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
• Article Data: 6

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

Description

3-Methyl-2(3H)-benzothiazolone is a five-membered heterocyclic compound with a distinctive chemical structure. Its crystals are characterized by the orthorhombic crystal system and space group Pbca, which contributes to its unique properties and potential applications in various fields.

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 
• 17890-34-5 N-(trimethylsilyl)phenyl(methyl)amine 
• 87463-11-4 O-methyl N-methyl-N-phenylcarbamothioate 
• 2757-23-5 chloro(chlorosulfanyl)methanone 
• 100-61-8 N-methylaniline 
• 87463-00-1 O-ethyl N-methyl-N-phenylthiocarbamate 
• 87463-10-3 (N,N'-dimethyl-N,N'-diphenylcarbamoyl)sulfenamide 
• 51480-12-7 Bis(N-methyl-N-phenylcarbamoyl)disulfane 
• 100244-42-6 O-isopropyl N-methyl-N-phenylthiocarbamate 

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 
• 70292-64-7 2-ethoxy-1,3-benzothiazole 
• 2254-94-6 3-methylbenzothiazole-2-thione 
• 133044-32-3 3-methyl-6-benzoyl-2(3H)-benzothiazolone 
• 133044-34-5 3-Methyl-6-(4-Chlorobenzoyl)Benzothiazolinone 
• 912266-38-7 5-butyryl-2-methylaminothiophenol 
• 912266-40-1 5-benzoyl-2-methylaminothiophenol 

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.

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.

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.