2985-79-7

Usage

Uses

Used in Plastics Industry:
4'-Chloro-2-hydroxybenzophenone is used as an additive for enhancing the photo-antioxidant abilities of 2-hydroxybenzoyl compounds. It serves to prevent the autooxidation of plastics when exposed to UV light, thereby improving the durability and stability of the materials.
Used in Pharmaceutical Industry:
4'-Chloro-2-hydroxybenzophenone is utilized as a key intermediate in the development of novel Azomethine Prodrugs of (R)-α-Methylhistamine. These prodrugs have potential applications in the treatment of various medical conditions, showcasing the versatility of 4'-chloro-2-hydroxybenzophenone in the pharmaceutical sector.

Preparation

Preparation by Fries rearrangement of phenyl p-chloro-benzoate, ? with aluminium chloride without solvent between 120° and 160°, (29%), at 200° for 20 min or in refluxing chlorobenzene for 10 h (53%); ? with trifluoromethanesulfonic acid at 45–55° (6%).

Upstream product

• 1871-38-1 phenyl 4-chlorobenzoate 
• 72083-18-2 5-tert-butyl-4'-chloro-2-methoxy-benzophenone 
• 108-90-7 chlorobenzene 
• 1441-87-8 salicyloyl chloride 
• 637-87-6 1-Chloro-4-iodobenzene 
• 90-02-8 salicylaldehyde 
• 89-95-2 2-methyl-benzyl alcohol 
• 46449-60-9 bis(4-chloro-phenyl)-iodonium cation 
• 69-72-7 salicylic acid 
• 122-01-0 4-chloro-benzoyl chloride 
• 108-95-2 phenol 
• 1679-18-1 4-Chlorophenylboronic acid 
• 106-48-9 4-chloro-phenol 
• 446-52-6 2-Fluorobenzaldehyde 

Downstream Products

• 1334334-91-6 2-((4-chlorophenyl)(imino)methyl)phenol 
• 1334247-23-2 (S)-2-(amino(4-chlorophenyl)methyl)phenol 
• 163837-57-8 (R)-(4-chlorophenyl)(phenyl)methylamine 
• 451503-28-9 (α¹R)-4-chloro-α-phenyl-benzenemethanamine hydrochloride 
• 57329-30-3 3-(4'-chlorophenyl)benzofuran 
• 1579264-47-3 C₂₁H₁₅ClO₂ 

Relevant academic research and scientific papers

Water-Tolerant ortho-Acylation of Phenols

A metal-free, water-tolerant, and one-pot process for ortho-acylation of phenols promoted by the iodine source/hydrogen peroxide system has been developed. This transformation undergoes ether formation, iodocyclization, C-C bond cleavage, and oxidative hydrolysis in a one-step manner, which is supported by control experiments.

Asymmetric Transfer Hydrogenation of o-Hydroxyphenyl Ketones: Utilizing Directing Effects That Optimize the Asymmetric Synthesis of Challenging Alcohols

A systematic range of o-hydroxyphenyl ketones were reduced under asymmetric transfer hydrogenation conditions using the C3-tethered catalyst 2. Two directing effects, i.e., an o-hydroxyphenyl coupled to a bulky aromatic on the opposite side of the ketone substrate, combine in a matched manner to deliver reduction products with very high enantiomeric excess.

Cu/Ag mediated peroxide-free synthesis of benzoylated naphthol derivatives

A peroxide-free methodology was developed for the synthesis of benzoylated naphthol/phenol derivatives through oxidative deamination reaction performed under aerobic reaction conditions. A synergistic combination of Cu(OTf)2 and Ag2O was used to convert the aminonaphthols and aminophenols to the corresponding benzoylated derivatives. The definite role of atmospheric oxygen to assist the reaction was proved by performing the reaction in the argon atmosphere.

