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

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

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

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

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.

Synthesis and application of oxalic acid monoester derivatives

The invention relates to synthesis and application of oxalic acid monoester-containing compounds as shown in a general formula (I) which is described in the specification. The compounds represent a broad-spectrum efficient insecticidal and bactericidal agent structure type. The oxalic acid monoester-containing compounds can well control aphids, plutella xylostella and spodoptera exigua when used as novel insecticidal bactericides; the compounds can also be used for preventing and treating cucumber brown blotch, cucumber bacterial angular leaf spot, cucumber fusarium wilt, cucumber downy mildew, cucumber powdery mildew, tomato bacterial leaf spot and rice sheath blight. R in the general formula (I) is as defined in the specification.

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.

A General Strategy Toward Highly Fluorogenic Bioprobes Emitting across the Visible Spectrum

A general approach toward highly fluorogenic probes across the visible spectrum for various analytes offers significant potential for engineering a wide range of bioprobes with diverse sensing and imaging functions. Here we show a facile and general strategy that involves introducing a new fluorogenic mechanism in boron dipyrromethene (BODIPY) dyes, based on the principle of stimuli-triggered dramatic reduction in the electron-withdrawing capabilities of the meso-substituents of BODIPYs. The fluorogenic mechanism has been demonstrated to be applicable in various BODIPYs with emission maxima ranging from green to far red (509, 585, and 660 nm), and the synthetic strategy allows access to a panel of highly fluorogenic bioprobes for various biomolecules and enzymes (H2O2, H2S, and protease) via introducing specific triggering motifs. The potency of the general design strategy is exemplified by its application to develop a mitochondria-targeting far-red probe capable of imaging of endogenous H2O2 in living cells.

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.

Ionic liquids based on oxalic acid mono amides

The present invention relates to monosubstituted oxalic acid amides of the general formula (I) ????????[A]+ [O-C(O)-C(O)-X]-?????(I) wherein the meaning is for [A]+ a cation made from an organic moiety A having a formally positively charged heteroatom selected from the group consisting of nitrogen, phosphorus and sulfur and X is the group -NRaRb, wherein Ra and Rb are the same or different and are independently from each other hydrogen or a C1 to C30 organic residue with the proviso that at least one of Ra and Rb is a C1 to C30 organic residue.

Design, synthesis and insecticidal activities of novel N-oxalyl derivatives of neonicotinoid compound

Ten novel neonicotinoid derivatives containing N-oxalyl groups were designed and synthesized, and their structures were characterized by 1H NMR, MS, IR, elemental analysis and single crystal X-ray diffraction analysis. The insecticidal activities of the new compounds were evaluated. The results of bioassays indicated that some of these title compounds exhibited excellent insecticidal activities.

Synthesis, crystal structure, and insecticidal activity of novel N-alkyloxyoxalyl derivatives of 2-arylpyrrole

Two series of novel N-alkyloxyoxalyl derivatives of 2-arylpyrrole were synthesized, and their structures were characterized by 1H NMR spectroscopy, elemental analysis, and single-crystal X-ray diffraction analysis. The insecticidal activities of the new compounds were evaluated. The results of bioassays indicated that some of these title compounds exhibited excellent insecticidal activities, and their insecticidal activities against oriental armyworm, mosquito, and spider mite are comparable to those of the commercialized Chlorfenapyr.

Asymmetric 1,3-dipolar cycloadditions of 2-diazocyclohexane-1,3-diones and alkyl diazopyruvates

The 1,3-dipolar cycloaddition reactions of 2-diazocyclohexane-1,3-dione (7a; Table 1) and of alkyl diazopyruvates (11a-e; Table 3) to 2,3-dihydrofuran and other enol ethers have been investigated in the presence of chiral transition metal catalysts. With RhII catalysts, the cycloadditions were not enantioselective, but those catalyzed by [RuIICl 2(1a)] and [RuIICl2(1b)] proceeded with enantioselectivities of up to 58% and 74% ee, respectively, when diazopyruvates 11 were used as substrates. The phenyliodonium ylide 7c yielded the adduct 8a in lower yield and poorer selectivity than the corresponding diazo precursor 7a (Table2) upon decomposition with [Ru(pybox)] catalysts. This suggests that ylide decomposition by RuII catalysts, contrary to that of the corresponding diazo precursors, does not lead to Ru-carbene complexes as reactive intermediates. Our method represents the first reproducible, enantioselective 1,3-cycloaddition of these types of substrates.