33992-80-2

Basic information

• Product Name: AKOS B018339
• Synonyms: AKOS B018339;CHEMBRDG-BB 3018339;ART-CHEM-BB B018339;(5E)-2-mercapto-5-(4-methylbenzylidene)-1,3-thiazol-4(5H)-one;Albb-009123;(5E)-2-mercapto-5-(4-methylbenzylidene)-1,3-thiazol-4(5H)-one(SALTDATA: FREE);(5Z)-5-(4-methylbenzylidene)-2-thioxo-thiazolidin-4-one;(5Z)-5-[(4-methylphenyl)methylene]-2-thioxo-4-thiazolidinone
• CAS NO: 33992-80-2
• Molecular Formula: C₁₁H₉NOS₂
• Molecular Weight: 235.33
• Mol File: 33992-80-2.mol

Chemical Properties

• Boiling Point: 377.1°C at 760 mmHg
• Flash Point: 181.9°C
• Appearance: /
• Density: 1.38g/cm³
• Vapor Pressure: 6.92E-06mmHg at 25°C
• Refractive Index: 1.708
• CAS DataBase Reference: AKOS B018339(CAS DataBase Reference)
• NIST Chemistry Reference: AKOS B018339(33992-80-2)
• EPA Substance Registry System: AKOS B018339(33992-80-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 33992-80-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H9NOS2/c1-7-2-4-8(5-3-7)6-9-10(13)12-11(14)15-9/h2-6H,1H3,(H,12,13,14)/b9-6+

Upstream product

• 141-84-4 2-thioxo-4-thiazolidinone 
• 104-87-0 4-methyl-benzaldehyde 

Downstream Products

• 1544402-06-3 (Z)-5-(4-methylbenzylidene)-2-(methylthio)thiazol-4(5H)-one 
• 1187463-28-0 (Z)-2'-[(5-amino-3-methyl-1-phenylpyrazol-4-yl)imino]-5'-(4-methylbenzylidene)thiazolidin-4-one 
• 1236049-22-1 N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-(4-methylphenylmethylene)-2-thioxo-4-thiazolidinone 
• 32730-02-2 5-(4-methyl-benzylidene)-thiazolidine-2,4-dithione 
• 32723-65-2 5-(4-methyl-benzylidene)-2-methylsulfanyl-thiazol-4-one 
• 33656-60-9 3-hydroxymethyl-5-(4-methyl-benzylidene)-2-thioxo-thiazolidin-4-one 

Relevant articles and documents

Facile synthesis of 5-arylidene rhodanine derivatives using Na2SO3 as an eco-friendly catalyst. Access to 2-mercapto-3-aryl-acrylic acids and a benzoxaborole derivative

A simple, efficient and environment-friendly procedure for the synthesis of 5-arylidene rhodanines derivatives via a Knoevenagel type reaction was developed using rhodanine, a variety of differently substituted aldehydes and Na2SO3 a

Introducing broadened antibacterial activity to rhodanine derivatives targeting enoyl-acyl carrier protein reductase

Broadened antibacterial activity was introduced to rhodanine derivatives targeting Mycobacterial tuberculosis enoyl-acyl carrier protein reductase (Mtb InhA) by recruiting feature of xacins to bring DNA Gyrase B inhibitory capability. This is significant for preventing further bacterial injections in the tuberculosis treatment. The most potent compound Cy14 suggested comparable bioactivity (IC50=3.18μM for Mtb InhA; IC50=10nM for DNA Gyrase B) with positive controls. Structure–activity relationship discussion and molecular docking model revealed the significance of rhodanine moiety and derived methoxyl on meta-position, pointing out orientations for future modification.

Solid acid TS-1 catalyst: an efficient catalyst in Knoevenagel condensation for the synthesis of 5-arylidene-2,4-thiazolidinediones/Rhodanines in aqueous medium

Abstract: TS-1 zeolite was prepared for the synthesis of 5-arylidene-2,4-thiazolidinediones/Rhodanines in aqueous medium by incorporating titanium(IV) cations in a silicate-1 framework using hydrothermal treatment and characterized by using XRD, EDX, BET, FT-IR and SEM techniques. The catalytic activity of the catalyst was tested for Knoevenagel condensation reaction. The condensation of active ethylene 2,4-thiazolidinedione with substituted aryl aldehydes under aqueous medium at 90?°C afforded the corresponding product in excellent yield up to 92% within 30?min. The present method offers several advantages over the reported methods such as easy separation of catalyst, simple work-up procedure, and an excellent yield of desired product. Furthermore, the catalyst could be reused without significant loss in activity. Graphical abstract: [Figure not available: see fulltext.]

