2786-62-1

Basic information

• Product Name: 3-METHYL-2(3H)-BENZOTHIAZOLONE
• Synonyms: 3-METHYL-2(3H)-BENZOTHIAZOLONE;3-METHYL-1,3-BENZOTHIAZOL-2(3H)-ONE;3-Methyl-3H-benzothiazol-2-one;3-Methyl-(2H)benzothiazolone, GC 98%;3-METHYL-2(3H)-BENZOTHIAZOLONE 98%;3-methyl-1,3-benzothiazol-2-one
• CAS NO: 2786-62-1
• Molecular Formula: C₈H₇NOS
• Molecular Weight: 165.21
• Product Categories: Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Thiazoles
• Mol File: 2786-62-1.mol

Chemical Properties

• Melting Point: 74-77 °C(lit.)
• Boiling Point: 294.3°Cat760mmHg
• Flash Point: 131.8°C
• Appearance: /
• Density: 1.315g/cm³
• Refractive Index: 1.672
• CAS DataBase Reference: 3-METHYL-2(3H)-BENZOTHIAZOLONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYL-2(3H)-BENZOTHIAZOLONE(2786-62-1)
• EPA Substance Registry System: 3-METHYL-2(3H)-BENZOTHIAZOLONE(2786-62-1)

Safety Data

• Hazardous Substances Data: 2786-62-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Methyl-2(3H)-benzothiazolone is used as a key intermediate in the synthesis of various pharmaceutical compounds. It plays a crucial role in the production of 2,3-dihydro-3-methyl-2-oxobenzo[d]oxazole-6-carbaldehyde and 2,3-dihydro-3-methyl-2-oxobenzo[d]thiazole-6-carbaldehyde, which are important for the development of new drugs.
Used in Antifungal Agents:
3-Methyl-2(3H)-benzothiazolone is used as a building block for the synthesis of imidazole derivatives that contain the 2(3H)-benzothiazolone moiety. These imidazole derivatives have potential antifungal properties, making them valuable in the development of new antifungal agents to combat fungal infections.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 5, p. 769, 1968 DOI: 10.1002/jhet.5570050605

InChI:InChI=1/C8H9NOS/c1-9-6-4-2-3-5-7(6)11-8(9)10/h2-5,8,10H,1H3

Upstream product

• 2786-31-4 3-methylbenzothiazolium iodide 
• 27825-90-7 3-methyl-2-methylthiobenzothiazolium methylsulfate 
• 4338-98-1 2-hydrazono-3-methyl-2,3-dihydrobenzo[d]thiazole hydrochloride 
• 100-61-8 N-methylaniline 
• 2757-23-5 chloro(chlorosulfanyl)methanone 
• 100244-42-6 O-isopropyl N-methyl-N-phenylthiocarbamate 
• 51480-12-7 Bis(N-methyl-N-phenylcarbamoyl)disulfane 
• 87463-10-3 (N,N'-dimethyl-N,N'-diphenylcarbamoyl)sulfenamide 
• 87463-00-1 O-ethyl N-methyl-N-phenylthiocarbamate 
• 87463-11-4 O-methyl N-methyl-N-phenylcarbamothioate 
• 17890-34-5 N-(trimethylsilyl)phenyl(methyl)amine 

Downstream Products

• 21749-63-3 2-(methylamino)benzenethiol 
• 2843-10-9 N-methyl-2-(10-methyl-10H-benzo[b]pyridazino[3,4-e][1,4]thiazin-4-ylsulfanyl)-aniline 
• 133044-32-3 3-methyl-6-benzoyl-2(3H)-benzothiazolone 
• 133044-34-5 3-Methyl-6-(4-Chlorobenzoyl)Benzothiazolinone 
• 13372-62-8 N-methyl-o-aminophenyl methyl sulphide 
• 91799-47-2 N-methyl-N-(2-(methylthio)phenyl)acetamide 
• 2783-66-6 1-methyl-2-phenylbenzothiazolium iodide 
• 93226-41-6 3-Methyl-2-brommethyl-benzthiazolium 
• 16622-21-2 2-benzyl-3-methyl-benzothiazolium; iodide 
• 2786-31-4 3-methylbenzothiazolium iodide 
• 2254-94-6 3-methylbenzothiazole-2-thione 
• 70292-64-7 2-ethoxy-1,3-benzothiazole 
• 4329-95-7 3-Methylbenzothiazolium 2-sulfonate 

