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CAS No. : | 42824-53-3 | MDL No. : | MFCD07644571 |
Formula : | C28H18O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZSLCDSMUKOZRPQ-UHFFFAOYSA-N |
M.W : | 418.44 | Pubchem ID : | 12149442 |
Synonyms : |
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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 |
---|---|---|
90% | With sodium hydroxide; In 1,4-dioxane; water; at 90℃; for 6h; | NaOH (0.8g, 20mmol) was added to a solution of compound 6 (250 mg, 0.56 mmol) in 1,4-dioxane/water(5:1, 30mL). The mixture was stirred vigorously and heated to reflux at 90 C for 6 h. After the starting material wascompletely consumed, the reaction was terminated. Then the 1,4-dioxane was removed under reduced pressure andthe suspension diluted by water and adjusted pH to 7 with HCl. The light yellow precipitation thus formed wasfiltered and dried to give compound A-1 (yiled:90%).1H NMR (400MHz, DMSO-d6) δ (ppm): 13.18 (s, 2H), 8.23 (d,J =7.9 Hz, 4H), 7.62 (d, J =7.9 Hz, 4H), 7.56 (m, 4H), 7.46 (m, 4H). |
90% | at 90℃; for 6h;Alkaline conditions; | NaOH (1.6 g, 40 mmol) was added to a solution of compound 4(580 mg, 1.3 mmol) in 1,4-dioxane and water (5:1, 60 mL). The mixturewas stirred vigorously and heated to refilux at 90 C for 6 h. The startingmaterial 4 was monitored with TLC, and the reaction was terminatedafter the consumption of compound 4. Then the 1,4-dioxane wasremoved under reduced pressure, and the suspension was diluted bywater and adjusted the pH to ca. 7 with HCl. The light yellow precipitationwas filtered and dried to give compound 5 (yield: 90%). 1H NMR(400 MHz, D2O) (ppm): 7.99 (d, J 8.1 Hz, 4H), 7.56 (dd, J 6.8, 3.3Hz, 4H), 7.29 (dd, J 6.9, 3.2 Hz, 4H), 7.26 (d, J 8.1 Hz, 4H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In a 35 ml vial, Zn(NO3)26H2O (237 mg, 0.80 mmol) and DMA (15 ml) werecombined. The reaction was treated with ultrasonification for5 min, followed by addition of 4,4'-(anthracene-9,10-diyl)dibenzoicacid (200 mg, 0.48 mmol). Trifluoroacetic acid (245 ml)was added as a modulator, and the vial was sealed and subjected to ultrasonification for 30 min. The vial was thenplaced in a pre-heated Pie block and held at 393 K overnight.The solution was cooled and the resulting crystals wereisolated by centrifugation, followed by washing with dichloromethane,and finally drying. Crystals of [Zn(abd)-(DMA)2]DMA}n were isolated manually from a mixture thatalso contained unidentified amorphous and microcrystallinespecies. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With water; potassium hydroxide; In tetrahydrofuran; for 24h;Reflux; | KOH pellets (54.68 g, 0.976 mols), water (65 ml), and THF(70 ml) were combined in a 250 ml RBF. Diethyl 4,40-(anthracene-9,10-diyl)dibenzoate (1.47 g, 3.30 mmol) was addedto this mixture, followed by heating under reflux for 24 h.Upon cooling, the solution was diluted slowly with 12.1 MHCl(aq) until the solution acidity was approximately pH = 1.After cooling in an ice bath, the resulting precipitate wasfiltered off, rinsed with additional deionized water (250 ml),followed by drying in an oven to give the product as an offwhitesolid that was consistent with data reported in theliterature (yield 1.24 g, 95%) (Hauptvogel et al., 2011). 