38533-19-6

Basic information

• Product Name: 2-phenyl-2H-1,4-benzothiazin-3(4H)-one
• Synonyms: 2-phenyl-3,4-dihydro-2H-1,4-benzothiazin-3-one
• CAS NO: 38533-19-6
• Molecular Formula: C₁₄H₁₁NOS
• Molecular Weight: 241.3082
• Mol File: 38533-19-6.mol

Chemical Properties

• Boiling Point: 452.7°C at 760 mmHg
• Flash Point: 227.6°C
• Density: 1.253g/cm³
• Vapor Pressure: 2.19E-08mmHg at 25°C
• Refractive Index: 1.646
• CAS DataBase Reference: 2-phenyl-2H-1,4-benzothiazin-3(4H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-phenyl-2H-1,4-benzothiazin-3(4H)-one(38533-19-6)
• EPA Substance Registry System: 2-phenyl-2H-1,4-benzothiazin-3(4H)-one(38533-19-6)

Safety Data

• Hazardous Substances Data: 38533-19-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-phenyl-2H-1,4-benzothiazin-3(4H)-one is used as an anti-tuberculosis agent for its ability to inhibit the growth of Mycobacterium tuberculosis, the bacteria that causes tuberculosis. It is particularly effective against both drug-susceptible and drug-resistant strains of the bacteria, making it a valuable asset in the fight against multi-drug resistant tuberculosis.
2-phenyl-2H-1,4-benzothiazin-3(4H)-one is used as a potential candidate for the development of new tuberculosis treatments due to its mechanism of action that involves blocking the biosynthesis of the mycobacterial cell wall, which is crucial for the survival and virulence of the bacteria.

Upstream product

• 4870-65-9 2-bromophenylacetic acid 
• 137-07-5 2-amino-benzenethiol 
• 37128-01-1 2-chloro-N-(2-methylsulfanyl-phenyl)-2-phenyl-acetamide 
• 2882-19-1 ethyl 2-phenyl-2-bromoacetate 
• 5325-20-2 2H-1,4-benzothiazin-3-one 
• 108-90-7 chlorobenzene 
• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 
• 100-52-7 benzaldehyde 
• 129200-96-0 (2E)-3-phenyl-2-(phenylsulfonyl)-2-propenenitrile 
• 22065-57-2 ethyl 2-phenyldiazoacetate 
• 2987-53-3 2-(Methylthio)aniline 
• 2912-62-1 α-chlorophenylacetyl chloride 
• 1155-00-6 bis(2-nitrophenyl)disulfide 

Downstream Products

• 95948-81-5 2-phenyl-4-(2-piperidin-1-yl-ethyl)-4H-benzo[1,4]thiazin-3-one 
• 78600-49-4 4-acetyl-2-acetoxymethyl-2-phenyl-2,3-dihydro-4H-1,4-benzothiazine 
• 78600-48-3 5-acetyl-3-acetoxy-3-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine 
• 78600-47-2 trans-4-Acetyl-2-methyl-2-phenyl-2,3-dihydro-4H-1,4 benzothiazine 1-oxide 
• 78600-47-2 cis-4-Acetyl-2-methyl-2-phenyl-2,3-dihydro-4H-1,4-benzothiazine 1-oxide 
• 93301-20-3 2-methyl-2-phenyl-2,3-dihydro-4H-1,4-benzothiazine 
• 95553-77-8 dimethyl-[1-methyl-2-(2-phenyl-2,3-dihydro-benzo[1,4]thiazin-4-yl)-ethyl]-amine 
• 95158-16-0 dimethyl-[2-(2-phenyl-2,3-dihydro-benzo[1,4]thiazin-4-yl)-ethyl]-amine 
• 94966-78-6 diethyl-[1-methyl-2-(2-phenyl-2,3-dihydro-benzo[1,4]thiazin-4-yl)-ethyl]-amine 
• 100598-56-9 ethyl 2-phenyl-2H-1,4-benzothiazin-3-one-4-acetate 
• 80838-95-5 4-methyl-2-phenyl-1,4(3H)-benzothiazine 
• 113342-90-8 3-methylthio-2-phenyl-1,4-(2H)-benzothiazine 
• 93301-41-8 5-acetyl-3-phenyl-2,5-dihydro-1,5-benzothiazepine 
• 93301-24-7 4-acetyl-2-methyl-2-phenyl-2,3-dihydro-4H-1,4-benzothiazine 

