ChemicalBook--->CAS DataBase List--->492-97-7

492-97-7

492-97-7 Structure

492-97-7 Structure
IdentificationMore
[Name]

2,2'-BITHIOPHENE
[CAS]

492-97-7
[Synonyms]

2,2'-BITHIENYL
2,2'-BITHIOPHENE
[2,2']BITHIOPHENYL
2,2'-DITHIENYL
2,2-DITHIENYL
2,2’-dlthienyl
2,2'-Dithiophene
Dithienyl
2,2'-Bithiophen
2,2'-Bithiophene,98%
2,2'-Bithiophene
2,2μ-Bithienyl, 2,2μ-Dithienyl
2-(2'-Thieno)thiophene
[EINECS(EC#)]

207-767-2
[Molecular Formula]

C8H6S2
[MDL Number]

MFCD00005414
[Molecular Weight]

166.26
[MOL File]

492-97-7.mol
Questions And AnswerBack Directory
[Synthesis]

2,2'-BITHIOPHENE can be obtained by first preparing a Grignard reagent from 2-bromothiophene, and then coupling it with 2-bromothiophene.

Synthesis of 492-97-7

At room temperature, Mg (3.5 g, 0.147 mol) was added to a three-necked flask, a condenser was added, and the reaction apparatus was sealed. The gas was evacuated (Ar gas) 3-5 times. 60 mL of anhydrous diethyl ether was injected into the three-necked flask with a syringe and stirred. Then, compound 4 (20 g, 0.123 mol) and 0.5 mL of 1,2-dibromoethane were added to an empty single-necked flask and dissolved with 30 mL of anhydrous diethyl ether. The reaction flask was then heated with a hair dryer. The dissolved mixture was added dropwise to the reaction flask with a syringe. After the addition was complete, the reaction apparatus was placed at 50 °C for 3 h. Another clean three-necked flask was taken, and compound 4 (16.7 g, 0.1 mol) and Ni(dppp)Cl2 were added to it. A condenser was added, and the reaction apparatus was sealed. The above reaction solution was then transferred to this three-necked flask with a syringe and heated to 50 °C overnight. The reaction solution was extracted with ethyl acetate, and the combined ethyl acetate phases were washed with distilled water and then dried with anhydrous sodium sulfate.

Ethyl acetate was removed by vacuum distillation, and the crude product was purified by silica gel column chromatography (eluent: petroleum ether) to give a white solid, 2,2'-BITHIOPHENE.
Chemical PropertiesBack Directory
[Appearance]

white to light yellow crystal powder
[Melting point ]

32-33 °C (lit.)
[Boiling point ]

260 °C (lit.)
[density ]

1.2455 (rough estimate)
[refractive index ]

1.6210 (estimate)
[Fp ]

>230 °F
[storage temp. ]

Keep in dark place,Inert atmosphere,Room temperature
[form ]

powder to lump to clear liquid
[color ]

White or Colorless to Light yellow to Green
[Water Solubility ]

Insoluble in water.
[Sensitive ]

Light Sensitive
[BRN ]

3039
[InChIKey]

OHZAHWOAMVVGEL-UHFFFAOYSA-N
[LogP]

3.750
[CAS DataBase Reference]

492-97-7(CAS DataBase Reference)
[EPA Substance Registry System]

2,2'-Bithiophene (492-97-7)
[Odor]

Yellowish liquid/solid
Hazard InformationBack Directory
[Description]

2,2'-bithiophene is an intermediate widely used for the synthesis of small molecules or polymer semiconductors in application of organic electronics.?It has proven that?2,2'-bithiophene exists as a mixture of the cis-like and the trans-like planar structures. 5,5'-positions of?2,2'-bithiophene are easily accessible for bromination and stannylation to give 5,5'-dibromo-2,2'-bithiophene or 5,5'-trimethylstannyl-2,2'-bithiophene, which can be used for direct arylation reactions.
[Chemical Properties]

white to light yellow crystal powder
[Uses]

2,2’Bithiophene is a reactant in the preparation of thienophenyl compounds.
[Application]

2,2'-Bithiophene is an organic compound composed of two thiophene rings connected by a single bond. These molecules possess a planar aromatic structure and unique electronic and optical properties, making them suitable for a variety of applications in electronics, optoelectronics, and sensing. Other studies have shown that novel complexes formed by 2,2'-bithiophene-derived ligands coordinating Ni(II) and Cu(II) have potential as antibacterial agents.
[Definition]

ChEBI: A thiophene derivative that consists of two thiophene rings connected by a 2,2'-linkage.
[Synthesis Reference(s)]

The Journal of Organic Chemistry, 51, p. 2627, 1986 DOI: 10.1021/jo00364a002
Synthetic Communications, 19, p. 307, 1989 DOI: 10.1080/00397918908050983
[General Description]

2,2′-Bithiophene is an electron transporting material with the π-electrons present in the system that facilitate charge mobility.
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H332-H335
[Precautionary statements ]

P261-P280-P305+P351+P338
[Hazard Codes ]

Xi,Xn
[Risk Statements ]

R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
[WGK Germany ]

3
[F ]

10-23
[Hazard Note ]

Irritant
[TSCA ]

T
[HazardClass ]

IRRITANT
[HS Code ]

29309090
Raw materials And Preparation ProductsBack Directory
[Raw materials]

dithiophen-2-ylmercury-->2-(2-Thienyl)pyridine
[Preparation Products]

2,2'-Bithiophene-5-boronic acid-->2,2'-Bithiophene-5-carboxaldehyde-->2,2'-Bithiophene, 5-(3,5-dibromophenyl)--->Thiophene(SIV) (9CI)-->4-(2-Ethylhexyl)-4H-dithieno[3,2-b:2',3'-d]pyrrole-->[2,2’]bithiophenyl-5,5'-dicarbaldehyde-->5-Bromo-2,2'-bithiophene-5'-carboxaldehyde-->alpha-Sexithiophene-->o-Quarterphenyl-->3,3'-Dibromo-5,5'-bis(trimethylsilyl)-2,2'-bithiophene-->4,4-Dioctyl-4H-silolo[3,2-b:4,5-b']dithiophene-->2-Thiopheneacetonitrile
Spectrum DetailBack Directory
[Spectrum Detail]

2,2'-BITHIOPHENE(492-97-7)MS
2,2'-BITHIOPHENE(492-97-7)1HNMR
2,2'-BITHIOPHENE(492-97-7)13CNMR
2,2'-BITHIOPHENE(492-97-7)IR1
2,2'-BITHIOPHENE(492-97-7)IR2
2,2'-BITHIOPHENE(492-97-7)Raman
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

2,2'-Bithiophene, 97%(492-97-7)
[Alfa Aesar]

2,2'-Bithiophene, 98%(492-97-7)
[Sigma Aldrich]

492-97-7(sigmaaldrich)
[TCI AMERICA]

2,2'-Bithiophene,>98.0%(GC)(492-97-7)
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