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Chemical Structure| 1231160-82-9

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Product Details of [ 1231160-82-9 ]

CAS No. :1231160-82-9
Formula : C14H19NO2S
M.W : 265.37
SMILES Code : O=C1C2=CSC=C2C(N1CC(CC)CCCC)=O
MDL No. :MFCD23703119
InChI Key :PCLDQMLVTDTSOU-UHFFFAOYSA-N
Pubchem ID :67246768

Safety of [ 1231160-82-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335-H412
Precautionary Statements:P261-P264-P270-P271-P273-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 1231160-82-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1231160-82-9 ]

[ 1231160-82-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 1231160-82-9 ]
  • [ 1231160-83-0 ]
YieldReaction ConditionsOperation in experiment
79% With N-Bromosuccinimide; sulfuric acid; trifluoroacetic acid; at 20℃;Inert atmosphere; Schlenk technique; 5-(2-ethylhexyl)-4,H-thieno[3,4-c]pyrrole-4,6(5H)-dione (0.27 g, 1.01 mmol) was dissolved in concentratedsulfuric acid (1.6 mL) and trifluoroacetic acid (3.4 mL). NBS (0.543 g,3.05 mmol) was added in one portion and the reaction mixturewasstirred at room temperature overnight. The resultant solution wasthen diluted with water (100 mL) and extracted with dichloromethane.The organic phase was washed with KOH solution,further dried over anhydrous magnesium sulfate and evaporated toafford the crude product as orange crystals. Purification by columnchromatography using silica gel and hexane/chloroform (3:2) gave1,3-dibromo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione (0.34 g, 79%) as pink solid. 1H NMR (400 MHz, CDCl3): delta 3.49(d, J 7.3 Hz, 2H), 1.81-1.76 (m, 1H), 1.35-1.27 (m, 8H), 0.93-0.88(t, 6H). 13C (100 MHz, CDCl3): delta 160.46, 134.46, 112.65, 42.26, 37.80,30.13, 28.13, 23.43, 22.54, 13.66, 9.95. Mp: 110.5-112 C. MALDITOF:calculated for C14H17Br2NO2S [M+H]+ 424.5344.
76.2% With N-Bromosuccinimide; sulfuric acid; trifluoroacetic acid; at 20℃; Compound 1 (1.40 g, 5.28 mmol) was dissolved in sulfuric acid (7.8 mL) and trifluoroaceticacid (26 mL). While stirring, NBS (2.81 g, 15.8 mmol) was added and the reaction mixturewas stirred at roomtemperature overnight. The mixture was poured into water and extractedwith dichloromethane. The organic phases were combined, washed with brine, and driedwithmagnesiumsulfate. The product was obtained by column chromatography using chloroform:hexane (2:1). Yield: 1.70 g (76.2%). 1H NMR (400 MHz, CDCl3): delta (ppm) 3.60 (d, 2H),1.37 (m, 9H), 0.90 (m, 6H).
75% With N-Bromosuccinimide; sulfuric acid; trifluoroacetic acid; at 20℃; To a solution of the 5-(2-ethylhexyl)thieno[3,4-c]pyrrole-4,6-dione (0.50 g, 1.88 mmol) in trifluoroacetic acid (5 mL) and conc.H2SO4 (2 mL) was added NBS (1.10 g, 6.18 mmol) in portions. Themixture was stirred at room temperature overnight. Then, waterwas added and the mixture was extracted with dichloromethanetwice. The organic phase was dried over Na2SO4. After removingsolvent under vacuum, the crude product was purified by silicacolumn to give the title compound as white powder with 75% yield.Mp: 104 C. FTIR (KBr) v/cm-1 2956, 2929, 1697, 1535, 1388, 1054,958,746, 680. 1H NMR (CDCl3, ppm): 3.52 (d, J 7.14 Hz, 2H),1.81e1.77 (m, 1H), 1.38-1.29 (m, 8H), 0.94-0.92 (m, 6H). 13C NMR(CDCl3, ppm): 160.87, 134.90, 113.13, 42.81, 38.36, 30.69, 28.72,24.00, 23.13, 14.26, 10.55. HRMS (ESI) (M+, C14H17Br2NO2S): calcd,420.9347; found, 420.9341.
  • 2
  • [ 1231160-82-9 ]
  • [ 1231160-83-0 ]
  • 5,5’,5’’-tris(2-ethylhexyl)-4H,4’H,4’’H-1,1’:3’,1’’-ter(thieno[3,4-c]-pyrrole)-4,4’,4’’,6,6’,6’’(5H,5’H,5’’H)-hexaone [ No CAS ]
 

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