1073-72-9

Usage

Uses

Used in Pharmaceutical Industry:
4-(Methylthio)phenol is used as a key intermediate in the synthesis of phosphoramidodithioate compounds, which are essential in the preparation of sulprofos amidate, a widely used insecticide.
Used in Chemical Synthesis:
4-(Methylthio)phenol is used as a reagent for the removal of benzyloxycarbonyl and O-benzyl protecting groups during acidolytic cleavage with trifluoroacetic acid. Its ability to accept benzyl groups makes it a valuable component in various chemical reactions and processes.

InChI:InChI=1/C7H8OS/c1-9-7-4-2-6(8)3-5-7/h2-5,8H,1H3

Upstream product

• 1879-16-9 1-methoxy-4-methylsulfanyl-benzene 
• 637-89-8 4-sulfanylphenol 
• 77-78-1 dimethyl sulfate 
• 624-92-0 Dimethyldisulphide 
• 108-95-2 phenol 
• 20828-73-3 methylsulfanylium 
• 5188-07-8 sodium thiomethoxide 
• 616-38-6 carbonic acid dimethyl ester 
• 74-88-4 methyl iodide 
• 106-46-7 para-dichlorobenzene 
• 123-09-1 4-chlorophenyl methyl sulfide 
• 106-54-7 p-Chlorothiophenol 
• 15267-49-9 4-(methylthio)phenoxyacetic acid 
• 98546-51-1 (4-thiomethoxyphenyl)boronic acid 

Downstream Products

• 101787-77-3 1,4-bis-(4-methylsulfanyl-phenoxy)-butane 
• 103155-23-3 1,5-bis-(4-methylsulfanyl-phenoxy)-pentane 
• 53559-55-0 4-methanesulfinyl-2,6-dinitro-phenol 
• 56773-30-9 4-chloromethylsulfonylphenol 
• 76330-17-1 2,6-dibromo-4-methylsulfanyl-phenol 
• 32279-04-2 (p-hydroxyphenyl)dimethylsulfonium methyl sulfate 
• 80724-09-0 3,5-dinitro-benzoic acid-(4-methylsulfanyl-phenyl ester) 
• 52407-91-7 C₁₄H₂₂NO₄PS₂ 
• 25562-87-2 2-[4-(methylsulfanyl)phenoxy]benzoic acid 
• 28248-45-5 Thiophosphoric acid O-(2-methoxy-1-methyl-ethyl) ester O'-methyl ester O''-(4-methylsulfanyl-phenyl) ester 
• 28248-48-8 Thiophosphoric acid O-(2-methoxy-propyl) ester O'-methyl ester O''-(4-methylsulfanyl-phenyl) ester 
• 28253-49-8 Thiophosphoric acid O-(2-ethoxy-ethyl) ester O'-methyl ester O''-(4-methylsulfanyl-phenyl) ester 
• 28248-56-8 Thiophosphoric acid O-(3-methoxy-propyl) ester O'-methyl ester O''-(4-methylsulfanyl-phenyl) ester 
• 28248-59-1 Thiophosphoric acid O-ethyl ester O'-(2-methoxy-1-methyl-ethyl) ester O''-(4-methylsulfanyl-phenyl) ester 

Relevant academic research and scientific papers

Sustainable oxidations with air mediated by gallic acid: Potential applicability in the reutilization of grape pomace

Gallic acid converts atmospheric oxygen into hydrogen peroxide, which is able to oxidize arylboronic acids as a proof of concept of sustainable oxidations. Moreover, tannic acid and grape pomace extract are also able to perform oxidations with air. Therefore this work unleashes an alternative method for reutilization and valorization of bio-wastes rich in tannins.

A Mild Heteroatom (O -, N -, and S -) Methylation Protocol Using Trimethyl Phosphate (TMP)-Ca(OH) 2Combination

A mild heteroatom methylation protocol using trimethyl phosphate (TMP)-Ca(OH)2combination has been developed, which proceeds in DMF, or water, or under neat conditions, at 80 °C or at room temperature. A series of O-, N-, and S-nucleophiles, including phenols, sulfonamides, N-heterocycles, such as 9H-carbazole, indole derivatives, and 1,8-naphthalimide, and aryl/alkyl thiols, are suitable substrates for this protocol. The high efficiency, operational simplicity, scalability, cost-efficiency, and environmentally friendly nature of this protocol make it an attractive alternative to the conventional base-promoted heteroatom methylation procedures.

Aryl phenol compound as well as synthesis method and application thereof

The invention discloses a synthesis method of an aryl phenol compound shown as a formula (3). All systems are carried out in an air or nitrogen atmosphere, and visible light is utilized to excite a photosensitizer for catalyzation. In a reaction solvent, ArNR1R2 as shown in a formula (1) and water as shown in a formula (2) are used as reaction raw materials and react under the auxiliary action of acid to obtain the aryl phenol compound as shown in a formula (3). The ArNR1R2 in the formula (1) can be primary amine and tertiary amine, can also be steroid and amino acid derivatives, and can also be drugs or derivatives of propofol, paracetamol, ibuprofen, oxaprozin, indomethacin and the like. The synthesis method has the advantages of cheap and easily available raw materials, simple reaction operation, mild reaction conditions, high reaction yield and good compatibility of substrate functional groups. The fluid reaction not only can realize amplification of basic chemicals, but also can realize amplification of fine chemicals, such as synthesis of drugs propofol and paracetamol. The invention has wide application prospect and use value.

