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CAS No. : | 652-12-0 | MDL No. : | MFCD00039697 |
Formula : | C8F4O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BJDDKZDZTHIIJB-UHFFFAOYSA-N |
M.W : | 220.08 | Pubchem ID : | 69545 |
Synonyms : |
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Chemical Name : | Tetrafluorophthalic anhydride |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | 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 |
---|---|---|
74%. | In chloroform; | Synthesis Example 2 Synthesis of (S)-2-(1-phenylethyl)-4,5,6,7-tetrafluoro-1H-isoindole-1,3-dione (Compound No.17) 220 mg of tetrafluorophthalic anhydride and 121 mg of (S)-α-methylbenzylamine were charged in an egg-plant type flask of 50 ml, followed by stirring under heating at a temperature of 180 C. for 2 hours. After cooled, the reaction product was dissolved in chloroform, purified by silica gel column chromatography (eluent; methylene chloride:methanol=30:1 v/v), recrystallized from a mixed solvent of n-hexane-ethyl acetate, to obtain 240 mg of the desired product as colorless needles. Yield: 74%. m.p. 95-96 C.; [α]20D=-42.2 (C=0.386 AcOEt); MS(EI+) 323(M)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65%. | In chloroform; | Synthesis Example 1 Synthesis of (R)-2-(1-phenylethyl)-4,5,6,7-tetrafluoro-1H-isoindole-1,3-dione (Compound No.18) 220 mg of tetrafluorophthalic anhydride and 121 mg of (R)-α-methylbenzylamine were charged in an egg-plant type flask of 50 ml, followed by stirring under heating at a temperature of 180 C. for 2 hours. After cooled, the reaction product was dissolved in chloroform, purified by silica gel column chromatography (eluent; methylene chloride:methanol=30:1 v/v), recrystallized from a mixed solvent of n-hexane-ethyl acetate, to obtain 210 mg of the desired product as colorless needles. Yield: 65%. m.p. 95.5-96 C.; [α]20D=41.5 (C=0.348 AcOEt); MS(EI+) 323(M)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Example 1 Synthesis of 1,2,3,4,8,9,10,11-octafluoro-5,7,12,14-tetrahydroxypentacen-6,13-dione (3) <strong>[652-12-0]4,5,6,7-tetrafluoroisobenzofuran-1,3-dione</strong> (2) (5.75 g, 26.1 mmol), 5,6,7,8-tetrafluoro-9,10-dihydroxy-2,3-dihydroanthracen-1,4-dione (1) (9.84 g, 31.3 mmol), aluminum chloride (1.53 g, 11.5 mmol), and sodium chloride (10.0 g, 171 mmol) were added to a 200-mL SUS autoclave and heated for 1 hour at 280 C. After completion of the reaction, cooling to room temperature was carried out and the reaction mixture was then introduced into dilute hydrochloric acid and was stirred for 1 hour at 100 C. The mixture was then filtered and the residue was washed with methanol, dichloromethane, toluene, and ether in the sequence given. The resulting solid was vacuum dried to give 11.5 g (85% yield) 1,2,3,4,8,9,10,11-octafluoro-5,7,12,14-tetrahydroxypentacen-6,13-dione (3). melting point: 300 C. (decomposition) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 5,5-dimethyl-1,3-cyclohexadiene; | EXAMPLE 9 350 g of crude tetrafluorophthalic acid are heated with 800 g of xylene using a water separator, until no further water passes(5 hours). The resulting suspension is allowed to cool and the anhydride which has precipitated is filtered off. 301 g of tetrafluorophthalic anhydride are obtained, the mother liquor, which still contains about 5 g of tetrafluorophthalic anhydride, being used for further dehydrations. | |
EXAMPLE 3 Synthesis of tetrafluorophthalic anhydride The amount of 20.0 g of tetrafluorophthalic acid (0.0840 mol) was dissolved and left standing for dehydration at temperatures of 160 to 170 C. for three hours. Thereafter, the dehydrated acid was left standing for sublimation at temperatures of 170 to 180 C. under a vacuum (5 Torrs). Consequently, there was obtained 18.0 g of tetrafluorophthalic anhydride. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With acetic acid; at 120℃; for 4h; | General procedure: To a 10 mL round-bottomed flask equipped with a stirring bar and refluxcondenser was charged the appropriate mono-, di-, or tetrafluorophthalicanhydride 1 (0.5-4 mmol, 1 equiv). Glacial AcOH (0.5-4mL) was then added, and to the stirred solution was added the appropriateamine 2 (0.55-4.4 mmol, 1.1 equiv). The solution was heated at120 C and allowed to stir at this temperature for 4-12 h, then theflask was allowed to cool to rt. The reaction mixture was taken in aseparatory funnel, treated with sat. aq Na2CO3 (4-30 mL), and extractedwith EtOAc (2 × 2.5-15 mL). The combined organic phases weredried (anhyd MgSO4) and concentrated. The crude product was purifiedby recrystallization or flash chromatography using silica gel withhexanes/EtOAc as eluents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With acetic acid; for 4h;Reflux; | A mixture of 4,5,6,7- tetrafluorophthalic anhydride 1 (4.4 g, 20mmol, 1.0 equiv.) and aniline (2.2 g, 24 mmol, 1.2 equiv.) in glacial acetic acid (20 mL) was refluxed for 4 h. The mixture was cooled to roomtemperature. The solids were filtered from the solution, and product 2 (4.8 g, 81%) was obtained as white crystal without further purification. M.p.: 199-200 C. 1H NMR (500 MHz, CDCl3): δ 7.52 (t, J = 7.6 Hz, 2H),7.45 (t, J = 7.4 Hz, 1H), 7.41-7.34 (m, 2H). 13C NMR (126 MHz, CDCl3): δ 161.4, 146.4 (m), 144.9 (m), 144.2 (m), 142.5 (m), 130.5, 129.4,128.9, 126.4, 113.5. High-resolution mass spectrometry (m/z): [M +H]+ calculated for C14H6F4NO2, 296.0329, found 296.0335. |
64% | With acetic acid; at 120℃; for 4h; | General procedure: To a 10 mL round-bottomed flask equipped with a stirring bar and refluxcondenser was charged the appropriate mono-, di-, or tetrafluorophthalicanhydride 1 (0.5-4 mmol, 1 equiv). Glacial AcOH (0.5-4mL) was then added, and to the stirred solution was added the appropriateamine 2 (0.55-4.4 mmol, 1.1 equiv). The solution was heated at120 C and allowed to stir at this temperature for 4-12 h, then theflask was allowed to cool to rt. The reaction mixture was taken in aseparatory funnel, treated with sat. aq Na2CO3 (4-30 mL), and extractedwith EtOAc (2 × 2.5-15 mL). The combined organic phases weredried (anhyd MgSO4) and concentrated. The crude product was purifiedby recrystallization or flash chromatography using silica gel withhexanes/EtOAc as eluents. |