Efficient visible-light photocatalytic aerobic oxidation of cyclic sulfamides to imines

A highly efficient photocatalytic aerobic oxidation of cyclic sulfamides to synthesize cyclic N-sulfonyl imines with Ir(ppy)2(dtbpy)PF6 as photocatalyst is reported. These environmentally friendly transformations exihibit good to excellent isolated yields and good generality with respect to both five-membered and six-membered cyclic sulfamides.

Ruthenium-Catalyzed Direct Asymmetric Reductive Amination of Diaryl and Sterically Hindered Ketones with Ammonium Salts and H2

A Ru-catalyzed direct asymmetric reductive amination of ortho-OH-substituted diaryl and sterically hindered ketones with ammonium salts is reported. This method represents a straightforward route toward the synthesis of synthetically useful chiral primary diarylmethylamines and sterically hindered benzylamines (up to 97 % yield, 93–>99 % ee). Elaborations of the chiral amine products into bioactive compounds and a chiral ligand were demonstrated through manipulation of the removable and convertible -OH group.

Deoxygenative Arylation of Carboxylic Acids by Aryl Migration

An unprecedented deoxygenative arylation of aromatic carboxylic acids has been achieved, allowing the construction of an enhanced library of unsymmetrical diaryl ketones. The synergistic photoredox catalysis and phosphoranyl radical chemistry allows for precise cleavage of a stronger C?O bond and formation of a weaker C?C bond by 1,5-aryl migration under mild reaction conditions. This new protocol is independent of substrate redox-potential, electronic, and substituent effects. It affords a general and promising access to 60 examples of synthetically versatile o-amino and o-hydroxy diaryl ketones under redox-neutral conditions. Furthermore, it also brings one concise route to the total synthesis of quinolone alkaloid, (±)-yaequinolone A2, and a viridicatin derivative in satisfying yields.

Efficient catalytic synthesis method of 2-hydroxybenzophenone compound

The invention discloses a 2-hydroxybenzophenone compound and a green catalytic synthesis method thereof. According to the method, under the conditions of using coumaranone and coumaranone derivativesas raw materials, using nickel chloride as a catalyst, using methylbenzene as a solvent, using di-tert-butyl peroxide as an oxidizing agent, and using sodium carbonate as alkali, the 2-hydroxybenzophenone compound is obtained at high yield. The method has the advantages that the cost is low; the yield is high; the operation is simple and convenient; no pollution is caused and the like. The potential industrial application prospects are realized. The method provides a cheap and green path for the preparation of the 2-hydroxybenzophenone compound.

Rhodium-Catalyzed Directing-Group-Assisted Aldehydic C–H Arylations with Aryl Halides

A rhodium-catalyzed general protocol for the directing-group-assisted arylation of aromatic aldehydic C–H bonds was developed. This method involves either hydroxy- or amino-group-directed aldehyde C–H arylation with various aryl halides. A broad synthetic scope for the preparation of 2-hydroxybenzophenones was established with electronically variant salicylaldehydes and aryl halides with chemo- and regioselective possibilities. The developed protocol was also applied in the synthesis of medicinally important 3-salicyloylpyridines in high yields.

Acylation of Csp2-H bond with acyl sources derived from alkynes: Rh-Cu bimetallic catalyzed CC bond cleavage

A Rh-Cu bimetallic catalyzed o-acylation of acyloxacetamide with alkynes has been described. This transformation provides a novel, concise way to synthesize ortho-acylphenols using functionalized alkynes as acylating reagents. Mechanistic studies revealed a Rh-Cu relay process, in which O2 plays a critical role for the formation of carbonyl compounds.

Iridium- and rhodium-catalyzed C-H activation and formyl arylation of benzaldehydes under chelation-assistance

Mild and efficient synthesis of benzophenones via Ir(iii)- and Rh(iii)-catalyzed, directing group-assisted formyl C-H arylation of benzaldehydes has been achieved using diaryliodonium salts, in which Rh(iii) and Ir(iii) catalysts exhibited a complementary