| Identification | More | [Name]
5,5'-Dibromo-2,2'-bithiophene | [CAS]
4805-22-5 | [Synonyms]
5,5'-DIBROMO-2,2'-BITHIOPHENE
SPECS AC-776/41252583
5,5'-dibromo-2,2'-dithiophene
5,5''-DIBROMO-2,2''-BITHIOPHENE: 99.8%
2,2'-Bi(5-bromothiophene) | [EINECS(EC#)]
695-323-2 | [Molecular Formula]
C8H4Br2S2 | [MDL Number]
MFCD00219110 | [Molecular Weight]
324.06 | [MOL File]
4805-22-5.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow shiny flakes or | [Melting point ]
144-146 °C(lit.)
| [Boiling point ]
318.6±37.0 °C(Predicted) | [density ]
1.951±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
powder to crystal | [color ]
White to Light yellow to Light orange | [Water Solubility ]
Slightly soluble in water. | [Usage]
A termination reagent for polymer ization | [InChI]
InChI=1S/C8H4Br2S2/c9-7-3-1-5(11-7)6-2-4-8(10)12-6/h1-4H | [InChIKey]
SXNCMLQAQIGJDO-UHFFFAOYSA-N | [SMILES]
C1(C2SC(Br)=CC=2)SC(Br)=CC=1 | [CAS DataBase Reference]
4805-22-5(CAS DataBase Reference) |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Diethyl ether-->Chloroform-->n-Butyllithium-->Cupric bromide-->2,5-Dibromothiophene-->2,2'-BITHIOPHENE-->Acetic acid-->N-Bromosuccinimide | [Preparation Products]
[2，2’]bithiophenyl-5,5'-dicarbaldehyde-->5-BROMO-2,2'-BITHIOPHENE-5'-CARBOXALDEHYDE-->ALPHA-SEXITHIOPHENE-->3,3'''-dioctyl-2,2':5',5'':2'',2'''-quaterthiophene-->5,5μ-Bis(3-dodecyl-2-thienyl)-2,2μ-bithiophene |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow shiny flakes or | [Uses]
A termination reagent for polymer ization | [Uses]
It is an active pharmaceutical ingredient and an OLED (organic light-emitting diode) intermediate. | [Synthesis]
Using 2,2'-bithiophene (5.40 g, 32.4 mmol) as starting material, the reaction was stirred with N-bromosuccinimide (NBS, 11.57 g, 64.8 mmol, 2 eq.) in a solvent mixture of chloroform/acetic acid (1:1 v/v, 300 mL) for 4 hours at 70 °C. Upon completion of the reaction, the reaction mixture was diluted with dichloromethane (50 mL) and saturated aqueous sodium carbonate solution (100 mL). The organic phase was separated and the aqueous phase was extracted with dichloromethane (3 x 50 mL). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give a light yellow solid. The solid was washed with acetone to give the pure product 5,5'-dibromo-2,2'-bithiophene (1a, 10.42 g, 98% yield). To further improve the purity, it was recrystallized from tetrahydrofuran (THF). The structure of the product was confirmed by the following characterization data: 1H NMR (DMSO-d6, 600 MHz) δ: 7.23-7.22 (d, J = 3.9 Hz, 2H), 7.15-7.14 (d, J = 3.9 Hz, 2H); 13C NMR (DMSO-d6, 100 MHz) δ: 136.86, 131.60, 136.86, 131.60, 135.22, 110.84 125.22, 110.84; MS (ESI+): m/z = 324.05; UV-Vis (DMSO) λmax = 325 nm; IR (ATR): 3069 cm-1 (Ar-H stretching), 1683 cm-1 (conjugated C=C stretching), 1416 cm -1 (R1-C=C-R2 cis stretching), 1293 cm-1 (C=C bending). Elemental analysis results: calculated C 29.65, H 1.24, S 19.79; measured C 30.03, H 1.40, S 18.13. | [References]
[1] Bulletin of the Chemical Society of Japan, 1991, vol. 64, # 8, p. 2566 - 2568
[2] Journal of the Chinese Chemical Society, 2018, vol. 65, # 7, p. 828 - 834
[3] Tetrahedron Letters, 2010, vol. 51, # 1, p. 205 - 208
[4] Tetrahedron Letters, 2015, vol. 56, # 2, p. 368 - 373
[5] Helvetica Chimica Acta, 1996, vol. 79, # 3, p. 755 - 766 |
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