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CAS No. : | 320573-10-2 | MDL No. : | MFCD32643321 |
Formula : | C22H24N2Si2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RHQJPUDVIJICOH-UHFFFAOYSA-N |
M.W : | 372.61 | Pubchem ID : | 21573440 |
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 |
---|---|---|
85% | With sodium hydroxide; copper(l) iodide; N-benzyl-N,N,N-triethylammonium chloride In benzene at 60℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With alkali metal carbonate In methanol | |
97% | With methanol; potassium carbonate at 20℃; for 1h; | |
95% | With potassium carbonate In methanol at 20℃; |
92% | With potassium fluoride In methanol at 20℃; | |
78% | With potassium hydroxide In tetrahydrofuran; methanol for 22h; | |
67% | With tetrabutyl ammonium fluoride In tetrahydrofuran for 0.333333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With sodium hydroxide; copper(l) iodide; N-benzyl-N,N,N-triethylammonium chloride In water; benzene at 60℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sodium hydroxide; tetrakis(triphenylphosphine) palladium(0); N-benzyl-N,N,N-triethylammonium chloride In benzene at 60℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2,4,6-trimethylphenyl bromide With n-butyllithium In diethyl ether; pentane at 0℃; for 1h; Stage #2: 3,8-bis(trimethylsilanylethynyl)-[1,10]phenanthroline In diethyl ether; pentane at 20℃; for 19h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: n-BuLi / pentane; diethyl ether / 1 h / 0 °C 1.2: pentane; diethyl ether / 19 h / 20 °C 2.1: 896 mg / MnO2 / CH2Cl2 / 3 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: n-BuLi / pentane; diethyl ether / 1 h / 0 °C 1.2: pentane; diethyl ether / 19 h / 20 °C 2.1: 896 mg / MnO2 / CH2Cl2 / 3 h 3.1: n-BuLi / hexane; diethyl ether / 3 h / 0 °C 3.2: hexane; diethyl ether / 48 h / 20 °C 4.1: 2.29 g / MnO2 / CH2Cl2 / 2 h 5.1: 98 percent / aq. KOH / tetrahydrofuran; methanol / 16 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 78 percent / aq. KOH / tetrahydrofuran; methanol / 22 h 2: 31 percent / Et3N; CuI / [PdCl2(PPh3)2] / benzene / 24 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: n-BuLi / pentane; diethyl ether / 1 h / 0 °C 1.2: pentane; diethyl ether / 19 h / 20 °C 2.1: 896 mg / MnO2 / CH2Cl2 / 3 h 3.1: n-BuLi / hexane; diethyl ether / 3 h / 0 °C 3.2: hexane; diethyl ether / 48 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: n-BuLi / pentane; diethyl ether / 1 h / 0 °C 1.2: pentane; diethyl ether / 19 h / 20 °C 2.1: 896 mg / MnO2 / CH2Cl2 / 3 h 3.1: n-BuLi / hexane; diethyl ether / 3 h / 0 °C 3.2: hexane; diethyl ether / 48 h / 20 °C 4.1: 2.29 g / MnO2 / CH2Cl2 / 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: n-BuLi / pentane; diethyl ether / 1 h / 0 °C 1.2: pentane; diethyl ether / 19 h / 20 °C 2.1: 896 mg / MnO2 / CH2Cl2 / 3 h 3.1: n-BuLi / hexane; diethyl ether / 3 h / 0 °C 3.2: hexane; diethyl ether / 48 h / 20 °C 4.1: 2.29 g / MnO2 / CH2Cl2 / 2 h 5.1: 98 percent / aq. KOH / tetrahydrofuran; methanol / 16 h 6.1: 31 percent / Et3N; CuI / [PdCl2(PPh3)2] / benzene / 18 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: n-BuLi / pentane; diethyl ether / 1 h / 0 °C 1.2: pentane; diethyl ether / 19 h / 20 °C 2.1: 896 mg / MnO2 / CH2Cl2 / 3 h 3.1: n-BuLi / hexane; diethyl ether / 3 h / 0 °C 3.2: hexane; diethyl ether / 48 h / 20 °C 4.1: 2.29 g / MnO2 / CH2Cl2 / 2 h 5.1: 98 percent / aq. KOH / tetrahydrofuran; methanol / 16 h 6.1: 36 percent / Et3N; CuI / [PdCl2(PPh3)2] / benzene / 28 