| Identification | Back Directory | [Name]
TETRAIODOPHTHALIC ANHYDRIDE | [CAS]
632-80-4 | [Synonyms]
TETRAIODOPHTHALIC ANHYDRIDE
Phthalicanhydride,tetraiodo-
3,4,5,6-Tetraiodophthalic anhydride
4,5,6,7-tetraiodo-3-isobenzofurandione
4,5,6,7-tetraiodo-1,3-Isobenzofurandione
4,5,6,7-tetraiodoisobenzofuran-1,3-dione
4,5,6,7-tetraiodo-2-benzofuran-1,3-dione
1,3-Isobenzofurandione,4,5,6,7-tetraiodo-
4,5,6,7-tetraiodoisobenzofuran-1,3-quinone | [Molecular Formula]
C8I4O3 | [MDL Number]
MFCD00083098 | [MOL File]
632-80-4.mol | [Molecular Weight]
651.7 |
| Chemical Properties | Back Directory | [Melting point ]
327.5°C | [Boiling point ]
584.2±50.0 °C(Predicted) | [density ]
3.1538 (estimate) | [storage temp. ]
2-8°C, protect from light | [Appearance]
Light yellow to green yellow Solid | [InChI]
InChI=1S/C8I4O3/c9-3-1-2(8(14)15-7(1)13)4(10)6(12)5(3)11 | [InChIKey]
UHIMKEGZFOQVHV-UHFFFAOYSA-N | [SMILES]
C1(=O)C2=C(C(I)=C(I)C(I)=C2I)C(=O)O1 | [EPA Substance Registry System]
1,3-Isobenzofurandione, 4,5,6,7-tetraiodo- (632-80-4) |
| Questions And Answer(Q&A) | Back Directory | [preparation]
CAUTION: This reaction should be carried out in a well-ventilated hood. <br/>To a flask equipped with a mechanical stirrer and an air condenser topped with a tube leading to a gas trap is added 74.0 gm (0.5 mole) of phthalic anhydride, 162 gm (0.638 mole) of iodine, and 300 ml of 60% fuming sulfuric acid (1.84 moles). The flask is gently heated to 45-50°C, at which point the reaction commences. If the reaction becomes too vigorous it may be necessary to use a ice bath to lower the temperature to 40-50°C. The reaction mixture is eventually (4 hr) heated up to 65°C until all visible reaction has ceased. The reaction mixture is cooled to 10-20°C and an additional 81.0 gm (0.318 mole) of iodine is added and the reaction again slowly heated up to 65°C (1½hr) and again when the reaction ceases it is cooled. Another 27.0 gm (0.107 mole) of iodine is added and the reaction is again heated up to 65°C (1 hr). The flask is heated with an oil bath to a bath temperature of 175-180°C, at which point the sulfur trioxide and iodine fumes evolve. After about 2 hr, when the gaseous evolution ceases, the flask is cooled to about 60°C and the mxiture then poured into a beaker of water. The contents are allowed to stand overnight at room temperature, filtered, washed with two 50-ml portions of cone, sulfuric acid and then with three 100 ml portions of water. The light yellow crystalline product is put into a beaker containing 1 liter of water and 10 gm of sodium bisulfite in order to remove the last traces of free iodine. The aqueous solution is decanted, the product washed five times with ½ liter of water, washed twice with 100 ml of acetone and then dried at 60°C to afford 260-268 gm (80-82%), m.p. 327-328°C.
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