7652-29-1

Basic information

• Product Name: 6-CHLORO-2H-1,4-BENZOXAZIN-3(4H)-ONE
• Synonyms: BUTTPARK 35\07-21;6-CHLORO-2H-1,4-BENZOXAZIN-3(4H)-ONE;6-CHLORO 2H[1,4]BENZOXAZINE-3-(4H)-ONE;6-CHLORO-2H-BENZO[B][1,4]OXAZIN-3(4H)-ONE;OTAVA-BB BB0128760740;TIMTEC-BB SBB003725;TOSLAB 154300;6-Chloro-2h-benzo[b][1,4]oxazin-3-one .
• CAS NO: 7652-29-1
• Molecular Formula: C₈H₆ClNO₂
• Molecular Weight: 183.59
• Product Categories: Benzoxazines;BenzoxazinesHeterocyclic Building Blocks;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 7652-29-1.mol
• Article Data: 31

Chemical Properties

• Melting Point: 215-219 °C
• Boiling Point: 363 °C at 760 mmHg
• Flash Point: 173.3 °C
• Appearance: /
• Density: 1.393 g/cm³
• Vapor Pressure: 1.87E-05mmHg at 25°C
• Refractive Index: 1.578
• Storage Temp.: 2-8°C
• PKA: 11.89±0.20(Predicted)
• CAS DataBase Reference: 6-CHLORO-2H-1,4-BENZOXAZIN-3(4H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLORO-2H-1,4-BENZOXAZIN-3(4H)-ONE(7652-29-1)
• EPA Substance Registry System: 6-CHLORO-2H-1,4-BENZOXAZIN-3(4H)-ONE(7652-29-1)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26
• WGK Germany: 2
• HazardClass: IRRITANT
• Hazardous Substances Data: 7652-29-1(Hazardous Substances Data)

Usage

General Description

6-Chloro-2H-1,4-benzoxazin-3(4H)-one is a chemical compound with the molecular formula C8H4ClNO2. It is a derivative of benzoxazinone, a heterocyclic compound with potential biological and pharmaceutical applications. 6-CHLORO-2H-1,4-BENZOXAZIN-3(4H)-ONE is known for its antimicrobial and antifungal properties, and it has also been studied for its potential as an herbicide. It is a pale yellow powder with a melting point of around 216-220°C and is sparingly soluble in water. 6-Chloro-2H-1,4-benzoxazin-3(4H)-one is commonly used in research and development for its potential agricultural and medicinal applications.

InChI:InChI=1/C8H6ClNO2/c9-5-1-2-7-6(3-5)10-8(11)4-12-7/h1-3H,4H2,(H,10,11)

Upstream product

• 21086-49-7 (4-chloro-2-nitro-phenoxy)-acetic acid 
• 35588-41-1 2-chloro-N-(5-chloro-2-methoxyphenyl)acetamide 
• 35588-38-6 2-chloro-N-(5-chloro-2-hydroxyphenyl)acetamide 
• 13212-63-0 6-chloro-4-hydroxy-(2H)-1,4-benzoxazin-3(4H)-one 
• 1982-42-9 2,4-dichlorophenoxyacetic acid amine 
• 79-04-9 chloroacetyl chloride 
• 95-85-2 2-hydroxy-5-chloro-aniline 
• 771-26-6 4-hydroxy-2H-1,4-benzoxazin-3-one 
• 173195-16-9 2-Bromo-N-(5-chloro-2-hydroxy-phenyl)-acetamide 
• 79-07-2 Chloroacetamide 
• 37682-31-8 ethyl o-nitrophenoxyacetate 
• 344443-67-0 ethyl 4-chloro-2-nitrophenoxyacetate 
• 122-88-3 4-Chlorophenoxyacetic acid 
• 56-37-1 N-benzyl-N,N,N-triethylammonium chloride 