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: n-BuLi / pentane; diethyl ether / 1 h / 0 °C 1.2: pentane; diethyl ether / 19 h / 20 °C 2.1: 896 mg / MnO2 / CH2Cl2 / 3 h 3.1: n-BuLi / hexane; diethyl ether / 3 h / 0 °C 3.2: hexane; diethyl ether / 48 h / 20 °C 4.1: 2.29 g / MnO2 / CH2Cl2 / 2 h 5.1: 98 percent / aq. KOH / tetrahydrofuran; methanol / 16 h 6.1: 36 percent / Et3N; CuI / [PdCl2(PPh3)2] / benzene / 28 h / 80 °C 7.1: 32 percent / Et3N; CuI / [PdCl2(PPh3)2] / benzene / 24 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: n-BuLi / pentane; diethyl ether / 1 h / 0 °C 1.2: pentane; diethyl ether / 19 h / 20 °C 2.1: 896 mg / MnO2 / CH2Cl2 / 3 h 3.1: n-BuLi / hexane; diethyl ether / 3 h / 0 °C 3.2: hexane; diethyl ether / 48 h / 20 °C 4.1: 2.29 g / MnO2 / CH2Cl2 / 2 h 5.1: 98 percent / aq. KOH / tetrahydrofuran; methanol / 16 h 6.1: 36 percent / Et3N; CuI / [PdCl2(PPh3)2] / benzene / 28 h / 80 °C 7.1: 28 percent / Et3N; CuI / [PdCl2(PPh3)2] / benzene / 24 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 57 percent / sulfur monochloride; bromine; pyridine / various solvent(s) / 13 h / Heating 2: 100 percent / diisopropylethylamine; CuI / PdCl2(PPh3)2 / benzene / 40 h / 95 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 67 percent / TBAF / tetrahydrofuran / 0.33 h 2: 21 percent / diisopropylethylamine; CuI / Pd(PPh3)2Cl2 / tetrahydrofuran / 24 h / 90 °C | ||
Multi-step reaction with 2 steps 1: alkali metal carbonate / methanol 2: copper(l) iodide; bis(dibenzylideneacetone)-palladium(0); triphenylphosphine; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 72 h / 60 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1: potassium carbonate; methanol / 1 h / 20 °C 2: copper(l) iodide; N-ethyl-N,N-diisopropylamine; bis(dibenzylideneacetone)-palladium(0); triphenylphosphine / tetrahydrofuran / 72 h / 60 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 92 percent / KF / methanol / 20 °C 2: 15 percent / iPr2NH / Pd(PPh3)4 / benzene / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 92 percent / KF / methanol / 20 °C 2: 20 percent / iPr2NH / Pd(PPh3)4 / benzene / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 95 percent / K2CO3 / methanol / 20 °C 2: 85 percent / Et3N; Pd(PPh3)4; CuI / tetrahydrofuran / 6 h / 60 °C | ||
Multi-step reaction with 2 steps 1: alkali metal carbonate / methanol 2: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 48 h / 60 °C | ||
Multi-step reaction with 2 steps 1: potassium carbonate; methanol / 1 h / 20 °C 2: copper(l) iodide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 48 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In methanol; ethanol under Ar, Schlenk technique; mixt. of Ru-complex and phenanthroline deriv. in EtOH refluxed for 12 h, cooled to room temp., soln. of NH4PF6 in MeOH added, mixt. stirred for 30 min; evapn. to dryness under vac., residue extd. with CH2Cl2, column chromy. (alumina, CH2Cl2/MeOH (100/1); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With KF In methanol; dichloromethane under Ar, Schlenk technique; mixt. of Pt-complex, phenanthroline deriv.,CuI, and KF in CH2Cl2/MeOH (2/1) refluxed for 1 d, cooled to room temp.; evapd. to dryness under vac., column chromy. (alumina, CH2Cl2/MeOH (100/1); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In toluene under Ar, Schlenk technique; mixt. of Re-complex and phenanthroline deriv. in toluene refluxed for 8 h, cooled to room temp.; solid filtered off, washed with hexane and ether, dried under vac.; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | In methanol; dichloromethane stoich. mixt. in CH2Cl2/MeOH (2/1, v/v), refluxed; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: alkali metal carbonate / methanol 2.1: copper(l) iodide; bis(dibenzylideneacetone)-palladium(0); triphenylphosphine; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 72 h / 60 °C / Inert atmosphere 3.1: dichloromethane; acetonitrile / 0.5 h / Inert atmosphere 3.2: 3 h / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: alkali metal carbonate / methanol 2.