39774-18-0

Usage

Uses

Used in Chemical Synthesis:
4-Chlorobenzoin is used as a key intermediate in the synthesis of various organic chemicals. Its unique structure, featuring a chlorine atom on the benzene ring, allows for versatile chemical reactions and transformations, making it a valuable component in the production of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-chlorobenzoin is used as a building block for the synthesis of various drug molecules. Its reactivity and functional groups enable the creation of new compounds with potential therapeutic applications, contributing to the development of novel medications.
Used in Agrochemical Industry:
4-Chlorobenzoin is also utilized in the agrochemical industry for the synthesis of active ingredients in pesticides and other crop protection products. Its chemical properties facilitate the development of new compounds with improved efficacy and reduced environmental impact.
Used in Specialty Chemicals:
4-Chlorobenzoin serves as a raw material in the production of specialty chemicals, such as dyes, fragrances, and flavorings. Its versatility in chemical reactions allows for the creation of a wide range of compounds with specific properties, catering to the diverse needs of various industries.

InChI:InChI=1/C14H11ClO2/c15-12-8-6-11(7-9-12)14(17)13(16)10-4-2-1-3-5-10/h1-9,13,16H

Upstream product

• 106-39-8 bromochlorobenzene 
• 532-28-5 (RS)-mandelonitrile 
• 100-52-7 benzaldehyde 
• 113348-33-7 phosphoric acid (4-chlorophenyl)(cyano)methyl ester diethyl ester 
• 7446-70-0 aluminium trichloride 
• 4998-15-6 4-chlorophenylglyoxal 
• 71-43-2 benzene 
• 104-88-1 4-chlorobenzaldehyde 
• 25438-37-3 phenyl(trimethylsiloxy)acetonitrile 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 71292-81-4 2-(4-chlorophenyl)-2-hydroxy-1-phenylethanone 
• 10359-09-8 2-(4-chlorophenyl)-1,3-dithiane 
• 1333394-46-9 (2-(4-chlorophenyl)-1,3-dithian-2-yl)(phenyl)methanol 
• 1889-71-0 4'-chloro-2-phenylacetophenone 

Downstream Products

• 109569-22-4 4-(4-chloro-phenyl)-5-phenyl-1⁽³⁾H-imidazole 
• 114379-74-7 4-(4-chloro-phenyl)-5-phenyl-1⁽³⁾H-imidazole-2-carboxylic acid anilide 
• 75116-28-8 3-[2-(4-chlorophenyl)-2-oxoethyl]-1,3-dimethylindolin-2-one 
• 312523-92-5 5-(4-chlorophenyl)-2-(3,5-dimethoxyphenyl)-4-phenyl-1H-imidazole 
• 119267-71-9 2-(4-chlorophenyl)-2-oxo-1-phenylethyl acetate 
• 1889-71-0 4'-chloro-2-phenylacetophenone 
• 1379799-72-0 dimethyl 4-(4-chlorophenyl)-5-phenylfuran-2,3-dicarboxylate 
• 1293372-52-7 (4S,5R)-4-(4-chlorophenyl)-5-phenyl-[1,2,3]oxathiazolidine 2,2-dioxide 
• 1293372-40-3 4-(4-chlorophenyl)-5-phenyl-5H-[1,2,3]oxathiazole 2,2-dioxide 
• 65-85-0 benzoic acid 
• 74-11-3 para-chlorobenzoic acid 
• 62086-75-3 (1RS,2SR)-1-(4'-chlorophenyl)-2-phenylethane-1,2-diol 
• 114679-00-4 2-(4-chlorophenyl)-2-oxo-1-phenylethyl benzoate 
• 6332-83-8 2-(4-chlorophenyl)-1-phenylethanone 

Relevant academic research and scientific papers

Green preparation method α - hydroxyketone

The invention relates to a green preparation method of alpha-hydroxyketone. The method comprises the following steps: adding ketone, iodine, 1,4-diazabicyclo[2.2.2]octane and methanol into a glass reaction bottle in sequence; then stirring and reacting for 14 to 30h at room temperature in an air atmosphere under the irradiation of a 23W compact type fluorescent lamp, so as to obtain a reaction mixture; carrying out silica gel column chromatographic separation to obtain the pure alpha-hydroxyketone. The green preparation method provided by the invention has the characteristics of greenness, high efficiency, simplicity in operation, moderate conditions, wide applicability and easiness for industrialization.

