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| | 5-Amino-2,4,6-triiodoisophthalic acid Basic information |
| Product Name: | 5-Amino-2,4,6-triiodoisophthalic acid | | Synonyms: | ATIPA;5-AMINO-2,4,6-IODOISOPHTHALIC ACID;5-AMINO-2,4,6-TRIIODOBENZENE-1,3-DICARBOXYLIC ACID;5-AMINO-2,4,6-TRIIODOISOPHTHALIC ACID;5-Amino-2,4,6-Triod-Isophthalic Acid;Aminoiodoisophthalicacid;5-Amino-2,4,6-triiodoisophtalic acid;5-AMINO-2,4,6-TRIIODOISOPHTHALIC ACID, 9 5% | | CAS: | 35453-19-1 | | MF: | C8H4I3NO4 | | MW: | 558.84 | | EINECS: | 252-575-4 | | Product Categories: | Intermediate of Ioversol;Pyrimidines;Amines;Aromatics;Sulfur & Selenium Compounds;Aromatic Amino Acids;Peptide Synthesis;Unnatural Amino Acid Derivatives;Organic acids;(intermediate of iohexol) | | Mol File: | 35453-19-1.mol |  |
| | 5-Amino-2,4,6-triiodoisophthalic acid Chemical Properties |
| Melting point | 265-270 °C (lit.) | | Boiling point | 539.4±50.0 °C(Predicted) | | density | 3.053±0.06 g/cm3(Predicted) | | vapor pressure | 10hPa at 20℃ | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | DMSO, Methanol | | pka | 0.83±0.10(Predicted) | | color | Beige | | Major Application | peptide synthesis | | InChI | InChI=1S/C8H4I3NO4/c9-3-1(7(13)14)4(10)6(12)5(11)2(3)8(15)16/h12H2,(H,13,14)(H,15,16) | | InChIKey | JEZJSNULLBSYHV-UHFFFAOYSA-N | | SMILES | C1(C(O)=O)=C(I)C(N)=C(I)C(C(O)=O)=C1I | | CAS DataBase Reference | 35453-19-1(CAS DataBase Reference) |
| Hazard Codes | Xn | | Risk Statements | 42/43 | | Safety Statements | 26-36/37/39 | | WGK Germany | 3 | | HS Code | 29224995 | | Storage Class | 11 - Combustible Solids |
| | 5-Amino-2,4,6-triiodoisophthalic acid Usage And Synthesis |
| Chemical Properties | Beige Solid | | Uses | Intermediate for nonionic iodinated X-ray contrast agents. | | Uses | 5-Amino-2,4,6-triiodoisophthalic Acid (Iohexol EP Impurity K) is an intermediate for nonionic iodinated X-ray contrast agents. | | reaction suitability | reaction type: solution phase peptide synthesis | | Synthesis | Example 1 Synthesis of 5-amino-2,4,6-triiodoisophthalic acid
In a 250 mL three-necked round-bottomed flask equipped with a thermometer, condenser, and magnetic stirrer, 5-aminoisophthalic acid (I) (3.86 g, 27.6 mmol) was dissolved in water (129.42 g), and pH was adjusted with 96% sulfuric acid (2 mL, 35.3 mmol) to 1. Subsequently, solid iodine (8.42 g, 33.2 mmol) was added, and the mixture was heated to 72 °C in an oil bath. An 18.65% (w/v) aqueous iodic acid solution (20 mL, 21.2 mmol) was slowly added via syringe pump over 5.2 h (addition rate 3.8 mL/h). After continuing the reaction at 72 °C for 1 h (total reaction time 6.2 h), the reaction mixture was cooled to room temperature and filtered. The resulting solid was washed with water and dried to afford 5-amino-2,4,6-triiodoisophthalic acid (II) (12.74 g, 22.8 mmol) as a pale pink solid in 82.6% yield. The product was analyzed by HPLC and compared with the standard to confirm that it meets the analytical specification of industrially produced 5-amino-2,4,6-triiodoisophthalic acid. | | References | [1] Patent: EP2243767, 2010, A1. Location in patent: Page/Page column 8
[2] Organic and Biomolecular Chemistry, 2006, vol. 4, # 19, p. 3611 - 3617
[3] Journal of Organic Chemistry, 1994, vol. 59, # 6, p. 1344 - 1350
[4] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 11, p. 3545 - 3554
[5] Patent: US2820814, 1955, |
| | 5-Amino-2,4,6-triiodoisophthalic acid Preparation Products And Raw materials |
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