125849-94-7

Basic information

• Product Name: 3,5-DICHLORO-6-METHYL-1,4-OXAZIN-2-ONE
• Synonyms: 3,5-DICHLORO-6-METHYL-1,4-OXAZIN-2-ONE;2H-1,4-Oxazin-2-one, 3,5-dichloro-6-methyl-
• CAS NO: 125849-94-7
• Molecular Formula: C₅H₃Cl₂NO₂
• Molecular Weight: 179.99
• Product Categories: API intermediates
• Mol File: 125849-94-7.mol

Chemical Properties

• Melting Point: 70 °C
• Boiling Point: 212℃
• Flash Point: 82℃
• Appearance: /
• Density: 1.62
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -4.14±0.40(Predicted)
• CAS DataBase Reference: 3,5-DICHLORO-6-METHYL-1,4-OXAZIN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DICHLORO-6-METHYL-1,4-OXAZIN-2-ONE(125849-94-7)
• EPA Substance Registry System: 3,5-DICHLORO-6-METHYL-1,4-OXAZIN-2-ONE(125849-94-7)

Safety Data

• Hazardous Substances Data: 125849-94-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3,5-Dichloro-6-methyl-1,4-oxazin-2-one is used as a reagent in organic synthesis for its high reactivity, facilitating the creation of a wide range of chemical products.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 3,5-Dichloro-6-methyl-1,4-oxazin-2-one is utilized as a precursor in the synthesis of various pharmaceuticals, contributing to the development of new medications.
Used in Agrochemical Industry:
3,5-Dichloro-6-methyl-1,4-oxazin-2-one is employed as a starting material in the production of agrochemicals, aiding in the formulation of effective crop protection agents.
Used in Biotechnology:
3,5-Dichloro-6-methyl-1,4-oxazin-2-one is used as a component in the development of antimicrobial agents, leveraging its biocidal properties to combat microbial infections.
Used in Chemical Research:
3,5-Dichloro-6-methyl-1,4-oxazin-2-one is also used in chemical research as a model for studying the reactivity and properties of electrophilic reagents, furthering scientific understanding and innovation in chemical synthesis.

Upstream product

• 79-37-8 oxalyl dichloride 
• 78-97-7 2-hydroxy-propionitrile 
• 75-44-5 phosgene 

Downstream Products

• 143033-58-3 4-Methoxy-5-methyl-oxazole-2-carboxylic acid methyl ester 
• 143721-95-3 (1R,2R,6R,7S)-1,11-Dichloro-7-methyl-4-phenyl-8-oxa-4,10-diaza-tricyclo[5.2.2.0^2,6]undec-10-ene-3,5,9-trione 
• 137520-98-0 2,6-Dichloro-3-methyl-4-phenethyl-pyridine 
• 137520-84-4 2,6-Dichloro-3-methyl-5-phenethyl-pyridine 
• 138944-46-4 2,6-Dichloro-3-methyl-4-[4-(tetrahydro-pyran-2-yloxy)-butyl]-pyridine 
• 138944-43-1 2,6-dichloro-5-methyl-3-<4-((tetrahydropyran-2-yl)oxy)butyl>pyridine 
• 137520-88-8 2,6-Dichloro-3-methyl-5-(3,4,5-trimethoxy-phenyl)-pyridine 
• 137521-02-9 2,6-Dichloro-3-methyl-4-(3,4,5-trimethoxy-phenyl)-pyridine 
• 155959-00-5 5-chloro-6-methyl-3-phenylsulfenyl-2(H)-1,4-oxazin-2-one 
• 125850-04-6 2,6-Dichloro-3-methyl-5-phenyl-pyridine 
• 137521-01-8 2,6-Dichloro-3-methyl-4-phenyl-pyridine 
• 142330-89-0 5-chloro-6-methyl-3-(phenylmethylthio)-2H-1,4-oxazin-2-one 
• 142330-90-3 5-chloro-6-methyl-3-(4-methylphenyl)-2H-1,4-oxazin-2-one 
• 137520-86-6 2,6-dichloro-5-methylnicotinic acid ethyl ester 

Relevant articles and documents

A Novel Diels-Alder Approach to Heavily Substituted Azasugars

Diels-Alder cycloaddition of an appropriately substituted 1,4-oxazin-2-one with vinylene carbonate followed by the chemical manipulation of the bridged bicyclic lactone cycloadduct affords a heavily functionalised azasugar ring.

