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[ CAS No. 25121-87-3 ]

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Chemical Structure| 25121-87-3
Chemical Structure| 25121-87-3
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CAS No. :25121-87-3 MDL No. :MFCD03931293
Formula : C6H2Br2S2 Boiling Point : 346.7°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :298.02 g/mol Pubchem ID :3597455
Synonyms :

Safety of [ 25121-87-3 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P301+P310 UN#:2811
Hazard Statements:H301 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 25121-87-3 ]

  • Upstream synthesis route of [ 25121-87-3 ]
  • Downstream synthetic route of [ 25121-87-3 ]

[ 25121-87-3 ] Synthesis Path-Upstream   1~6

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YieldReaction ConditionsOperation in experiment
99% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; Thienothiophene(2.01 g of Tokyo Chemical Industry Co., Ltd.) and 30 mL of dimethylformamide (DMF) were placed in a reaction vessel.After stirring at room temperature to confirm dissolution,6.10 g (2.4 eq) of N-bromosuccinimide (NBS) was put in a powder state.After confirming the disappearance of the raw materials, n-hexane and ion-exchanged water were added to the reaction solution.Perform liquid separation.After washing the organic layer with ion-exchanged water and saturated saline once,Drying was carried out using Na2SO4.Distilling off the solvent under reduced pressure and dryingThiophenethiophene dibromide4.21g (99percent yield).
95% With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃; for 12 h; Added to the reactor 30 mlDMF, thieno [3, 2 - b] thiophene (2.31 g, 16.5 mmol), followed by cooling to 0 °C, adding NBS (8.81 g, 49.5 mmol), light reaction 12 h, NaHSO reaction after the conclusion3Washing, removing the upper layer solvent, congeals the organic phase concentration, over silica gel column purification to obtain compound C - 21 - 1 (4.67 g, 95percent).
88% With N-Bromosuccinimide In DMF (N,N-dimethyl-formamide) at 20℃; for 3 h; N-bromosuccinimide (1.24 g, 6.94 mmol) was added to a solution of thieno [3,2-b]thiophene (1.0 g, 6.94 mmol) in DMF (30 ml) at room temperature and this mixture was stirred for 3h. After this water ( 100 ml) was added and the precipitate formed was filtrated off, washed with water and dried to give 2 as a white solid (1.87 g, 88 percent). 1H NMR (300 MHz, CDCl3): 8 (ppm) 7.14 (s, 2H, Ar-H); 13C NMR (75 MHz, CDC13): 8 (ppm) 138.3 (quat.), 121.8 (CH), 113.7 (quat.)
85% at 20℃; Inert atmosphere A solution of 1.55 g (8.7 mmol) of N-bromosuccinimide (NBS) in 1 ml of DMF was slowly added in a stirred solution of 0.61 g (4.35 mmol) of thieno[3,2-b]thiophene in 9 ml of DMF. The reaction mixture was stirred overnight. The product was extracted with dichloromethane and the organic phase was washed 3 times with water, dried with MgSO4 and the organic solvent was removed with roto-evaporation. The resulting crude residue was purified by column chromatography on silica gel with hexane/dichloromethane 9/1 to give a white solid (1 g, 85percent yield). (m.p. 116.4-118.6 °C) δH (200 MHz, CDCl3) 7.19 (1H, s, 1-H), δC (50 MHz, CDCl3) 128.6, 122.2, 114.4.
68% With N-Bromosuccinimide In tetrahydrofuran at 10℃; for 80 h; Inert atmosphere In a 150 mL 3-neckedflask, a solution of thienothiophene(TT) (11.2 g, 80 mmol) in dry THF (100 mL) was cooled to 10 °C under a nitrogenatmosphere. NBS (35.6 g, 200 mmol) was addedslowly in portions and allowed to stir for 8 h at approximately 10 °C. Thereaction mixture was then poured into dichloromethane (DCM).The organic layer was washed with water and dried over anhydrous MgSO4. After removing thesolvent, the crude product was recrystallized from petroleum ether (PE, boiling range: 60-90 C) to give a colorless solid(16.2 g, 68percent yield). 1H NMR (300 MHz, CDCl3):δ (ppm) 7.14 (s, 2H). 13C NMR (75 MHz, CDCl3):δ (ppm) 138.31, 121.75, 113.64. GC-MS (EI, m/z) calcd for (C6H2Br2S2):297.79, found: 297.77.

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[2] Chemistry - A European Journal, 2011, vol. 17, # 3, p. 866 - 872
[3] Angewandte Chemie - International Edition, 2013, vol. 52, # 10, p. 2920 - 2924[4] Angew. Chem., 2013, vol. 125, # 10, p. 2992 - 2996,5
[5] Tetrahedron Letters, 2009, vol. 50, # 51, p. 7148 - 7151
[6] Patent: CN107056798, 2017, A, . Location in patent: Paragraph 0061; 0062; 0063; 0064
[7] Journal of Nanoscience and Nanotechnology, 2010, vol. 10, # 10, p. 6800 - 6804
[8] Journal of Organic Chemistry, 2015, vol. 80, # 20, p. 10127 - 10133
[9] Macromolecules, 2013, vol. 46, # 3, p. 727 - 735
[10] Patent: WO2005/121150, 2005, A1, . Location in patent: Page/Page column 33
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[13] Polymer, 2012, vol. 53, # 12, p. 2334 - 2346
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[15] Dalton Transactions, 2005, # 5, p. 874 - 883
[16] Molecules, 2012, vol. 17, # 10, p. 12163 - 12171
[17] Journal of the American Chemical Society, 2013, vol. 135, # 6, p. 2040 - 2043
[18] Patent: US8779204, 2014, B2, . Location in patent: Page/Page column 13; 14
[19] Patent: KR101540066, 2015, B1, . Location in patent: Paragraph 0021; 0022; 0023
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Reference: [1] Molecules, 2012, vol. 17, # 10, p. 12163 - 12171
[2] Patent: KR101540066, 2015, B1,
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  • [ 201004-08-2 ]
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Reference: [1] Molecules, 2012, vol. 17, # 10, p. 12163 - 12171
[2] Patent: KR101540066, 2015, B1,
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Reference: [1] Molecules, 2012, vol. 17, # 10, p. 12163 - 12171
[2] Patent: KR101540066, 2015, B1,
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Reference: [1] Macromolecules, 2013, vol. 46, # 3, p. 727 - 735
[2] Organic Letters, 2007, vol. 9, # 6, p. 1005 - 1008
[3] Macromolecules, 2016, vol. 49, # 7, p. 2541 - 2548
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  • [ 61676-62-8 ]
  • [ 924894-85-9 ]
Reference: [1] Journal of Materials Chemistry, 2011, vol. 21, # 25, p. 9224 - 9231
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