O₉Si 
• 1629188-65-3 C₁₁H₁₁ClO₂ 
• 1402841-30-8 (E)-ethyl 2-(2-chlorophenyl)-2-((trimethylsilyl)methylimino)acetate 
• 1392008-13-7 (R,E)-ethyl 3-(tert-butyldiazenyl)-2-(2-chlorophenyl)-2-hydroxypropanoate 
• 27993-91-5 3-(2-chlorophenyl)quinoxalin-2(1H)-one 
• 421545-87-1 ethyl 2-(2-chlorophenyl)-2-hydroxyacetate 
• 871836-58-7 ethyl 2-chloromandelate 
• 85905-83-5 (2-Chloro-phenyl)-triisobutylsilanyloxy-acetic acid ethyl ester 
• 26118-14-9 o-chlorobenzoylformic acid 
• 1196988-57-4 (S)-iso-propyl α-hydroxy-α-(2-chlorophenyl)acetate 
• 1242001-70-2 (R)-isopropyl 2-(2-chlorophenyl)-2-hydroxyacetate. 
• 62123-77-7 isopropyl-2-(2-chlorophenyl)-2-oxoacetate 

Relevant academic research and scientific papers

Tris(pentafluorophenyl)borane-Catalyzed Oxygen Insertion Reaction of α-Diazoesters (α-Diazoamides) with Dimethyl Sulfoxide

A tris(pentafluorophenyl)borane-catalyzed oxidation reaction of α-diazoesters (α-diazo amides) with dimethyl sulfoxide has been developed. The reaction proceeds under metal free conditions to afford a series α-ketoesters and α-ketoamides. The synthetic utility of this protocol is demonstrated through synthetic transformations and scaled-up synthesis. (Figure presented.).

Palladium-Catalyzed Asymmetric Hydroesterification of α-Aryl Acrylic Acids to Chiral Substituted Succinates

A palladium-catalyzed asymmetric hydroesterification of α-aryl acrylic acids with CO and alcohol was developed, preparing a variety of chiral α-substituted succinates in moderate yields with high ee values. The kinetic profile of the reaction progress revealed that the alkene substrate first underwent the hydroesterification followed by esterification with alcohol. The origin of the enantioselectivity was elucidated by density functional theory computation.

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.

Exploiting Cofactor Versatility to Convert a FAD-Dependent Baeyer–Villiger Monooxygenase into a Ketoreductase

Cyclohexanone monooxygenases (CHMOs) show very high catalytic specificity for natural Baeyer–Villiger (BV) reactions and promiscuous reduction reactions have not been reported to date. Wild-type CHMO from Acinetobacter sp. NCIMB 9871 was found to possess an innate, promiscuous ability to reduce an aromatic α-keto ester, but with poor yield and stereoselectivity. Structure-guided, site-directed mutagenesis drastically improved the catalytic carbonyl-reduction activity (yield up to 99 %) and stereoselectivity (ee up to 99 %), thereby converting this CHMO into a ketoreductase, which can reduce a range of differently substituted aromatic α-keto esters. The improved, promiscuous reduction activity of the mutant enzyme in comparison to the wild-type enzyme results from a decrease in the distance between the carbonyl moiety of the substrate and the hydrogen atom on N5 of the reduced flavin adenine dinucleotide (FAD) cofactor, as confirmed using docking and molecular dynamics simulations.

Controllable chemoselectivity in the coupling of bromoalkynes with alcohols under visible-light irradiation without additives: Synthesis of propargyl alcohols and α-ketoesters

The chemoselectivity of visible-light-induced coupling reactions of bromoalkynes with alcohols can be controlled by simple changes to the reaction atmosphere (N2 or O2). A N2 atmosphere favours propargyl alcohols via a direct C-C coupling process, whereas an O2 atmosphere results in the generation of α-ketoesters through the oxidative CC/C-O coupling pathway.

Copper-catalyzed TEMPO oxidative cleavage of 1,3-diketones and β-keto esters for the synthesis of 1,2-diketones and α-keto esters

A copper-catalyzed efficient and practical method has been developed for the synthesis of 1,2-diketones and α-keto esters. TEMPO was used as a radical initiator and scavenger, oxidizing the cleavage of α-methylene of 1,3-diketones and β-keto esters to form 1,2-diketones and α-keto esters. This method provided a general way for the formation of 1,2-dicarbonyl compounds.

A novel method for synthesis of α-keto esters with phenyliodine(III) diacetate

A rapid and efficient synthesis of α-keto esters from β-ketonitriles using phenyliodine(III) diacetate is reported. This protocol gave α-keto esters in good yields. This is the first time to report the application of hypervalent iodine(III) reagents in the synthesis of α-keto esters. A plausible reaction mechanism is proposed.

Simply air: Vanadium-catalyzed oxidative kinetic resolution of methyl o-chloromandelate by ambient air

Vanadium-catalyzed oxidative kinetic resolution (OKR) of methyl o-chloromandelate 2a, key intermediate of the well-known oral antiplatelet agent (S)-clopidogrel, was achieved by ambient air for the first time. The air oxidation system, which was composed of vanadium and tridentate Schiff base ligands derived from amino alcohols and salicylaldehyde derivatives, afforded an efficient and economic approach to the target intermediate with high enantioselectivities (>99% ee).

CeCl3·7H2O: An effective additive in ru-catalyzed enantioselective hydrogenation of aromatic α-ketoesters

(Chemical Equation Presented) In the presence of catalytic amounts of CeCl3·7H2O, [RuCl(benzene)(S)-SunPhos]Cl is a highly effective catalyst for the asymmetric hydrogenation of aromatic α-ketoesters. A variety of ethyl α-hydroxy-α-arylacetates have been prepared in up to 98.3% ee with a TON up to 10 000. Challenging aromatic α-ketoesters with ortho substituents are also hydrogenated with high enantioselectivities. The addition of CeCl3·7H2O not only improves the enantioselectivity but also enhances the stability of the catalyst. The ratio of CeCl3·7H2O to [RuCl(benzene)(S)-SunPhos]Cl plays an important role in the hydrogenation reaction with a large substrate/catalyst ratio.

Highly efficient chemoenzymatic synthesis of methyl (R)-o-chloromandelate, a key intermediate for clopidogrel, via asymmetric reduction with recombinant Escherichia coli

Methyl (R)-o-chloromandelate [(R)-1], which is an intermediate for a platelet aggregation inhibitor named clopidogrel, was obtained in >99% ee by the asymmetric reduction of methyl o-chlorobenzoylformate (2) with recombinant Escherichia coli overproducing