1,1-Dimethoxyethane

Base Information

• Chemical Name: 1,1-Dimethoxyethane
• CAS No.: 534-15-6
• Molecular Formula: C4H10 O2
• Molecular Weight: 90.1222
• Hs Code.: 2911 00 00
• European Community (EC) Number: 208-589-8
• UN Number: 2377
• UNII: ZO2AW8UR5T
• DSSTox Substance ID: DTXSID7027178
• Nikkaji Number: J6.336C
• Wikidata: Q27295796
• Metabolomics Workbench ID: 44184
• ChEMBL ID: CHEMBL3183607
• Mol file: 534-15-6.mol

Synonyms:1,1-dimethoxyethane;dimethyl acetal

Chemical Property of 1,1-Dimethoxyethane

Chemical Property:

• Appearance/Colour: clear colorless liquid
• Vapor Pressure: 187mmHg at 25°C
• Melting Point: -113 ºC
• Refractive Index: n20/D 1.367(lit.)
• Boiling Point: 64 ºC
• Flash Point: -17 ºC
• PSA: 18.46000
• Density: 0.85
• LogP: 0.62520
• Storage Temp.: Flammables area
• Sensitive.: Moisture Sensitive
• Solubility.: Chloroform (Sparingly)
• Water Solubility.: Soluble
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 90.068079557
• Heavy Atom Count: 6
• Complexity: 24.7
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

1,1-Dimethoxyethane ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F
• Statements: 11
• Safety Statements: 9-16-33

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Acetals
• Canonical SMILES: CC(OC)OC
• General Description: 1,1-Dimethoxyethane, also known as dimethyl acetal or acetaldehyde dimethyl acetal, serves as a key reactant in the synthesis of enantiopure α-methoxy carboxyl derivatives when combined with chiral titanium enolates. It acts as an electrophilic reagent, particularly under Lewis acid catalysis (e.g., BF3·OEt2 or SnCl4), facilitating stereoselective transformations at low temperatures (-78°C). The resulting adducts can be further processed to yield chiral α-methoxy carboxyl compounds, which are valuable intermediates in natural product synthesis. The compound's role highlights its utility in asymmetric synthesis and the production of enantiomerically enriched building blocks.

Technology Process of 1,1-Dimethoxyethane

There total 59 articles about 1,1-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: 97.0%

methanol (67-56-1) + acetaldehyde (75-07-0,9002-91-9) → 1,1-dimethoxyethane (534-15-6)

Guidance literature:

With 1-(n-butyl)-3-methylimidazolium tetrachlorogallate; at 20 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2005.08.059

Reference yield: 94.0%

1-bromo-2,2-dimethoxyethane (7252-83-7) → 1,1-dimethoxyethane (534-15-6)

Guidance literature:

With formic acid; tributyl-amine; 10-phenyl-10H-phenothiazine; In acetonitrile; at 20 ℃; for 9h; Inert atmosphere; UV-irradiation;

DOI:10.1039/c5cc04677g

Reference yield: 78.0%

(4aS,4bR,7aS,8aR)-Hexahydro-furo[3',2':3,4]cyclopenta[1,2-d][1,3]dioxin-6-one (109122-52-3) → (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one (32233-40-2) + 1,1-dimethoxyethane (534-15-6)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 75 - 80 ℃; for 4h;

DOI:10.1016/S0040-4020(01)88339-3

upstream raw materials:

methanol

methoxyethene

vinyl acetate

ethanol

Downstream raw materials:

1,3-dimethoxy-1-phenylbutane

1,1,3-trimethoxybutane

1.1.3.5-tetramethoxy-hexane

3,9-Dimethyl-2,4,8,10-tetraoxaspiro<5,5>undecan

Refernces

Enantiopure β-methoxy carboxyl derivatives from a chiral titanium enolate and dimethyl acetals

10.1016/S0040-4039(01)00829-2

The research focuses on the development of a synthetic approach to enantiopure α-methoxy carboxyl derivatives using a chiral titanium enolate and dimethyl acetals. The main reactants involved are (S)-N-acetyl-4-isopropyl-1,3-thiazolidine-2-thione and various dimethyl acetals. The experiments utilized Lewis acids, such as BF3·OEt2 and SnCl4, to enhance the electrophilicity of the acetals and improve the stereoselectivity and yield of the process. The reactions were conducted at low temperatures (-78°C) and monitored using HPLC analysis to determine the diastereomeric ratios and overall yields. The adducts obtained were then transformed into a range of enantiopure α-unsubstituted α-methoxy carboxyl derivatives through the removal of the chiral thiazolidine-2-thione auxiliary, which was achieved using mild conditions and resulted in high yields. The analyses used to confirm the structures and absolute configurations of the adducts included spectroscopic and analytical data, as well as chemical correlation. The methodology described provides an efficient way to synthesize chiral building blocks useful in the total synthesis of natural products.