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50-65-7

Basic Information
CAS No.: 50-65-7
Name: Niclosamide
Article Data: 24
Cas Database
Molecular Structure:
Molecular Structure of 50-65-7 (Niclosamide)
Formula: C13H8Cl2N2O4
Molecular Weight: 327.124
Synonyms: Fenasal;Vermitid;2,5-Dichlor-4-nitro-salizylsaeureanilid [German];Chemagro 2353;N-(2-Chloro-4-nitrophenyl)-5-chlorosalicylamide;Nitrophenyl chlorsalicylamide;Benzamide, 5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxy-;HL 2447;Salicylanilide, 2,5-dichloro-4-nitro-, compd. with 2-aminoethanol (1:1);2, 5-Dichlor-4-nitro-salizylsaeureanilid;Mansonil;Benzamide, 5-chloro-N- (2-chloro-4-nitrophenyl)-2-hydroxy-;Lintex;Benzamide, 5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxy-, compd with 2-aminoethanol (1:1);Vermitin;5-Chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide;Prestwick_354;Phenasal;2,5-Dichloro-4-nitrosalicylanilide;5,2-Dichloro-4-nitrosalicylanilide, ethanolamine salt;Bayer 2353;Phenasal ethanolamine salt;5-Chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide compd with 2-aminoethanol;Niclosamide [BSI:ISO];2, 5-Dichloro-4-nitrosalicylanilide;Sulqui;Niclosamide-(2-hydroxyethyl)ammonium;WR 46234;Radeverm;SR 73;B 2353;2,5-Dichloro-4-nitrosalicyloylanilide ethanolamine salt;Benzamide,5-chloro-N-(2-chloro-4- nitrophenyl)-2-hydroxy-;Niclocide (TN);1420-04-8;Helmiantin;
EINECS: 200-056-8
Density: 1.616 g/cm3
Melting Point: 225-230oC
Boiling Point: 413.905 °C at 760 mmHg
Flash Point: 204.122 °C
Solubility: 13.32mg/L(25 oC)
Appearance: white to yellowish odourless crystalline powder
Hazard Symbols: N/A
Risk Codes: 50
Safety: 29
Transport Information: UN 3077 9/PG 3
PSA: 95.15000
LogP: 4.45570
Synthetic route
321-14-2

5-chloro-2-hydroxybenzoic acid

121-87-9

2-Chloro-4-nitroaniline

50-65-7

Niclosamide

Conditions
ConditionsYield
With phosphorus trichloride In chlorobenzene at 135℃; for 3h; Concentration; Solvent;68.7%
With thionyl chloride In 5,5-dimethyl-1,3-cyclohexadiene at 78℃; for 6.1h; Temperature; Reflux;
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;
With phosphorus trichloride In 5,5-dimethyl-1,3-cyclohexadiene for 4h; Reflux;
6626-92-2

5-chloro-N-(2-chlorophenyl)-2-hydroxybenzamide

50-65-7

Niclosamide

Conditions
ConditionsYield
With 3-(ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium bis(trifluoromethanesulfonyl)imide at 20℃; for 5h; Ionic liquid;48%

niclosamide-2-O-glucuronide

50-65-7

Niclosamide

Conditions
ConditionsYield
With β-glucuronidase for 0.333333h;
15216-81-6

5-chloro-2-hydroxybenzoyl chloride

121-87-9

2-Chloro-4-nitroaniline

50-65-7

Niclosamide

Conditions
ConditionsYield
With dmap; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; dichloromethane
In dichloromethane at 25℃; Inert atmosphere;
321-14-2

5-chloro-2-hydroxybenzoic acid

50-65-7

Niclosamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 12 h / 25 °C
2: dichloromethane / 25 °C / Inert atmosphere
View Scheme
50-65-7

Niclosamide

79-44-7

N,N-Dimethylcarbamoyl chloride

1187819-29-9

4-chloro-2-((2-chloro-4-nitrophenyl)carbamoyl)phenyl dimethylcarbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran Reflux;100%
With pyridine; dmap Reflux;
50-65-7

Niclosamide

N-(4-amino-2-chloro-phenyl)-5-chloro-2-hydroxy-benzamide

Conditions
ConditionsYield
With ammonium chloride; zinc In methanol at 0 - 20℃; for 16h;100%
With ammonium chloride; zinc In methanol; water at 0 - 20℃; for 16h; Inert atmosphere;100%
With palladium 10% on activated carbon; hydrogen In methanol; ethyl acetate at 20℃; under 3000.3 Torr; for 3h;99.9%
50-65-7

Niclosamide

762-04-9

phosphonic acid diethyl ester

4-chloro-2-((2-chloro-4-nitrophenyl)carbamoyl)phenyl diethyl phosphate

Conditions
ConditionsYield
With dmap; N-ethyl-N,N-diisopropylamine In tetrachloromethane; N,N-dimethyl-formamide at 0℃; for 2h;96.2%
110-91-8

morpholine

50-00-0

formaldehyd

50-65-7

Niclosamide

860032-69-5

5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxy-3-(morpholinomethyl)benzamide