1HNMR (400 MHz, DMSO-d6): δ 13.13 (br s, 2H), 8.22 (d, J =8.2 Hz, 4H), 7.62 (d, J = 8.2 Hz, 4H), 7.55 (dd, J = 6.9, 3.2 Hz,4H), 7.46 (dd, J = 6.9, 3.3 Hz, 4H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In a 35 ml vial, Zn(NO3)26H2O(237 mg, 0.80 mmol) and DMF (15 ml) were combined. The reaction was subjected to ultrasonification for 5 min, followedby addition of <strong>[42824-53-3]4,4'-(anthracene-9,10-diyl)dibenzoic acid</strong>(200 mg, 0.48 mmol). Trifluoroacetic acid (245 ml) was addedas a modulator, and the vial was sealed and subjected toultrasonification for an additional 30 min. The vial was thenplaced in a pre-heated Pie block and held at 393 K overnight.The solution was cooled and the resulting solid were isolatedby centrifugation, followed by washing with dichloromethane,and drying. Crystals of [Zn(abd)(DMF)2]n were isolatedmanually from a mixture that also contained unidentifiedamorphous and microcrystalline species. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70.5% | In water; at 180℃; for 72h;Autoclave; High pressure; | A mixture of Cd(NO3)24H2O (0.123 g, 0.4 mmol), 9,10-anthracene dibenzoic acid (0.084 g, 0.2 mmol), pyridine-3-carboxylic acid (0.012 g, 0.1 mmol), pyridine-4-carboxylicacid (0.012 g, 0.1 mmol), and H2O (15.0 mL) in a 25mLTeflon-lined autoclave was heated at 180 C for 3 days. Afterthe mixture was cooled slowly to ambient temperature, yellowblock crystals were obtained. The crystals were filtered,washed with distilled water and dried at ambient temperature.The yield of the reaction, determined from the weightof the solvent-free material (0.132 g), is 70.5% based on9,10-anthracene dibenzoic acid. Anal. Calcd (%) for C68H40N2O12Cd3: C, 57.75; H, 2.85; N, 1.98. Found: C, 57.71;H, 2.82; N, 2.02. IR data (KBr pellet, t/cm1): 3446(s),3116(w), 2363(w), 1568(s), 1483(s), 1402(s), 1375(m),1072(m), 854(m), 773(m), 668(m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 20℃; for 24h; | Compound 5 (330 mg, 0.8 mmol) and the compound 3 (610 mg,0.16 mmol) were dissolved in 50.0 mL dry THF, then HOBT (220 mg,1.6 mmol), DCC (420 mg, 1.7 mmol) were added. The mixture wasstirred at room temperature for 24 h. The solvent was removed in vacuum,and residue was subjected to a column chromatography on silicagel with DCM: EA: MeOH 1:1: 0.1 as the elution, white solid wascollected as the target product (220 mg, yield, 24.0%).1H NMR (400MHz, CDCl3) (ppm): 8.02 (d, J 8.2 Hz, 4H), 7.65-7.62 (m, 4H), 7.56(d, J 8.2 Hz, 4H), 7.35-7.27 (m, 4H), 6.77 (s, 2H), 3.92 (s, 12H), 3.80(t, J 6.2 Hz, 12H), 3.68 (s, 18H), 2.62 (t, J 6.2 Hz, 12H). HRMS(ESI): m/z calcd for C60H72N2O20Na [MNa], 1163.4571, found[MNa], 1163.4547. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52.8% | In water; at 120℃; for 48h;Autoclave; | A mixture of H2ADBA (20.9 mg, 0.05 mmol) and Zn(Ac)22H2O (11.0mg, 0.05 mmol) was dissolved in 6 mL of mixed solvent of DMF/H2O/CH3OH (1:1:1, v/v/v). The mixture was sealed in a 10 mL Teflon-lined stainless-steel autoclave and heated at 120 C for 48 h. After cooling to room temperature at a rate of 5 C h1, yellow block crystals were collected, washed with DMF and H2O, and dried in air. Yield: 52.8% (based on H2ADBA). Elemental analysis (EA) calcd. for Zn-ADBA (C61H52N2O9Zn, Mr 1022.42): C 71.65%, H 5.12%, N 2.73%; Found: C71.21%, H, 4.99%, N 2.58%. IR (KBr, cm1): 3424(m), 3064(m), 2438(w), 1600(vs), 1523(vs), 1379(vs), 1172(m), 1016(m) 837(m),749(m), 660(m). |