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31431-39-7

Basic Information
CAS No.: 31431-39-7
Name: Mebendazole
Article Data: 10
Molecular Structure:
Molecular Structure of 31431-39-7 (Mebendazole)
Formula: C16H13N3O3
Molecular Weight: 295.298
Synonyms: Methyl 5-benzoyl-2-benzimidazolecarbamate;2-Benzimidazolecarbamic acid, 5-benzoyl-, methyl ester;Sufil;R 17635;Equivurm Plus;MBDZ;Methyl 5-benzoyl benzimidazole-2-carbamate;Versid;(5-Benzoyl-1H-benzimidazol-2-yl)carbamic acid methyl ester;Mebex;Verpanyl;Mebendazole (JAN/USP);2-Benzimidazolecarbamic acid, 5-benzoyl-, methyl ester (8CI);Mebutar;5-Benzoyl-2-benzimidazolecarbamic acid methyl ester;Telmin;Vermox (TN);R 17,635;Bantenol;Telluryl compoundsTelmin;Vermox;R 17, 635;Lomper;Pantelmin;Methyl 5-benzoyl-2-benzimidazolylcarbamate;
EINECS: 250-635-4
Density: 1.388 g/cm3
Melting Point: 288.5 °C
Boiling Point: 436.98°C (rough estimate)
Solubility: 35.4mg/L(25 oC)
Appearance: white to yellowish powder
Hazard Symbols: HarmfulXn
Risk Codes: 22
Safety: 36
Transport Information: UN 2811
PSA: 84.08000
LogP: 3.04520
Synthetic route
39070-63-8

4-benzoylbenzene-1,2-diamine

40943-37-1

O-methyl-N-(methoxycarbonyl)-isourea

31431-39-7

mebendazole

Conditions
ConditionsYield
With acetic acid In toluene95%
With hydrogenchloride In chloroform Cooling with ice; Reflux;
52329-60-9

(2-amino-1H-benzimidazol-5-yl)(phenyl)methanone

79-22-1

methyl chloroformate

A

104663-13-0

isomebendazole

B

31431-39-7

mebendazole

Conditions
ConditionsYield
With pyridine Ambient temperature; Yield given. Yields of byproduct given;
With pyridine Ambient temperature;A 0.5 g
B 0.1 g
57070-71-0

(3,4-diaminophenyl)phenylmethanone hydrochloride

31431-39-7

mebendazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 6 g / sodium hydroxide / H2O / 12 h / Heating
2: 0.1 g / pyridine / Ambient temperature
View Scheme

[Ru(η6-p-cymene)Cl2(mebendazole)]

C26H27Cl2N3O3Ru

67-68-5

dimethyl sulfoxide

A

115543-07-2

[Ru(η6-p-cymene)(dmso)Cl2]

B

31431-39-7

mebendazole

Conditions
ConditionsYield
In chloroform
528-45-0

3,4-dinitrobenzoic acid

31431-39-7

mebendazole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: thionyl chloride / N,N-dimethyl-formamide / 0 °C
2: aluminum (III) chloride / dichloromethane / 3 h / Reflux; Inert atmosphere
3: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 20 °C
4: hydrogenchloride / chloroform / Cooling with ice; Reflux
View Scheme
24376-18-9

3,4-dinitrobenzoyl chloride

31431-39-7

mebendazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aluminum (III) chloride / dichloromethane / 3 h / Reflux; Inert atmosphere
2: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 20 °C
3: hydrogenchloride / chloroform / Cooling with ice; Reflux
View Scheme
33609-48-2

3,4-dinitrobenzophenone

31431-39-7

mebendazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 20 °C
2: hydrogenchloride / chloroform / Cooling with ice; Reflux
View Scheme
39259-32-0

methyl N-(1-methylthio-1-iminomethyl)-carbamate

39070-63-8

4-benzoylbenzene-1,2-diamine

31431-39-7

mebendazole

Conditions
ConditionsYield
With acetic acid In methanol at 75 - 80℃;
106-43-4

para-chlorotoluene

31431-39-7

mebendazole

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: nitric acid / 70 °C
2: nitric acid / 50 °C
3: thionyl chloride / N,N-dimethyl-formamide / 75 - 80 °C
4: ammonia / 130 - 135 °C / 4500.45 - 5250.53 Torr
5: sulfur; sodium hydroxide / methanol / 78 - 80 °C
6: acetic acid / methanol / 75 - 80 °C
View Scheme
74-11-3

para-chlorobenzoic acid

31431-39-7

mebendazole

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: nitric acid / 50 °C
2: thionyl chloride / N,N-dimethyl-formamide / 75 - 80 °C
3: ammonia / 130 - 135 °C / 4500.45 - 5250.53 Torr
4: sulfur; sodium hydroxide / methanol / 78 - 80 °C
5: acetic acid / methanol / 75 - 80 °C
View Scheme
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Chemistry

