33402-67-4

Usage

Uses

Used in Pharmaceutical Industry:
Sodium alpha-hydroxy-p-methoxytoluene-alpha-sulphonate is used as an intermediate in the synthesis of Ambucetamide (A575935) for its antispasmodic properties. Ambucetamide is particularly effective for the relief of menstrual pain, providing a targeted solution for this common issue.
Used in Chemical Synthesis:
In the field of chemical synthesis, sodium alpha-hydroxy-p-methoxytoluene-alpha-sulphonate serves as a crucial component in the production of various compounds. Its unique structure allows it to participate in different chemical reactions, contributing to the development of new substances with potential applications in various industries.
Used in Research and Development:
Due to its versatile nature, sodium alpha-hydroxy-p-methoxytoluene-alpha-sulphonate is also utilized in research and development. Scientists and researchers use sodium alpha-hydroxy-p-methoxytoluene-alpha-sulphonate to explore new chemical pathways, develop innovative products, and enhance existing ones. Its role in R&D is essential for advancing knowledge and creating new solutions in various fields.

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 80493-71-6 2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-amine 
• 91437-83-1 5-chloro-2-(4-methoxyphenyl)-1H-benzo[d]imidazole 
• 14629-56-2 trimethyl(4-methoxybenzyloxy)silane 
• 161374-07-8 ethyl 4-(4-methoxyphenyl)-6-methyl-1,2,3,4-tetrahydropyrimidin-2-one-5-carboxylate 
• 5429-22-1 4-(4-methoxybenzylidene)-2-phenyl-5(4H)-oxazolone 
• 1147718-32-8 5,6-dichloro-1-cyclopentyl-2-(4-methoxyphenyl)-1H-benzimidazole 
• 1147718-54-4 5-chloro-1-cyclopentyl-2-(4-methoxyphenyl)-1H-benzimidazole 
• 122439-15-0 N-(4-methoxybenzyl)pyrrolidine 
• 24932-54-5 N,N-diethyl-4-methoxy-benzenemethanamine 
• 747356-47-4 2-(4-Methoxy-phenyl)-1H-benzoimidazole-5-carbonyl chloride 
• 174422-17-4 2-(4-methoxyphenyl)-1H-benzo[d]imidazole-5-carboxylic acid 
• 40655-15-0 5-amino-2-(4-methoxyphenyl)-1H-benzimidazole 
• 690697-75-7 C₂₁H₁₇N₃O₂ 
• 263021-75-6 C₂₁H₁₆N₄O₄ 

Relevant academic research and scientific papers

Kinetics, Thermodynamics, and Mechanism of the Formation of Benzaldehyde-S(IV) Adducts

The kinetics and mechanism of the formation of α-hydroxyphenylmethanesulfonate (HPMS) by the addition of bisulfite to benzaldehyde were studied at low pH.A three-term rate law was observed as d/dt = (k1α2 + (k2 + k3KH- (H+))α1)t where α1 = ->/, α2 = 2->/, and KH is the proton association constant of benzaldehyde.The rate-limiting steps of each term appeared to be the nucleophilic attack of SO32- on the carbonyl carbon of benzaldehhyde, the attack of HSO3- on the carbonyl carbon, and the attack by HSO3- on the protonated carbon of the carbocation, C6H5C+H(OH), respectively.Over the pH range of most natural systems, only the k1 and k2 steps contribute to adduct formation while the k3 term becomes important for pH 1 = (2.15 +/- 0.09) * 104 M-1 s-1, k2 = (0.71 +/- 0.03) M-1 s-1, k3 ca./= 2.5 * 107 M-1 s-1.Para-substitution on the benzaldehyde ring resulted in a slight increase in reactivity for p-NO2- and p-Cl-, and a decrease for p-OH-, p-OCH3-, and p-CH3-C6H5CHO.The equilibrium association constant, K = ->/-> , at 25 deg C was determined to be 4.8 (+/-0.8) * 103 at μ = 0.1 M and 0.98 (+/-0.11) * 103 M-1 at μ = 1.0 M. ΔH deg and ΔS deg were determined to be -64.6 kJ mol-1 and -146 J mol-1 deg-1, respectively.

