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CAS No. : | 325810-07-9 | MDL No. : | MFCD22200540 |
Formula : | C55H48CuF3P3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ADEZRALRKPUAPZ-UHFFFAOYSA-N |
M.W : | 922.43 | Pubchem ID : | 12057354 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 | UN#: | |
Hazard Statements: | H315-H319 | Packing Group: | |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In tetrahydrofuran byproducts: Me3SiOCH(CF3)2; (N2 or Ar); stirred at 50°C for 12 h; evapd. (vac.), washed (cold hexane), dried (vac.), recrystd. (THF); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90 %Spectr. | With 4,4'-di-tert-butyl-2,2'-bipyridine In toluene at 80℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water-d2 In toluene at 50℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 50 %Spectr. 2: 15 %Spectr. | With 4,4'-di-tert-butyl-2,2'-bipyridine In N,N-dimethyl-formamide at 100℃; for 2h; | |
1: 20 %Spectr. 2: 80 %Spectr. | In acetonitrile at 70℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65 %Spectr. | With 4,4'-di-tert-butyl-2,2'-bipyridine In toluene at 80℃; for 22h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 60 %Spectr. 2: > 5 %Spectr. | With 4,4'-di-tert-butyl-2,2'-bipyridine In toluene at 100℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60 %Spectr. | With 4,4'-di-tert-butyl-2,2'-bipyridine In toluene at 80℃; for 22h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60 %Spectr. | With 4,4'-di-tert-butyl-2,2'-bipyridine In toluene at 80℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70 %Spectr. | With 4,4'-di-tert-butyl-2,2'-bipyridine In toluene at 80℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | In dichloromethane soln. of phen in CH2Cl2 added to soln. of Cu compd. in CH2Cl2, Et2O added after 30 min; solid sepd. by decantation, washed with Et2O, dried under vac.; elem. anal.; | |
65% | In dichloromethane for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In methanol mixt. of CuF2*3H2O and PPh3 in MeOH stirred under reflux in air overnight, filtration, filtrate evapd. to dryness under vac., residue dried under vac. overnight, treated with THF and CF3SiMe3 in glove box, mixt. stirred under Ar for 2 h; solid quickly filtered off in air, washed successively with dry THF and hexane, dried under vac.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran at 4℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | In tetrahydrofuran at 50℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In tetrahydrofuran at 22℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In tetrahydrofuran at 50℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In tetrahydrofuran at 22℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | In tetrahydrofuran at 22℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | In tetrahydrofuran at 50℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | In tetrahydrofuran at 22℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | In tetrahydrofuran at 50℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | In tetrahydrofuran at 22℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | In tetrahydrofuran at 50℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | In tetrahydrofuran at 22℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | Stage #1: 1-(4-methoxyphenyl)-2-propyn-1-ol With 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic anhydride In tetrahydrofuran for 0.333333h; Stage #2: tris(triphenylphosphane)(trifluoromethyl)copper(I) In tetrahydrofuran at 22℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | In tetrahydrofuran at 22℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In tetrahydrofuran at 50℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | In tetrahydrofuran at 22℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In tetrahydrofuran at 22℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In