Product Name

  • Name

    Rafoxanide

  • EINECS 245-148-9
  • CAS No. 22662-39-1
  • Article Data9
  • CAS DataBase
  • Density 2.05 g/cm3
  • Solubility
  • Melting Point 169ºC
  • Formula C19H11Cl2I2NO3
  • Boiling Point 526.6 °C at 760 mmHg
  • Molecular Weight 626.016
  • Flash Point 272.3 °C
  • Transport Information
  • Appearance COA
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 22662-39-1 (Rafoxanide)
  • Hazard Symbols
  • Synonyms Salicylanilide,3'-chloro-4'-(p-chlorophenoxy)-3,5-diiodo- (8CI);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;Benzamide,N-[3-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3,5-diiodo-;
  • PSA 58.56000
  • LogP 7.02580

Synthetic route

2-hydroxy-3,5-diiodobenzoic acid chloride

2-hydroxy-3,5-diiodobenzoic acid chloride

4-amino-2-chlorophenyl-p-chlorophenyl ether

4-amino-2-chlorophenyl-p-chlorophenyl ether

rafoxanide
22662-39-1

rafoxanide

Conditions
ConditionsYield
at 20 - 40℃; for 1h;92.1%
3,4-dichloronitrobenzene
99-54-7

3,4-dichloronitrobenzene

rafoxanide
22662-39-1

rafoxanide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium hydroxide / N,N-dimethyl-formamide / 0.33 h / 35 °C
1.2: 5 h / Reflux
2.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 2 h / 55 °C / 150.01 Torr / Inert atmosphere
3.1: 1 h / 20 - 40 °C
View Scheme
2-chloro-4-nitrophenyl-p-chlorophenyl ether

2-chloro-4-nitrophenyl-p-chlorophenyl ether

rafoxanide
22662-39-1

rafoxanide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 2 h / 55 °C / 150.01 Torr / Inert atmosphere
2: 1 h / 20 - 40 °C
View Scheme
3-chloro-4-(4-chlorophenoxy)-benzenamine
24900-79-6

3-chloro-4-(4-chlorophenoxy)-benzenamine

3,5-diiodosalicylic acid
133-91-5

3,5-diiodosalicylic acid

rafoxanide
22662-39-1

rafoxanide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 14h;
rafoxanide
22662-39-1

rafoxanide

C19H13Cl2I2NO2

C19H13Cl2I2NO2

Conditions
ConditionsYield
Stage #1: rafoxanide With tris(pentafluorophenyl)borate; methylphenylsilane In toluene at 27 - 50℃; for 25h; Inert atmosphere; Sealed tube;
Stage #2: With tetrabutyl ammonium fluoride In toluene at 0 - 27℃; for 1h; Inert atmosphere; Sealed tube; chemoselective reaction;		93%
rafoxanide
22662-39-1

rafoxanide

3-[3-chloro-4-(4-chlorophenoxy)phenyl]-6,8-diiodo-2H-1,3-benzoxazine-2,4(3H)-dione

3-[3-chloro-4-(4-chlorophenoxy)phenyl]-6,8-diiodo-2H-1,3-benzoxazine-2,4(3H)-dione

Conditions
ConditionsYield
With 1,1'-carbonyldiimidazole In dimethyl sulfoxide at 20 - 22℃; for 0.5h; Cooling with ice;58%
rafoxanide
22662-39-1

rafoxanide

3-(3-chloro-4-(4-chlorophenoxy)phenyl)-6,8-diiodobenzo[e][1,2,3]oxathiazin-4(3H)-one-2,2-dioxide

3-(3-chloro-4-(4-chlorophenoxy)phenyl)-6,8-diiodobenzo[e][1,2,3]oxathiazin-4(3H)-one-2,2-dioxide

Conditions
ConditionsYield
Stage #1: rafoxanide With triethylamine In acetonitrile at 20℃; for 0.166667h;
Stage #2: With 1-(fluorosulfuryl)-2,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate In acetonitrile for 1h; Inert atmosphere;		56%
Stage #1: rafoxanide With triethylamine In acetonitrile at 20℃; for 0.166667h;
Stage #2: With 1-(fluorosulfuryl)-2,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate In acetonitrile for 1h;		55%

Rafoxanide Chemical Properties

Molecular Structure of Rafoxanide (CAS NO.22662-39-1):

IUPAC Name: N-[3-Chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3,5-diiodobenzamide
Canonical SMILES: C1=CC(=CC=C1OC2=C(C=C(C=C2)NC(=O)C3=CC(=CC(=C3O)I)I)Cl)Cl
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
Molecular Weight: 626.01048 [g/mol]
Molecular Formula: C19H11Cl2I2NO3
XLogP3-AA: 7
H-Bond Donor: 2
H-Bond Acceptor: 3
EINECS: 245-148-9
Product Categories: Rafoxanide
Appearance: slight yellowish brown injectable solution &white oral solution
Solubility in water: in oily solutes
Melting Point: 169 °C
storage temp.: 0-6 °C 
Index of Refraction: 1.752
Molar Refractivity: 124.75 cm3
Molar Volume: 305.3 cm3
Surface Tension: 67.7 dyne/cm
Density: 2.05 g/cm3
Flash Point: 272.3 °C
Enthalpy of Vaporization: 83.11 kJ/mol
Boiling Point: 526.6 °C at 760 mmHg
Vapour Pressure: 1.05E-11 mmHg at 25 °C
Classification Code: Agricultural Chemical; Anthelmintic; Anthelmintics; Anti-Infective Agents; Antinematodal agents; Antiparasitic Agents; Antiplatyhelmintic agents; Insect attractant, repellent and chemosterilant

Rafoxanide Uses

 Rafoxanide (CAS NO.22662-39-1) is a salicylanilide used as an antiparasitic agent.

Rafoxanide Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cattle LDLo unreported 80mg/kg (80mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Revue d'Elevage et de Medicine Veterinaire des Pays Tropicaux. Vol. 29, Pg. 31, 1976.

Rafoxanide Safety Profile

Safety Information of Rafoxanide (CAS NO.22662-39-1):
RTECS: VN7870000 

Rafoxanide Specification

 Rafoxanide (CAS NO.22662-39-1), its Synonyms are 3'-Chlor-4'-(4-chlorphenoxy)-3,5-diiodsalicylanilid ; 3'-Chloro-4'-(p-chlorophenoxy)-3,5-diiodosalicylanilide ; Benzamide, N-(3-chloro-4-(4-chlorophenoxy)phenyl)-2-hydroxy-3,5-diiodo- ; Bovanide ; Disalan ; Duofas ; Rafoxanidum .

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