632-80-4

Usage

Preparation

CAUTION: This reaction should be carried out in a well-ventilated hood.
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 (1?hr) 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 ? 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.

InChI:InChI=1/C8I4O3/c9-3-1-2(8(14)15-7(1)13)4(10)6(12)5(3)11

Upstream product

• 85-44-9 phthalic anhydride 
• 7664-93-9 sulfuric acid 
• 7553-56-2 iodine 

Downstream Products

• 101098-38-8 3,5-diiodo-4-(4,5,6,7-tetraiodo-1,3-dioxo-isoindolin-2-yl)-benzoic acid 
• 101439-62-7 4,5,6,7-tetraiodo-2-(2,4,5-trimethyl-phenyl)-isoindoline-1,3-dione 
• 105911-95-3 2-(4-amino-3,5-diiodo-benzenesulfonyl)-4,5,6,7-tetraiodo-isoindoline-1,3-dione 
• 100526-65-6 3,5-diiodo-4-(4,5,6,7-tetraiodo-1,3-dioxo-isoindolin-2-yl)-benzenesulfonic acid amide 
• 107917-78-2 4,5,6,7-tetraiodo-2-(2-methoxy-phenyl)-isoindoline-1,3-dione 
• 107916-15-4 4,5,6,7-tetraiodo-2-(4-methoxy-phenyl)-isoindoline-1,3-dione 
• 100913-87-9 4-(4,5,6,7-tetraiodo-1,3-dioxo-isoindolin-2-yl)-benzoic acid 
• 109258-44-8 N-(4-carboxy-phenyl)-3,4,5,6-tetraiodo-phthalamic acid 
• 99066-68-9 2,3,4,5-tetraiodo-benzoic acid-(2-hydroxy-ethyl ester) 
• 131516-70-6 2-(3,4-dimethyl-phenyl)-4,5,6,7-tetraiodo-isoindoline-1,3-dione 
• 100526-57-6 2-(2-chloro-phenyl)-4,5,6,7-tetraiodo-isoindoline-1,3-dione 
• 101081-04-3 2-(4-ethoxy-phenyl)-4,5,6,7-tetraiodo-isoindoline-1,3-dione 
• 861782-37-8 2,3,4,5-tetraiodo-6-p-toluoyl-benzoic acid 
• 131516-69-3 2-(2,4-dimethyl-phenyl)-4,5,6,7-tetraiodo-isoindoline-1,3-dione 

Relevant academic research and scientific papers

The i.r. and Raman spectra of tetraiodophthalic anhydride, potassium tetraiodophthalimide, tetraiodophthalimide and N-d-tetraiodophthalimide

The i.r. (4000-170 cm-1) and Raman (4000-40 cm-1) spectra were reported for polycrystalline tetraiodophthalic anhydride, potassium tetraiodophthalimide, tetraiodophthalimide and N-d-tetraiodophthalimide.The observed bands of C6I4(CO)2X, where X = O, N-, NH and ND, were tentatively assigned in comparison with those of C6H4(CO)2X, C6Cl4(CO)2X and C6Br4(CO)2X, on the basis of C2ν molecular symmetries.A normal coordinate analysis was carried out to confirm the vibrational assignment and obtain the force constants on an assumption of the valence force field.

Synthesis and Fluorescent Properties of Tetra-Biphenyl N-Substituted Phthalimides

A series of tetra(biphenyl-4-yl)phthalimide (TBPPI) derivatives with different N-substituents (n-butyl, phenyl, p-methyl phenyl, and p-acetyl phenyl moieties for compounds 7–10, respectively) were prepared to examine their fluorescent behavior under various conditions. The chemical structure of compound 7 has been successfully confirmed by single crystal X-ray diffraction analysis. The photoluminescence (PL) spectra in different ratios of CH2Cl2/EtOH mixture solutions revealed that compounds 7 and 8 exhibited both aggregation-induced emission (AIE) and aggregation-caused quenching (ACQ) behaviors, while compounds 9 and 10 displayed AIE and aggregation-induced emission enhancement (AIEE) properties, respectively.

Divinyl compounds and chromogenic recording-material prepared by using thereof

Disclosed herein are novel divinyl compounds represented by the formula (I): STR1 and a recording-material prepared by utilizing the divinyl compounds. The present divinyl compound is in itself almost colorless, extremely stable in the atmosphere and develops rapidly blakish color by a developer. The color image given by the present divinyl compound is excellect in light-resistance and moisture-resistance and the letters developed can be read by an optical letter-reading apparatus or a barcord reading apparatus.

Direct Aromatic Periodination

Periodic acid and iodine in concentrated sulfuric acid exhaustively iodinated unactivated aromatic substrates.Thus benzene, nitrobenzene, benzoic acid, chlorobenzene, phthalic anhydride, and toluene were all converted to their periodo derivatives.Benzonitrile was converted to pentaiodobenzamide.This direct method compared favorably with the only general periodination procedure available, a mercuration/iododemercuration sequence.Partially iodinated products were obtained under less vigorous conditions.Thus, triiodo derivatives were obtained from nitrobenzene, benzo-ic acid, and toluene; tetraiodo derivatives were obtained from benzene, chlorobenzene, and trifluorobenzene.