3,3-diethyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine

Base Information

• Chemical Name: 3,3-diethyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine
• CAS No.: 259139-19-0
• Molecular Formula: C11H16O2S
• Molecular Weight: 212.30900
• DSSTox Substance ID: DTXSID90471346
• Nikkaji Number: J1.162.448K
• Wikidata: Q82299838
• Mol file: 259139-19-0.mol

Synonyms:259139-19-0;3,3-diethyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine;3,4-(2',2'-Diethylpropylene)dioxythiophene;3,3-diethyl-2,4-dihydrothieno[3,4-b][1,4]dioxepine;2H-Thieno[3,4-b][1,4]dioxepin, 3,3-diethyl-3,4-dihydro-;3,4-(2 inverted exclamation marka,2 inverted exclamation marka-Diethylpropylene)dioxythiophene;3,4-(2',2'-Diethylpropylene)dioxythiophene, 97%;3,4-(2,2-Diethylpropylene)dioxythiophene,97%;SCHEMBL2754120;DTXSID90471346;HMKHKPKUPVRLOW-UHFFFAOYSA-N;MFCD08705267;SB67116;CS-0450451;J-016176;3, 3-diethyl-2, 4-dihydrothieno[3, 4-b][1, 4]dioxepine

Chemical Property of 3,3-diethyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine

Chemical Property:

• Vapor Pressure: 0.008mmHg at 25°C
• Refractive Index: n20/D 1.534
• Boiling Point: 276.101oC at 760 mmHg
• Flash Point: 120.782oC
• PSA: 46.70000
• Density: 1.109 g/mL at 25oC
• LogP: 3.32570
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 212.08710092
• Heavy Atom Count: 14
• Complexity: 176

Purity/Quality:

98%Min ^*data from raw suppliers

3,4-(2′,2′-Diethylpropylene)dioxythiophene 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1(COC2=CSC=C2OC1)CC

Technology Process of 3,3-diethyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine

There total 4 articles about 3,3-diethyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine 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: 80.0%

2,3-dimethoxythiophene (51792-34-8) + 2,2-diethyl-1,3-propanediol (115-76-4) → 3,4-(2,2-diethylpropane-1,3-diyldioxy)thiophene (259139-19-0)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; at 110 ℃; for 24h;

Reference yield:

3,3-diethyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine-6,8-dicarboxylic acid → 3,4-(2,2-diethylpropane-1,3-diyldioxy)thiophene (259139-19-0)

Guidance literature:

With quinoline; copper chromite; at 150 ℃; for 12h;

DOI:10.1039/b205907j

Reference yield:

2,2-diethyl-1,3-propanediol (115-76-4) → 3,4-(2,2-diethylpropane-1,3-diyldioxy)thiophene (259139-19-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / PBu₃; diethyl azodicarboxylate / tetrahydrofuran / Heating

2: aq. NaOH / 6 h / 70 °C

3: copper chromite; quinoline / 12 h / 150 °C

With quinoline; sodium hydroxide; copper chromite; tributylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1: Mitsunobu reaction;

DOI:10.1039/b205907j

upstream raw materials:

2,3-dimethoxythiophene

2,2-diethyl-1,3-propanediol

3,3-diethyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine-6,8-dicarboxylic Acid Diethyl Ester

Downstream raw materials:

3,4-(2,2-diethylpropane-1,3-diyldioxy)-2,5-bis(hydroxyphenylmethyl)thiophene

Refernces

• 1、 Agarwal, Neeraj,Mishra, Sarada Prasad,Hung, Chen-Hsiung,Kumar, Anil,Ravikanth, Mangalampalli. "The synthesis and crystal structure of β-substituted thiaporphyrins with novel cyclic substituents". . p. 1173 - 1180. Retrieved 2007/10/03.
• 2、 Zong, Kyukwan,Madrigal, Luis,Groenendaal,Reynolds, John R.. "3,4-Alkylenedioxy ring formation via double Mitsunobu reactions: An efficientroute for the synthesis of 3,4-ethylenedioxythiophene (EDOT) and 3,4-propylenedioxythiophene (ProDOT) derivatives as monomers for electron-rich conducting polymers". . p. 2498 - 2499. Retrieved 2007/10/03.