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

Base Information

• Chemical Name: 5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine
• CAS No.: 174508-31-7
• Molecular Formula: C6H4Br2O2S
• Molecular Weight: 299.971
• Hs Code.: 29349990
• European Community (EC) Number: 803-069-2
• DSSTox Substance ID: DTXSID00397083
• Nikkaji Number: J1.371.574B
• Wikidata: Q72464175
• Mol file: 174508-31-7.mol

Synonyms:5,7-dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine;174508-31-7;2,5-dibromo-3,4-ethylenedioxythiophene;5,7-dibromo-2H,3H-thieno[3,4-b][1,4]dioxine;Thieno[3,4-b]-1,4-dioxin, 5,7-dibromo-2,3-dihydro-;MFCD01651770;5,7-Dibromo-2,3-dihydrothieno[3,4-b]-1,4-dioxine;DBEDOT;SCHEMBL1413215;DTXSID00397083;FHMRWRBNAIDRAP-UHFFFAOYSA-N;AMY10871;AKOS015913090;CS-W002815;PS-7132;AC-22786;SY019162;D4056;FT-0660060;2,5-Dibromo-3,4-ethylenedioxythiophene, 95%;2,5-Dibromo-3,4-ethylenedioxythiophene, 97%;A811650;J-516553;350037-71-7

Chemical Property of 5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine

Chemical Property:

• Vapor Pressure: 0.00139mmHg at 25°C
• Melting Point: 98 °C
• Refractive Index: 1.644
• Boiling Point: 306.528 °C at 760 mmHg
• Flash Point: 139.184 °C
• PSA: 46.70000
• Density: 2.14 g/cm³
• LogP: 3.04430
• Storage Temp.: ?20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 299.82783
• Heavy Atom Count: 11
• Complexity: 142

Purity/Quality:

98%,99%, ^*data from raw suppliers

5,7-Dibromo-2,3-dihydrothieno[3,4-b]-1,4-dioxine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 22-26-36/37/39-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COC2=C(SC(=C2O1)Br)Br
• Uses: 5,7-Dibromo-2,3-dihydrothieno[3,4-b]-1,4-dioxine is used in the preparation of 3,4-ethylenedioxythiophene oligomers with optical and redox properties. Used as a monomer in the synthesis of poly(3,4-ethylenedioxythiophene) (PEDOT) polymer which are used in electrochromic devices.

Technology Process of 5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine

There total 3 articles about 5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine 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: 100.0%

3,4-(ethylenedioxy)thiophene (126213-50-1) → 5,7-dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine (174508-31-7)

Guidance literature:

With N-Bromosuccinimide; acetic acid; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/ja000752t

Reference yield:

2,3-dihydro-thieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid diethyl ester (154934-13-1) → 5,7-dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine (174508-31-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / KOH / ethanol / 3 h / Heating

2: 68 percent / CuO; quinoline / 5 h / 200 °C

3: NBS; AcOH / CH₂Cl₂ / 3 h / 0 °C

With quinoline; potassium hydroxide; N-Bromosuccinimide; acetic acid; copper(II) oxide; In ethanol; dichloromethane;

DOI:10.1039/b511075k

Reference yield:

3,4-ethylenedioxythiophene-2,5-dicarboxyllic acid (18361-03-0) → 5,7-dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine (174508-31-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / CuO; quinoline / 5 h / 200 °C

2: NBS; AcOH / CH₂Cl₂ / 3 h / 0 °C

With quinoline; N-Bromosuccinimide; acetic acid; copper(II) oxide; In dichloromethane;

DOI:10.1039/b511075k

upstream raw materials:

3,4-(ethylenedioxy)thiophene

2,3-dihydro-thieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid diethyl ester

3,4-ethylenedioxythiophene-2,5-dicarboxyllic acid

Downstream raw materials:

5-bromo-2-(mesitylthio)-3,4-ethylenedioxythiophene

5-chloro-3,4-ethylenedioxythiophene-2-carbaldehyde

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

Refernces

• 1、 Wu, Fan,Xu, Zhuanghu,Wang, Yuan,Wang, Mingyang. "Electromagnetic interference shielding properties of solid-state polymerization conducting polymer". . p. 38797 - 38803. Retrieved 2014.
• 2、 Turbiez, Mathieu,Frere, Pierre,Roncali, Jean. "Stable and soluble oligo(3,4-ethylenedioxythiophene)s end-capped with alkyl chains". . p. 5357 - 5360. Retrieved 2003.
• 3、 Zhu, Shengbo,An, Zhongwei,Chen, Xinbing,Chen, Pei,Liu, Qianfeng. "Cyclic thiourea functionalized dyes with binary π-linkers: Influence of different π-conjugation segments on the performance of dye-sensitized solar cells". . p. 146 - 154. Retrieved 2015.
• 4、 Zhu, Yongbao,Wolf, Michael O.. "Charge transfer and delocalization in conjugated (ferrocenylethynyl)oligothiophene complexes". . p. 10121 - 10125. Retrieved 2000.
• 5、 Wu, Wei,Ali, Ahmat,Jamal, Ruxangul,Abdulla, Mihray,Bakri, Tursunnisahan,Abdiryim, Tursun. "A bromine-catalysis-synthesized poly(3,4-ethylenedioxythiophene)/graphitic carbon nitride electrochemical sensor for heavy metal ion determination". . p. 34691 - 34698. Retrieved 2019.
• 6、 Cheng, Jun,Zhang, Fang,Li, Ke,Li, Jie,Lu, Xiaoqing,Zheng, Jingxia,Guo, Kunpeng,Yang, Shihe,Dong, Qingchen. "A planar dithiafulvene based sensitizer forming J-aggregates on TiO2 photoanode to enhance the performance of dye-sensitized solar cells". . p. 97 - 103. Retrieved 2017.
• 7、 Gupta, Sonal,Kumar, Rachana,Mishra, Anamika,Patra, Asit. "Solid-state synthesis of conjugated doped poly(3,4-ethylenedioxythiophene): An effective adsorbent for selective anionic dye removal". . . Retrieved 2021/07/19.
• 8、 Forgione, Pat,Hase, Hannes,Liu, Jiang Tian,Salzmann, Ingo,Taylor, Sarah. "Approaching the Integer-Charge Transfer Regime in Molecularly Doped Oligothiophenes by Efficient Decarboxylative Cross-Coupling". supporting information. p. 7146 - 7153. Retrieved 2020/03/23.