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CAS No. : | 2715-43-7 | MDL No. : | MFCD00017271 |
Formula : | C11H12O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DYSXJBCEIBVGJU-UHFFFAOYSA-N |
M.W : | 176.21 | Pubchem ID : | 10866858 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501 | UN#: | |
Hazard Statements: | H315-H319-H335 | 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 |
---|---|---|
95% | With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 12h;Inert atmosphere; | Ethyl 4-vinyl benzoate was synthesized according to a reported modified procedure. 1H NMR match previously reported data. Under a nitrogen atmosphere, 4-vinyl benzoic acid (1.00 g, 6.75 mmol), 1,3-dicyclohexyl-carbodiimide (1.67 g, 8.10 mmol), and 4-dimethylaminopyridine (82.5 mg, 0.675 mmol) were added to a 100 mL round-bottom flask equipped with a magnetic stir bar. To this mixture were added CH2Cl2 (50 mL) and ethanol (2.90 g, 67.5 mmol). The resulting solution was stirred under nitrogen for 12 h at RT, filtered through a Celite pad, and evaporated to near dryness under vacuum. Chromatography of the crude product on silica (Hexane: EtOAc=30:1), followed by concentration gave a primrose yellow oil (1.13 g, 95%). 1H NMR (400 MHz, CDCl3): delta 7.78 (d, 2H, J = 8.5 Hz, ArH), 7.24 (d, 2H, J = 8.0 Hz, ArH), 6.51 (dd, 1H, J1 = 11 Hz, J2 = 18 Hz, CH=CH2), 5.63 (d, 1H, J = 18 Hz, CH=CH2), 5.16 (d, 1H, J = 11 Hz, CH=CH2), 4.16 (q, 2H, J = 7.5 Hz, CH2CH3), 1.19 (t, 3H, J = 7.0 Hz, CH2CH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; N-Methyldicyclohexylamine; tri tert-butylphosphoniumtetrafluoroborate In tetrahydrofuran Reflux; | |
82% | With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; N-Methyldicyclohexylamine; tri tert-butylphosphoniumtetrafluoroborate In tetrahydrofuran Reflux; | Synthesis of 1,2,4,5-Tetrakis[(1E)-2'-(ethyl 4''-benzoate)vinyl] benzene: 1,2,4,5-tetrabromobenzene (255.8 mg, 0.66 mmol), ethyl-4-vinylbenzoate (498.6 mg, 2.83 mmol), Pd2(dba)3·CHCl3 (69.2 mg, 0.07 mmol), [(t-Bu)3PH]BF4 (75.4 mg, 0.26 mmol), Cy2NMe (0.8 mL) in THF (8 mL) were heated at reflux overnight. The THF was removed under reduced pressure, and the product was purified by flash chromatography with CH2Cl2/MeOH (100:0-99:1) as the eluent. The crude material was recrystallized from CH2Cl2/EtOH to give yellow ester (541.2 mg, 82%) as a bright yellow solid. 1H NMR (600 MHz, CDCl3): δ 1.42 (t, J= 7.1 Hz, 12H, CH3), 4.41 (q, J= 7.1 Hz, 8H, CH2), 7.14 (d, J= 16 Hz, 4H, vinyl CH), 7.57 (d, J= 16.1 Hz, 4H, vinyl CH), 7.61 (d, J= 8.3 Hz, 8H, ArH), 7.86 (s, 2H, core ArH), 8.07(d, J= 8.3 Hz, 8H, ArH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; N-Methyldicyclohexylamine; tri tert-butylphosphoniumtetrafluoroborate In tetrahydrofuran Reflux; | |
97% | With N-Methyldicyclohexylamine; tri tert-butylphosphoniumtetrafluoroborate In tetrahydrofuran for 17h; Reflux; | 1 Standard Conditions for Heck Cross-Coupling ProcedureTo a flame-dried schienk flask was added the halobenzene (1 equiv), Pd2(dba)3.CHCl3 (2-15 mol %) and [(t-Bu)3PH]BF4 (10-60 mol %) which were subsequently dried under vacuum for 15 minutes before being dissolved in dry THF. N-Methyldicyclohexylamine (4 equiv) and ethyl 4-vinylbenzoate 7 (3.3 equiv) were added via syringe and the reaction monitored by TLC (neat CH2Cl2). Upon completion of the reaction the residual THF was removed in vacuo, the crude material redissolved in CH2Cl2 and filtered to remove any insoluble material before being absorbed onto fine silica and eluting with 0:100 to 2:98 MeOH/CH2Cl2; 1,3,5-Tris[(1E)-2'-(ethyl 4-benzoate)vinyl]benzene (10)Prepared as per, the standard procedure using 1,3,5-tribromobenzene 8 (1010 mg, 3.21 mmol), Pd2(dba)3.CHCl3 (882 mg, 0.85 mmol), t-Bu3PHBF4 (560 mg, 1.93 mmol), Cy2NMe (3.0 mL), ethyl 