Conditions
ConditionsYield
In ethanol; water for 2h; Mannich reaction; Heating;95%
In ethanol; water Mannich reaction; Reflux;95%
50-65-7

Niclosamide

74-88-4

methyl iodide

32060-31-4

5-chloro-N-(2-chloro-4-nitrophenyl)-2-methoxybenzamide

Conditions
ConditionsYield
With potassium carbonate In acetone for 15h; Reflux; Sealed tube; Inert atmosphere;94%
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    Chemical Name: Niclosamide CAS No.: 50-65-7 Molecular Fomula:C13H8Cl2N2O4 Chemical Structure: Molecular weight: 327.12 Appearance: White or light yellow Crystalline Powder Assay:99.0 %min Appearance:Yellowish fine crystals Storage:Store in cool

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    Name:niclosamide CAS NO: 50-65-7 Grade:Medical scientific research and export Molecular formula:C13H8Cl2N2O4 Molecular weight:327.1196 Product Quality 12 years of chemical raw materials Mature operation of the industry System stability Da

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Chemistry

IUPAC Name: 5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide 
Empirical Formula: C13H8Cl2N2O4
Molecular Weight: 327.1196g/mol
EINECS: 200-056-8 
Structure of Niclosamide (CAS NO.50-65-7):

Index of Refraction: 1.709
Molar Refractivity: 79.04 cm3
Molar Volume: 202.4 cm3
Polarizability: 31.33×10-24cm3
Surface Tension: 71.6 dyne/cm
Density: 1.615 g/cm3
Flash Point: 210.5 °C
Enthalpy of Vaporization: 70.52 kJ/mol
Boiling Point: 424.5 °C at 760 mmHg
Vapour Pressure: 8.35E-08 mmHg at 25°C 
Product Categories: Veterinaries;API's 
Canonical SMILES: C1=CC(=C(C=C1[N+](=O)[O-])Cl)NC(=O)C2=C(C=CC(=C2)Cl)O
InChI: InChI=1S/C13H8Cl2N2O4/c14-7-1-4-12(18)9(5-7)13(19)16-11-3-2-8(17(20)21)6-10(11)15/h1-6,18H,(H,16,19)
InChIKey: RJMUSRYZPJIFPJ-UHFFFAOYSA-N

Uses

  Niclosamide (CAS NO.50-65-7) is used as a piscicide.It is stressed that while anthelmintics are a drug family used to treat worm infections, Niclosamide is used specifically to treat tapeworms and is not effective against worms such as pinworms or roundworms.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD oral > 1gm/kg (1000mg/kg)   French Medicament Patent Document. Vol. #2628M,
mouse LD50 intravenous 7500ug/kg (7.5mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 884, 1960.
mouse LD50 oral 1gm/kg (1000mg/kg)   "Wirksubstanzen der Pflanzenschutz und Schadlingsbekampfungsmittel," Perkow, W., Berlin, Verlag Paul Parey, 1971-1976Vol. -, Pg. -, 1971/1976.
rabbit LD oral > 5gm/kg (5000mg/kg)   French Medicament Patent Document. Vol. #2628M,
rat LD50 intraperitoneal 250mg/kg (250mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Zeitschrift fuer Tropenmedizin und Parasitologie. Vol. 13, Pg. 1, 1962.
rat LD50 oral 2500mg/kg (2500mg/kg)   "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A297, Pg. 1983,

Safety Profile

RIDADR: UN 3077 9/PG 3
WGK Germany: 2
RTECS: VN8400000

Specification

  Niclosamide , its cas register number is 50-65-7. It also can be called 2',5-Dichlor-4'-nitro-salizylsaeureanilid ; 2',5-Dichloro-4'-nitrosalicylanilide ; 2-Chloro-4-nitrophenylamide-6-chlorosalicylic acid ; 2-Hydroxy-5-chloro-N-(2-chloro-4-nitrophenyl)benzamide ; 5-Chloro-2'-chloro-4'-nitrosalicylanilide ; 5-Chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide ; 5-Chlorosalicyloyl-(o-chloro-p-nitranilide) ; Atenase ; Bayluscid ; Cestocid ; Devermine ; Dichlosale ; Fedal-Telmin ; Fenasal ; Helmiantin ; Lintex ; Mansonil ; Mato ; N-(2'-Chlor-4'-nitrophenyl)-5-chlorsalicylamid ; Nasemo ; Niclosamida ; Niclosamide ; Niclosamidum ; Nitrophenyl chlorsalicylamide ; Sagimid ; Salicylanilide, 2',5-dichloro-4'-nitro- ; Sulqui ; Vermitid ; Vermitin ;Yomesan ; Zestocarp .