5325-20-2

Basic information

• Product Name: (2H)1,4-BENZOTHIAZIN-3(4H)-ONE
• Synonyms: 4H-1,4-benzothiazin-3-one;BenzothiazinHone;(2H)-1,4-Benzothiazin-3-(4H)-one 98%;2H-1,4-BENZOTHIAZIN-3(4H)-ONE, 99+%;2H-1,4-Benzothiazine-3-ol;3,4-Dihydro-2H-1,4-benzothiazine-3-one;1,4-Benzothiazin-3(4H)-one;3,4-Dihydro-2H-1,4-benzothiazin-3-one
• CAS NO: 5325-20-2
• Molecular Formula: C₈H₇NOS
• Molecular Weight: 165.21
• EINECS: 226-197-5
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Thiazines
• Mol File: 5325-20-2.mol
• Article Data: 31

Chemical Properties

• Melting Point: 176-178 °C(lit.)
• Boiling Point: 272.25°C (rough estimate)
• Flash Point: 169.5 °C
• Appearance: almost white to light beige-grey crystalline powder
• Density: 1.1979 (rough estimate)
• Vapor Pressure: 3.36E-09mmHg at 25°C
• Refractive Index: 1.6458 (estimate)
• Storage Temp.: 2-8°C
• PKA: 12.90±0.20(Predicted)
• BRN: 131642
• CAS DataBase Reference: (2H)1,4-BENZOTHIAZIN-3(4H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (2H)1,4-BENZOTHIAZIN-3(4H)-ONE(5325-20-2)
• EPA Substance Registry System: (2H)1,4-BENZOTHIAZIN-3(4H)-ONE(5325-20-2)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 5325-20-2(Hazardous Substances Data)

Usage

Chemical Properties

ALMOST WHITE TO LIGHT BEIGE-GREY CRYST. POWDER

General Description

2H-1,4-Benzothiazin-3(4H)-one derivatives were synthesized and tested for calcium antagonistic and calmodulin antagonistic activities.

InChI:InChI=1/C16H20ClNO5/c1-4-22-14(20)16(18-11(3)19,15(21)23-5-2)10-12-8-6-7-9-13(12)17/h6-9H,4-5,10H2,1-3H3,(H,18,19)

Upstream product

• 149-30-4 2-thioxo-3H-1,3-benzothiazole 
• 74-93-1 methylthiol 
• 93808-89-0 bis-[2-(2-chloro-acetylamino)-phenyl]-disulfide 
• 109-79-5 n-butanethiol 
• 6375-65-1 (2-nitro-phenylsulfanyl)-acetic acid 
• 79-08-3 bromoacetic acid 
• 137-07-5 2-amino-benzenethiol 
• 105-39-5 chloroacetic acid ethyl ester 
• 79-11-8 chloroacetic acid 
• 1141-88-4 2-Aminophenyl disulfide 
• 30248-11-4 (2-amino-phenylsulfanyl)-acetic acid; sodium salt 
• 73112-11-5 2,3-dihydro-3-imino-4H-1,4-benzothiazine hydrochloride 
• 24231-81-0 4-(2-chloro-acetylamino)-2-imino-3-phenyl-2,3-dihydro-thiazole-5-carboxylic acid ethyl ester 
• 21201-23-0 4-acetoxy-4H-benzo[1,4]thiazin-3-one 

Downstream Products

• 145549-29-7 4-benzoyl-4H-benzo[1,4]thiazin-3-one 
• 100621-01-0 (2⁽⁴⁾H-benzo[1,4]thiazin-3-yl)-phenyl-amine 
• 98589-44-7 (2-cyano-phenylsulfanyl)-acetic acid 
• 3080-99-7 3,4-dihydro-2H-benzo[1,4]thiazine 
• 37142-87-3 4-methyl-1,4-benzothiazin-3(4H)-one 
• 37012-79-6 3-(3-oxo-2H-benzo[b][1,4]thiazin-4(3H)-yl)propanoic acid 
• 103110-40-3 3-oxo-4-phenyl-3,4-dihydro-2H-1,4-benzothiazine 
• 112183-35-4 4-Phenethyl-4H-benzo[1,4]thiazin-3-one 
• 95476-30-5 2-(4-methyl-benzylidene)-4H-benzo[1,4]thiazin-3-one 
• 54874-85-0 2-(4-chloro-benzylidene)-4H-benzo[1,4]thiazin-3-one 
• 24545-07-1 2-benzylidene-2H-1,4-benzothiazin-3(4H)-one 
• 95476-37-2 2-(4-methoxy-benzylidene)-4H-benzo[1,4]thiazin-3-one 
• 54874-84-9 2-[1-(4-Bromo-phenyl)-meth-(E)-ylidene]-4H-benzo[1,4]thiazin-3-one 
• 6431-73-8 4-benzyl-2H-benzo[b][1,4]thiazin-3(4H)-one 

Relevant articles and documents

Design, synthesis and in vitro anticancer evaluation of new 2h-benzo[b][1,4]thiazin-3(4h)-one based 1,2,3-Triazoles

A series of novel 2H-benzo[b][1,4]thiazin-3(4H)-one derived from 1,4-disubstituted 1,2,3-triazole derivatives (4a-j and 5a-j) were synthesized using Cu(I) catalyzed azide alkyne cyclization (CuAAC) reaction of the compounds 2 and 3 with various aromatic azides. The examination of in vitro anticancer activity revealed that the compounds 4d and 5d were found to possess a broad spectrum of anticancer activity against three cell lines MCF-7, HeLa and IMR-32 with IC50 values ranging from 26. 28 ± 1. 5 to 32. 06 ± 0. 3 M mL-1, respectively. The remaining compounds have shown good to moderate activity against the tested cell lines.

Novel benzothiazine-piperazine derivatives by peptide-coupling as potential anti-proliferative agents

In an attempt to develop potential and selective anti-proliferative agents, a series of novel benzothiazine-piperazine derivatives 8a–i and 10a–g were synthesized by coupling of 2H-1,4-benzothiazin-3(4H)-one with various amines 7a–i and 9a–g in excellent yields and evaluated for their in vitro anti-proliferative activity against four cancer cell lines, HeLa (cervical), MIAPACA (pancreatic), MDA-MB-231 (breast) and IMR32 (neuroblastoma). In vitro inhibitory activity indicated that compounds 8a, 8d, 8g, 10a, 10b, 10e, 10f were found to be good anti-proliferative agents. Among them the derivatives 8g, 10e and 10f were found to be the most active members exhibiting remarkable growth inhibitory activity. Molecular docking was undertaken to investigate the probable binding mode and key active site interactions in HDAC8 and EHMT2 proteins. The docking results are complementary to the experimental results.

Efficient synthesis of benzene-fused 6/7-membered amides: Via Xphos Pd G2 catalyzed intramolecular C-N bond formation

An efficient approach for benzene-fused 6/7-membered amides via intramolecular amidation of aryl chlorides catalyzed by a Buchwald-Hartwig second generation Pd catalyst (Xphos Pd G2) has been successfully developed. This catalyst system allows the primary amides which have only modest nucleophilicity to be coupled successfully even with electron rich aryl chlorides in short reaction time. The intramolecular amidation reaction also has good chemoselectivity and excellent functional group compatibility.