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

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 Information

Hazard Codes 

Xn

Risk Statements 

42/43

Safety Statements 

26-36/37/39

WGK Germany 

3

HS Code 

29224995

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-Amino-2,4,6-triiodoisophthalic acid Usage And Synthesis

Chemical Properties

Beige Solid

Uses

5-Amino-2,4,6-triiodoisophthalic Acid (Iohexol EP Impurity K) is an intermediate for nonionic iodinated X-ray contrast agents.

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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