Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 245116-57-8 | MDL No. : | MFCD22374551 |
Formula : | C14H18O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IYVCKZLBCVNHFV-UHFFFAOYSA-N |
M.W : | 250.29 | Pubchem ID : | 640088 |
Synonyms : |
|
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: |
* 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 |
---|---|---|
38% | With sodium hydroxide In ethanol at 60℃; for 60h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | Stage #1: 1,4-dibromo-2,5-dipropoxybenzene With n-butyllithium In diethyl ether; hexane at -15℃; for 0.5h; Stage #2: N,N-dimethyl-formamide In diethyl ether; hexane for 0.5h; | |
62% | With n-butyllithium | |
51.3% | Stage #1: 1,4-dibromo-2,5-dipropoxybenzene With n-butyllithium In diethyl ether; hexane at 0℃; for 2h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In diethyl ether; hexane at 0℃; for 1h; Inert atmosphere; | Compound 3b The synthesis of 3b has previously been reported [1] but the following method is convenient. Compound 3a (2.00 g, 5.68 mmol, 1.0 eq) was dissolved in dry Et2O (100 mL) and the solution was cooled to 0 °C under N2. nBuLi (15% in hexanes, 1.6 M, 14.2 mL, 22.7 mmol, 4.0 eq) was added at 0 °C over a period of 15 min and the reaction mixture was stirred at 0 °C for 2 h. Dry DMF (1.8 mL, 23 mmol, 4.0 eq) was added and the reaction mixture was stirred at 0 °C for 1 h. The now light yellow suspension was quenched by the addition of saturated aqueous NH4Cl (150 mL) and subsequently extracted with chloroform (3 x 100 mL). The organic layers were combined, dried over MgSO4 and concentrated in vacuo. The crude material was purified by column chromatography (silica, EtOAc in cyclohexane 0-20% gradient). After removal of solvent from the fraction collected, the yellow solid was recrystallized from petroleum ether (25 mL). The yellow solution was allowed to slowly cool to room temperature and was left to crystallize for 18 h. The resultant crystals were collected by filtration, washed with petroleum ether and dried in vacuo. The filtrate was cooled to -20 °C to yield a second crop of crystalline product which was collected by filtration, washed with petroleum ether and dried in vacuo. The product crops were combined to give 3b (729 mg, 2.91 mmol, 51.3%) as a yellow crystalline solid. 1H NMR (500 MHz, CDCl3): δ/ppm 10.53 (s, 2H, HCHO), 7.43 (s, 2H, H3), 4.06 (t, J = 6.5 Hz, 4H, Ha), 1.93 - 1.82 (m, 4H, Hb), 1.06 (t, J = 7.4 Hz, 6H, Hc). 13C{1H} NMR (126 MHz, CDCl3): δ/ppm 189.6 (CCHO), 155.4 (C2), 129.5 (C1), 111.8 (C3), 70.9 (Ca), 22.6 (Cb), 10.7 (Cc). The NMR spectroscopic data agreed with the literature [1]. |
40% | Stage #1: 1,4-dibromo-2,5-dipropoxybenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With sodium hydroxide In ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | With sodium hydroxide In ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With sodium hydroxide In ethanol at 75℃; for 96h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With potassium <i>tert</i>-butylate In tetrahydrofuran; <i>tert</i>-butyl alcohol at 20℃; for 0.25h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17.1% | In dichloromethane at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 17.5 percent / Br2; KOAc / acetic acid / 3 h / 17 °C 2.1: n-BuLi / hexane; tetrahydrofuran / 2 h / -78 °C 2.2: 40 percent / hexane; tetrahydrofuran / -78 - 20 °C | ||
Multi-step reaction with 2 steps 1.1: 88 percent / Br2 / CCl4 2.1: 1.6 M nBuLi / diethyl ether; hexane / 0.5 h / -15 °C 2.2: 74 percent / diethyl ether; hexane / 0.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: NaOH / dimethylsulfoxide 2.1: 17.5 percent / Br2; KOAc / acetic acid / 3 h / 17 °C 3.1: n-BuLi / hexane; tetrahydrofuran / 2 h / -78 °C 3.2: 40 percent / hexane; tetrahydrofuran / -78 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | Stage #1: (4-(bis(4-(hexyloxy)phenyl)amino)benzyl)triphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Stage #2: 2,5-dipropoxybenzene-1,4-dicarbaldehyde In tetrahydrofuran Reflux; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.1% | With sodium methylate In ethanol for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97.6% | With sodium methylate In ethanol for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With sodium methylate In ethanol at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 100 °C / Inert atmosphere 2.1: n-butyllithium / diethyl ether; hexane / 2 h / 0 °C / Inert atmosphere 2.2: 1 h / 0 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22.2% | Stage #1: methyl-3-pyridylketone; 2,5-Dipropoxyterephthaldialdehyd With potassium hydroxide In ethanol at 20℃; Stage #2: With ammonium hydroxide In ethanol at 20℃; for 72h; | General procedure for the synthesis of the bis(3,2′:6′,3″-terpyridine) ligands General procedure: The appropriate 2,5-dialkyloxybenzene-1,4-dicarbaldehyde (1.0 eq) was placed at roomtemperature in EtOH (25-50 mL). 3-Acetylpyridine (5.0 eq) and crushed KOH (5.0 eq) werethen added. Immediate color change upon the addition of KOH from yellow to orange/redobserved. Then slow addition of aqueous NH3 solution (32%, 120 eq) followed and thereaction mixture was stirred at room temperature for 21-96 h. The fine precipitate thatformed was collected by filtration and washed with H2O (3 x 7-15 mL), followed by EtOH (3 x7-15 mL) and Et2O (2x 7-15 mL) and then dried in vacuo. The off-white/ light yellow crudesolid was recrystallized/ reprecipitated from a mixture of EtOH and CHCl3, MeOH and CHCl3or EtOH to give the desired bis(3,2′:6′,3″-terpyridine) ligand. |