New spiro-oxindole constructed with pyrrolidine/thioxothiazolidin-4-one derivatives: Regioselective synthesis, X-ray crystal structures, Hirshfeld surface analysis, DFT, docking and antimicrobial studies

In this work, polycyclic heterocycles containing spirooxindole, pyrrolidine, and thioxothiazolidin-4-one rings have been synthesized via the regioselective 1,3-dipolar cycloaddition of azomethine ylide, which is generated in situ by the condensation of th

[Et3NH][HSO4] catalyzed efficient synthesis of 5-arylidene-rhodanine conjugates and their antitubercular activity

Abstract: We have described a highly efficient, safer protocol for the synthesis of 5-arylidene-rhodanine conjugates catalyzed by Bronsted acidic ionic liquid [Et3NH][HSO4] in excellent yields. The protocol offers cost-effective, environmentally benign, solvent-free conditions and recycle–reuse of the catalyst. The synthesized 5-arylidene-rhodanine conjugates were characterized on the basis of 1H NMR, 13C NMR and HRMS spectral data. A series of 5-arylidene-rhodanine derivatives 3a–h, 4a–h were synthesized and evaluated for their in vitro antitubercular activity against dormant Mycobacterium tuberculosis H37Ra and M. bovis BCG strains. Moreover, compounds 3a, 3b, 3e, 3f, 3g, 3h and 4f exhibited good antitubercular activity and were also evaluated for anti-proliferative activity against MCF-7, A549 and HCT116 cell lines using modified MTT assay and found to be noncytotoxic. Compounds 3a–h and 4f were further screened for their antibacterial activity against four bacteria strains to assess their selectivity towards M. tuberculosis. Furthermore, in silico ADME prediction of all the tested compounds followed the criteria for orally active drug and, therefore, these compounds may have a good potential for eventual development as oral agents. Graphical Abstract: [Figure not available: see fulltext.]

A facile synthesis of (Z)-5-(substituted)-2-(methylthio)thiazol-4(5H)-one using microwave irradiation and conventional method

A new effective approach to the synthesis of some new (Z)-5-(substituted)- 2-thioxothiazolidin-4-one 3a-l and (Z)-5-(substituted)-2-(methylthio)thiazol- 4(5H)-one 5a-l is reported under microwave irradiation as well as conventional conditions.

A facile synthesis of (Z)-5-(substituted)-2-(methylthio)thiazol-4(5H)-one using microwave irradiation and conventional method

A new effective approach to the synthesis of some new (Z)-5-(substituted)-2-thioxothiazolidin-4-one 3a-l and (Z)-5-(substituted)-2-(methylthio)thiazol-4(5H)-one 5a-l is reported under microwave irradiation as well as conventional conditions.

Facile and convenient synthesis of 5-arylalkylidenerhodanines by electrocatalytic crossed aldol condensation

An electrochemically induced catalytic crossed Aldol condensation of one equivalent of rhodanine with various aromatic aldehydes and ketones in ethanol in an undivided cell in the presence of sodium bromide as an electrolyte results in the formation of th

Urea/thiourea catalyzed, solvent-free synthesis of 5-arylidenethiazolidine- 2,4-diones and 5-arylidene-2-thioxothiazolidin-4-ones

An efficient and organo-catalyzed method has been developed for the synthesis of 5-arylidenethiazolidine-2,4-diones and 5-arylidene-2- thioxothiazolidin-4-ones via Knoevenagel condensation of arylaldehydes 1 and 2,4-thiazolidinedione 2a/2-thioxothiazolidin-4-one 2b under mild conditions. Urea-adduct 4 and azomethine 5 also afford arylidene-products 3 by reacting with 2a-b via addition-elimination reaction. This protocol has the features of use of inexpensive, ecofriendly readily available, effective catalyst system viz. urea/thiourea, avoidance of volatile solvents, excellent yield and simple work-up procedure.

CHARGE CONTROLLING AGENT AND TONER USING SAME

The present invention provides a charge control agent containing, as an active substance(s), one or two or more rhodanine compounds represented by the following formula (1). where R1 represents a hydrogen atom, etc.; R2 represents a hydrogen atom, a linea