2942-13-4

Basic information

• Product Name: 6-METHOXY-1,3-BENZOTHIAZOLE
• Synonyms: 6-METHOXY-1,3-BENZOTHIAZOLE;6-METHOXYBENZOTHIAZOLE;Benzothiazole, 6-methoxy- (7CI,8CI,9CI);Benzothiazole,6-Methoxy-;6-Methoxybenzo[d]thiazole;NSC 508406
• CAS NO: 2942-13-4
• Molecular Formula: C₈H₇NOS
• Molecular Weight: 165.21
• Product Categories: BENZOTHIAZOLE
• Mol File: 2942-13-4.mol

Chemical Properties

• Melting Point: 72.5-73℃
• Boiling Point: 274.4 °C at 760 mmHg
• Flash Point: 119.8 °C
• Appearance: /
• Density: 1.268 g/cm³
• Vapor Pressure: 0.00906mmHg at 25°C
• Refractive Index: 1.645
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 1.60±0.10(Predicted)
• CAS DataBase Reference: 6-METHOXY-1,3-BENZOTHIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-METHOXY-1,3-BENZOTHIAZOLE(2942-13-4)
• EPA Substance Registry System: 6-METHOXY-1,3-BENZOTHIAZOLE(2942-13-4)

Safety Data

• Hazardous Substances Data: 2942-13-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of Medicinal Chemistry, 16, p. 1314, 1973 DOI: 10.1021/jm00269a026

InChI:InChI=1/C8H7NOS/c1-10-6-2-3-7-8(4-6)11-5-9-7/h2-5H,1H3

Upstream product

• 1747-60-0 6-methoxybenzothiazol-2-ylamine 
• 108-98-5 thiophenol 
• 2941-59-5 2-iodo-6-methoxybenzo[d]thiazole 
• 67-68-5 dimethyl sulfoxide 
• 191348-14-8 2-iodo-4-methoxylaniline 
• 68-12-2 N,N-dimethyl-formamide 
• 6274-29-9 2-amino-5-methoxy-thiophenol 
• 124-38-9 carbon dioxide 
• 119072-55-8 tert-butylisonitrile 
• 4274-42-4 2-amino-5-methoxy-benzenethiol; hydrochloride 
• 127-19-5 N,N-dimethyl acetamide 
• 7732-36-7 bis(2-amino-5-methoxyphenyl)disulfide 
• 64-18-6 formic acid 
• 2258-42-6 formyl acetic anhydride 

Downstream Products

• 30132-86-6 6-methoxy-7-aminobenzothiazole 
• 798548-58-0 6-methoxy-7-nitro-2-phenyl-benzothiazole 
• 13244-33-2 2-amino-5-methoxybenzenesulfonic acid 
• 101078-51-7 6-methoxy-2-(4-tolyl)-1,3-benzothiazole 
• 65840-58-6 1-(6-methoxy-benzothiazol-2-yl)-ethanone 
• 10205-69-3 6-methoxy-2-phenylbenzothiazole 
• 1730-44-5 2-chloro-7-methoxy-10H-phenothiazine 
• 1771-19-3 3-methoxy-10H-phenothiazine 
• 1730-43-4 3,7-dimethoxy-10H-phenothiazine 
• 1617537-48-0 1-benzyl-3-(6-methoxybenzo[d]thiazol-2-yl)quinolin-4(1H)-one 
• 92161-47-2 2-(4-chlorophenyl)-6-methoxybenzo[d]thiazole 
• 1122521-71-4 6-methoxy-2-(2-methoxyphenyl)-1,3-benzothiazole 
• 101078-50-6 5-methoxy-2-(4′-tolyl)benzo[d]thiazole 
• 1398308-42-3 6-methoxy-2-(5-(4-(trifluoromethyl)phenyl)thiazol-2-yl)benzo[d]thiazole 

Relevant articles and documents

Iodine-promoted ring-opening methylation of benzothiazoles with dimethyl sulfite

A halogen-bond promoted ring-opening methylation of benzothiazoles has been developed using dimethyl sulphite as a methylating reagent in the presence of a base. This approach represents a simple and efficient synthesis ofN-methyl-N-(o-methylthio)phenyl amides, and features direct construction of both N-Me and S-Me bonds in a one-pot reaction through the decomposition of easily prepared benzothiazoles.

Photoelectrochemical cross-dehydrogenative coupling of benzothiazoles with strong aliphatic C-H bonds

A photoelectrochemical strategy for the cross-dehydrogenative coupling of unactivated aliphatic hydrogen donors (e.g.alkanes) with benzothiazoles is reported. We used tetrabutylammonium decatungstate as the photocatalyst to activate strong C(sp3)-H bonds in the chosen substrates, while electrochemistry scavenged the extra electrons.

