Name | 2,2'-Bithiophene |
Synonyms | 2TH Dithienyl 2,2'-dlthienyl 2,2'-Bithiophen 2,2'-Bithiophene 2,2'-Dithiophene 2,2zzhlxy-Bithiophene 2-(2'-Thieno)thiophene 2,2μ-Bithienyl, 2,2μ-Dithienyl |
CAS | 492-97-7 |
EINECS | 207-767-2 |
InChI | InChI=1/C8H6S2/c1-3-7(9-5-1)8-4-2-6-10-8/h1-6H |
InChIKey | OHZAHWOAMVVGEL-UHFFFAOYSA-N |
Molecular Formula | C8H6S2 |
Molar Mass | 166.26 |
Density | 1.2455 (rough estimate) |
Melting Point | 32-33 °C (lit.) |
Boling Point | 260 °C (lit.) |
Flash Point | >230°F |
Water Solubility | Insoluble in water. |
Vapor Presure | 0.0203mmHg at 25°C |
Appearance | White to bright yellow crystalline powder |
Color | White or Colorless to Light yellow to Green |
Odor | Yellowish liquid/solid |
BRN | 3039 |
Storage Condition | Keep in dark place,Inert atmosphere,Room temperature |
Sensitive | Light Sensitive |
Refractive Index | 1.6210 (estimate) |
MDL | MFCD00005414 |
Risk Codes | R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | 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 |
FLUKA BRAND F CODES | 10-23 |
TSCA | T |
HS Code | 29309090 |
Hazard Class | IRRITANT |
EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
Preparation | Dithiophene can be obtained by using 2-bromothiophene as raw material, first preparing Grignard reagent, and then coupling with 2-bromothiophene. Mg(3.5g,0.147mol) is added to the three-mouth bottle at normal temperature, a condenser tube is added and the reaction device is sealed, air exchange (Ar gas) is carried out for 3-5 times, 60mL of anhydrous ether is injected into the three-mouth bottle with a syringe, stirring, compound 4(20g,0.123mol) and 0.5 mL1, 2-dibromoethane are added to the empty single-mouth bottle and dissolved with 30mL anhydrous ether, and then the reaction bottle is blown hot with a hair dryer, add the dissolved mixed solution dropwise into the reaction bottle with a syringe, and place the reaction device at 50 ℃ for 3h after the dropwise addition is completed. Take another clean three-mouth bottle, add compound 4(16.7g,0.1mol) and Ni(dppp)Cl2 into it, add a condenser tube and seal the reaction device, then transfer the reaction liquid to the three-mouth bottle with a syringe, heat at 50 ℃, and react overnight; the reaction liquid was extracted with ethyl acetate, and the combined ethyl acetate phase was washed with distilled water and then dried with anhydrous sodium sulfate. The ethyl acetate was distilled under vacuum, and the crude product was purified with a silica gel chromatography column (the eluent was petroleum ether) to obtain a white solid dithiophene. |
Use | Used for a rhodium-catalyzed C- H arylation reaction matrix of iso-aromatic hydrocarbons and aryl iodides |