4-vinylbenzoate 7 (1870 mg, 10.61 mmol) and THF (40 mL). The product was eluted with 2:98 MeOH/CH2Cl2 and recrystallized from CH2Cl2/EtOH to give 10 as an off white powder, 1.86 g (97%).1H NMR (600 MHz, CDCl3): δ1.42 (t, J=7.1 Hz, 9H, CH3), 4.40 (q, J=7.1 Hz, 6H, CH2), 7.24 (AB quartet, 6H, vinyl), 7.60 (d, J=8.3 Hz, 6H, ArH), 7.61 (s, 3H, ArH), 8.06 (d, J=8.3 Hz, 6H, ArH).13C NMR (150 MHz, CDCl3): δ 14.51 (CH3), 61.13 (CH2), 125.0 (CH), 126.5 (CH), 128.7 (CH), 129.7 (C), 130.2 (CH), 130.5 (CH), 137.9 (C), 141.5 (C), 166.5 (CO).IR (KBr): ν (cm-1) 2979, 2929, 1713, 1604, 1279, 1178, 1105, 762, 698HR-EI+-MS: C39H36O6 requires 600.2512 amu. found 600.2513.EI+-MS: MI=C39H36O6; m/z: 600.3 (100%)=MI+, 555.2 (7%)=[MI-EtO]+.UV-Vis (CH2Cl2): λ (nm) [log ε(M-1 cm-1)] 258 [4.49], 330 [4.28]Fluorescence (CH2Cl2): excitation (nm) [emission (nm)] 258 [397, 418, 518], 330 [397, 418]; (cyclohexane) 328 [393, 413] |
97% | With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; N-Methyldicyclohexylamine; tri tert-butylphosphoniumtetrafluoroborate In tetrahydrofuran for 17h; Inert atmosphere; Schlenk technique; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With bis(cyclooctatetraene)(1-isocyanoadamantane)iron; 1-adamantyl isocyanide In neat (no solvent) at 50℃; for 23h; | |
92% | With iron(II) pivalate; 1-adamantanecarbonitrile In neat (no solvent) at 50℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | Stage #1: (vinyl)trimethoxylsilane; Ethyl 4-bromobenzoate With (1,2-dimethoxyethane)dichloronickel(II); tetrabutylammonium triphenyldifluorosilicate In N,N-dimethyl acetamide at 35℃; for 12h; Inert atmosphere; Stage #2: In N,N-dimethyl acetamide | General Procedure 2 General procedure: In a nitrogen-filled glove box, aromatic halide (0.2 mmol, 1.0equiv), TBAT (270 mg, 0.5 mmol, 2.5 equiv), NiCl2(glyme) (4.4mg, 0.02 mmol, 10 mol%), and DMA (1.0 mL) were charged to an8 mL vial equipped with a magnetic stirrer bar. The vinyltrimethoxysilane(59.1 mg, 0.4 mmol, 2.0 equiv) was added. The vialwas removed from the glove box, and the reaction mixture wasstirred at rt (35 °C) for 12 h. The reaction mixture was thendiluted with EtOAc and washed with water. The organic phasewas dried over Na2SO4, filtered, and concentrated, and theresidue was purified by column chromatography on silica gel togive the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | Stage #1: phenyl cyclopropyl ketone; 4-ethenylbenzoic acid, ethyl ester With bis((-)pinanediolato)diboron; 3-pentyl isonicotinate; methoxybenzene at 100℃; for 12h; Inert atmosphere; Schlenk technique; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol at 80℃; for 3h; Inert atmosphere; Schlenk technique; diastereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13% | With 4-dimethylaminopyridine; 10-(3,5-dimethoxyphenyl)-9-mesityl-1,3,6,8-tetramethoxyacridin-10-ium tetrafluoroborate In methanol; propan-2-one for 16h; Sealed tube; Inert atmosphere; Irradiation; Green chemistry; | General procedure for Giese reaction in batch General procedure: An oven dried 5-mL microwave tube equipped with a magnetic stirring bar was charged with [4-(4- ethoxyphenyl)phenyl]boronic acid 1a (40 mg, 0.165 mmol), photoredox catalyst (Mes-Acr; 2.6 mg, 0.004 mmol), DMAP (5.0 mg, 0.041 mmol). The vial was sealed with a septum and 3 cycles vacuum/Argon were performed. A 1:1 acetone/MeOH solvent mixture (purged with argon for 15 minutes) (2 mL), and methylviny ketone 2a (46 mg, 0.660 mmol) were added. The tube was irradiated with Penn PhD Photoreactor M2 (450 nm) for 1 h. The reaction, assayed by HPLC/MS, was concentrated in vacuo, reconstituted in DCM, and purified through flash chromatography (AcOEt/Hexane: 0% for 4 CV then to 90% in 12 CV). 4-[4-(4-ethoxyphenyl)phenyl]butan-2-one 3aa was isolated as white solid (25 mg, y: 56 %). |