2,2'-BITHIOPHENE-5-CARBOXALDEHYDE

Base Information

• Chemical Name: 2,2'-BITHIOPHENE-5-CARBOXALDEHYDE
• CAS No.: 3779-27-9
• Molecular Formula: C9H6OS2
• Molecular Weight: 194.278
• Hs Code.: 29349990
• Mol file: 3779-27-9.mol

Synonyms:2,2'-Bithienyl-5-carbaldehyde;5-(2-Thienyl)-2-thiophenecarboxaldehyde;5-(Thiophen-2-yl)thiophene-2-carbaldehyde;5-Formyl-2,2'-bithienyl;5-Formyl-2,2'-bithiophene;5-Formyl-2,2'-dithienyl;NSC 630688;[2,2']Bithiophenyl-5-carbaldehyde;[2,2']Bithiophenyl-5-carboxaldehyde;

Chemical Property of 2,2'-BITHIOPHENE-5-CARBOXALDEHYDE

Chemical Property:

• Appearance/Colour: yellow-brown to brown crystalline powder
• Melting Point: 55-58 °C(lit.)
• Boiling Point: 340 °C at 760 mmHg
• Flash Point: 159.4 °C
• PSA: 73.55000
• Density: 1.336g/cm³
• LogP: 3.28910
• Storage Temp.: Refrigerator (+4°C)

Purity/Quality:

99% ^*data from raw suppliers

2,2''-Bithiophene-5-Carboxaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: 2,2′-Bithiophene-5-carboxaldehyde may be used in the synthesis of the following:boron dipyrromethene(BODIPY)oligothiophenes via a multi-step reaction process(2,2′-bithiophene-5-carbaldehyde)-4-nitrophenylhydrazone(BT-NPH) via reaction with 4-nitrophenylhydrazinebithiophene fulleropyrrolidine obtained via refluxing with sarcosine and fullereneazomethine phthalic diimides by heating with N,N-bis(4-amino-2,3,5,6-tetramethylphenyl)naphthalene-1,4,5,8-dicarboximide (DANDI)

Technology Process of 2,2'-BITHIOPHENE-5-CARBOXALDEHYDE

There total 19 articles about 2,2'-BITHIOPHENE-5-CARBOXALDEHYDE 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: 94.0%

5-bromo-2-thiophencarboxaldehyde (4701-17-1) + thiophene boronic acid (6165-68-0) → 2,2'-bithiophene-5-carboxaldehyde (3779-27-9)

Guidance literature:

With palladium diacetate; potassium carbonate; XPhos; In water; acetonitrile; at 25 ℃; Inert atmosphere;

DOI:10.1039/c2ob26627j

Reference yield: 94.0%

2,2'-Bithiophene (492-97-7) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 2,2'-bithiophene-5-carboxaldehyde (3779-27-9)

Guidance literature:

With trichlorophosphate;

DOI:10.1016/S0040-4039(00)02317-0

Reference yield: 85.0%

5-bromo-2-thiophencarboxaldehyde (4701-17-1) + tributyl(thien-2-yl)stannane (54663-78-4) → 2,2'-bithiophene-5-carboxaldehyde (3779-27-9)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; at 80 - 90 ℃; for 24h;

upstream raw materials:

2,2'-Bithiophene

thiophene

5-iodothiophene-2-carbaldehyde

tributyl(thien-2-yl)stannane

Downstream raw materials:

3c-[2,2']bithienyl-5-yl-2-phenyl-acrylonitrile

3c-[2,2']bithienyl-5-yl-2-(3,4-dichloro-phenyl)-acrylonitrile

(E)-5-styryl-2,2'-bithiophene

4-[2,2']bithiophenyl-5-ylmethylene-2-phenyl-4H-oxazol-5-one

Refernces

• 1、 Chen, Jianbin,Hu, Tingting,Li, Chunpeng,Li, Tianduo,Niu, Qingfen,Qin, Xuyang,Wei, Tao,Yin, Pengcheng. "Rapid and sensitive detection of hypochlorite in ~100% aqueous solution using a bithiophene-based fluorescent sensor: Application to water analysis and live-cell imaging". . . Retrieved 2020.
• 2、 Chen, Jianbin,Hu, Tingting,Li, Chunpeng,Li, Tianduo,Niu, Qingfen,Qin, Xuyang,Wei, Tao,Yang, Lan. "A novel dual-function bithiophene-Meldrum's acid based chemosensor for highly sensitive, colorimetric and fluorimetric detection of cyanide and hypochlorite and its applications". . . Retrieved 2020.
• 3、 Chen, Jianbin,Li, Chunpeng,Li, Tianduo,Niu, Qingfen,Qin, Xuyang,Wang, Jingui,Wei, Tao,Yang, Qingxin. "Bithiophene-based fluorescent sensor for highly sensitive and ultrarapid detection of Hg2+ in water, seafood, urine and live cells". . . Retrieved 2020.
• 4、 Cortizo-Lacalle, Diego,Howells, Calvyn T.,Pandey, Upendra K.,Cameron, Joseph,Findlay, Neil J.,Inigo, Anto Regis,Tuttle, Tell,Skabara, Peter J.,Samuel, Ifor D. W.. "Solution processable diketopyrrolopyrrole (DPP) cored small molecules with BODIPY end groups as novel donors for organic solar cells". . p. 2683 - 2695. Retrieved 2014.
• 5、 Grisorio, Roberto,De Marco, Luisa,Allegretta, Giovanni,Giannuzzi, Roberto,Suranna, Gian Paolo,Manca, Michele,Mastrorilli, Piero,Gigli, Giuseppe. "Anchoring stability and photovoltaic properties of new D(-π-A) 2 dyes for dye-sensitized solar cell applications". . p. 221 - 231. Retrieved 2013.
• 6、 Benitz, Alejandro,D’Souza, Francis,Jang, Youngwoo,Nesterov, Vladamir,Thomas, Michael B. "Synthesis and photoinduced charge stabilization in molecular tetrads featuring covalently linked triphenylamine-oligothiophene-BODIPY-C60". . . Retrieved 2021/07/16.