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CAS No. : | 1719-83-1 | MDL No. : | MFCD00082228 |
Formula : | C12H8O6 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XLOGCGOPKPCECW-UHFFFAOYSA-N |
M.W : | 248.19 | Pubchem ID : | 102679 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
21.23 g | With pyridine; In 1-methyl-pyrrolidin-2-one; at 180℃; for 168h;Inert atmosphere; | To a stirred solution of <strong>[341-58-2]2,2'-bis(trifluoromethyl)benzidine</strong> (77.43 g, 241.8 mmole, 4 equivalents) in pyridine (30 ml) and N-methylpyrrolidinone (150 ml) was added portionwise a suspension of bicyclooctenetetracarboxylic dianhydride (15 g, 60.45 mmole) in 50 ml N- methylpyrrolidinone under nitrogen atmosphere. Resulting mixture heated at 180C for 7 days. The mixture was cooled down to ambient (0660) temperature, solvents distilled off using rotary evaporator, the residue extracted several times with hot mixture of 10% ethyl acetate and heptane to recover excess of <strong>[341-58-2]2,2'-bis(trifluoromethyl)benzidine</strong>. The residue was absorbed onto celite and subjected to chromatography on silica gel using gradient eluation with mixtures of ethyl acetate and hexanes. Fractions containing diimide-diamine combined, eluent evaporated, dried in vacuum to give 21.23 g of compound 5. 1H-NMR (DMSO-de, 500 MHz): 3.49 (s, 4H), 3.57 (br. S, 2H), 5.72 (s, 4H), 6.37 (t, 2H, J = 4 Hz), 6.78 (dd, 2H, J1 = 8Hz, J2 = 2 Hz), 6.95-6.97 (m, 4H), 7.43 (d, 2H, J = 8 Hz), 7.47 (dd, 2H, J1 = 8 Hz, J2 = 2 Hz), 7.61 (d, 2H, J = 2 Hz). 13C-NMR (DMSO-de, 125 MHz): 176.9, 149.6, 138.5, 133.5, 133.9, 132.6, 132.0, 131.6, 129.9, 129.0, 128.7, 128.2, 128.0, 125.7, 125.0, 124.2, 123.5, 122.8, 122.1 , (0661) 116.2, 110.6, 43.0, 34.5. 19F-NMR (DMSO-de, 470 MHz): 57.4, 57.1. (0662) MALDI TOF MS: 853.1654 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14.8 g; 8.75 g | With pyridine; In 1-methyl-pyrrolidin-2-one; at 180℃; for 144h;Inert atmosphere; | A mixture of <strong>[341-58-2]2,2'-bis(trifluoromethyl)benzidine</strong> (77.43 g, 241.8 mmole, 2 equivalents), pyridine (20 ml), N-methylpyrrolidinone (100 ml) and bicyclooctenetetracarboxylic dianhydride (15 g, 60.45 mmole) was stirred with heating at 180C under nitrogen atmosphere for 6 days. The mixture was cooled down to ambient temperature, solvents distilled off using rotary evaporator, the residue absorbed onto celite and subjected to chromatography on silica gel using gradient eluation with mixtures of ethyl acetate and hexanes. Fractions containing diimide-diamine combined, eluent evaporated, dried in vacuum to give 14.8 g of compound 5. (0666) Fractions containing tetraimide-diamine combined, eluent evaporated, dried in vacuum to give 8.75 g of compound 7. Compound 7: 1 H-NMR (DMSO-de, 500 MHz): 3.50 (s, 4H), 3.51 (s, 4H), 3.58 (br. S, 4H), 5.72 (s, 4H), 6.38 (t, 4H, J = 4 Hz), 6.78 (dd, 2H, J1 = 8 Hz, J2 = 2 Hz), 6.95-6.97 (0667) (m, 4H), 7.43 (d, 2H, J = 8 Hz), 7.47 (dd, 2H, J1 = 8 Hz, J2 = 2 Hz), 7.56- 7.61 (m, 6H), 7.72 (s, 2H). 13C-NMR (DMSO-de, 125 MHz): 176.92, 176.86, 149.6, 138.6, 136.1 , 133.9, 133.0, 132.9, 132.6, 132.0, 131 .7, 130.2, 129.9, 128.2, 128.0, 125.7, 1245.0, 124.8, 124.5, 124.4, 124.2, 123.5, 122.8, 122.6, 122.1 , 1 16.2, 1 10.67, 1 10.62, 48.9, 43.00, 42.96, (0668) 34.5. 19F-NMR (DMSO-de, 470 MHz): 57.4, 57.2, 57.1 . MALDI TOF MS: 1385.2532 (MH+). |
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