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50-65-7

Basic Information
CAS No.: 50-65-7
Name: Niclosamide
Molecular Structure:
Molecular Structure of 50-65-7 (Niclosamide)
Formula: C13H8Cl2N2O4
Molecular Weight: 327.12
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:
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%
50-65-7

Niclosamide

139115-91-6

2-(2-tert-butyloxycarbonylaminoethoxy)ethanol

(2-{2-[4-chloro-2-(2-chloro-4-nitro-phenylcarbamoyl)-phenoxy]-ethoxy}-ethyl)carbamic acid tert-butyl ester

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 2h;93%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 2h; Mitsunobu Displacement; Inert atmosphere;
50-00-0

formaldehyd

50-65-7

Niclosamide

124-40-3

dimethyl amine

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

Conditions
ConditionsYield
In ethanol; water for 2h; Mannich reaction; Heating;92%
50-65-7

Niclosamide

77279-24-4

tert-butyl 4-(2-hydroxyethyl)piperazine-1-carboxylate

1420290-97-6

4-{2-[4-chloro-2-(2-chloro-4-nitro-phenylcarbamoyl)-phenoxy]-ethyl}-piperazine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 2h;91%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 2h; Mitsunobu Displacement; Inert atmosphere;
50-00-0

formaldehyd

50-65-7

Niclosamide

109-89-7

diethylamine

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

Conditions
ConditionsYield
In ethanol; water for 2h; Mannich reaction; Heating;90%
50-65-7

Niclosamide

108-24-7

acetic anhydride

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

Conditions
ConditionsYield
With dmap In N,N-dimethyl-formamide at 0℃;88.2%
With phosphoric acid at 70℃; for 1h;83%
With dmap In dichloromethane at 20℃; for 18h;
110-89-4

piperidine

50-00-0

formaldehyd

50-65-7

Niclosamide

164589-62-2

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

Conditions
ConditionsYield
In ethanol; water for 2h; Mannich reaction; Heating;87%
In ethanol; water Mannich reaction; Reflux;87%
371-62-0

2-fluoroethanol

50-65-7

Niclosamide

1420290-80-7

5-chloro-N-(2-chloro-4-nitro-phenyl)-2-(2-fluoro-ethoxy)benzamide

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 16h; Mitsunobu Displacement; Inert atmosphere;86%
590-97-6

acetoxymethyl bromide

50-65-7

Niclosamide

acetic acid 4-chloro-2-(2-chloro-4-nitrophenylcarbamoyl)phenoxymethyl ester

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃;86%
124-22-1

n-Dodecylamine

50-65-7

Niclosamide

1619232-16-4

dodecan-1-aminium 4-chloro-2-[(2-chloro-4-nitrophenyl)carbamoyl]phenoxide

Conditions
ConditionsYield
In ethanol at 20℃; for 336h;84%
55750-53-3

2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-hexanoic acid

50-65-7

Niclosamide

(4-chloro-2-((2-chloro-4-nitrophenyl)carbamoyl)phenyl-6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoate)

Conditions
ConditionsYield
With triethylamine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere;82%
15159-40-7

4-morpholinocarbonyl chloride

50-65-7

Niclosamide

1243092-32-1

4-chloro-2-((2-chloro-4-nitrophenyl)carbamoyl)phenyl morpholine-4-carboxylate

Conditions
ConditionsYield
With pyridine at 60℃;81%
With pyridine; dmap for 3h; Reflux;
143-27-1

hexadecylamine

50-65-7

Niclosamide

1619232-17-5

hexadecan-1-aminium 4-chloro-2-[(2-chloro-4-nitrophenyl)carbamoyl]phenoxide

Conditions
ConditionsYield
In ethanol at 20℃; for 336h;81%
50-65-7

Niclosamide

23238-76-8

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

Conditions
ConditionsYield
With Lawessons reagent In acetonitrile for 24h; Reflux;80%
50-65-7

Niclosamide

77544-68-4

8-tosyloxy-3,6-dioxaoctanol

1046321-41-8

O-(2-[2-(2-hydroxyethoxy)ethoxy]ethyl)niclosamide

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium carbonate In 1,4-dioxane at 79.99℃; for 12h;79%
With tetrabutylammomium bromide; potassium carbonate In 1,4-dioxane at 85℃; for 6h; Reflux;78%
1189-71-5

isocyanate de chlorosulfonyle

50-65-7

Niclosamide

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

Conditions
ConditionsYield
Stage #1: isocyanate de chlorosulfonyle With formic acid at 0℃;
Stage #2: Niclosamide With pyridine In dichloromethane at 50℃; for 6h;
76%
50-65-7

Niclosamide

112-67-4

n-hexadecanoyl chloride

4-chloro-2-(2-chloro-4-nitroanilinocarbonyl)phenyl hexadecanoate

Conditions
ConditionsYield
With pyridine In chloroform at 0℃; for 3h;75%
50-65-7

Niclosamide

540-51-2

2-bromoethanol

1046321-35-0

2-(2-bromoethoxy)-5-chloro-N-(2-chloro-4-nitrophenyl)benzamide

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 16h; Mitsunobu Displacement; Inert atmosphere;75%
140-31-8

aminoethylpiperazine

50-65-7

Niclosamide

4-(2-ammonioethyl)piperazin-1-ium bis-{4-chloro-2-[(2-chloro-4-nitrophenyl)carbamoyl]phenoxide}

Conditions
ConditionsYield
In ethanol at 20℃; for 337.92h;74%
26690-80-2

2-(N-tert-butoxycarbonylamino)ethanol

50-65-7

Niclosamide

{2-[4-chloro-2-(2-chloro-4-nitro-phenylcarbamoyl)-phenoxy]-ethyl}-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃;71%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran45%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 2h; Mitsunobu Displacement; Inert atmosphere;
50-65-7

Niclosamide

77544-60-6

p-toluenesulfonic acid 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethyl ester

2-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}ethoxyl niclosamide

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium carbonate In 1,4-dioxane at 79.99℃; for 12h;70%
50-00-0

formaldehyd

50-65-7

Niclosamide

58556-46-0

glycine acetate

3'-(N-glycinomethyl)-2,5'-dichloro-4-nitrosalicylanilide

Conditions
ConditionsYield
In ethanol; water 1.) reflux, 5 h, 2.) r.t., overnight;65%
50-65-7

Niclosamide

6-chloro-3-(2-chloro-4-nitrophenyl)benzo[e][1,2,3]oxathiazin-4(3H)-one 2,2-dioxide

Conditions
ConditionsYield
Stage #1: Niclosamide With N-ethyl-N,N-diisopropylamine In acetonitrile
Stage #2: With potassium fluoride; N,N`-sulfuryldiimidazole; trifluoroacetic acid In water at 20℃; for 18h;
64%
50-65-7

Niclosamide

C13H6(2)H2Cl2N2O4

Conditions
ConditionsYield
With rhodium(III) chloride; water-d2 In N,N-dimethyl-formamide at 108℃;60%
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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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    Product Name: Niclosamide CAS NO.: 50-65-7 EINECS NO.: 200-056-8 MF: C13H8Cl2N2O4 MW: 327.12 Melting point: 225-230℃ Appearance: light yellow powder Niclosamide is a teniacide in the anthelmintic family especia

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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 .