5,5'-Dimethyl-2,2'-bithiophene

Base Information

• Chemical Name: 5,5'-Dimethyl-2,2'-bithiophene
• CAS No.: 16303-58-5
• Molecular Formula: C10H10S2
• Molecular Weight: 194.321
• Hs Code.: 29309099
• NSC Number: 140317
• DSSTox Substance ID: DTXSID20300993
• Nikkaji Number: J540.958F
• Wikidata: Q82044478
• Mol file: 16303-58-5.mol

Synonyms:5,5'-dimethyl-2,2'-bithiophene;16303-58-5;5,5'-Dimethyl-2,2'-bithiophenyl;2-methyl-5-(5-methylthiophen-2-yl)thiophene;MFCD01927313;2,2'-Bithiophene, 5,5'-dimethyl-;2-Methyl-5-(5-methyl-2-thienyl)thiophene;5,5/'-DIMETHYL-2,2/'-BITHIOPHENYL;NSC140317;Boc-Glu-Glu-Leumethylester;SCHEMBL29764;YSCK0533;DTXSID20300993;GEO-01160;AKOS005259599;NSC-140317;5,5'-DIMETHYL-(2,2')BITHIOPHENYL;AI-942/13331366;W-200151

Chemical Property of 5,5'-Dimethyl-2,2'-bithiophene

Chemical Property:

• Appearance/Colour: yellow to light brown crystals
• Melting Point: 65-68 °C
• Boiling Point: 262.9 °C at 760 mmHg
• Flash Point: 81.8 °C
• PSA: 56.48000
• Density: 1.169 g/cm³
• LogP: 4.09340
• Storage Temp.: Refrigerator (+4°C)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 194.02239267
• Heavy Atom Count: 12
• Complexity: 140

Purity/Quality:

98% ^*data from raw suppliers

5,5'-DIMETHYL-2,2'-BITHIOPHENYL 95.00% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(S1)C2=CC=C(S2)C

Technology Process of 5,5'-Dimethyl-2,2'-bithiophene

There total 42 articles about 5,5'-Dimethyl-2,2'-bithiophene 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: 97.0%

(5-methylthiophen-2-yl)boronic acid (162607-20-7) → 5,5'-dimethyl-2,2'-dithiophene (16303-58-5)

Guidance literature:

With C₅₄H₇₄Cl₂N₄O₂Pd₂; In ethanol; at 22 ℃; for 6h;

DOI:10.1055/s-0036-1591602

Reference yield: 91.0%

2-iodo-5-methylthiophene (16494-36-3) → 5,5'-dimethyl-2,2'-dithiophene (16303-58-5)

Guidance literature:

2-iodo-5-methylthiophene; With diethylzinc; phosphazene base-P₄-tert-butyl; In hexane; N,N-dimethyl acetamide; at 20 ℃; for 24h; Inert atmosphere;

With chloranil; In hexane; N,N-dimethyl acetamide; at 20 ℃; for 20h; Inert atmosphere;

DOI:10.1039/c0nj00202j

Reference yield: 85.0%

2-Methylthiophene (554-14-3) → 5,5'-dimethyl-2,2'-dithiophene (16303-58-5)

Guidance literature:

With oxygen; palladium diacetate; trifluoroacetic acid; In dimethyl sulfoxide; at 20 ℃; under 760.051 Torr; regioselective reaction; Sealed tube;

DOI:10.1021/ol501019y

upstream raw materials:

2-iodo-5-methylthiophene

5-methyl-2,2'-bithiophene-5'-carboxaldehyde

2-bromo-5-methyl thiophene

5-methyl-2-thienylmagnesium iodide

Refernces

• 1、 Masui, Kentaro,Ikegami, Haruka,Mori, Atsunori. "Palladium-Catalyzed C-H Homocoupling of Thiophenes: Facile Construction of Bithiophene Structure". . p. 5074 - 5075. Retrieved 2004.
• 2、 Korenaga, Toshinobu,Nitatori, Kaoru,Muraoka, Hiroki,Ogawa, Satoshi,Shimada, Kazuaki. "Perfluorocyclopentadienyl Radical Derivative as an Organocatalyst for Oxidative Coupling of Aryl- and Thienylmagnesium Compounds under Atmospheric Oxygen". . p. 4835 - 4839. Retrieved 2018.
• 3、 Lotz, Monica D.,Camasso, Nicole M.,Canty, Allan J.,Sanford, Melanie S.. "Role of silver salts in palladium-catalyzed arene and heteroarene C-H functionalization reactions". . p. 165 - 171. Retrieved 2017.
• 4、 Xing, Liwen,Liu, Ji-Ren,Hong, Xin,Houk, Kendall N.,Luscombe, Christine K.. "An Exception to the Carothers Equation Caused by the Accelerated Chain Extension in a Pd/Ag Cocatalyzed Cross Dehydrogenative Coupling Polymerization". . p. 2311 - 2322. Retrieved 2022/02/09.