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 48 h / 60 °C 3.1: dichloromethane; acetonitrile / 0.5 h / Inert atmosphere 3.2: 3 h / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | In dichloromethane; acetonitrile for 1h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: C27H37N3O4; copper(II) acetate monohydrate; 3,8-bis(trimethylsilanylethynyl)-[1,10]phenanthroline In methanol for 1h; Stage #2: potassium hexafluorophosphate In methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 65℃; for 72h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 60℃; for 96h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In dichloromethane at 30℃; for 16h; Inert atmosphere; | 2.3. Preparation of Pt(3,8-Phen≡TMS)Cl2 Platinum complex Pt(DMSO)Cl2 (422 mg, 1.0 mmol) was dissolvedin dry CH2Cl2 (100 ml). The solution was added 3,8-Phen≡TMS (327 mg, 1.0 mmol) and stirred at 30C for 16 h. Thesolution was added CH3CN (20 ml) and CH2Cl2 was removed byreduced pressure. The precipitate in CH3CN was filtered throughfilter paper and the pale orange powder was obtained. The powderwas dried at 60C under vacuum for 3 h. Yield: 536 mg (84%).FT-IR (KBr, cm1) n(Phen-C≡C): 2159, n(-CH3): 2852, 2923, 2961. UV/VIS (CH2Cl2): labs nm (ε 105), 287 (0.46), 328 (0.31), 362(0.28), 420 (0.03). 1H NMR (CD3Cl, 400 MHz, ppm): d 9.85 (d,J 1.6 Hz, 2H, Phen-H2 and H9), 8.63 (d, J 1.6 Hz, 2H, Phen-H4and H7), 7.95 (s, 2H, Phen-H5 and H6), 0.34 (s, 18H, ≡TMS). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: n-butyllithium / diethyl ether; hexane / 6 h / 0 - 20 °C / Inert atmosphere 1.2: 12 h / 20 °C / Inert atmosphere 1.3: 3 h / 20 °C 2.1: n-butyllithium / diethyl ether; hexane / 6 h / 0 - 20 °C / Inert atmosphere 2.2: 12 h / 20 °C / Inert atmosphere 2.3: 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: n-butyllithium / diethyl ether; hexane / 6 h / 0 - 20 °C / Inert atmosphere 1.2: 12 h / 20 °C / Inert atmosphere 1.3: 3 h / 20 °C 2.1: n-butyllithium / diethyl ether; hexane / 6 h / 0 - 20 °C / Inert atmosphere 2.2: 12 h / 20 °C / Inert atmosphere 2.3: 3 h / 20 °C 3.1: potassium carbonate; methanol / tetrahydrofuran; water / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | Stage #1: 2-bromo-1,3,5-trimethoxybenzene With n-butyllithium In diethyl ether; hexane at 0 - 20℃; for 6h; Inert atmosphere; Stage #2: 3,8-bis(trimethylsilanylethynyl)-[1,10]phenanthroline In diethyl ether; hexane at 20℃; for 12h; Inert atmosphere; Stage #3: With manganese(IV) oxide In dichloromethane at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In acetonitrile at 50℃; for 24h; | 1-3 [3,8-Bis-(trimethylsilylethynyl)-1,10-phenanthroline] platinum dichloride preparation: Weigh 3,8-bis-(trimethylsilylethynyl)-1,10-phenanthroline (37mg, 0.1mmol),Dimethyl sulfoxide platinum chloride (42mg, 0.1mmol) and 100mL reaction flask,Add 20 mL of anhydrous acetonitrile, and heat the reaction at 50°C for 24 hours. Drain the reaction solution,The product was extracted with dichloromethane and separated on a silica gel column with a yield of 85%. |