19093-34-6

Usage

Uses

Used in Pharmaceutical Industry:
2-(METHYLSULFINYL)BENZENECARBOXYLIC ACID is used as a β-lactamase inhibitor for enhancing the efficacy of β-lactam antibiotics. It is employed to treat a variety of bacterial infections, including respiratory, urinary tract, and skin infections, by inhibiting the enzymes produced by bacteria that can degrade these antibiotics, thus allowing the antibiotics to effectively kill the bacteria.
Used in Combination Therapy for Severe Infections:
2-(METHYLSULFINYL)BENZENECARBOXYLIC ACID is used in combination with other antibiotics to treat severe or life-threatening infections caused by resistant bacteria. Its role as a β-lactamase inhibitor is crucial in overcoming bacterial resistance and improving the therapeutic outcomes in such critical cases.

InChI:InChI=1/C8H8O3S/c1-12(11)7-5-3-2-4-6(7)8(9)10/h2-5H,1H3,(H,9,10)

Upstream product

• 3724-10-5 2-(methylthio)benzoic acid 

Downstream Products

• 4850-73-1 methyl 2-methylsulfinylbenzoate 
• 33963-55-2 2-(methylsulfonyl)benzoic acid 
• 49639-13-6 2-methylsulfonylbenzoyl chloride 
• 844442-77-9 cis-[Pt(PPh₃)2(2-(methylsulfinyl)benzoate)2] 
• 3724-10-5 2-(methylthio)benzoic acid 
• 88375-86-4 2-Methanesulfinyl-benzoic acid benzhydryl ester 

Relevant academic research and scientific papers

Method for preparing 2-(methylsulfinyl)benzoic acid

The invention relates to the technical field of fine chemical engineering, and discloses a method for preparing 2-(methylsulfinyl)benzoic acid. The method comprises the specific steps: by taking 2-(methylthio)benzoic acid as a reaction raw material and 1-chloromethyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane bis(tetrafluoroborate) salt as an additive, carrying out a reaction in a methanol solvent atthe temperature of 20 DEG C for 24 hours, filtering a reaction solution after the reaction is finished, carrying out reduced pressure distillation, and collecting to obtain the target product 2-(methylsulfinyl)benzoic acid. The method is simple and convenient to operate, 2-(methylthio)benzoic acid is used as a reaction raw material, the target product is efficiently synthesized in one step, the use of a toxic reagent chloroform, an acid with strong corrosivity and a transition metal salt is avoided, and the method has potential application value.

Enantioselective oxidation of thioethers to sulfoxides by means of a structural template with chiral-at-metal ruthenium complexes

Treatment of cis-[Ru(bpy)2Cl2]·2H2O or Δ/Λ-[Ru(bpy)2(py)2]2+ (bpy=2,2′-bipyridine, py=pyridine) with the prochiral thioether ligands 2-alkylthiobenzoic acid (HOS-R) produces the corresponding thioether complexes rac-[Ru(bpy)2(OS-R)](PF6) (R=Me (rac-1), iPr (rac-2), 2-benzylthiobenzonate (Bn) (rac-3)) and Δ/Λ-[Ru(bpy)2(OS-R)](PF6) (R=Me (Δ-1/Λ-1), iPr (Δ-2/Λ-2), Bn (Δ-3/Λ-3)) with retention of the configurations at chiral metal centers. In situ oxidation of the thioether complexes by metachloroperoxybenzoic acid provides the corresponding sulfoxide complexes rac-[Ru(bpy)2(OSO-R)](PF6) (OSO-R is 2-alkylsulfinylbenzonate, R=Me (rac-1a), iPr (rac-2a), Bn (rac-3a)), Δ-[Ru(bpy)2{(R)-OSO-R}](PF6) (R=Me (Δ-1a), iPr (Δ-2a), Bn (Δ-3a)), and Λ-[Ru(bpy)2{(S)-OSO-R}](PF6) (R=Me (Λ-1a), iPr (Λ-2a), Bn (Λ-3a)) in yields of 95% with 98% ee values. The absolute configurations at the metal centers and sulfur atoms were determined by means of X-ray crystallography. The results indicate that the configurations of the metal centers are retained and have the function of controlling sulfoxide chirality during the oxidation process. The Δ metal-centered configuration enantioselectively generates an R-configuration sulfoxide, and the Λ configuration enantioselectively forms an S-configuration sulfoxide in the course of the in situ oxidation reaction, thereby resulting in a predetermined chirality of the sulfoxide ligands. The predetermined chirality of sulfoxides (S)-HOSO-R and (R)-HOSO-R were obtained by the treatments of the corresponding sulfoxide complexes Δ-[Ru(bpy)2{(R )-OSO-R}](PF6) and Λ-[Ru(bpy)2{(S)-OSO-R}](PF6) with trifluoroacetic acid in yields of 90% with 83.5-92.9% ee values.

