4807-55-0

Basic information

• Product Name: 3-METHYLRHODANINE
• Synonyms: 3-Methyl-2-thioxo-1,3-thiazolidin-4-one;3-methyl-2-thioxo-4-thiazolidinon;3-Methylrhodanide;3-methyl-rhodanin;3-Methylrodanin;4-Thiazolidinone, 3-methyl-2-thioxo-;Methylrhodanine;n-methyl-rhodanin
• CAS NO: 4807-55-0
• Molecular Formula: C₄H₅NOS₂
• Molecular Weight: 147.22
• EINECS: 225-367-6
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Thiazoles;Building Blocks;C3 to C7;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 4807-55-0.mol
• Article Data: 16

Chemical Properties

• Melting Point: 69-71 °C(lit.)
• Boiling Point: 213.4°C at 760 mmHg
• Flash Point: 82.9°C
• Appearance: /
• Density: 1.344 (estimate)
• Vapor Pressure: 0.164mmHg at 25°C
• Refractive Index: 1.5130 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -1.76±0.20(Predicted)
• CAS DataBase Reference: 3-METHYLRHODANINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYLRHODANINE(4807-55-0)
• EPA Substance Registry System: 3-METHYLRHODANINE(4807-55-0)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-28-36/37/39-45
• WGK Germany: 3
• RTECS: VI8400000
• Hazardous Substances Data: 4807-55-0(Hazardous Substances Data)

Usage

General Description

3-Methylrhodanine, also known as 2-amino-3-methylimidazo[4,5-f]azepine-4-carboxamide, is a chemical compound with a molecular formula of C7H7N3O. It is a heterocyclic compound and a derivative of rhodanine. The chemical structure of 3-Methylrhodanine consists of a five-membered ring with nitrogen and sulfur atoms. 3-Methylrhodanine has been studied for its potential pharmacological activities, including as an anti-cancer agent, as well as for its use in the synthesis of pharmaceuticals. Additionally, 3-Methylrhodanine has been researched for its potential use in the synthesis of novel materials and as a building block in organic chemistry. Studies have also shown that this compound has antioxidant and radical scavenging properties, making it of interest for potential use in the field of health and wellness.

InChI:InChI=1/C4H5NOS2/c1-5-3(6)2-8-4(5)7/h2H2,1H3

Upstream product

• 21160-95-2 methyl-dithiocarbamic acid; methylamine salt 
• 79-11-8 chloroacetic acid 
• 75-15-0 carbon disulfide 
• 74-89-5 methylamine 
• 137-42-8 sodium N-methyldithiocarbamate 
• 105-39-5 chloroacetic acid ethyl ester 
• 598-52-7 1-(methyl)-thiourea 
• 68-11-1 mercaptoacetic acid 
• 13558-70-8 methyl N-(chloroacetyl)carbamate 
• 2365-48-2 Methyl thioglycolate 
• 556-61-6 methyl thioisocyanate 
• 6326-83-6 bis(carboxymethyl)trithiocarbonate 
• 593-51-1 methylamine hydrochloride 
• 63906-52-5 thiocyanatoacetic acid, Na-salt 

Downstream Products

• 123021-26-1 5-[2-(3-carboxypropoxy)-1-naphthylmethylene]-3-methyl-4-oxo-2-thioxothiazolidine 
• 113059-39-5 3-methyl-5-[2-(1-methyl-1H-[2]quinolylidene)-1-phenyl-ethylidene]-2-thioxo-thiazolidin-4-one 
• 61854-69-1 Isatyliden-3-N-methylrhodanin 
• 28996-47-6 (Z)-3-methyl-5-(4-nitrobenzylidene)-2-thioxothiazolidin-4-one 
• 5685-07-4 1,3-thiazoline-2-thione 
• 1133953-94-2 (Z)-5-(3',5'-diiodo-4'-hydroxybenzylidene)-3-methyl-2-thioxothiazolidin-4-one 
• 1133954-14-9 (Z)-5-(biphenyl-2'-ylmethylene)-3-methyl-2-thioxothiazolidin-4-one 
• 34709-43-8 (Z)-3-methyl-5-(4'-methylbenzylidene)-2-thioxothiazolidin-4-one 
• 1133954-19-4 (Z)-3-methyl-5-(2'-phenylethylidene)-2-thioxothiazolidin-4-one 
• 1133954-06-9 (Z)-5-(4'-fluorobenzylidene)-3-methyl-2-thioxothiazolidin-4-one 
• 1133953-96-4 (Z)-5-(4'-hydroxybenzylidene)-3-methyl-2-thioxothiazolidin-4-one 
• 1133954-00-3 (Z)-5-(4'-methoxybenzylidene)-3-methyl-2-thioxothiazolidin-4-one 

Relevant articles and documents

A facile one-pot, four-component synthesis of (Z)-isomer of rhodanine-oxindole derivatives under environmentally benevolent conditions

Herein, an efficient and sustainable one-pot, four-component access to rhodanine-oxindole derivatives is achieved by a reaction between primary amines, carbon disulfide, ethyl chloroacetate, and cyano-substituted alkenyl oxindoles. The reaction was conducted without any harsh conditions as well as exhausting workup in polyethylene glycol (PEG) as a green solvent at room temperature and delivered rhodanine-oxindole products in high yield. This publication is the first easy protocol to be reported for the rapid construction of new rhodanine-oxindole derivatives at room temperature without harsh conditions and via multicomponent reaction.

A concise approach to n-substituted rhodanines through a base-assisted one-pot coupling and cyclization process

An efficient approach to obtain functionalized rhodanines was developed through a base-assisted one-pot coupling and continuous cyclization of a primary amine, carbon disulfide, and methyl (2-chloroacetyl)carbamate. This conversion tolerates a broad range of functional groups and can be used to scale the preparation of N-substituted rhodanines in excellent yields.

Thiazolidinone-peptide hybrids as dengue virus protease inhibitors with antiviral activity in cell culture

The protease of dengue virus is a promising target for antiviral drug discovery. We here report a new generation of peptide-hybrid inhibitors of dengue protease that incorporate N-substituted 5-arylidenethiazolidinone heterocycles (rhodanines and thiazolidinediones) as N-terminal capping groups of the peptide moiety. The compounds were extensively characterized with respect to inhibition of various proteases, inhibition mechanisms, membrane permeability, antiviral activity, and cytotoxicity in cell culture. A sulfur/oxygen exchange in position 2 of the capping heterocycle (thiazolidinedione-capped vs rhodanine-capped peptide hybrids) has a significant effect on these properties and activities. The most promising in vitro affinities were observed for thiazolidinedione-based peptide hybrids containing hydrophobic groups with Ki values between 1.5 and 1.8 μM and competitive inhibition mechanisms. Rhodanine-capped peptide hybrids with hydrophobic substituents have, in correlation with their membrane permeability, a more pronounced antiviral activity in cell culture than the thiazolidinediones.