2,3-Dihydrothieno[3,4-b][1,4]dioxine-5-carbaldehyde

Base Information

• Chemical Name: 2,3-Dihydrothieno[3,4-b][1,4]dioxine-5-carbaldehyde
• CAS No.: 204905-77-1
• Molecular Formula: C7H6O3S
• Molecular Weight: 170.189
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID90393458
• Nikkaji Number: J1.162.502I
• Wikidata: Q72466288
• Mol file: 204905-77-1.mol

Synonyms:2,3-dihydrothieno[3,4-b][1,4]dioxine-5-carbaldehyde;204905-77-1;2H,3H-thieno[3,4-b][1,4]dioxine-5-carbaldehyde;3,4-ethylenedioxythiophene-2-carbaldehyde;3,4-Ethylenedioxythiophene-2-carboxaldehyde;Thieno[3,4-b]-1,4-dioxin-5-carboxaldehyde, 2,3-dihydro-;2,3-Dihydrothieno[3,4-b]-1,4-dioxin-5-carbaldehyde;2,3-dihydrothieno(3,4-b)(1,4)dioxine-5-carbaldehyde;2,3-Dihydrothieno[3,4-b][1,4]dioxine-5-carboxaldehyde;SCHEMBL1525869;DTXSID90393458;GNVXYRDVJKJZTO-UHFFFAOYSA-N;AMY42344;BCP17568;MFCD01651766;2-formyl-3,4-ethylene dioxythiophene;AKOS006227729;DS-1425;BP-10372;A4460;CS-0060824;E1150;FT-0706321;EN300-135907;J-507023;2,3-dihydrothieno[3,4-b][1,4]dioxine-5-carbaldehy;F8880-7230;Z1198157321;2,3-dihydrothieno[3,4-b][1,4]dioxine-5-carbaldehyde, AldrichCPR

Chemical Property of 2,3-Dihydrothieno[3,4-b][1,4]dioxine-5-carbaldehyde

Chemical Property:

• Vapor Pressure: 0.000572mmHg at 25°C
• Melting Point: 138 °C
• Refractive Index: 1.623
• Boiling Point: 311.199 °C at 760 mmHg
• Flash Point: 142.009 °C
• PSA: 63.77000
• Density: 1.424 g/cm³
• LogP: 1.33180
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 170.00376522
• Heavy Atom Count: 11
• Complexity: 162

Purity/Quality:

99.0% ^*data from raw suppliers

2,3-Dihydrothieno[3,4-b][1,4]dioxine-5-carbaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COC2=C(SC=C2O1)C=O

Technology Process of 2,3-Dihydrothieno[3,4-b][1,4]dioxine-5-carbaldehyde

There total 2 articles about 2,3-Dihydrothieno[3,4-b][1,4]dioxine-5-carbaldehyde 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: 22.0%

bromodichloromethane (75-27-4) + 3,4-(ethylenedioxy)thiophene (126213-50-1) → 2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxaldehyde (211235-87-9) + 3,4-ethylenedioxythiophene-2-carboxaldehyde (204905-77-1)

Guidance literature:

bromodichloromethane; 3,4-(ethylenedioxy)thiophene; With 1,1'-bis-(diphenylphosphino)ferrocene; potassium phosphate; palladium diacetate; acetic anhydride; silver carbonate; In acetonitrile; at 60 ℃; for 48h; Schlenk technique; Inert atmosphere;

With hydrogenchloride; In dichloromethane; at 30 ℃; Overall yield = 66 %;

DOI:10.1016/j.tetlet.2018.07.013

Reference yield:

N,N-dimethyl-formamide (68-12-2,33513-42-7) + 3,4-(ethylenedioxy)thiophene (126213-50-1) → 2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxaldehyde (211235-87-9) + 3,4-ethylenedioxythiophene-2-carboxaldehyde (204905-77-1)

Guidance literature:

With n-butyllithium; potassium tert-butylate; lithium bromide; Yield given; Multistep reaction. Yields of byproduct given; 1.) THF, hexane, -90 deg C, 30 min, 2.) -90 deg c to room temperature;

DOI:10.1021/jo981312b

Reference yield: 93.0%

5,5-difluoro-10-mesityl-1,3,7,9-tetramethyl-5H-4λ4,5λ4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine (1308671-66-0) + 3,4-ethylenedioxythiophene-2-carboxaldehyde (204905-77-1) → C36H33BF2N2O4S2 + C29H29BF2N2O2S

Guidance literature:

With piperidine; toluene-4-sulfonic acid; In toluene; Reflux; Dean-Stark;

DOI:10.1016/j.electacta.2018.03.044

upstream raw materials:

N,N-dimethyl-formamide

3,4-(ethylenedioxy)thiophene

bromodichloromethane

Downstream raw materials:

7-bromo-2,3-dihydrothieno[3,4-b][1,4]dioxine-5-carbaldehyde

3,4-ethylenedioxythenyl alcohol

C₂₂H₂₆N₂O₇S

1-{4-[2,5-di(2-thienyl)pyrrol-1-yl]phenyl}-3-(3,4-ethylenedioxythien-2-yl)prop-2-en-1-one

Refernces

• 1、 Akoudad, Said,Frere, Pierre,Mercier, Nicolas,Roncali, Jean. "Low Oxidation Potential Tetrathiafulvalene Analogues Based on 3,4-Dialkoxythiophene π-Conjugating Spacers". . p. 4267 - 4272. Retrieved 2007/10/03.