Downstream Products

• 55894-78-5 2-benzylidene-6-chloro-4H-benzo[1,4]oxazin-3-one 
• 52042-27-0 6-chloro-4-(2,3-dihydroxy-propyl)-4H-benzo[1,4]oxazin-3-one 
• 105492-48-6 6-Chloro-4-(2-oxo-2-phenyl-ethyl)-4H-benzo[1,4]oxazin-3-one 
• 105492-49-7 6-Chloro-4-(2-oxo-2-p-tolyl-ethyl)-4H-benzo[1,4]oxazin-3-one 
• 105492-50-0 6-Chloro-4-[2-(4-chloro-phenyl)-2-oxo-ethyl]-4H-benzo[1,4]oxazin-3-one 
• 105492-51-1 6-Chloro-4-[2-(4-methoxy-phenyl)-2-oxo-ethyl]-4H-benzo[1,4]oxazin-3-one 
• 116862-22-7 6-chloro-7-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one 
• 6239-11-8 [4-Chloro-2-(3-trifluoromethyl-benzoylamino)-phenoxy]-acetic acid 
• 6239-09-4 4-Chlor-2-benzamido-phenoxyessigsaeure 
• 6239-10-7 [4-Chloro-2-(4-chloro-benzoylamino)-phenoxy]-acetic acid 
• 6529-97-1 [4-Chloro-2-(4-methoxy-benzoylamino)-phenoxy]-acetic acid 
• 6239-17-4 [4-Chloro-2-(3,4-dichloro-benzoylamino)-phenoxy]-acetic acid 
• 104829-96-1 Benzoic acid N'-(6-chloro-3-oxo-2,3-dihydro-benzo[1,4]oxazine-4-carbonyl)-hydrazide 
• 104971-81-5 8-Chloro-2-phenyl-4H-5-oxa-3,9b-diaza-cyclopenta[a]naphthalene 

Relevant articles and documents

Intramolecular cyclization of N-hydroxy-2-phenoxyacetamides and 3-phenoxypropanamides

Abstract: A novel route for the preparation of 2H-1,4- benzoxazin-3(4H)one and 1,5 benzoxazepinones by intramolecular cyclization of N-hydroxy 2-phenoxyacetamide and N-hydroxy -3 phenoxypropanamide using PPA and Lewis acid has been discussed. Graphical abstract: [Figure not available: see fulltext. Caption: Preparation of 2H-1,4- benzoxazin-3(4H)one and 1,5 benzoxazepinones by electrophilic aromatic substitution from N-hydroxy 2-phenoxyacetamide and N-hydroxy -3 phenoxypropanamide and their acetyl and benzoyl derivatives using PPA and Lewis acids.]

Synthesis and biological evaluation of potential acetylcholinesterase inhibitors based on a benzoxazine core

With the purpose of expanding the structural variety of chemical compounds available as pharmacological tools for the treatment of Alzheimer's disease, we synthesized and evaluated a novel series of indole-benzoxazinones (Family I) and benzoxazine-arylpiperazine derivatives (Family II) for potential human acetylcholinesterase (hAChE) inhibitory properties. The most active compounds 7a and 7d demonstrated effective inhibitory profiles with Ki values of 20.3 ± 0.9 μM and 20.2 ± 0.9 μM, respectively. Kinetic inhibition assays showed non-competitive inhibition of AChE by the tested compounds. According to our docking studies, the most active compounds from both series (Families I and II) showed a binding mode similar to donepezil and interact with the same residues.

Using gene expression database to uncover biology functions of 1,4-disubstituted 1,2,3-triazole analogues synthesized via a copper (I)-catalyzed reaction

We have synthesized bioactive 1,4-disubstituted 1,2,3-triazole analogues containing 2H-1,4-benzoxazin-3-(4H)-one derivatives via 1,3-dipolar cycloaddition in the presence of CuI. All the reactions proceeded smoothly and afforded its desired products in excellent yields. Among these analogues, 3y exhibited a better cytotoxic effect on human hepatocellular carcinoma (HCC) Hep 3B cells and displayed less cytotoxicity on normal human umbilical vein endothelial cells, compared with Sorafenib, a targeted therapy for advanced HCC. 3y also induced stronger apoptosis and autophagy. Addition of curcumin enhanced 3y-induced cytotoxicity by further induction of autophagy. Using gene expression signatures of 3y to query Connectivity Map, a glycogen synthase kinase-3 inhibitor (AR-A014418) was predicted to display similar molecular action of 3y. Experiments further demonstrate that AR-A014418 acted like 3y, and vice versa. Overall, our data suggest the chemotherapeutic potential of 3y on HCC.