5685-06-3

Basic information

• Product Name: 4-methylthiazole-2(3H)-thione
• Synonyms: 4-methylthiazole-2(3H)-thione;4-Methyl-4-thiazoline-2-thione;2(3H)-Thiazolethione, 4-methyl-;4-Methyl-2(3H)-thiazolethione;4-Methyl-2-mercaptothiazole;4-Methyl-2-thiazolethiol;4-Methylthiazoline-2-thione;4-Thiazoline-2-thione, 4-methyl-
• CAS NO: 5685-06-3
• Molecular Formula: C₄H₅NS₂
• Molecular Weight: 131.2192
• EINECS: 227-152-2
• Mol File: 5685-06-3.mol

Chemical Properties

• Melting Point: 89.3°C
• Boiling Point: 203.4 °C at 760 mmHg
• Flash Point: 76.8 °C
• Appearance: /solid
• Density: 1.263 (estimate)
• Vapor Pressure: 0.278mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• PKA: 8?+-.0.40(Predicted)
• CAS DataBase Reference: 4-methylthiazole-2(3H)-thione(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methylthiazole-2(3H)-thione(5685-06-3)
• EPA Substance Registry System: 4-methylthiazole-2(3H)-thione(5685-06-3)

Safety Data

• Hazardous Substances Data: 5685-06-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
4-Methylthiazole-2(3H)-thione is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs with diverse therapeutic properties.
Used in Dye Production:
In the dye industry, 4-Methylthiazole-2(3H)-thione is utilized as a component in the production of dyes, where its chemical structure imparts specific color characteristics to the final products.
Used in Pesticide Formulation:
4-Methylthiazole-2(3H)-thione is employed as a component in the formulation of pesticides, leveraging its chemical properties to enhance the effectiveness of these agricultural chemicals.
Used in Antimicrobial Applications:
4-Methylthiazole-2(3H)-thione is used as an antimicrobial agent due to its potential biological activities, which can help in controlling the growth of microorganisms in various settings.
Used in Anticancer Research:
In the field of oncology, 4-Methylthiazole-2(3H)-thione is studied for its potential anticancer properties, with the aim of developing new therapeutic agents for the treatment of cancer.
Used in Flavor and Fragrance Industry:
4-Methylthiazole-2(3H)-thione is investigated as a precursor to flavor and fragrance compounds, where its unique sulfur-containing structure could contribute to the creation of novel scents and tastes.
Overall, 4-Methylthiazole-2(3H)-thione is a multifaceted chemical with a broad spectrum of applications across different industries, from healthcare to agriculture, and from colorants to fragrances.

InChI:InChI=1/C4H5NS2/c1-3-2-7-4(6)5-3/h2H,1H3,(H,5,6)

Upstream product

• 513-74-6 ammonium dithiocarbamate 
• 78-95-5 chloroacetone 
• 108-31-6 maleic anhydride 
• 89861-47-2 4-methyl-3-[(1-oxohexadecyl)oxy]-2(3H)-thiazolethione 
• 23826-98-4 bis(4-methylthiazol-2-yl) disulfide 
• 147727-23-9 C₁₅H₁₄N₂O₂ 
• 152732-30-4 (2S,3R)-3-(3-Cyano-indol-1-ylmethyl)-oxirane-2-carboxylic acid 4-methyl-2-thioxo-thiazol-3-yl ester 
• 693-95-8 4-Methylthiazole 
• 60-29-7 diethyl ether 
• 64-17-5 ethanol 
• 1095-04-1 triphenyl thiophosphite 
• 110907-36-3 4-Methyl-2-phenyldisulfanyl-thiazole 
• 100780-08-3 3-(3,3-diphenylpropionoxy-)-4-methylthiazole-2(3H)-thione 
• 57658-34-1 2-mercapto-4-methylthiazole-5-carboxylic acid 