tetrahydrofuran at 22℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | Stage #1: trifluoromethan With potassium <i>tert</i>-butylate; copper(l) chloride In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Stage #2: triphenylphosphine In N,N-dimethyl-formamide Inert atmosphere; | 34 Example 34; To a 0.31 M solution of stabilized CuCF3 in DMF (2.5 mL; 0.78 mmol) was added a solution of PPh3 (617 mg; 2.35 mmol) in dry DMF (1 .5 mL). After stirring overnight the mixture was treated with ether (10 mL). The white precipitate of [(Ph3P)3Cu(CF3)] was separated by filtration, washed with ether (3 * 5 mL), and dried under vacuum. The yield was 347 mg (48%). NMR (CH2CI2, 25 °C): 31 P, δ = -0.6 ppm (br,s); 19F, δ = -25.4 ppm (s). Purity (19F with an internal standard): 97%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | In chloroform-d1 at 55℃; for 18h; Glovebox; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | In chloroform-d1 at 55℃; for 18h; Glovebox; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In chloroform-d1 at 20℃; for 18h; Glovebox; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | In chloroform-d1 at 20℃; for 18h; Glovebox; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | In chloroform-d1 at 20℃; for 18h; Glovebox; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | In chloroform-d1 at 20℃; for 18h; Glovebox; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | In chloroform-d1 at 20℃; for 18h; Glovebox; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | In chloroform-d1 at 55℃; for 18h; Glovebox; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | In chloroform-d1 at 55℃; for 18h; Glovebox; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | In chloroform-d1 at 55℃; for 18h; Glovebox; Inert atmosphere; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In chloroform-d1 at 20℃; for 18h; Glovebox; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | Stage #1: tris(triphenylphosphane)(trifluoromethyl)copper(I); 2-benzyloxy-7-iodo-3-methoxy-3-(t rif luoromethyl)-isoindolin-1-one With 4,4'-di-tert-butyl-2,2'-bipyridine In toluene at 80℃; for 20h; Stage #2: With 4,4'-di-tert-butyl-2,2'-bipyridine In toluene at 80℃; for 4h; | 2-Benzyloxy-3-methoxy-3,7-bistrifluoromethylisoindolin-1-one (18) The mixture of iodide 16 (100 mg, 0.216 mmol),(PPh3)3CuCF3 (218 mg, 0.237 mmol) and 4,4'-di-tert-butyl-2,2'-bipyridyl (4,4-dtbpy) (63.6 mg, 0.237 mmol) in toluene(2.2 mL) was stirred for 20 h at 80°C. To the mixture,(PPh3)3CuCF3 (39.7 mg, 0.0432 mmol) and 4,4-di-tertbutyl-2,2-bipyridyl (11.6 mg, 0.0432 mmol) were added and themixture was stirred for 4 h at 80°C. The mixture was dilutedwith EtOAc, washed with H2O, 28% NH3 aq., H2O and brine,dried over Na2SO4, filtered and evaporated under reducedpressure. The residue was purified with flash column chromatography(SiO2, n-hexane-EtOAc=19 : 19 : 1) to afford trifluoromehylatedcompound 18 (41.7 mg, 48%). White powder;1H-NMR (400 MHz, CDCl3) δ: 7.94 (dd, J=4.3 Hz, 1H), 7.81(d, J=4.3 Hz, 2H), 7.54 (d, J=5.9 Hz, 2H), 7.32-7.44 (m, 3H),5.32 (d, J=9.7 Hz, 1H), 5.13 (d, J=9.7 Hz, 1H); 13C-NMR(100 MHz, CDCl3) δ: 162.44, 137.00, 134.30, 133.52, 129.63(2C), 129.23 (q, J=4.8 Hz), 129.04 (2C), 128.53, 127.74, 127.83,(q, J=28.8 Hz), 127.81, 122.00 (q, J=274.8 Hz), 121.86 (q,J=286.7 Hz), 97.78 (q, J=36.0 Hz), 79.20, 51.49; 19F-NMR(368 MHz, CDCl3) δ: -60.96 (s, 3F), -77.67 (s, 3F); IR (KBr,cm-1) ν: 3584, 3388, 2918, 2847, 1755, 1604, 1325, 1173, 989,760, 641; LR-MS (ESI): m/z 428 [M+Na]+; HR-MS (ESI): m/zCalcd for C18H13F6NO3Na [M+Na]+ 428.0692. Found 428.0701. