2,3-Dihydrothieno[3,4-b][1,4]dithiine

Base Information

• Chemical Name: 2,3-Dihydrothieno[3,4-b][1,4]dithiine
• CAS No.: 158962-92-6
• Molecular Formula: C6H6S3
• Molecular Weight: 174.312
• Hs Code.: 2934999090
• European Community (EC) Number: 663-169-5
• DSSTox Substance ID: DTXSID00454968
• Nikkaji Number: J1.757.894D
• Wikidata: Q72466291
• Mol file: 158962-92-6.mol

Synonyms:2,3-Dihydrothieno[3,4-b][1,4]dithiine;158962-92-6;3,4-ethylenedithiothiophene;2,3-dihydro-Thieno[3,4-b]-1,4-dithiin;Thieno[3,4-b]-1,4-dithiin, 2,3-dihydro-;C6H6S3;3,4-Etylenedithiathiophene;SCHEMBL14863540;AMY7292;DTXSID00454968;MFCD23098725;AKOS016005614;DS-18344;2,3-Dihydrothieno[3,4-b]-1,4-dithiin;CS-0060829;FT-0697763;2H,3H-THIENO[3,4-B][1,4]DITHIINE;W16898;A883335;158962-93-7

Chemical Property of 2,3-Dihydrothieno[3,4-b][1,4]dithiine

Chemical Property:

• Refractive Index: n20/D 1.685
• Boiling Point: 288.7±29.0 °C(Predicted)
• Flash Point: 105°C
• PSA: 78.84000
• Density: 1.374g/mLat 25℃
• LogP: 2.94590
• Storage Temp.: 2-8°C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 173.96316371
• Heavy Atom Count: 9
• Complexity: 92.5

Purity/Quality:

98%, 99% ^*data from raw suppliers

3,4-Ethylenedithiothiophene ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CSC2=CSC=C2S1
• Uses: EDTT can be electrochemically oxidized in acetonitrile to form poly(EDTT) films on the surface of the electrodes, which can be used in the fabrication of organic light emitting diodes (OLEDs) and organic photovoltaics (OPVs).

Technology Process of 2,3-Dihydrothieno[3,4-b][1,4]dithiine

There total 2 articles about 2,3-Dihydrothieno[3,4-b][1,4]dithiine 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: 90.0%

2,3-dimethoxythiophene (51792-34-8) + ethane-1,2-dithiol (540-63-6) → 3,4-ethylenedisulfanylthiophene (158962-92-6)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; at 90 ℃; Inert atmosphere;

DOI:10.1002/pola.25971

Reference yield: 70.0%

ethylene dibromide (106-93-4) + 3,3'-(thiophene-3,4-diylbis(sulfanediyl))dipropanenitrile (437711-56-3) → 3,4-ethylenedisulfanylthiophene (158962-92-6)

Guidance literature:

3,3'-(thiophene-3,4-diylbis(sulfanediyl))dipropanenitrile; With cesium hydroxide; In methanol; N,N-dimethyl-formamide; at 0 ℃; for 0.0833333h;

ethylene dibromide; In methanol; N,N-dimethyl-formamide; at 0 - 20 ℃; for 1.33333h; Further stages.;

DOI:10.1021/jo025627+

Reference yield: 23.0%

chloro-diphenylphosphine (1079-66-9,74391-44-9) + 3,4-ethylenedisulfanylthiophene (158962-92-6) → 2,5-bis(diphenylphosphoryl)-3,4-ethylenedithiothiophene

Guidance literature:

3,4-ethylenedisulfanylthiophene; With n-butyllithium; In tetrahydrofuran; at -80 ℃; for 3.25h;

chloro-diphenylphosphine; In tetrahydrofuran; at -80 - 20 ℃; for 14h;

With dihydrogen peroxide; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1246/cl.190752

upstream raw materials:

2,3-dimethoxythiophene

ethane-1,2-dithiol

ethylene dibromide

3,3'-(thiophene-3,4-diylbis(sulfanediyl))dipropanenitrile

Downstream raw materials:

5-(4-(diphenylamino)phenyl)-3,4-(ethylenedithio)thiophene-2-carbaldehyde

2-cyano-3-{5-[4-(diphenylamino)phenyl]-3,4-(ethylenedithio)thiophene-2-yl}acrylic acid

Refernces

• 1、 Goldoni, Francesca,Langeveld-Voss, Bea M. W.,Meijer. "Convenient synthesis of 3,4-bis(alkylthio) thiophenes". . p. 2237 - 2244. Retrieved 1998.
• 2、 Chen, Shuai,Lu, Baoyang,Duan, Xuemin,Xu, Jingkun. "Systematic study on chemical oxidative and solid-state polymerization of poly(3,4-ethylenedithiathiophene)". experimental part. p. 1967 - 1978. Retrieved 2012/07/17.