Molecular Structure of Mebendazole (CAS NO.31431-39-7):

IUPAC Name: methyl N-(6-Benzoyl-1H-benzimidazol-2-yl)carbamate
Canonical SMILES: COC(=O)NC1=NC2=C(N1)C=C(C=C2)C(=O)C3=CC=CC=C3
InChI: InChI=1S/C16H13N3O3/c1-22-16(21)19-15-17-12-8-7-11(9-13(12)18-15)14(20)10-5-3-2-4-6-10/h2-9H,1H3,(H2,17,18,19,21)
InChIKey: OPXLLQIJSORQAM-UHFFFAOYSA-N
Molecular Formula: C16H13N3O3
Molar mass: 295.2927 g/mol
Index of Refraction: 1.702
Molar Refractivity: 82.43 cm3
Molar Volume: 212.6 cm3
Surface Tension: 66.7 dyne/cm
Density: 1.388 g/cm3
Melting point: 288.5 °C
storage temp: 0-6 °C
Water solubility: insoluble
Appearance: White Amorphous Powder
Product Categories: Intermediates & Fine Chemicals; Miscellaneous Natural Products; Miscellaneous Enzyme; Pharmaceuticals

Uses

 Mebendazole (CAS NO.31431-39-7) is used to treat infestations by worms including pinworms, roundworms, tapeworms, hookworms, and whipworms.

Production

Take o-dichlorobenzene and benzoyl chloride as raw materials,the product can be derived by condensation, amination, cyclization.

Toxicity Data With Reference

cat LD50 oral > 640mg/kg (640mg/kg)   Toxicology and Applied Pharmacology. Vol. 24, Pg. 371, 1973.
chicken LD50 unreported > 40mg/kg (40mg/kg)   United States Patent Document. Vol. #3657267,
dog LD intramuscular > 2gm/kg (2000mg/kg)   Drugs in Japan Vol. -, Pg. 1207, 1990.
dog LD50 oral 1280mg/kg (1280mg/kg)   Drugs in Japan Vol. -, Pg. 1207, 1990.
domestic animals - goat/sheep LD50 oral > 80mg/kg (80mg/kg)   United States Patent Document. Vol. #3657267,
guinea pig LD50 oral > 1280mg/kg (1280mg/kg)   Toxicology and Applied Pharmacology. Vol. 24, Pg. 371, 1973.
mouse LD50 intraperitoneal 712mg/kg (712mg/kg)   Meditsinskaya Parazitologiya i Parazitarnye Bolezni. Medical Parasitology and Parasitic Diseases. Vol. 48(4), Pg. 29, 1979.
mouse LD50 oral 620mg/kg (620mg/kg)   Meditsinskaya Parazitologiya i Parazitarnye Bolezni. Medical Parasitology and Parasitic Diseases. Vol. 47(6), Pg. 48, 1978.
rabbit LD50 oral > 640mg/kg (640mg/kg)   Toxicology and Applied Pharmacology. Vol. 24, Pg. 371, 1973.
rat LD50 intramuscular 350mg/kg (350mg/kg)   Drugs in Japan Vol. -, Pg. 1207, 1990.
rat LD50 oral 714mg/kg (714mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 19, Pg. 735, 1988.

Consensus Reports

EPA Genetic Toxicology Program.

Safety Profile

Moderately toxic by ingestion and intraperitoneal routes. Human mutation data reported. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx.
Safety Information of Mebendazole (CAS NO.31431-39-7):
Hazard Codes: Xn
Risk Statements:
22:  Harmful if swallowed 
Safety Statements:
36:  Wear suitable protective clothing
RIDADR: UN 2811
WGK Germany: 3
RTECS: EY8600000

Specification

 Mebendazole (CAS NO.31431-39-7), its Synonyms are (5-Benzoyl-1H-benzimidazol-2-yl)-carbamic acid methyl ester ; 2-Benzimidazolecarbamic acid, 5-benzoyl-, methyl ester ; 5-Benzoyl-2-benzimidazolecarbamic acid methyl ester ; Bantenol ; Besantin ; Mebendazolum ; Methyl 5-benzoyl-2-benzimidazolecarbamate ; Methyl 5-benzoyl-2-benzimidazolylcarbamate ; Methyl N-(5-benzoyl-2-benzimidazolyl)carbamate ; N-(Benzoyl-5, benzimidazolyl)-2, carbamate de methyle ; N-2 (5-Benzoyl-benzimidazole) carbamate de methyle .