Synthesis, bioevaluation and docking studies of some 2-phenyl-1H-benzimidazole derivatives as anthelminthic agents against the nematode Teladorsagia circumcincta

Gastrointestinal nematode infections are the main diseases in herds of small ruminants. Resistance to the main established drugs has become a worldwide problem. The purpose of this study is to obtain and evaluate the in vitro ovicidal and larvicidal activity of some 2-phenylbenzimidazole derivatives on susceptible and resistant strains of Teladorsagia circumcincta. Compounds were prepared by known procedures from substituted o-phenylenediamines and arylaldehydes or intermediate sodium 1-hydroxyphenylmethanesulfonate derivatives. Egg Hatch Test (EHT), Larval Mortality Test (LMT) and Larval Migration Inhibition Test (LMIT) were used in the initial screening of compounds at 50 μM concentration, and EC50 values were determined for the most potent compounds. Cytotoxicity evaluation of compounds was conducted on human Caco-2 and HepG2 cell lines to calculate their Selectivity Indexes (SI). At 50 μM concentration, nine out of twenty-four compounds displayed more than 98% ovicidal activity on a susceptible strain, and four of them showed more than 86% on one resistant strain. The most potent ovicidal benzimidazole (BZ) 3 showed EC50 = 6.30 μM, for the susceptible strain, while BZ 2 showed the lowest EC50 value of 14.5 μM for the resistant strain. Docking studies of most potent compounds in a modelled Teladorsagia tubulin indicated an inverted orientation for BZ 1 in the colchicine binding site, probably due to its fair interaction with glutamic acid at codon 198, which could justify its inactivity against the resistant strain of T. circumcincta.

1 H -Benzimidazole-5-carboxamidine derivatives: Design, synthesis, molecular docking, DFT and antimicrobial studies

In this study, 15 new N-(cyclohexyl)-2-substituted-1H-benzimidazole-5-carboxamidine derivatives that could be new antimicrobial agents were synthesized and their antimicrobial activities were determined using the microdilution method. Some of the derivatives showed significant efficacy against MRSA and VREF with an MIC value of 8 μg mL-1 compared to reference drugs. Molecular docking studies of the compounds against PBP4 and active and allosteric regions of PBP2a were performed and estimated ADME profiles were calculated. The nitrogens of the amidine group of M7, one of the most effective antimicrobial compounds compared to reference drugs, formed two separate hydrogen bonds with ASP275 (1.77 ?) and ASP295 (1.83 ?) in the allosteric region of PBP2a. Geometric optimization parameters, MEP analysis, and HUMO and LUMO quantum parameters of M7 were calculated using DFT/B3LYP theory and the 6-311G(d,p) basis set and the results are displayed.

Formal synthesis of (+)-lactacystin from l-serine

A formal, stereocontrolled synthesis of lactacystin has been completed from t-Bu-O-l-serine, providing the key intermediate 13, also useful for the generation of a range of C-9 analogues.

Facile utilisation of aldehyde bisulfite adducts: Synthesis of (E)-1,2- diphenylethenes

Background: A one-pot coupling reaction of aldehyde bisulfite adducts was developed for McMurry reaction using Zn-TiCl4 in 1,4-dioxane solvent medium. The treatment of sodium hydroxy(phenyl)methane sulfonate (2a) with TiCl4 in 1,4-dioxane favoured the deprotection of the bisulfite adduct 2a, and the in situ regeneration of benzaldehyde (1a) underwent reductive coupling to afford stilbene 3a in a relatively good yield, thus leading to an improved synthesis of a series of (E)-1,2- diphenylethenes 3. The present approach provides a new solution to the inherent instability of aldehydes and also provides a direct access to C'C bond formation for the synthesis of 1,2-diphenylethenes from aryl aldehyde bisulfite adducts. Methods: All reactions were performed at 70-80o and the synthesized compounds were characterized by IR, 1H NMR, 13C NMR, and mass spectrometric techniques. Results: The present approach provides a new solution to the instability of aldehydes and also provides a direct access to C'C bond formation for the synthesis of 1,2-diphenylethenes from aryl aldehyde bisulfite adducts. Conclusion: In the present work, we have reported an efficient method for the synthesis of 1,2- diphenylethene derivatives. Aldehydes are commonly used as the starting materials in the McMurry reaction, which affords the stilbene derivatives, the core skeleton of various valuable compounds. To increase the stability of the aldehydes, bisulfite adducts are usually employed, but the deprotection process causes loss of process efficiency. To address this issue, we developed a method based on the single-pot reaction of aromatic bisulfite adduct using TiCl4/Zn in 1,4-dioxane.