Relevant articles and documents

A Forgotten Chiral Spiro Compound Revisited: 3,3'-Dimethyl-3H,3'H-2,2'-spirobi[[1,3]benzothiazole]

The title compound was obtained as a side product during dimerization-oxidation steps of the carbene generated from N-methylbenzothiazolium iodide. Chromatography on (S,S)-Whelk O1 column showed on cooling a typical plateau shape chromatogram indicating an exchange between two enantiomers on the column. The thermal barrier to racemization was determined (85 kJ.mol-1 at 10 C) by dynamic high-performance liquid chromatography (DHPLC).The absolute configuration of the first (M) and second eluted (P) enantiomers on the (S, S)-Whelk O1 column was established by comparing the reconstructed circular dichroism (CD) spectra from the CD detector signal and the calculated CD spectrum of the (P) enantiomer. Mass spectrometry revealed that 3,3'-dimethyl-3H,3'H-2,2'-spirobi[[1,3]benzothiazole] can be viewed as a masked thiophenate attached to a benzothiazolium framework. Chirality 27:716-721, 2015.

Synthetic routes to, transformations of, and rather surprising stabilities of (N-Methyl-N-phenylcarbamoyl)sulfenyl Chloride, ((N-Methyl-N-phenylcarbamoyl) dithio)carbonyl chloride, and related compounds

(Figure presented) The title compound classes, (carbamoyl)sulfenyl chlorides and ((carbamoyl)dithio)carbonyl chlorides, have been implicated previously as unstable, albeit trappable, intermediates in organosulfur chemistry. The presentwork reports for each of these functional groups: (i) several routes to prepare it in the N-methylaniline family; (ii) its direct structural characterization by several spectroscopic techniques; (iii) its rather unexpected stability and its ultimate fatewhen it decomposes; (iv) a series of further chemical transformations that give highly stable derivatives, each in turn subject to thorough characterization. Relevant kinetic and mechanistic experiments were carried out, including some with p-methyl- and 2,6-dimethyl-substituted N-methylanilines. Given that the title compounds can be isolated and are relatively stable, they may find applications in the preparation of thiolyzable and/or photolabile protecting groups for the sulfhydryl function of cysteine and for the development of new protein synthesis and modification reagents

o-Iodoxybenzoic Acid (IBX) as a Viable Reagent in the Manipulation of Nitrogen- and Sulfur-Containing Substrates: Scope, Generality, and Mechanism of IBX-Mediated Amine Oxidations and Dithiane Deprotections

o-Iodoxybenzoic acid (IBX), a highly versatile hypervalent iodine(V) reagent, was found to efficiently mediate the dehydrogenation of amines in addition to facilitating the oxidative cleavage of dithioacetals and dithioketals. Through the development of relevant IBX-based protocols, a plethora of useful synthetic intermediates, including imines, oximes, ketones, and aromatic N-heterocycles, were found to be readily accessible under notably mild conditions. Further investigation of these transformations led to the elucidation of valuable mechanistic details, resulting in the conclusion that they proceed via ionic rather than single electron transfer (SET) pathways.

The reaction of 3-methylthiazolium derivatives with superoxide

3-Methylbenzothiazolium salts were allowed to react with superoxide to afford dimeric bis[o-(N-formyl-N-methylamino)phenyl]disulfides and 3-methyl-2-benzothiazolones. The reaction was applied to monocyclic thiazolium salts, and novel ten-membered ring com

Preparation of 1,4-Dienes from 2-(2-Hydroxyalkylseleno)benzothiazoles by the Reaction Involving Se -> O Azaaromatic Ring Rearrangement

The reactions of 2-(2-oxoalkylseleno)benzothiazoles with allylic Grignard reagents in the presence of BF3*OEt2 gave the corresponding 2-benzothiazoles which, on treatment with Ph3P and NaH, afforded 1,4-dienes in good to excellent yields.

THE REACTION OF 3-METHYLBENZOTHIAZOLIUM SALTS WITH SUPEROXIDE

3-Methylbenzothiazolium salts reacted with superoxide to afford dimeric bisdisulfides and 3-methyl-2-benzothiazolones.The reaction was entirely specific for superoxides, and is of interest from the biological and mechanis