Iron-catalyzed tandem oxidative coupling and acetal hydrolysis reaction to prepare formylated benzothiazoles and isoquinolines

The aldehyde group is one of the most versatile intermediates in synthetic chemistry, and the introduction of an aldehyde group into heteroarenes is important for the transformation of molecular structure. Herein, we achieved the direct formylation of benzothiazo/les and isoquinolines. The reaction features a novel iron-catalyzed Minisci-type oxidative coupling process using commercially available 1,3-dioxolane as a formylated reagent followed by acetal hydrolysis without a separation process. The reaction can be performed under exceedingly mild reaction conditions and exhibits broad functional group tolerance.

K2S as Sulfur Source and DMSO as Carbon Source for the Synthesis of 2-Unsubstituted Benzothiazoles

We describe a three-component reaction of o-iodoanilines with K2S and DMSO that provides 2-unsubstituted benzothiazoles in moderate to good isolated yields with good functional group tolerance. Electron-rich aromatic amines and o-phenylenediamines instead of o-iodoanilines provided 2-unsubstituted benzothiazoles and 2-unsubstituted benzimidazoles with and without K2S under similar conditions. Notably, DMSO plays three vital roles: carbon source, solvent, and oxidant.

Synthetic method of ammonium acetate-mediated benzothiazole compound

The invention discloses a synthetic method of an ammonium acetate-mediated benzothiazole compound . The synthetic method comprises the steps: adding an o-haloaniline derivative, potassium sulfide, dimethyl sulfoxide, a catalyst, an additive 1 and an additive 2 into a reaction tube, carrying out a stirring reaction at the temperature of 130-150 DEG C, cooling to room temperature after the reactionis finished, and separating and purifying the product to obtain the benzothiazole compound. The invention provides the synthetic method of the benzothiazole compound by taking K2S as a sulfur source,DMSO as a carbon source and an oxidizing agent, an o-haloaniline derivative as a substrate and an ammonium acetate mediated three-component one-pot method. The method has the advantages of fewer reaction steps, mild reaction conditions, good functional group tolerance and the like.

Method for synthesizing benzothiazole by microwave radiation of benzothioamide compound in aqueous phase

The invention discloses a method for synthesizing benzothiazole by microwave radiation of a benzothioamide compound in an aqueous phase. The method includes the steps: adding the benzothioamide compound into the aqueous phase under microwave conditions; performing cyclization under alkaline conditions to generate the benzothiazole. The method for preparing the benzothiazole is environmentally friendly, simple and convenient in operation, safe, cheap and efficient. Compared with the prior art, the method is applicable to a lot of functional groups, high in yield, few in by-products, simple in operation, safe, low in cost and environmentally friendly.

Heterogeneous copper-catalyzed synthesis of S-arylated 2-aminothiophenols via ring opening of benzothiazoles and C-S coupling using aryl halides

Chelate resins, which are polystyrene-divinylbenezene-based polymers bearing iminodiacetic acids or polyamines as ligands, supported copper catalysts (Cu/CR11 or Cu/CR20) in effectively catalyzing the ring cleaving S-arylation of benzothiazole with aryl i

Synthesis of benzothiazoles from 2-aminobenzenethiols in the presence of a reusable polythiazolium precatalyst under atmospheric pressure of carbon dioxide

Synthesis of benzothiazoles from 2-aminobenzenethiols and carbon dioxide was carried out using poly(3,4-dimethyl-5-vinylthiazolium) iodide as a precatalyst to in situ generation of NHCs by deprotonation. The reaction was successfully carried out under mild conditions (1 atm of CO2 and 60–70 °C) with a broad substrate scope and functional group tolerance. The precatalyst salt was recovered and reused for several times without any loss of activity.

HEMOGLOBIN MODIFIER COMPOUNDS AND USES THEREOF

Described herein are compounds, including pharmaceutically acceptable salts thereof, methods of making such compounds, pharmaceutical compositions comprising such compounds, and methods of using such compounds to treat, prevent or diagnose blood-based diseases, disorders or conditions.

Thermolysis and radiofluorination of diaryliodonium salts derived from anilines

Aniline-derived diaryliodonium salts were synthesized and functionalized in good to excellent yields by judicious utilization of electron-withdrawing protecting groups. This simple approach opens another route to radiolabeling amino arenes in relatively complex molecules, such as flutemetamol.