Relevant articles and documents

Enhancing the Extent of Enolization for α-C-H Bonds of Aliphatic Carboxylic Acid Equivalents via Ion Pair Catalysis: Application toward α-Chalcogenation

In general, the α-functionalization of carboxylic acid derivatives requires either a transition metal catalyst or a stoichiometric activating agent/strong base/external additive. A transition metal free α-chalcogenation of aliphatic carboxylic acid equivalents is reported herein via ion pair formation using K3PO4 as a catalyst. Mild conditions, broad scope, scalability of the process, attaining bioactive glucokinase activators, and some synthetic intermediates establish merits of the strategy.

Catalytic Enantioselective Access to Dihydroquinoxalinones via Formal α-Halo Acyl Halide Synthon in One Pot

An enantioselective one-pot catalytic strategy to dihydroquinoxalinones, featuring novel 1-phenylsulfonyl-1-cyano enantioenriched epoxides as masked α-halo acyl halide synthons, followed by a domino ring-opening cyclization (DROC), is documented. A popula

DABCO mediated one pot synthesis of sulfoxonium ylides under blue LED

DABCO mediated practical and convenient one pot method has been developed to access sulfoxonium ylides under photoredox and metal free conditions at room temperature. The protocol explored the reactivity of DMSO and α-aryl-α-diazo esters in presence of DABCO under blue LED condition. We demonstrated the generality of this protocol by synthesizing a variety of sulfoxonium ylides in very good yields. The practicality of the protocol has been demonstrated by the gram scale synthesis as well as by the extension of this protocol to synthesize precursors of biologically active compounds. This straightforward and practical method offers an alternative route to access very useful sulfoxonium ylides from α-aryl-α-diazoacetates.

Expeditious synthesis of C2- or N4-aryl-1,4-benzothiazin-3-one via orthogonal Pd-catalyzed C-arylation and Cu-catalyzed N-arylation

Direct, chemo-specific arylation at C-2 or N-4 of 1,4-benzothiazin-3-one with aryl halides, based on Pd or Cu catalyst system, respectively, provided easy entry to arylated derivatives, a class of molecules not easily accessible via existing methods. Under Pd-catalysis conditions with LiHMDS as the base, N-arylation of 1,4-benzothiazin-3-one was inhibited leading to Cα-arylation of a secondary amide without the need for protection and de-protection of more acidic amido NH.

LXR modulators

A compound of formula I wherein A, X, q, R1, R2a, R2b, R2c, R3a, and R3b are defined herein.

Regioselective one pot synthesis of 2-alkyl/aryl-4H-benzo[1,4]thiazine-3- one via microwave irradiation

A series of 2-alkyl/aryl-4H-benzo[1,4]thiazine-3-ones have been synthesized by microwave irradiation of ethyl-2-bromo-2-alkyl/aryl acetate and 2-amino thiophenol in the presence of 1,8-diazabicyclo-[5.4.0]undec-7-ene and N-methylpiperidine. All compounds were characterized by 1H NMR, 13C NMR and elemental analyses, and by X-ray crystallography in the case of 2-methyl-4H-benzo[1,4]thiazin-3-one.

Synthesis of 2H-1,4-benzothiazin-3(4H)-ones and 2H-1,4-benzoselenazin-3(4H)-ones with the aid of samarium(II) iodide

Bis(o-nitrophenyl) disulfides or diselenides were easy to reduce by samarium(II) iodide to produce the active intermediates 2 in situ, which readily react with α-halocarboxylic derivatives to yield the corresponding products 2H-1,4-benzothiazin-3(4H)-ones and 2H-1,4-benzoselenazin-3(4H)-ones, respectively, in moderate to high yields under mild conditions.

A Convenient and General Synthesis of 2-Aryl- and 2-Pyridyl-3-oxo-3,4-dihydro-2H-1,4-benzothiazines

The reaction of bis(2-aminophenyl) disulphide 1 with methyl or ethyl aryl- or pyridylacetates and sodium hydride gives the title compounds in good yield and high purity.The reaction is general, the starting materials easily available and the workup is simple and rapid.

Heterocyclic aldose reductase inhibitors and methods of using them

The invention relates to new compounds of the formula: STR1 Aldose reductase inhibitors. Treatment of certain complications of diabetes.