The development of an environmentally benign sulfide oxidation procedure and its assessment by green chemistry metrics

Different Iron (III) species were used as catalysts in sulfoxidation reactions giving excellent yields and high chemoselectivity. Among the iron (III) species, the best one was a solid β-cyclodextrin-FeBr3 complex. Sulfoxidation takes place wit

Cis-platinum complexes with chelating amines and sulphinyl carboxylates

STR1 Platinum (II) complexes of formula (I) where: Am is a monodentate amine, or (Am)2 is a bidentate amine, B represents a straight or branched alkyl residue or a single bond, R is selected from the group of hydrogen, (C3 -C8) cycloalkyl, phenyl or naphthyl which may be substituted by halogens (I, Br, Cl, F), trihalomethane, hydroxyl, (C1 -C4)-alkoxyl, (C1 -C7)-acylamino, (C1 -C7)-sulphamido, allyl, phenoxyl, haloalkoxyl, nitro, cyano, azido, with condition that when R is hydrogen B is different from a single bond, Q is a residue of formula --(CH2)n1 --CRa Rb --(CH2)n2 --, 1,2- or 2,3-naphthalene, benzo-1,3-dioxolan-5,6-diyl, substituted or unsubstituted 1,2-phenylene, Ra and Rb are selected independently of each other from the group of hydrogen, allyl, linear or branched (C1 -C8)-alkyl, --(CH2)p OH, --(CH2 CH2 O)q --CH3, or taken together with the carbon atom to which they are bonded form a (C3 -C8) cycloalkyl, or heterocyclic tetrahydropyran-4,4-diyl, n1 and n2 are independently zero or the integer 1, p is an integer from 2 to 6, and q is an integer from 1-3, X- is a biocompatible anion such as chloride, bromide, iodide, nitrate, perchlorate, or one equivalent of sulphate or phosphate, or an anion of a monovalent C1 -C4 organic acid such as acetate, propionate or chloroacetate, or of an aromatic acid such as benzoate, or of a heteroaromatic acid such as nicotinate are described. The compounds are useful as anti-tumor drugs.

Lipase-catalyzed kinetic resolution of a series of esters having a sulfoxide group as the stereogenic centre

A series of methyl 2-(alkylsulfinyl)benzoates (alkyl = C1, n-C4, n-C8, n-C12 and n-C16) was investigated with respect to substrate behaviour and enantioselectivity in a lipase (Candida rugosa)-catalyz

NEIGHBOURING-GROUP PARTICIPATION IN THE OXIDATION OF SULPHIDES WITH HYDROGEN PEROXIDE

Using a set of sulphides (o- and p-XC6H4SMe), the electronic effect, steric hindrance and anchimeric assistance for the O-transfer by H2O2 have been investigated by a kinetic method.The steric effect and anchimeric assistance were evaluated by comparing t

MECHANISM OF THE OXIDATION OF ORGANIC SULPHIDES BY PERMANGANATE ION

The kinetics of the oxidation of number of aryl methyl, alkyl phenyl, dialkyl and diphenyl sulphides by permanganate ion to yield the sulphoxides, have been studied.The reaction is first order with respect to the sulphide and permanganate and is independe

Kinetics of the Oxidation of Organic Sulphides by Pyridinium Fluorochromate

The kinetics of the oxidation of a number of monosubstituted aryl methyl, alkyl phenyl, dialkyl, and diphenyl sulphides by pyridinium fluorochromate (PFC) to yield the corresponding sulphoxides have been studied.The reaction is first order with respect to

Pyridinium Chlorochromate Oxidation of ortho-Substituted Phenyl Methyl Sulphides

Bimolecular rate constants for the pyridinium chlorochromate oxidation of several ortho-substituted phenyl methyl sulphides have been determined spectrophotometrically in 60percent (v/v) aqueous acetic acid.Correlation of rate constants at 30 deg C by ext

Mechanism of the Oxidation of Sulphides with Sodium Periodate

The kinetics of the oxidation of RSAr, R2S, and (CH2)nS sulphides with NaIO4 yielding sulphoxides were investigated in ethanol-water solutions, and the rate equation v = k2 was found to be valid.The observed substituent (ρ -1