5781-53-3

Basic information

• Product Name: METHYL OXALYL CHLORIDE
• Synonyms: MONO-METHYL OXALYL CHLORIDE;CHLOROGLYOXYLIC ACID METHYL ESTER;METHYL CHLOROFORMYLFORMATE;METHYL CHLOROGLYOXALATE;METHYL CHLOROGLYOXYLATE;METHYL CHLOROOXOACETATE;METHYL OXALYL CHLORIDE;Acetic acid, chlorooxo-, methyl ester
• CAS NO: 5781-53-3
• Molecular Formula: C₃H₃ClO₃
• Molecular Weight: 122.51
• EINECS: 227-307-4
• Product Categories: Organics
• Mol File: 5781-53-3.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 118-120 °C(lit.)
• Flash Point: 116 °F
• Appearance: Clear/Liquid
• Density: 1.332 g/mL at 25 °C(lit.)
• Vapor Pressure: 16.3mmHg at 25°C
• Refractive Index: n20/D 1.419(lit.)
• Storage Temp.: Flammables area
• Water Solubility: Miscible with water.
• Sensitive: Moisture Sensitive
• BRN: 1071541
• CAS DataBase Reference: METHYL OXALYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL OXALYL CHLORIDE(5781-53-3)
• EPA Substance Registry System: METHYL OXALYL CHLORIDE(5781-53-3)

Safety Data

• Hazard Codes: C,F
• Statements: 34-37-10-36-14
• Safety Statements: 26-36/37/39-45-16
• RIDADR: UN 2920 8/PG 2
• WGK Germany: 3
• F: 9-21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 5781-53-3(Hazardous Substances Data)

Usage

Description

METHYL OXALYL CHLORIDE is a clear liquid that serves as an important organic intermediate (building block) for the synthesis of various substituted methyl oxalyl products. It is widely utilized in the chemical industry due to its versatile reactivity and ability to participate in a range of chemical reactions.

Uses

Used in Pharmaceutical Industry:
METHYL OXALYL CHLORIDE is used as a synthetic reagent for the regioselective synthesis of fused coumarins, which are important compounds with a range of biological activities, including anti-inflammatory, antioxidant, and anticoagulant properties.
Used in Chemical Synthesis:
METHYL OXALYL CHLORIDE is used as a synthetic reagent for the cyclization to form substituted isoxazoles and heterocycles. These compounds are valuable in the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Organic Chemistry:
METHYL OXALYL CHLORIDE is used as a synthetic reagent in intramolecular Wittig reactions, which are crucial for the formation of complex molecular structures, particularly in the synthesis of natural products and pharmaceuticals.
Used in Silyl Enol Ether Acylation:
METHYL OXALYL CHLORIDE is used as a synthetic reagent in silyl enol ether acylation, a reaction that allows for the formation of carbon-carbon bonds and is essential for the synthesis of various organic compounds.
Used in Material Science:
METHYL OXALYL CHLORIDE is used as a synthetic reagent in the iron-mediated cleavage of C-C bonds, a process that is important for the development of new materials and the modification of existing ones.

InChI:InChI=1/C3H3ClO3/c1-7-3(6)2(4)5/h1H3

Upstream product

• 67-56-1 methanol 
• 79-37-8 oxalyl dichloride 
• 589-57-1 diethyl phosphorylchloridite 
• 17640-25-4 methyl 2,2-dichloro-2-methoxyacetate 
• 89281-72-1 Dichlor-propyloxy-essigsaeure-methylester 
• 553-90-2 Dimethyl oxalate 

Downstream Products

• 108982-03-2 7-hydroxy-4-oxo-3-phenyl-4H-chromene-2-carboxylic acid methyl ester 
• 101446-06-4 5,7-dihydroxy-4-oxo-3-phenyl-4H-chromene-2-carboxylic acid methyl ester 
• 100612-62-2 (4-butyl-phenyl)-glyoxylic acid methyl ester 
• 855398-32-2 3-(N-methoxyoxalyl-anilino)-3-phenyl-propionic acid methyl ester 
• 111033-85-3 (2RS,3RS)-2-hydroxy-3-methoxyoxalyloxy-2,3-diphenyl-propionic acid methyl ester 
• 34404-83-6 methyl 2,4,6-trimethylphenylgloxylate 
• 42022-57-1 Methyl-N-(1-adamantyl)oxamat 
• 42022-53-7 methyl 2-((2,6-diisopropylphenyl)amino)-2-oxoacetate 
• 72030-81-0 dimethyl oxazole-4,5-dicarboxylate 
• 89464-63-1 dimethyloxalylglycine 
• 5781-55-5 methoxalic anhydride 
• 54166-71-1 2'-carbamoyl-3'-methoxyoxanilic acid methyl ester 
• 22979-34-6 Methyl-p-methoxyphenylglyoxylat-hydrazon 
• 13797-22-3 methyl N-phenyloxamate 

Relevant articles and documents

A continuous flow synthesis of [1.1.1]propellane and bicyclo[1.1.1]pentane derivatives

A continuous flow process to generate [1.1.1]propellane on demand is presented rendering solutions of [1.1.1]propellane that can directly be derivatised into various bicyclo[1.1.1]pentane (BCP) species. This was realised in throughputs up to 8.5 mmol h-1providing an attractive and straightforward access to gram quantities of selected BCP building blocks. Lastly, a continuous photochemical transformation of [1.1.1]propellane into valuable BCPs bearing mixed ester/acyl chloride moieties was developed.

METHOD OF MAKING PRODRUG FOR SUSTAINED AND CONTROLLED RELEASE

A novel ROS-responsive prodrug is provided. The prodrug utilizes a unique modified oxalate linker conjugated to 4-aminophenol, which can enhance the reaction kinetics for intracellular ROS within tumor tissues while keeping the modified oxalate backbone stable with amide bond under very low ROS level.

BODIPY-based high-sensitivity fluorescent probe and synthesis method and application thereof

The invention relates to a BODIPY-based high-sensitivity fluorescent probe and a synthesis method and application thereof. A structural general formula of the probe is shown as (I), wherein Trigger is stimulant triggering groups, R1 and R2 are groups for regulating and controlling fluorescent transmission wavelength of the probe and introducing organelle targeting, and R1 and R2 are defined in the description. By the probe, detection of different substrates can be realized without changing mother nucleus structure of the probe by only changing different Trigger groups. In addition, according to different needs on wavelength and targeting, the mother nucleus structure of the probe can be quickly modified. By changing R1 and R2, maximum fluorescent emission wavelength of the probe can be changed, and the probe can target mitochondrion to realize detection of active substances in the mitochondrion. The probe has good biocompatibility, thereby being applicable to detecting biological systems. Application value of the fluorescent probe in the aspect of detecting bioactive molecules and protease over-expressed in inflammatory or tumor tissue has potential social benefit and economic benefit.