Synthesis of spirocyclic pyridoazepines as analogues of galanthamine by nucleophilic aromatic substitution of 3-substituted 2-chloropyridines

In this report we describe the synthesis of spirocyclic pyridoazepines starting from easily available precursors. The key step of our synthesis is an intramolecular nucleophilic aromatic substitution of the appropriate 3-substituted 2-chloropyridines. The final compounds, designed as simplified analogues of the alkaloid galanthamine, showed significant acetylcholinesterase inhibition activity. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Spirocyclic pyridoazepine analogues of galanthamine: Synthesis, modelling studies and evaluation as inhibitors of acetylcholinesterase

Spirocyclic pyridoazepines, designed as simplified analogues of the alkaloid galanthamine, were synthesised and evaluated as inhibitors of acetylcholinesterase. The key cyclisation step involved internal displacement of 2-chloro or 2-iodopyridine by either nucleophilic aromatic substitution or a Heck reaction. The target compounds showed significant inhibition of acetylcholinesterase but lower than that of galanthamine. This result could be rationalised by comparative docking simulation studies based on the known crystal structure of the acetylcholinesterase-galanthamine complex; multiple hydrogen bonding of a cocrystallised water molecule to both the receptor and the ligand was found to be of crucial importance for effective binding to the active site of the enzyme. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

6,6-FUSED HETEROARYL PIPERIDINE ETHER ALLOSTERIC MODULATORS OF THE M4 MUSCARINIC ACETYLCHOLINE RECEPTOR

The present invention is directed to 6,6-fused heteroarylpiperidine ether compounds which are allosteric modulators of the M4 muscarinic acetylcholine receptor. The present invention is also directed to uses of the compounds described herein in the potential treatment or prevention of neurological and psychiatric disorders and diseases in which M4 muscarinic acetylcholine receptors are involved. The present invention is also directed to compositions comprising these compounds. The present invention is also directed to uses of these compositions in the potential prevention or treatment of such diseases in which M4 muscarinic acetylcholine receptors are involved.

HETEROARYL PIPERIDINE ETHER ALLOSTERIC MODULATORS OF THE M4 MUSCARINIC ACETYLCHOLINE RECEPTOR

The present invention is directed to heteroarylpiperidine ether compounds which are allosteric modulators of the M4 muscarinic acetylcholine receptor. The present invention is also directed to uses of the compounds described herein in the potential treatment or prevention of neurological and psychiatric disorders and diseases in which M4 muscarinic acetylcholine receptors are involved. The present invention is also directed to compositions comprising these compounds. The present invention is also directed to uses of these compositions in the potential prevention or treatment of such diseases in which M4 muscarinic acetylcholine receptors are involved.

AZABICYCLO[4.1.0]HEPTANE ALLOSTERIC MODULATORS OF THE M4 MUSCARINIC ACETYLCHOLINE RECEPTOR

The present invention is directed to azabicyclo[4.1.0]heptane compounds which are allosteric modulators of the M4 muscarinic acetylcholine receptor. The present invention is also directed to uses of the compounds described herein in the potential treatmen

6,5-FUSED HETEROARYL PIPERIDINE ETHER ALLOSTERIC MODULATORS OF THE M4 MUSCARINIC ACETYLCHOLINE RECEPTOR

The present invention is directed to 6,5-fused heteroarylpiperidine ether compounds which are allosteric modulators of the M4 muscarinic acetylcholine receptor. The present invention is also directed to uses of the compounds described herein in the potential treatment or prevention of neurological and psychiatric disorders and diseases in which M4 muscarinic acetylcholine receptors are involved. The present invention is also directed to compositions comprising these compounds. The present invention is also directed to uses of these compositions in the potential prevention or treatment of such diseases in which M4 muscarinic acetylcholine receptors are involved.

6,7-DIHYDRO-5H-PYRROLO[3,4-B]PYRIDIN-5-ONE ALLOSTERIC MODULATORS OF THE M4 MUSCARINIC ACETYLCHOLINE RECEPTOR

The present invention is directed to 6,7-dihydro-5H-pyrrolo[3,4-b]pyridine-5-one compounds which are allosteric modulators of the M4 muscarinic acetylcholine receptor. The present invention is also directed to uses of the compounds described herein in the potential treatment or prevention of neurological and psychiatric disorders and diseases in which M4 muscarinic acetylcholine receptors are involved. The present invention is also directed to compositions comprising these compounds. The present invention is also directed to uses of these compositions in the potential prevention or treatment of such diseases in which M4 muscarinic acetylcholine receptors are involved.

POSITIVE ALLOSTERIC MODULATORS OF MGLUR2

The present invention is directed to 5-substituted 1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide and 1,3-dihydro[1,2,5]thiadiazolo[3,4-b]pyridine 2,2,-dioxide derivatives which are potentiators of metabotropic glutamate receptors, particularly the mGluR2 receptor, and which are useful in the treatment or prevention of neurological and psychiatric disorders associated with glutamate dysfunction and diseases in which metabotropic glutamate receptors are involved. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which metabotropic glutamate receptors are involved

Synthesis of 5,5′-dialkyl-6,6′-dichloro-2, 2′-bipyridines

5,5′-Dialkyl-6,6′-dichloro-2,2′-bipyridines were synthesized starting from 3-substituted 2-chloro-6-iodopyridines using Pd-catalyzed coupling conditions. 6-Alkyl-3,5-dichloro-2H-1,4-oxazin-2-ones were excellent precursors for the synthesis of these functionalized 2-iodo-6-chloropyridines. Copyright Taylor & Francis Group, LLC.