4837-14-3

Usage

Appearance

White to light yellow crystalline solid
A physical characteristic describing the color and form of the compound in its solid state.

Usage in organic synthesis

Building block for various organic compounds
A role in the creation of other chemical compounds, contributing to the formation of complex molecules.

Application in industries

Pharmaceuticals and agricultural chemicals
A potential use in the production of products for medical and agricultural purposes.

Specific functional groups

Bromine atom at the 1-position, difluoromethylthio group at the 4-position
The presence of these groups at specific positions on the benzene ring contributes to the compound's unique properties.

Handling precautions

Handle with care
A need for careful handling to avoid hazards or unwanted reactions.

Storage conditions

Cool, dry place away from heat and direct sunlight
The optimal environment for preserving the compound's stability and preventing degradation.

Upstream product

• 353-59-3 halon-1211 
• 106-53-6 para-bromobenzenethiol 
• 75-61-6 dibromodifluoromethane 
• 5335-84-2 bis(4-bromophenyl)disulfide 
• 365-00-4 2,2-difluoro-1,3-diphenyl-1,3-propanedione 
• 65864-64-4 trimethyl(difluoromethyl)silane 
• 354-08-5 bromodifluoroacetic acid 
• 275818-95-6 sodium difluoromethanesulfinate 
• 5467-74-3 4-Bromophenylboronic acid 
• 589-87-7 1,4-bromoiodobenzene 
• 106-40-1 4-bromo-aniline 
• 3226-41-3 4-bromobenzenediazonium tetrafluoroborate 
• 673-40-5 4-bromobenzenediazonium tetrafluoroborate 
• 115262-00-5 [chloro(difluoro)methyl]trimethylsilane 

Downstream Products

• 51679-57-3 1-bromo-4-[(difluoromethyl)sulfonyl]benzene 
• 4837-26-7 4-((difluoromethyl)thio)benzoic acid 
• 1451998-62-1 tert-butyl 3-(4-((difluoromethyl)sulfonyl)phenyl)-3-fluoroazetidine-1-carboxylate 
• 1451998-40-5 tert-butyl 3-(4-((difluoromethyl)thio)phenyl)-3-fluoroazetidine-1-carboxylate 
• 1451993-09-1 (5-amino-3,4-dimethylthieno[2,3-c]pyridazin-6-yl)(3-(4-((difluoromethyl)sulfonyl)phenyl)-3-fluoroazetidin-1-yl)methanone 
• 1451998-52-9 (4-((difluoromethyl)sulfonyl)phenyl)methanamine 
• 1236079-27-8 4-((difluoromethyl)sulfonyl)benzonitrile 
• 1451993-19-3 5-amino-N-(4-((difluoromethyl)sulfonyl)benzyl)-3,4-dimethylthieno[2,3-c]pyridazine-6-carboxamide 
• 1451998-39-2 tert-butyl 3-(4-((difluoromethyl)thio)phenyl)-3-hydroxyazetidine-1-carboxylate 
• 51679-53-9 2-[4-(Difluoro-methanesulfonyl)-phenylamino]-benzoic acid 
• 51679-50-6 N-(4-Difluoromethylthiophenyl)anthranilic acid 
• 4837-25-6 4-[(difluoromethyl)thio]benzonitrile 

Relevant academic research and scientific papers

Difluoromethylation of Phenols and Thiophenols with the S-(Difluo-romethyl)sulfonium Salt: Reaction, Scope, and Mechanistic Study

A facile and practical approach for the difluoromethylation of phenols and thiophenols was described. Making use of the recently developed bench-stable S-(difluoromethyl)sulfonium salt as the difluorocarbene precursor, a wide variety of diversely functionalized phenols and thiophenols were readily converted to their corresponding aryl difluoromethyl ethers in good to excellent yields in the presence of lithium hydroxide. Chemoselectivity of various O,S-nucleophiles toward difluorocarbene was systematically studied, suggesting the reactivity order ArS- > RS-, ArO- > ROH > RO-, ArSH, ArOH, RSH.

Radical Difluororomethylation of Thiols with Difluoromethylphosphonium Triflate under Photoredox Catalysis

A convenient, visible light-induced radical difluoromethylation of aryl-, heteroaryl-, and alkylthiols with difluoromethyltriphenylphosphonium triflate was developed to afford various difluoromethyl thioethers in moderate to excellent yields. The key reaction features include the use of a readily available CF2H radical source, mild reaction conditions, and excellent chemoselective thiol-difluoromethylation.

Visible-Light Photoredox Difluoromethylation of Phenols and Thiophenols with Commercially Available Difluorobromoacetic Acid

A simple and efficient visible-light photoredox one-pot method for difluoromethylation of phenols and thiophenols has been developed. The protocol uses commercially available, inexpensive, and easy handling difluorobromoacetic acid as the difluoromethylating agent, and the diverse O- and S-difluoromethylated products were prepared in good yields with tolerance of many functional groups.

