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Chemical Structure| 945717-57-7 Chemical Structure| 945717-57-7

Structure of 945717-57-7

Chemical Structure| 945717-57-7

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Product Details of [ 945717-57-7 ]

CAS No. :945717-57-7
Formula : C6H2ClF3IN
M.W : 307.44
SMILES Code : FC(C1=NC(Cl)=CC=C1I)(F)F
MDL No. :MFCD16610547

Safety of [ 945717-57-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 945717-57-7 ]

* 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 [ 945717-57-7 ]

[ 945717-57-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 945717-57-7 ]
  • [ 205444-22-0 ]
YieldReaction ConditionsOperation in experiment
69% With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -75 - -72℃; for 1.83333h; To a stirred solution of 3.05 ml of n-BuLi (1.6 M in hexane, 4.88 mmol) under argon at -75 C. was added 0.69 ml of diisopropylamine (4.88 mmol) in 2.5 ml THF over 5 min (temperature between -72 and -75 C.). After 10 min at -75 C. a solution of 1.5 g of 6-chloro-3-iodo-2-trifluoromethyl-pyridine (4.88 mmol) in 3.5 ml THF was added dropwise over 20 min at the same temperature. After 1.5 hours stirring at -75 C., 6 ml 2M aqueous HCl were added (temperature was allowed to raise to RT). The mixture was then diluted with water, extracted with diethylether and the combined organic phases were successively washed with saturated NaHCO3 solution and brine, dried over magnesium sulfate, filtered off and concentrated in vacuo. The residue was purified by silicagel chromatography (eluent:heptane/AcOEt 95:5) leading to 1.145 g (69%) of 2-chloro-4-iodo-6-trifluoromethyl-pyridine as a white powder. MS: 307.0
  • 2
  • [ 39890-95-4 ]
  • [ 945717-57-7 ]
  • [ 205444-22-0 ]
YieldReaction ConditionsOperation in experiment
To a cooled (-100C) solution of diisopropylamine (14.5 mL, 104 mmol) in 80 mL of THF under inert atmosphere was added dropwise n-butyllithium (65 mL of a 1.6 M solution in hexanes, 104 mmol) followed by a lOmL of THF solution of 2-chloro-6- (trifluoromethyl) pyridine (9.5 g, 52 mmol). After two hours, the temperature was raised to -78C and a 10 mL solution of iodine in THF (13 g, 52 mmol) was added. After 1 hour, the reaction was poured into water and extracted with DCM. The combined DCM layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo to provide 14.9 g of a mixture of 6-chloro-3-iodo-2-(trifluoromethyl)pyridine and 2-chloro-4-iodo-6- (trifluoromethyl)pyridine. This crude material was resubjected to LDA as follows. To a cooled (-78C) solution of diisopropylamine (14.5 mL, 104 mmol) in 80 mL of THF under inert atmosphere was added dropwise n-butyllithium (65 mL of a 1.6 M solution in hexanes, 104 mmol) followed by a 30 mL solution of the preceding crude mixture in THF. After three hours, the reaction mixture was poured in water and extracted with DCM. The DCM layers were washed with brine, dried (MgSC^), concentrated in vacuo, and purified via silica gel chromatography (0-20% EtOAc/hexanes) to afford Intermediate 9A as a white solid (6.9 g, 42%). l NMR (CDC13): delta 7.96 (s, 1H), 7.95 (s, 1H).
 

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