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| CAS No.: | 50-65-7 |
|---|---|
| Name: | Niclosamide |
| Article Data: | 24 |
| Molecular Structure: | |
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| 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 |
| Risk Codes: | 50 |
| Safety: | 29 |
| Transport Information: | UN 3077 9/PG 3 |
| PSA: | 95.15000 |
| LogP: | 4.45570 |
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| Conditions | Yield |
|---|---|
| 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; |
| Conditions | Yield |
|---|---|
| With 3-(ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium bis(trifluoromethanesulfonyl)imide at 20℃; for 5h; Ionic liquid; | 48% |
- 50-65-7
Niclosamide
| Conditions | Yield |
|---|---|
| With β-glucuronidase for 0.333333h; |
| Conditions | Yield |
|---|---|
| With dmap; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; dichloromethane | |
| In dichloromethane at 25℃; Inert atmosphere; |
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With N-ethyl-N,N-diisopropylamine In tetrahydrofuran Reflux; | 100% |
| With pyridine; dmap Reflux; |
- 50-65-7
Niclosamide
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With potassium carbonate In acetone for 15h; Reflux; Sealed tube; Inert atmosphere; | 94% |
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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 .