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | Stage #1: tris(triphenylphosphane)(trifluoromethyl)copper(I); 2-benzyloxy-7-iodo-3-(2,2,2-trifluoroethoxy)-3-trifluoromethylisoindolin-1-one With 4,4'-di-tert-butyl-2,2'-bipyridine In toluene at 80℃; for 20h; Stage #2: With 4,4'-di-tert-butyl-2,2'-bipyridine In toluene at 80℃; for 4h; | 2-Benzyloxy-3-methoxy-3,7-bistrifluoromethylisoindolin-1-one (18) General procedure: The mixture of iodide 16 (100 mg, 0.216 mmol),(PPh3)3CuCF3 (218 mg, 0.237 mmol) and 4,4'-di-tert-butyl-2,2'-bipyridyl (4,4-dtbpy) (63.6 mg, 0.237 mmol) in toluene(2.2 mL) was stirred for 20 h at 80°C. To the mixture,(PPh3)3CuCF3 (39.7 mg, 0.0432 mmol) and 4,4-di-tertbutyl-2,2-bipyridyl (11.6 mg, 0.0432 mmol) were added and themixture was stirred for 4 h at 80°C. The mixture was dilutedwith EtOAc, washed with H2O, 28% NH3 aq., H2O and brine,dried over Na2SO4, filtered and evaporated under reducedpressure. The residue was purified with flash column chromatography(SiO2, n-hexane-EtOAc=19 : 19 : 1) to afford trifluoromehylatedcompound 18 (41.7 mg, 48%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | Stage #1: tris(triphenylphosphane)(trifluoromethyl)copper(I); 7-iodo-2-(4-methoxybenzyloxy)-3-(2-oxo-2-phenylethyl)-3-trifluoromethylisoindolin-1-one With 4,4'-di-tert-butyl-2,2'-bipyridine In toluene at 80℃; for 20h; Stage #2: With 4,4'-di-tert-butyl-2,2'-bipyridine In toluene at 80℃; for 4h; | 2-Benzyloxy-3-methoxy-3,7-bistrifluoromethylisoindolin-1-one (18) The mixture of iodide 16 (100 mg, 0.216 mmol),(PPh3)3CuCF3 (218 mg, 0.237 mmol) and 4,4'-di-tert-butyl-2,2'-bipyridyl (4,4-dtbpy) (63.6 mg, 0.237 mmol) in toluene(2.2 mL) was stirred for 20 h at 80°C. To the mixture,(PPh3)3CuCF3 (39.7 mg, 0.0432 mmol) and 4,4-di-tertbutyl-2,2-bipyridyl (11.6 mg, 0.0432 mmol) were added and themixture was stirred for 4 h at 80°C. The mixture was dilutedwith EtOAc, washed with H2O, 28% NH3 aq., H2O and brine,dried over Na2SO4, filtered and evaporated under reducedpressure. The residue was purified with flash column chromatography(SiO2, n-hexane-EtOAc=19 : 19 : 1) to afford trifluoromehylatedcompound 18 (41.7 mg, 48%). White powder;1H-NMR (400 MHz, CDCl3) δ: 7.94 (dd, J=4.3 Hz, 1H), 7.81(d, J=4.3 Hz, 2H), 7.54 (d, J=5.9 Hz, 2H), 7.32-7.44 (m, 3H),5.32 (d, J=9.7 Hz, 1H), 5.13 (d, J=9.7 Hz, 1H); 13C-NMR(100 MHz, CDCl3) δ: 162.44, 137.00, 134.30, 133.52, 129.63(2C), 129.23 (q, J=4.8 Hz), 129.04 (2C), 128.53, 127.74, 127.83,(q, J=28.8 Hz), 127.81, 122.00 (q, J=274.8 Hz), 121.86 (q,J=286.7 Hz), 97.78 (q, J=36.0 Hz), 79.20, 51.49; 19F-NMR(368 MHz, CDCl3) δ: -60.96 (s, 3F), -77.67 (s, 3F); IR (KBr,cm-1) ν: 3584, 3388, 2918, 2847, 1755, 1604, 1325, 1173, 989,760, 641; LR-MS (ESI): m/z 428 [M+Na]+; HR-MS (ESI): m/zCalcd for C18H13F6NO3Na [M+Na]+ 428.0692. Found 428.0701. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
< 10 %Chromat. | With 4,4'-di-tert-butyl-2,2'-bipyridine In N,N-dimethyl-formamide at 80℃; Sealed tube; | Reaction conditions employing [(PPh3)3CuCF3] (systemC1): A vial was charged with 0.31 mmol of 4-iodobiphenyl,264 mg (0.29 mmol) of (PPh3)3CuCF3, and 85.0 mg(0.32 mmol) of dtbpy in 5.4 mL of toluene with 60.5 µL(0.29 mmol) of undecane, as internal standard. After the solution was allowed to stir for five minutes, 0.6 mL aliquots weretaken and transferred into 5 mL air-tight ampules. The ampuleswere sealed and placed in an oil bath at 80 °C. The reactionswere removed from the oil bath at various time intervals andquenched with 0.6 mL of methanol in air. Aliquots of each solution were injected into a GC-FID and the reactions were monitored for the formation of the 4-trifluoromethylbiphenylproduct. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | Stage #1: copper (II)-fluoride; triphenylphosphine In methanol Reflux; Stage #2: (trifluoromethyl)trimethylsilane In tetrahydrofuran for 2h; Inert atmosphere; |
Tags: 325810-07-9 synthesis path| 325810-07-9 SDS| 325810-07-9 COA| 325810-07-9 purity| 325810-07-9 application| 325810-07-9 NMR| 325810-07-9 COA| 325810-07-9 structure
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H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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