Downstream Products

• 5316-68-7 2-ethylsulfanyl-4-methyl-thiazole 
• 5316-72-3 2-(benzylthio)-4-methylthiazole 
• 5685-17-6 (4-Methyl-thiazol-2-ylmercapto)-essigsaeure 
• 55578-40-0 2-(4-methyl-thiazol-2-ylmercapto)-hydroquinone 
• 693-95-8 4-Methylthiazole 
• 113411-23-7 4-methylthiazole-2-sulfonamide 
• 23826-98-4 bis(4-methylthiazol-2-yl) disulfide 
• 71371-10-3 3-oxo-5-methyl-2-phenyl-2,3-dihydro-thiazolo[2,3-b]thiazolylium betaine 
• 16914-21-9 3-benzyl-2-benzylsulfanyl-4-methyl-thiazolium; bromide 
• 55379-29-8 2-benzoylsulfanyl-4-methyl-thiazole 
• 55379-12-9 4-methyl-2-(4-nitro-benzylsulfanyl)-thiazole 
• 93284-11-8 4-methyl-2-((2-nitrophenyl)disulfanyl)thiazole 
• 2591-05-1 2-(4-methyl-thiazol-2-ylsulfanyl)-1-phenyl-ethanone 
• 90356-75-5 4-nitro-3-trifluoromethyl-N-[2-hydroxy-2-methyl-3-(4-methylthiazol-2-ylthio)propionyl]aniline 

Relevant articles and documents

Synthesis of novel azabicyclo derivatives containing a thiazole moiety and their biological activity against pine-wood nematodes

To explore a new skeleton with nematicidal activity, a series of novel azabicyclo derivatives containing a thiazole moiety were designed, synthesized and evaluated for their nematicidal activities. The bioassay results against pine-wood nematodes (Bursaphelenchus xylophilus) showed that most of the title compounds displayed nematicidal activity at a concentration of 40 mg/L. Especially, the title compounds2-((8-methyl-8-azabicyclo[3.2.1]octan-3-yl)oxy)-4-(4-chlorophenyl)thiazole (7e), 2-((8-methyl-8-azabicyclo[3.2.1]octan-3-yl)thio)-4-phenylthiazole (10a) and 2-((8-methyl-8-azabicyclo [3.2.1]octan-3-yl)thio)-4-(4-chlorophenyl)thiazole (10e) exhibited more than 90% mortality against Bursaphelenchus xylophilus.

Decarboxylation method for heterocyclic carboxylic acid compounds

The invention relates to a decarboxylation method for heterocyclic carboxylic acid compounds. The method comprises the following steps: dissolving the heterocyclic carboxylic acid compounds in an aprotic polar solvent N,N-dimethylformamide, and performing decarboxylation at 85-150 DEG C with an organic acid as a catalyst. The method in the invention allows the yield of decarboxylation products obtained after a reaction to be higher than the yield of the products obtained through decarboxylation methods in the prior art, and does not need an expensive metal catalyst; and the solvent (DMF) in the present invention is more stable than DMSO, is not prone to decompose at a high temperature, and it can be recycled, so the cost is reduced. The method has the advantages of simple operation process, zero pollution, greenness, environmental protection and excellent application prospect.

A process for the preparation method of thiabendazole

The invention relates to a new method for synthesizing thiabendazole. Acetone and chlorine are taken as starting materials to synthesize chloroacetone, chloroacetone not subjected to separation can directly react with thiocarbamide to obtain 2-Amino-4-methylthiazole which is subjected to diazotization to obtain 4-methylthiazole, and 4-methylthiazole is oxidized to produce 4-thiazolecarboxylic acid, and finally, 4-thiazolecarboxylic acid reacts with o-phenylenediamine to obtain the target object thiabendazole. The thiabendazole is a broad-spectrum anthelmintic, can repel roundworms, hookworms, whipworms, pinworms, strongyloises stercoralis and trichinization, is also a broad-spectrum efficient disinfectant and is widely used as a fruit fresh-keeping agent and a bactericidal mildew inhibitor in various fields over the past decade in China.

5 - Hydroxy indoles containing heterocyclic ring derivative and its use

The present invention relates to a heterocyclic ring-containing 5-hydroxy indole derivative as represented by formula I, comprising a racemate of the derivative, an optical isomer of same, and a pharmaceutically acceptable salt and/or hydrate thereof, where substituent R1, R2, X, Y, and Z have the meanings as provided in the description. The compound of formula I is applicable in preparing a medicament for treatment and/or prevention of viral infections, and particularly for preparing an anti-hepatitis B virus medicament and anti-influenza virus medicament.

QUINAZOLINE DERIVATIVES AS TAM FAMILY KINASE INHIBITORS

Disclosed are compounds, compositions and methods for treating diseases, syndromes, conditions and disorders that are affected by the modulation of the activity of, e.g., the inhibition of, one or more members of the TAM family kinases.