Antituberculosis agents bearing the 1,2-disubstituted benzimidazole scaffold

Abstract: The emergence of drug-resistant strains in recent years has fueled the epidemic of tuberculosis. This necessitates the development of new chemical scaffolds to curb resistant tuberculosis for effective control of this disease. In this study, we have designed and synthesized two series of benzimidazole derivatives. Their antimycobacterial activities were initially evaluated using Mycobacterium tuberculosis H37RV strains. The most potent analog (6h) was further assessed using various drug-resistant M. tuberculosis strains. This report described the importance of benzimidazoles as new antitmycobacterial agents targeting both the M. tuberculosis H37RV as well as the drug-resistant-tuberculosis strains. The trifluoromethyl group which was essential for antimycobacterial activity was also highlighted. Graphical Abstract: Two series of benzimidazole derivatives and their antimycobacterial activities were evaluated using M. tuberculosis H37RV (MTB-H37RV) strains. Compound 6h was identified as the most potent among all synthesized compounds. The most potent analog was further assessed using various drug-resistant MTB strains. In addition, the trifluoromethyl was identified as an important substitution in giving good antimycobacterial effect. [InlineMediaObject not available: see fulltext.]

Synthesis of 3-Formylbenzenesulfonyl Chloride Derivatives

A synthetic route to 3-formylbenzenesulfonyl chloride derivatives from the corresponding benzaldehydes has been developed. The key step in this procedure is the conversion of aldehyde bisulfite adducts to target compounds via a two-stage reaction in the presence of Na 2 SO 4. A series of 3-formylbenzenesulfonyl chloride derivatives were prepared by this method and identified by chemical derivatization method.

Liquid-Liquid Extraction Protocol for the Removal of Aldehydes and Highly Reactive Ketones from Mixtures

The reaction of the bisulfite ion with aldehydes to form charged bisulfite adducts is a well-established method for the purification of aldehydes. This reaction has been modified to create a convenient liquid-liquid extraction method for the removal of aldehydes from mixtures. The use of a water-miscible solvent allows the reaction to occur during a simple 30 s shaking protocol by increasing the contact between the bisulfite ion and the aldehyde. The introduction of an immiscible solvent allows for the extraction of the uncharged organic components away from the bisulfite adduct. The developed protocol is applicable to a wide range of aldehydes, including sterically hindered neopentyl aldehydes. Sterically unhindered cyclic and linear ketones, as well as highly electrophilic ketones, are also removed using this protocol. The mild conditions tolerate a wide range of functional groups, allowing for excellent aldehyde contaminant removal rates with high levels of recovery of the desired component.

Reduction of Weinreb amides to aldehydes under ambient conditions with magnesium borohydride reagents Dedicated to the memory of Professor Sheldon Shore

Chloromagnesium dimethylaminoborohydride (ClMg+ [H3BNMe2]-, MgAB) is an analogue of the versatile lithium dialkylaminoborohydrides (LAB reagents), prepared by the reaction of dimethylamine-borane with methylmagnesium chloride. MgAB is a partial reducing agent for Weinreb amides under ambient conditions and is complementary to the commonly utilized lithium aluminum hydride (LiAlH4) and diisobutylaluminum hydride (DIBAL) reagents, while exhibiting enhanced chemoselectivity. To prevent over-reduction, the aldehyde products are readily isolated in good yields by forming the sodium bisulfite adducts. Aldehyde products can both be stored and later used as the bisulfite adducts, or can be regenerated from the bisulfite adducts by treatment with aqueous formaldehyde.

Synthesis and evaluation of antimycobacterial activity of new benzimidazole aminoesters

Abstract A total of 51 novel benzimidazoles were synthesized by a 4-step reaction starting from basic compound 4-fluoro-3-nitrobenzoic acid under relatively mild reaction conditions. The structure of the novel benzimidazoles was confirmed by mass spectra as well as 1H NMR spectroscopic data. Out of the 51 novel synthesized compounds, 42 of them were screened for their antimycobacterial activity against Mycobacterium tuberculosis H37Rv strain using BacTiter-Glo Microbial Cell Viability (BTG) method. Results of activity screened using Alamar Blue method was also provided for comparison purposes. Two of the novel benzimidazoles synthesized showed moderately good activity with IC50 of less than 15 μM. Compound 5g, ethyl 2-(4-(trifluoromethyl)phenyl)-1-(2-morpholinoethyl)-1H-benzo[d]imidazole-5-carboxylate, was found to be the most active with IC50 of 11.52 μM.