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Chemical Structure| 1446909-29-0
Chemical Structure| 1446909-29-0
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Product Details of [ 1446909-29-0 ]

CAS No. :1446909-29-0 MDL No. :N/A
Formula : C27H19N Boiling Point : -
Linear Structure Formula :- InChI Key :YLKOFCYTHCZTEG-UHFFFAOYSA-N
M.W : 357.45 Pubchem ID :145926283
Synonyms :

Safety of [ 1446909-29-0 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1446909-29-0 ]

* 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 [ 1446909-29-0 ]

[ 1446909-29-0 ] Synthesis Path-Downstream   1~11

  • 1
  • [ CAS Unavailable ]
  • [ 1446909-29-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C / Inert atmosphere 1.2: 6 h / 20 °C 2.1: toluene-4-sulfonic acid / toluene / 12 h / Reflux 3.1: N,N-dimethyl-formamide / 60 h / Inert atmosphere; Reflux
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / 0 °C / Inert atmosphere 1.2: 6 h / 20 °C / Inert atmosphere 2.1: toluene-4-sulfonic acid / toluene / 4 h / Reflux 3.1: N,N-dimethyl-formamide / 15 h / Reflux
  • 2
  • [ 90-90-4 ]
  • [ 1446909-29-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C / Inert atmosphere 1.2: 6 h / 20 °C 2.1: toluene-4-sulfonic acid / toluene / 12 h / Reflux 3.1: N,N-dimethyl-formamide / 60 h / Inert atmosphere; Reflux
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / 0 °C / Inert atmosphere 1.2: 6 h / 20 °C / Inert atmosphere 2.1: toluene-4-sulfonic acid / toluene / 4 h / Reflux 3.1: N,N-dimethyl-formamide / 15 h / Reflux
  • 3
  • [ 34699-28-0 ]
  • [ CAS Unavailable ]
  • [ 1446909-29-0 ]
YieldReaction ConditionsOperation in experiment
48% In N,N-dimethyl-formamide for 15h; Reflux;
In N,N-dimethyl-formamide for 60h; Inert atmosphere; Reflux; 1 Synthesis of 4- (1, 2, 2-triphenylvinyl) benzonitrile (TPE-CN) TPE-Br (820 mg) , CuCN (268 mg) , and DMF (10 mL) were added into a two-necked round bottom flask. The mixture was heated at reflux for 60 hours under nitrogen condition and then suspended into 300 mL water. After ethylenediamine (10 mL) was added, the resulting mixture was stirred at 100 for 1 hour and was then filtered. The precipitated solid was extracted with dichloromethane (3 × 150 mL) and the combined organic phase was dried with anhydrous magnesium sulfate. After filtration and solvent evaporation, the residue was purified by silica gel column chromatography with hexane and dichloromethane (v/v, 1/1) as eluent to give TPE-CN as white powder in 53%yield.1H NMR (400 MHz, CDCl3) : δ 7.40 (d, 2H, J = 8.4 Hz) , 7.15 (m, 11H) , 7.03 (m, 6H) .13C NMR (100 MHz, CDCl3) : δ 149.0, 143.5, 143.0, 142.9, 142.8, 139.3, 132.1, 131.7, 131.4, 131.3, 128.2, 128.0, 127.4, 127.2, 119.2, 110.0. HRMS (MALDI-TOF) , m/z calcd. for C30H20N16Na+: 357.1517; found 357.1536
  • 4
  • [ 1446909-29-0 ]
  • [ 2323541-74-6 ]
YieldReaction ConditionsOperation in experiment
82% With sodium azide; zinc dibromide In 1-methyl-pyrrolidin-2-one; water at 150℃; 1 Synthesis of TPE-1TTZ Into a 10 mL round-bottomed flask were added sodium azide (138 mg, 2mmol) , zinc bromide (225 mg, 2 mmol) and 0.5 mL of water. TPE-CN (357 mg, 1mmol) was dissolved in 4.5 mL of N-Methylpyrrolidone (NMP) and injected into the solution. The reaction mixture was stirred at 150 . The mixture was acidified to pH 1 with aqueous HCl solution (3M) and was stirred vigorously for 30 minutes. The organic mixture was extracted with ethyl acetate (20 mL x 2) , washed with 3M HCl (50 mL x 2) and concentrated to yield a crude product. This crude product was added into NaOH solution (0.25M, 40 mL) and stirred vigorously until a white precipitate of zinc hydroxide was observed. The resulting suspension was filtered to remove zinc hydroxide. The filtrate was washed with ethylacetate (10 mL x 2) and acidified to pH 1 with 3 M HCl. The product precipitated upon stirring, which was again extracted into 20 mL ethyl acetate and the organic layer was separated. The aqueous layer was washed with ethyl acetate (20 mL x 2) . The organic layers were combined, concentrated and dried under vacuum to yield pure product as a white powder (82%) .1H NMR (400 MHz, DMSO) : δ 7.80 (d, 2H, J = 8.4 Hz) , 7.20-7.13 (m, 11H) , 7.03-6.98 (m, 6H) . HRMS (MALDI-TOF) , m/z calcd. for C27H20N4: 400.1722; found 400.1762
