1,2-Dimethoxyethane

Base Information

• Chemical Name: 1,2-Dimethoxyethane
• CAS No.: 110-71-4
• Deprecated CAS: 173201-80-4,144808-02-6,144808-03-7,52755-96-1,847145-59-9,1194542-96-5,890090-87-6
• Molecular Formula: C4H10O2
• Molecular Weight: 90.1222
• Hs Code.: 29091900
• European Community (EC) Number: 203-794-9,607-475-9
• ICSC Number: 1568
• NSC Number: 60542
• UN Number: 2252
• UNII: GXS24JF5IW
• DSSTox Substance ID: DTXSID0025286
• Nikkaji Number: J5.099G
• Wikidata: Q416271
• Metabolomics Workbench ID: 56454
• ChEMBL ID: CHEMBL1232411
• Mol file: 110-71-4.mol

Synonyms:1,2-dimethoxyethane;1,2-dimethoxyethane, conjugate monoacid;dimethoxyethane;ethylene glycol dimethyl ether

Chemical Property of 1,2-Dimethoxyethane

Chemical Property:

• Appearance/Colour: water-white Liquid
• Vapor Pressure: 48 mm Hg ( 20 °C)
• Melting Point: -69 °C
• Refractive Index: n20/D 1.379(lit.)
• Boiling Point: 84.5 °C at 760 mmHg
• Flash Point: 0 °C
• PSA: 18.46000
• Density: 0.839 g/cm³
• LogP: 0.27920
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Solubility.: 1000g/l soluble
• Water Solubility.: Miscible
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 90.068079557
• Heavy Atom Count: 6
• Complexity: 17.5
• Transport DOT Label: Flammable Liquid

Purity/Quality:

98% ^*data from raw suppliers

1,2-Dimethoxyethane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T
• Hazard Codes: F,T
• Statements: 60-61-11-19-20-38
• Safety Statements: 53-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Solvents -> Glycol Ethers (Glymes)
• Canonical SMILES: COCCOC
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Long Term Exposure: Animal tests show that this substance possibly causes toxicity to human reproduction or development.
• Uses: Solvent commonly employed in organometallic reactions,1 particularly organolithium reactions.2 May also function as a ligand.3 Monoglyme is used in the electrolyte solutions for lithium batteries. 1,2-Dimethoxyethane is widely used as a solvent for electrolyte of lithium batteries, polysilicones, oligo- and polysaccharides. It plays an important role in Grignard reactions, Suzuki reactions and Stille couplings in organometallic chemistry and in pharmaceutical synthesis. It is a higher boiling point solvent and is used as an alternative to diethyl ether and tetrahydrofuran. It is used for the etching of synthetic polymers like polytetrafluoroethylene and other fluoropolymers with alkali metal dispersions.

Technology Process of 1,2-Dimethoxyethane

There total 90 articles about 1,2-Dimethoxyethane 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: 62.0%

→ 1,2-dimethoxyethane (110-71-4) + 2-chloroethyl methyl ether (627-42-9)

Guidance literature:

Reference yield:

2-methoxy-ethanol (109-86-4,95507-80-5) + 1-butyl-1-nitrosourea (869-01-2) → 1,2-dimethoxyethane (110-71-4) + butyl methyl ether (628-28-4) + 2-Butoxyethanol (111-76-2,9004-77-7) + 2-(1-Methylpropoxy)ethanol (7795-91-7) + 1-(2-methoxy-ethoxy)-butane (13343-98-1) + 2-(2-Methoxyethoxy)butan

Guidance literature:

With potassium carbonate; for 0.0833333h; Product distribution; Mechanism; Ambient temperature; further reagent: NaHCO₃, further reactions with EtOCH₂CH₂OH, MeOH-oxirane, -oxetane, -tetrahydrofuran;

Reference yield:

Dimethyl ether (115-10-6,157621-61-9) → methanol (67-56-1) + formaldehyd (50-00-0,30525-89-4,61233-19-0) + 1,2-dimethoxyethane (110-71-4) + Methyl formate (107-31-3)

Guidance literature:

With oxygen; at 325 ℃; Reagent/catalyst; Temperature; Catalytic behavior; Flow reactor; Gas phase;

DOI:10.1016/j.mencom.2017.01.023

upstream raw materials:

2-methoxy-ethanol

chloromethyl methyl ether

ethanol

ethylene glycol

Downstream raw materials:

(5-fluoro-pentyl)-methyl ether

methoxyacetaldehyde

(4-methoxy-phenyl)-[1,4]dioxane

trityllithium

Refernces

• 1、 Noh, Wontae,Girolami, Gregory S.. "X-ray crystal structure of the tetra(tert-butyl)erbate anion and attempts to prepare tetravalent organolanthanide complexes". . p. 3865 - 3870. Retrieved 2007.
• 2、 Khusnutdinov,Shchadneva,Mayakova. "Reactions of diols with dimethyl carbonate in the presence of W(CO) 6 and Co2(CO)8". . p. 948 - 952. Retrieved 2014.
• 3、 Schumann, Herbert,Nickel, Siegbert,Loebel, J?rg,Pickardt, Joachim. "Organometallic compounds of the lanthanides. 42. Bis(dimethoxyethane)lithium bis(cyclopentadienyl)bis(trimethylsilyl)lanthanide complexes". . p. 2004 - 2009. Retrieved 1988.
• 4、 Jensen, James A.,Gozum, John E.,Pollina, Deborah M.,Girolami, Gregory S.. "". . p. 1643 - 1644. Retrieved 1988.
• 5、 Hunter, Roger,Hutchings, Graham J.,Pickl, Wolfgang. "Mechanistic Studies on Initial C-C Bond Formation in the Zeolite ZSM-5 Catalysed Methanol Conversion Reaction: Evidence against a Radical Pathway". . p. 843 - 844. Retrieved 1987.
• 6、 Zhang, Junhao,Du, Jin,Qian, Yitai,Xiong, Shenglin. "Synthesis, characterization and properties of carbon nanotubes microspheres from pyrolysis of polypropylene and maleated polypropylene". . p. 15 - 20. Retrieved 2010.
• 7、 Tada, Akio,Yoshino, Takumi,Itoh, Hidenobu. "Decomposition of Methanol to Syngas over AlPO4-Supported Nickel Catalyst". . p. 419 - 422. Retrieved 1987.
• 8、 Von Kugelgen, Stephen,Bellone, Donatela E.,Cloke, Ryan R.,Perkins, Wade S.,Fischer, Felix R.. "Initiator Control of Conjugated Polymer Topology in Ring-Opening Alkyne Metathesis Polymerization". . p. 6234 - 6239. Retrieved 2016.
• 9、 Sun, Kai,Wu, Yingquan,Tan, Minghui,Wang, Liyan,Yang, Guohui,Zhang, Min,Zhang, Wei,Tan, Yisheng. "Ethanol and Higher Alcohols Synthesis from Syngas over CuCoM (M=Fe, Cr, Ga and Al) Nanoplates Derived From Hydrotalcite-Like Precursors". . p. 2695 - 2706. Retrieved 2019.
• 10、 Tinnermann, Hendrik,Sung, Simon,Csókás, Dániel,Toh, Zhi Hao,Fraser, Craig,Young, Rowan D.. "Alkali Metal Adducts of an Iron(0) Complex and Their Synergistic FLP-Type Activation of Aliphatic C-X Bonds". supporting information. p. 10700 - 10708. Retrieved 2021/07/31.