| Identification | More | [Name]
5-Amino-2,4,6-triiodoisophthalic acid | [CAS]
35453-19-1 | [Synonyms]
5-AMINO-2,4,6-IODOISOPHTHALIC ACID
5-AMINO-2,4,6-TRIIODOBENZENE-1,3-DICARBOXYLIC ACID
5-AMINO-2,4,6-TRIIODOISOPHTHALIC ACID
ATIPA
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%
5-amino-2,4,6-triiodo isophthalic aicd
Amino-2,4,6-triiodoisophthalicAcid
5-AMINO-2,4,6-TRIIODO-1,3-BENZENEDICARBOXYLIC ACID
5-Amino-2,4,6-triiodo
5-amino-2,4,6-triiodoisophthalic acid (intermediate of iohexol)
2,4,6-Triodo Isophthalic Acid (ATIPA)
2,4,6-Triiodo-5-aminoisophthalic acid | [EINECS(EC#)]
252-575-4 | [Molecular Formula]
C8H4I3NO4 | [MDL Number]
MFCD00190167 | [Molecular Weight]
558.84 | [MOL File]
35453-19-1.mol |
| Chemical Properties | Back Directory | [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 | [form ]
neat | [pka]
0.83±0.10(Predicted) | [color ]
Beige | [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) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R42/43:May cause sensitization by inhalation and skin contact . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3
| [HS Code ]
29224995 |
| Hazard Information | Back Directory | [Chemical Properties]
Beige Solid | [Uses]
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, |
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