Nickel Hydride Catalyzed Cleavage of Allyl Ethers Induced by Isomerization

This report discloses the deallylation of O - and N -allyl functional groups by using a combination of a Ni-H precatalyst and excess Bronsted acid. Key steps are the isomerization of the O - or N -allyl group through Ni-catalyzed double-bond migration followed by Bronsted acid induced O/N-C bond hydrolysis. A variety of functional groups are tolerated in this protocol, highlighting its synthetic value.

Rongalite-promoted metal-free aerobic ipso-hydroxylation of arylboronic acids under sunlight: DFT mechanistic studies

A novel rongalite-promoted metal-free aerobic ipso-hydroxylation of arylboronic acids has been developed. This method employs low-cost rongalite as a radical initiator and O2 as a green oxidizing agent for ipso-hydroxylation. This protocol is compatible with a wide variety of functional groups with good to excellent yields at room temperature. Furthermore, mechanistic insight into the role of superoxide radical anions in C-B cleavage has also been provided based on DFT studies.

Method for preparing alcohol and phenol through aerobic hydroxylation reaction of boric acid derivative in absence of photocatalyst

The invention discloses a method for preparing alcohol and phenol through aerobic hydroxylation reaction of a boric acid derivative in the absence of a photocatalyst, wherein the boric acid derivativeis aryl boronic acid or alkyl boronic acid, and the corresponding target compounds are respectively a phenol-based compound and an alcohol-based compound. According to the method, by using a boric acid derivative as a reaction substrate, an additive is added under a solvent condition, and a hydroxylation reaction is performed under aerobic and illumination conditions to obtain a corresponding target compound. According to the invention, the new strategy is provided for the synthesis of phenols through aerobic hydroxylation of aryl boronic acid without a photocatalyst; the catalyst-free aerobic hydroxylation method for photocatalysis of aryl boronic acid or alkyl boronic acid by using triethylamine as an additive is firstly disclosed; and the new method has advantages of photocatalyst-freecondition, wide substrate range and good functional group compatibility.

Palladium-Catalyzed Hydroxylation of Aryl Halides with Boric Acid

Boric acid, B(OH)3, is proved to be an efficient hydroxide reagent in converting (hetero)aryl halides to the corresponding phenols with a Pd catalyst under mild conditions. Various phenol products were obtained in good to excellent yields. This transformation tolerates a broad range of functional groups and molecules, including base-sensitive substituents and complicated pharmaceutical (hetero)aryl halide molecules.

Enantioselective Synthesis of 3-Fluorochromanes via Iodine(I)/Iodine(III) Catalysis

The chromane nucleus is common to a plenum of bioactive small molecules where it is frequently oxidized at position 3. Motivated by the importance of this position in conferring efficacy, and the prominence of bioisosterism in drug discovery, an iodine(I)/iodine(III) catalysis strategy to access enantioenriched 3-fluorochromanes is disclosed (up to 7:93 e.r.). In situ generation of ArIF2 enables the direct fluorocyclization of allyl phenyl ethers to generate novel scaffolds that manifest the stereoelectronic gauche effect. Mechanistic interrogation using deuterated probes confirms a stereospecific process consistent with a type IIinv pathway.

B2cat2-Mediated Reduction of Sulfoxides to Sulfides

An efficient and operationally simple method for the reduction of sulfoxides to sulfides has been developed using bis(catecholato)diboron (B2cat2) as a reducing agent. The present method accommodates various functional groups which are generally prone to reduction: halides, alkynes, carbonyls, nitriles, and heterocycles are totally intact, and only sulfoxide moieties undergo reduction chemoselectively. Moreover, the remaining diboron and the resulting boron-containing wastes are readily removable, the practicality of this protocol being thus demonstrated.

Photocatalytic Deoxygenation of Sulfoxides Using Visible Light: Mechanistic Investigations and Synthetic Applications

The photocatalytic deoxygenation of sulfoxides to generate sulfides facilitated by either Ir[(dF(CF3)ppy)2(dtbbpy)]PF6 or fac-Ir(ppy)3 is reported. Mechanistic studies indicate that a radical chain mechanism operates, which proceeds via a phosphoranyl radical generated from a radical/polar crossover process. Initiation of the radical chain was found to proceed via two opposing photocatalytic quenching mechanisms, offering complementary reactivity. The mild nature of the radical deoxygenation process enables the reduction of a wide range of functionalized sulfoxides, including those containing acid-sensitive groups, in typically high isolated yields.