Dimethyl diglycolate

Base Information

• Chemical Name: Dimethyl diglycolate
• CAS No.: 7040-23-5
• Molecular Formula: C6H10O5
• Molecular Weight: 162.142
• DSSTox Substance ID: DTXSID30220673
• Nikkaji Number: J802.855I
• Wikidata: Q83098023
• Mol file: 7040-23-5.mol

Synonyms:Dimethyl diglycolate;dimethyl 2,2'-oxydiacetate;7040-23-5;methyl 2-(2-methoxy-2-oxoethoxy)acetate;diglycolic acid dimethyl ester;Diglycolic acid, dimethyl ester;Acetic acid, oxydi-, dimethyl ester;Dimethyl 2,2'-oxybisacetate;DimethylDiglycolate-d4;TL 150;Acetic acid, oxybis-, dimethyl ester;BRN 1775710;AI3-10584;Acetic acid, 2,2'-oxybis-, dimethyl ester;3-03-00-00380 (Beilstein Handbook Reference);dimethyl2,2'-oxydiacetate;Oxybis(acetic acid methyl);SCHEMBL1335833;DTXSID30220673;AMY41876;MFCD01026217;AKOS006240219;AS-19988;D5721

Chemical Property of Dimethyl diglycolate

Chemical Property:

• Melting Point: 36 °C
• Refractive Index: 1.4230 (estimate)
• Boiling Point: 211.3oC at 760 mmHg
• Flash Point: 84.1oC
• PSA: 61.83000
• Density: 1.15g/cm3
• LogP: -0.65100
• Solubility.: DCM, Ethyl Acetate, Methanol
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 162.05282342
• Heavy Atom Count: 11
• Complexity: 126

Purity/Quality:

99%, ^*data from raw suppliers

DimethylDiglycolate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)COCC(=O)OC
• Uses: Dimethyl Diglycolate is an starting material in the manufacture of unsaturated polyester resins and plasticizers.

Technology Process of Dimethyl diglycolate

There total 3 articles about Dimethyl diglycolate 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:

methyl 2-(methoxymethoxy)acetate (50918-08-6) + boron trifluoride (7637-07-2) → glycolic acid methyl ester (96-35-5) + methyl methoxyacetate (6290-49-9) + dimethyl diglycolate (7040-23-5)

Guidance literature:

at 75 - 100 ℃; under 147102 - 514855 Torr;

Reference yield:

chloro-trimethyl-silane (75-77-4) + diglycolyl chloride (21062-20-4) + dibutyldimethoxytin (1067-55-6,235102-07-5) + 2,2-dibutyl[1,3,2]dioxastannolane (3590-59-8) → 2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane (7381-30-8) + dimethyl diglycolate (7040-23-5)

Guidance literature:

Multistep reaction; 1.) CHCl₃, 5-7 deg C; 2.) CHCl₃, r.t.;

Reference yield:

methanol (67-56-1) + formaldehyd (50-00-0,30525-89-4,61233-19-0) + carbon monoxide (201230-82-2) → glycolic acid methyl ester (96-35-5) + dimethyl diglycolate (7040-23-5)

Guidance literature:

formaldehyd; carbon monoxide; With phosphotungstic acid; In sulfolane; at 140 ℃; under 60006 Torr; Autoclave;

methanol; With nitric acid; for 4h; Reflux;

DOI:10.1007/s10562-011-0616-0

upstream raw materials:

chloro-trimethyl-silane

diglycolyl chloride

dibutyldimethoxytin

2,2-dibutyl[1,3,2]dioxastannolane

Downstream raw materials:

1,1,1',1'-tetraphenyl-2,2'-oxydiethanol

N,N'-bis[(1S)-1-benzyl-2-hydroxyethyl]diglycolyldiamide

TODGA

3,4-dihydroxyfuran-2,5-dicarboxylic acid dimethyl ester

Refernces

• 1、 Roelens, Stefano. "Organotin-mediated Synthesis of Macrocyclic Polyesters: Mechanism and Selectivity in the Reaction of Dioxastannolanes with Diacyl Dichlorides". . p. 1617 - 1626. Retrieved 2007/10/02.