Silver-catalyzed fluoroalkylation of thiols using fluoroalkanesulfinates

A practical sliver-catalyzed fluoroalkylation of aryl-, heteroaryl- and alkylthiols has been developed. The reaction has a good functional-group tolerance and excellent selectivity. A variety of stable and solid fluoroalkanesulfinates including di- and perfluoroalkanesulfinates can be employed. This methodology provides a straightforward and streamlined access to perfluoroalkylthiolated organic molecules. [Figure presented]

Difluoromethyl bioisostere: Examining the lipophilic hydrogen bond donor concept

There is a growing interest in organic compounds containing the difluoromethyl group, as it is considered a lipophilic hydrogen bond donor that may act as a bioisostere of hydroxyl, thiol, or amine groups. A series of difluoromethyl anisoles and thioanisoles was prepared and their druglike properties, hydrogen bonding, and lipophilicity were studied. The hydrogen bond acidity parameters A (0.085-0.126) were determined using Abraham's solute 1H NMR analysis. It was found that the difluoromethyl group acts as a hydrogen bond donor on a scale similar to that of thiophenol, aniline, and amine groups but not as that of hydroxyl. Although difluoromethyl is considered a lipophilicity enhancing group, the range of the experimental Δlog P(water-octanol) values (log P(XCF2H) - log P(XCH3)) spanned from -0.1 to +0.4. For both parameters, a linear correlation was found between the measured values and Hammett σ constants. These results may aid in the rational design of drugs containing the difluoromethyl moiety.

A Route to α-Fluoroalkyl Sulfides from α-Fluorodiaroylmethanes

α,α-Difluorodiaroylmethane can be used as a nucleophilic difluoromethylation reagent for generating α-thioaryl-α,α-difluoroacetophenones (Ar1COCF2SAr) and difluoromethylthiolated arenes (ArSCF2H) under transition-metal-free conditions. The reaction selectivity is mainly dependent on temperature. The method has also been extended to the synthesis of α-thioaryl-α-monofluoroacetophenones using α-monofluorodibenzoylmethane. Moreover, the benzoyl cation derived from α,α-difluorodibenzoylmethane can react with nucleophiles to afford the desired products in a one-pot process.

PhSO2SCF2H: A Shelf-Stable, Easily Scalable Reagent for Radical Difluoromethylthiolation

A new shelf-stable and easily scalable difluoromethylthiolating reagent S-(difluoromethyl) benzenesulfonothioate (PhSO2SCF2H) was developed. PhSO2SCF2H is a powerful reagent for radical difluoromethylthiolation of aryl and alkyl boronic acids, decarboxylative difluoromethylthiolation of aliphatic acids, and a phenylsulfonyl-difluoromethylthio difunctionalization of alkenes under mild reaction conditions.

Preparation of difluoromethylthioethers through difluoromethylation of disulfides using TMS-CF2H

We report an operationally simple, metal-free approach for the late-stage introduction of the important lipophilic hydrogen-bond donor motif, SCF2H. This reaction converts diaryl- and dialkyl-disulfides into the corresponding aryl/alkyl-SCF2H through the nucleophilic transfer of a difluoromethyl group with good functional group tolerance. This method is notable for its use of commercially available TMSCF2H, and does not rely on the need for handling of sensitive metal complexes.

Palladium-catalyzed difluoromethylthiolation of heteroaryl bromides, iodides, triflates and aryl iodides

A palladium-catalyzed difluoromethylthiolation of heteroaryl halides and triflates under mild conditions was described. A vast range of heteroaryl halides such as pyridyl, quinolinyl, benzothiazolyl, thiophenyl, carbazolyl and pyazolyl halides could be difluoromethylthiolated efficiently, thus providing medicinal chemists with new tools for their search of new lead compounds for drug discovery. Likewise, aryl iodides were difluoromethylthiolated in high yields under a modified reaction condition.

Direct S-difluoromethylation of thiols using the Ruppert-Prakash reagent Dedicated to Prof. Veronique Gouverneur on the occasion of receiving the ACS Award for Creative Work in Fluorine Chemistry.

Direct S-difluoromethylation of aryl and aliphatic thiols using the Ruppert-Prakash reagent is demonstrated. The reaction produces trimethylsilyldifluoromethyl sulfides, which upon cleavage with fluoride produces the difluoromethyl sulfides. The key reaction features are the use of relatively inexpensive and commercially available starting materials, shorter reaction times, ambient temperatures, easy reaction procedure, and selective S-difluoromethylation in the presence of -OH, -NH2 and -CO2H functional groups. Furthermore, one-pot arylthiodifluoromethyl transfer to PhCHO is also demonstrated.