UV light-mediated difunctionalization of alkenes through aroyl radical addition/1,4-/1,2-Aryl shift cascade reactions

UV light-mediated difunctionalization of alkenes through an aroyl radical addition/1,4-/1,2-aryl shift has been described. The resulted aroyl radical from a photocleavage reaction added to acrylamide compounds followed by cyclization led to the formation of oxindoles, whereas the addition to cinnamic amides aroused a unique 1,4-aryl shift reaction. Furthermore, the difunctionalization of alkenes of prop-2-en-1-ols was also achieved through aroyl radical addition and a sequential 1,2-aryl shift cascade reaction.

Mechanism of α-ketol-type rearrangement of benzoin derivatives under basic conditions

The mechanism of base-catalyzed rearrangement of ring-substituted benzoins in aqueous methanol was examined by kinetic and product analyses. Substituent effects on the rate and equilibrium constants revealed that the kinetic process has a different electron demand compared to the equilibrium process. Reactions in deuterated solvents showed that the rate of H/D exchange of the α-hydrogen is similar to the overall rate toward the equilibrium state. A proton-inventory experiment using partially deuterated solvents showed a linear dependence of the rate on the deuterium fraction of the solvent, indicating that only one deuterium isotope effect contributes to the overall rate process. All these results point to a mechanism in which the rearrangement is initiated by the rate-determining α-hydrogen abstraction rather than a mechanism with initial hydroxyl hydrogen abstraction as in the general α-ketol rearrangement.

Chemoenzymatic synthesis of chiral unsymmetrical benzoin esters

A chemoenzymatic Dynamic Kinetic Resolution (DKR) of unsymmetrical benzoins (Ar1≠Ar2) has been carried out, by using Pseudomonas stutzeri lipase stereorecognition pattern. After studying this lipase behaviour, a high preference towards acylation of those benzoins containing substituents in the phenyl ring rather than in the benzoyl moiety was observed. This fact allowed the development of the DKR process of this kind of substrates, avoiding the accumulation of secondary products derived from the in situ racemization mediated by Shvo's catalyst action, and allowing the synthesis of enantiopure unsymmetrical benzoins acetates (not previously described) in very good yields (60-95%) and excellent enantiomeric excess values (always >99%).

Oxidation of benzoins to benzils using sodium hydride

A highly efficient and eco-friendly oxidation of benzoins 1 to benzils 2 using sodium hydride has been developed.

Antibody-Catalyzed Benzoin Oxidation as a Mechanistic Probe for Nucleophilic Catalysis by an Active Site Lysine

Aldolase antibody 24H6, which was obtained by reactive immunization against a 1,3-diketone hapten, is shown to catalyze additional reactions, including H/D exchange and oxidation reactions. Comparison of the H/D exchange reaction at the α-position of a wide range of aldehydes and ketones by 24H6 and by other aldolase antibodies, such as 38C2, pointed at the significantly larger size of the 24H6 active site. This property allowed for the catalysis of the oxidation of substituted benzoins to benzils by potassium ferricyanide. This reaction was used as a mechanistic probe to learn about the initial steps of the 24H6-catalyzed aldol condensation reaction. The Hammett correlation (ρ=4.7) of log(kcat) versus the substituent constant, σ, revealed that the reaction involves rapid formation of a Schiff base intermediate from the ketone and an active site lysine residue. The rate-limiting step in this oxidation reaction is the conversion of the Schiff base to an enamine intermediate. In addition, linear correlation (ρ= 3.13) was found between log(KM) and σ, indicating that electronic rather than steric factors are dominant in the antibody-substrate binding phenomenon and confirming that the reversible formation of a Schiff base intermediate comprises part of the substrate-binding mechanism.

Application of Cyanophosphates in Organic Synthesis. Reactivity of α-Cyano-α-diethylphosphonooxy Anions

The utility of the cyanohydrin diethylphosphates derived from aldehydes (arylaldehydes,crotonaldehyde, and cinnamaldehyde) as an acyl anion equivalent was examined.Deprotonation of cyanophosphates with n-butyllithium in the presence of tetramethylethylene

Reduction of Unsymmetrical Benzils Using Sodium Dithionite

Contrary to a previous report, reduction of unsymmetrical benzils by sodium dithionite (sodium hydrosulfite) in general yields a mixture of isomeric benzoins.Whereas the reduction of aldehydes and ketones by dithionite apparently takes place by a nucleophilic addition mechanism, the reduction of benzils proceeds by an electron-transfer mechanism.The initial product of the reduction is the (Z)-α,α'-stilbenediol which is produced stereospecifically.The ultimate benzoin products, then, result from the two different modes of ketolization of the stilbenediol intermediate.