  • 5
  • [ 1240902-16-2 ]
  • [ 1446909-29-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / toluene / 12 h / Reflux 2: N,N-dimethyl-formamide / 60 h / Inert atmosphere; Reflux
  • 6
  • [ 1607-57-4 ]
  • [ 126747-14-6 ]
  • [ 1446909-29-0 ]
YieldReaction ConditionsOperation in experiment
85% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 20h; Inert atmosphere; Reflux; 1 Example 1Synthesis of target compound p-CN (general structural formula I) Bromotristyrene (3.35 g, 10 mmol), 4-cyanophenylboronic acid (2.2 g, 15 mmol) and 0.18 g of tetrakis (triphenylphosphine) palladium were placed in a 100 mL two-necked round bottom flask, and the reaction system was deoxygenated. 15mL K2CO3 (6.21g, 45mmol) aqueous solution and 45mL tetrahydrofuran were deoxygenated and poured into a round-bottom flask. The reaction was refluxed under nitrogen for 20 hours. After the reaction was completed, it was cooled to room temperature, 100 mL of water was added, extracted with dichloromethane (100 mL × 3), and the organic phases were combined. The organic phase was dried over anhydrous sodium sulfate and filtered, and the crude product was obtained by rotary evaporation under reduced pressure. The crude product was purified by silica gel column chromatography using petroleum ether and methylene chloride as eluents to obtain 3.03 g of white powder with a yield of 85%.
71% Stage #1: Triphenylvinyl bromide With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In tetrahydrofuran; water at 85℃; for 0.5h; Inert atmosphere; Stage #2: 4-cyanophenylboronic acid In tetrahydrofuran; water at 85℃; for 24h; Inert atmosphere; 2.2.1. 2,6-Diflluoro-4-(1,2,2-triphenylvinyl)benzaldehyde (6) General procedure: A mixture of 2-bromo-1,1,2-triphenylethylene 5 (168 mg, 0.5 mmol),Pd(PPh3)2Cl2 (30 mg, 0.05 mmol) and K2CO3 (690 mg, 5 mmol) in 20mL of THF/H2O (4:1) was stirred in refllux at 85 C under N2. Thecoupling reagent, 3,5-difluoro-4-formylphenyl boronic acid (111 mg,0.6 mmol), was dissolved in THF and added to the reaction mixture after30 min using a syringe. The reaction was followed by thin layer chromatographyusing a mixture of hexane/ethyl acetate (5:1) as eluent. Assoon as the reaction was completed (24 h), the reaction mixture wasfiltered in vacuum over Celite to remove metal catalyst. After that, 30mL of water was added and extracted twice with 15 mL of dichloromethane.The organic phase was dried over anhydrous magnesiumsulfate and the solvent evaporated under reduced pressure. The productwas purified by column chromatography on silica gel, using dichloromethane/hexane (1/2) as eluent. The product was obtained as a lightyellow solid (163 mg, = 82%).
  • 7
  • [ 1391632-33-9 ]
  • [ 1446909-29-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / toluene / 4 h / Reflux 2: N,N-dimethyl-formamide / 15 h / Reflux
  • 8
  • [ 34619-03-9 ]
  • [ 1446909-29-0 ]
  • [ 2734780-01-7 ]
YieldReaction ConditionsOperation in experiment
70% Stage #1: 4-(1,2,2-triphenylvinyl)benzonitrile With lithium hexamethyldisilazane In tetrahydrofuran at -20 - 20℃; Inert atmosphere; Stage #2: tert-butyldicarbonate With sodium hydroxide In tetrahydrofuran; water at 20℃; for 24h;
  • 9
  • [ 1446909-29-0 ]
  • [ 2734780-03-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / -20 - 20 °C / Inert atmosphere 1.2: 24 h / 20 °C / pH 8 - 10 2.1: hydrogenchloride / water; diethyl ether / 0.17 h / 0 °C
  • 10
  • [ 1446909-29-0 ]
  • [ 2734780-02-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / -20 - 20 °C / Inert atmosphere 1.2: 24 h / 20 °C / pH 8 - 10 2.1: hydrogenchloride / water; diethyl ether / 0.17 h / 0 °C 3.1: sodium hydroxide / water / 0 °C
  • 11
  • [ CAS Unavailable ]
  • [ 1446909-29-0 ]
YieldReaction ConditionsOperation in experiment
80% With bis(trichloromethyl) carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 4h;
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