1,1-Dichlorodimethyl ether

Base Information

• Chemical Name: 1,1-Dichlorodimethyl ether
• CAS No.: 4885-02-3
• Molecular Formula: C2H4Cl2O
• Molecular Weight: 114.959
• Hs Code.: 29091990
• European Community (EC) Number: 225-498-9
• NSC Number: 91480
• UNII: M68H5X8887
• DSSTox Substance ID: DTXSID2063636
• Nikkaji Number: J34.756F
• Wikipedia: Dichloromethyl_methyl_ether
• Wikidata: Q158543
• Mol file: 4885-02-3.mol

Synonyms:Ether,dichloromethyl methyl (6CI,7CI,8CI);1,1-Dichloromethyl methyl ether;Chloromyl;Dichloromethoxymethane;Dichloromethyl methyl ether;Methoxydichloromethane;Methyl a,a-dichloromethyl ether;NSC 91480;alpha,alpha-Dichloromethyl methyl ether;

Chemical Property of 1,1-Dichlorodimethyl ether

Chemical Property:

• Appearance/Colour: Colorless liquid
• Vapor Pressure: 79mmHg at 25°C
• Melting Point: 85ºC
• Refractive Index: n20/D 1.431(lit.)
• Boiling Point: 84.999 °C at 760 mmHg
• Flash Point: 42.222 °C
• PSA: 9.23000
• Density: 1.263 g/cm³
• LogP: 1.39400
• Storage Temp.: 2-8°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 113.9639201
• Heavy Atom Count: 5
• Complexity: 21.6

Purity/Quality:

99% ^*data from raw suppliers

Dichloromethyl Methyl Ether ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,F,C
• Hazard Codes: C,T,F
• Statements: 10-20/22-34-37-33-23/24-40-36-23/24/25
• Safety Statements: 26-36/37/39-45-24/25-16-27-7/9

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(Cl)Cl
• Uses: Common formylating reagent for aromatic compounds, chlorinating agent for carboxylic acids, and reactant with borinic esters for the preparation of alkenones.

Technology Process of 1,1-Dichlorodimethyl ether

There total 6 articles about 1,1-Dichlorodimethyl ether 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: 71.0%

oxalyl dichloride (79-37-8) + Methyl formate (107-31-3) → Dichloromethyl methyl ether (4885-02-3)

Guidance literature:

With N-methyl-N-phenylformamide; at 25 - 30 ℃; for 31h;

DOI:10.1016/j.tetlet.2017.10.052

Reference yield:

Methyl formate (107-31-3) → Dichloromethyl methyl ether (4885-02-3)

Guidance literature:

With phosphorus pentachloride;

DOI:10.1007/BF00810110

Reference yield:

phosgene (75-44-5) + Methyl formate (107-31-3) → Dichloromethyl methyl ether (4885-02-3)

Guidance literature:

With triphenylphosphine; In 1,2-dichloro-benzene;

upstream raw materials:

Methyl formate

3-chloro-3-methoxy-diazirine

chlorine

chloromethyl methyl ether

Downstream raw materials:

Dichlorodiphenylmethane

α-chlorobenzyl methyl ether

benzylidene dichloride

4,4'-methylene-bis(N,N-dimethylaniline)

Refernces

A practical and highly efficient synthesis of lennoxamine and related isoindolobenzazepines

10.1016/j.tet.2004.03.049

The research presents a highly efficient synthesis method for lennoxamine and related isoindolobenzazepines, which are alkaloids derived from the Chilean plant Berberis darwinii. The study focuses on an improved approach to synthesizing these compounds through intramolecular condensation of aldehyde isoindolones under basic conditions, followed by catalytic hydrogenation of the resulting dehydroisoindolobenzazepines. Key reactants in the synthesis include aldehyde isoindolones, which are derived from the alkylation-acylation of arylethylamines with ethyl 2-chloromethylbenzoate derivatives. The synthesis involves formylation using dichloromethyl methyl ether and titanium tetrachloride, and the cyclization is performed in refluxing methanolic KOH. The dehydro intermediates are then catalytically hydrogenated to yield the final products. Analyses of the synthesized compounds were conducted using techniques such as 1H and 13C NMR spectroscopy, mass spectrometry, and infrared spectroscopy, with purification through column chromatography and recrystallization from methanol. The research also discusses the structural requirements for successful synthesis, such as the facilitative role of methoxy groups in the cyclization process.

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