Synthesis and characterisation of N-coordinated pentafluorophenyl gold(I) thiazole-derived complexes and an unusual self-assembly to form a tetrameric gold(I) complex

Treatment of [Au(C6F5)(SC4H8)] (1) (SC4H8 = tetrahydrothiophene or tht) with HC=NC(CH3)=C(H)S, CH3SC=NC(CH3)=C(H)S, (I) or piperidine yields the neutral mononuclear imine complexes [Au(C6F5)-{N=C(H)SC(H)=CCH3}] (2) and [Au(C6F5){N=C(SCH3)SC(H)=CCH3}] (3), or the amine complex [Au(C6F5){N(H)CH2(CH2)3CH 2}] (4). The reaction of 1 with S=CN(H)C(CH3)=C(H)S, (II) affords the thione complex [Au(C6F5){S=CN(H)C(CH3)=C(H)S}] (5), which, in CH2Cl2 via spontaneous intermolecular deprotonation of the thione ligand, self-assembles to an unique tetramer of Au(I), [Au{S=CNC(CH3)=C(H)S}]4 (6) containing a folded rectangle of Au-atoms with aurophlilic interactions [av. Au ... Au distance, 3.02(4) A and av. Au-Au-Au angle, 87(2)°]. N-coordination of the imine complexes has been confirmed by 15N NMR and the crystal structure determination of 2 which exhibits the expected linear N-coordination and intermolecular Au ... Au [3.345(1) A] contacts. The crystal structure of 5 shows thione S-coordination of II to the central Au atom.

Intramolecular Addition of a Dioxolanyl Radical to the Indole Nucleus: Preparation of Enantiomerically Pure, Oxygenated Perhydro-3H-pyrroloindoles

The cyclization of dioxolanyl radicals, which were generated by the Barton tartrate-derived thiohydroxamate ester (mixed anhydride) procedure, with an indole nucleus has been explored.The products derived from these reactions have been identified and their chemistry investigated with the goal of uncovering new entries into enantiomerically pure, mitomycin-like structures.Thus, the photolysis of 1-hydroxy-2-thiopyridone ester 8c and 1-hydroxy-4-methylthiazole-2(3H)-thione ester 8d has been conducted with UV and visible light.The photochemistry of the products, namely, dimer 9, dihydroindole 12a, indole 11, and thiazole 13c, derived from the thiohydroxamate esters and putative intermediates 18a and 18b, was also explored.

A Route to Chiral Epoxypyrroloindoles via Oxiranyl Radical Cyclization

An oxiranyl radical has been generated from a glycidic acid via the thiohydroxamic acid anhydride route.The radical has been shown to undergo cyclization, a process, which to our knowledge, has not been reported previously.The structure and the reactivity of the indole and dihydroindole products of the cyclization are discussed.

THE INVENTION OF RADICAL REACTIONS. PART XVIII. DECARBOXYLATIVE RADICAL ADDITION TO ARSENIC, ANTIMONY, AND BISMUTH PHENYLSULPHIDES - A NOVEL SYNTHESIS OF NOR-ALCOHOLS FROM CARBOXYLIC ACIDS

Carbon centered radicals obtained by decarboxylative transformation of suitable thiohydroxamate esters react with group Va trisphenylsulphides to give intermediates of general formula R-M(SPh)2 (M= As, Sb, Bi).These react spontaneously with air to give the corresponding alcohols.This procedure is especially useful in the case where M=Sb.It is thus sufficient to stir the thiohydroxamate ester with tris(phenylthio)antimony under air to obtain the nor alcohol directly and in high yield.The intermediate organometalloid could also be oxidised with nitrogen dioxide to give the expected nitroalkane albeit in only modest yield.The corresponding organobismuth intermediate derived from 3,3-diphenylpropionic acid could actually be isolated thereby providing strong evidence for the proposed mechanism.

The Invention of New Radical Chain Reactions. Part 9. Further Radical Chemistry of Thiohydroxamic Esters; Formation of Carbon-Carbon Bonds

Carbon radicals derived from the esters of several types of thiohydroxamic acids have been trapped in a number of different ways.Particular attention has been paid to carbon-carbon bond formation by addition to suitably activated ethylenic linkages.Carboxylic acids can be conveniently converted into homo- and bishomo-acids by free radical chemistry based on thiohydroxamic esters.In a coda the tautomerism of the thiohydroxamic acids have been examined by physical methods.It is confirmed that the esters used are derivatives of the thione tautomer.