N-[3-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3,5-diiodobenzamide

• ChemBase ID: 157399
• Molecular Formular: C19H11Cl2I2NO3
• Molecular Mass: 626.01048
• Monoisotopic Mass: 624.82054458
• SMILES: c1cc(ccc1Oc1ccc(cc1Cl)NC(=O)c1cc(cc(c1O)I)I)Cl
• Canonical SMILES: Clc1ccc(cc1)Oc1ccc(cc1Cl)NC(=O)c1cc(I)cc(c1O)I
• InChI: InChI=1S/C19H11Cl2I2NO3/c20-10-1-4-13(5-2-10)27-17-6-3-12(9-15(17)21)24-19(26)14-7-11(22)8-16(23)18(14)25/h1-9,25H,(H,24,26)
• InChIKey: NEMNPWINWMHUMR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[3-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3,5-diiodobenzamide
• IUPAC Traditional name: rafoxanide
• Synonyms: N-[3-Chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3,5-diiodobenzamide; 3,5-Diiodo-3'-chloro-4'-(p-chlorophenoxy)salicylanilide; 3,5-Diodo-3'-chloro-4'-(p-chlorophenoxy)salicylanilide; 3'-Chloro-4'-(4-chlorophenoxy)-3,5-diiodosalicylanilide; 3'-Chloro-4'-(p-chlorophenoxy)-3,5-diiodosalicylanilide; Disalan; NSC 355278; Ranide; Rafoxanide; 3′-Chloro-4′-(4-chlorophenoxy)-3,5-diiodosalicylanilide; Rafoxanide; 3′-氯-4′-(4-氯苯氧基)-3,5-二碘水杨酰苯胺; 雷复尼特

Database IDs

• CAS Number: 22662-39-1
• EC Number: 245-148-9
• MDL Number: MFCD00682899
• PubChem SID: 24860810; 162251536
• PubChem CID: 31475

CALCULATED PROPERTIES

• Acid pKa: 6.4124484
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 7.278168
• LogD (pH = 7.4): 6.3328013
• Log P: 7.327831
• Molar Refractivity: 126.1478 cm^3
• Polarizability: 48.178898 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Ethyl Aceate
• Apperance: White to Off-White Solid
• Melting Point: 165-167°C

Safety Information

• Storage Condition: Refrigerator
• RTECS: VN7870000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Grade: PESTANAL®, analytical standard
• Empirical Formula (Hill Notation): C19H11Cl2I2NO3

DETAILS

Sigma Aldrich - 34042

Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

Toronto Research Chemicals - R073500

Rafoxanide is a thyroid hormone receptor.

REFERENCES

• Bernal, J., et al.: Vitam. Horm., 71, 95 (2005)
• Fujimoto, N., et al.: J. Endocrinol., 181, 77 (2005)
• Hamers, T., et al.: Toxicol. Sci., 92, 157 (2005)
• Jugan, M., et al.: Biochem. Pharmacol., 79, 939 (2005)