Methyl chloroglyoxylate

Base Information

• Chemical Name: Methyl chloroglyoxylate
• CAS No.: 5781-53-3
• Molecular Formula: C3H3 Cl O3
• Molecular Weight: 122.508
• Hs Code.: 29171900
• European Community (EC) Number: 227-307-4
• UNII: 42Z6XG83RQ
• DSSTox Substance ID: DTXSID9064003
• Nikkaji Number: J218.045F
• Wikidata: Q72489213
• Mol file: 5781-53-3.mol

Synonyms:5781-53-3;Methyl oxalyl chloride;Methyl chloroglyoxylate;Methyl chlorooxoacetate;methyl 2-chloro-2-oxoacetate;Acetic acid, chlorooxo-, methyl ester;Methyl (Chlorocarbonyl)formate;Chloroglyoxylic Acid Methyl Ester;Methyloxalylchloride;methoxalyl chloride;methyl 2-chloro-2-oxo-acetate;C3H3ClO3;42Z6XG83RQ;Acetic acid, 2-chloro-2-oxo-, methyl ester;EINECS 227-307-4;methyl chloro(oxo)acetate;methylchlorooxoacetate;MFCD00000705;methyl chlorooxalate;methylchloroglyoxylate;ClCOCO2Me;methyl chloro-oxoacetate;methyl cloro(oxo)acetate;methoxyglyoxyloyl chloride;Methyl Chloro-oxo-acetate;Mono methyl oxalyl chloride;methyl(chlorocarbonyl)formate;methyl2-chloro-2-oxoacetate;UNII-42Z6XG83RQ;SCHEMBL51376;methyl-2-chloro-2-oxoacetate;Methyl chlorooxoacetate, 96%;chloro-oxalic acid methyl ester;chlorooxoacetic acid methyl ester;DTXSID9064003;chloro-oxoacetic acid methyl ester;chloro-oxo-acetic acid methyl ester;AKOS009031376;FS-3799;A8231;FT-0628771;EN300-20687;F0001-1507

Chemical Property of Methyl chloroglyoxylate

Chemical Property:

• Appearance/Colour: clear liquid
• Vapor Pressure: 16.3mmHg at 25°C
• Refractive Index: n20/D 1.419(lit.)
• Boiling Point: 119°Cat760mmHg
• Flash Point: 46.7°C
• PSA: 43.37000
• Density: 1.36g/cm³
• LogP: -0.07520
• Storage Temp.: Flammables area
• Sensitive.: Moisture Sensitive
• Water Solubility.: Miscible with water.
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 121.9770716
• Heavy Atom Count: 7
• Complexity: 98.4

Purity/Quality:

99%min ^*data from raw suppliers

Methyl chlorooxoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): CCF
• Hazard Codes: C,F
• Statements: 34-37-10-36-14
• Safety Statements: 26-36/37/39-45-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C(=O)Cl
• Uses: Methyl oxalyl chloride is an important organic intermediate (building block) to synthetize substituted methyl oxalyl products. It can be used for regioselective synthesis of fused coumarins, cyclization to form substituted isoxazoles and heterocycles, intramolecular Wittig reactions, silyl enol ether acylation, and iron-mediated cleavage of C-C bonds. Methyl oxalyl chloride is used as a synthetic reagent. It serves as a reagent in the synthesis of fused coumarins, substituted isoxazoles and heterocycles. Further, it is used in intramolecular Wittig reactions, and iron-mediated cleavage of C-C bonds. Reactant involved in:Regioselective synthesis of fused coumarinsCyclization to form substituted isoxazoles and heterocyclesIntramolecular Wittig reactionsSilyl enol ether acylationIron-mediated cleavage of C-C bonds

Technology Process of Methyl chloroglyoxylate

There total 9 articles about Methyl chloroglyoxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

diethyl phosphorylchloridite (589-57-1) + methyl 2,2-dichloro-2-methoxyacetate (17640-25-4) → monomethyl oxalyl chloride (5781-53-3) + Dimethyl oxalate (553-90-2) + chloroethane (75-00-3) + phosphonic dichloride (66298-75-7) + methyl phosphonochloridate (74813-29-9) + ethyl phosphonochloridate (74813-30-2)

Guidance literature:

With iron(III) chloride; at 105 - 110 ℃; for 1.16667h; Product distribution;

Reference yield: 93.0%

methanol (67-56-1) + oxalyl dichloride (79-37-8) → monomethyl oxalyl chloride (5781-53-3)

Guidance literature:

In diethyl ether; at 0 ℃; for 2h;

Reference yield:

→ monomethyl oxalyl chloride (5781-53-3)

Guidance literature:

With thionyl chloride;

DOI:10.1021/ja01175a083

upstream raw materials:

methyl 2,2-dichloro-2-methoxyacetate

Dimethyl oxalate

Dichlor-propyloxy-essigsaeure-methylester

diethyl phosphorylchloridite

Downstream raw materials:

7-hydroxy-4-oxo-3-phenyl-4H-chromene-2-carboxylic acid methyl ester

5,7-dihydroxy-4-oxo-3-phenyl-4H-chromene-2-carboxylic acid methyl ester

(4-butyl-phenyl)-glyoxylic acid methyl ester

3-(N-methoxyoxalyl-anilino)-3-phenyl-propionic acid methyl ester

Refernces

• 1、 -. "Synthesis and application of oxalic acid monoester derivatives". Paragraph 0015-0018. . Retrieved 2020/12/08.
• 2、 Chen, Haoliang,He, Xiujing,Su, Meihui,Zhai, Wenhao,Zhang, Hao,Li, Changhua. "A General Strategy Toward Highly Fluorogenic Bioprobes Emitting across the Visible Spectrum". supporting information. p. 10157 - 10163. Retrieved 2017/08/02.