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43210-67-9 Usage

Chemical Properties

Gray light brown crystalline powder. Melting point 233 ℃ (decomposition). Soluble in dimethyl sulfoxide (DMSO), slightly soluble in common organic solvents, insoluble in water. Odorless, tasteless.

Definition

ChEBI: A member of the class of benzimidazoles that is 1H-benzimidazole which is substituted at positons 2 and 5 by (methoxycarbonyl)amino and phenylsulfanediyl groups, respectively. A broad-spectrum anthelmintic, it is used, particularly in v terinary medicine, for the treatment of nematodal infections.

Uses

An anthelmintic (Nematodes)

Aofendazuo

Aofendazuo is a benzimidazole anthelmintic, also known as the Austrian phenol metronidazole, oxfendazole, benzene etomidate sulfoxide, benzene sulfur oxygen imidazole ,it is the sulfoxide form of Fenbendazole , white or off-white powder at room temperature, slight special smell, it can damage the microtubules of the worms epithelial cells of the gastrointestinal tract, and inhibit the worms uptake of glucose from the intestine.
Aofendazuo is used for the treatment and control of gastrointestinal adults and larvae, it has a good effect on the treatment of in vivo roundworms and lung worms in pigs and sheep , including Oster nematodes (Ostertagia), Haemonchus , Trichostrongylus, Nematodirus , Cooper nematode (Cooperia), capillary nematodes (Capillaria), toothed Oesophagostomum (Oesophagostomum), Chabertia, Trichuris nematodes form (Trichuris) and dictyocaulasis ( Dictyocaulus) and so on.
The above information is edited by the chemicalbook of Tian Ye.

Production method

5-chloro-2-nitroaniline reacts with benzene thiol, to thereby obtain 5-phenylthio-2-nitroaniline in 91% yield.Generate 3-phenylthio-o-phenylenediamine by ferrous sulfate-iron reduction in 90% yield. Finally, cyclize it with the S-methyl-melamine Methyl to obtain fenbendazole.

Chemical Properties

Off-White Solid

Uses

Anthelmintic. Broad-spectrum, high efficiency, low toxicity, antiparasitic. It has a strong killing effect on Roundworm, nematodes, tapeworms, cysticercosis , Fasciola and other parasites, not only killing worms, especially having a great effect on Transitional larvae ehich are hazardous to the liver, lungs and intestines .Fenbendazole is a benzimidazole anthelmintic, not only having a highly anthelmintic activity for gastrointestinal nematodes adults and larvae , but also having a good effect on dictyocaulasis, flukes and tapeworms, in addition,it has a strong killing eggs effect.

Benzimidazole anthelmintics

Fenbendazole is a benzimidazole anthelmintic with a broad spectrum,high efficiency and low toxicity ,in the structure,it has a strong affinity with the parasite tubulin ,by influencing cell transport and energy metabolism,it plays a role in preventing the polymerization of micro tubes, which ultimately destroys the integrity of parasite cells and energy transmission.
Fenbendazole is used to drive and to kill the animal gastrointestinal parasites, it not only has a highly anthelmintic activity on animal gastrointestinal roundworms, hookworms, whipworms, some tapeworms and nematodes , but also has a preferred effect on the part of the bronchial tree and lung parasites (Aelurostrongylus abstrutus and lung fluke) .

Brand name

Panacur (Hoechst-Roussel).
InChI:InChI=1/C15H13N3O2S/c1-20-15(19)18-14-16-12-8-7-11(9-13(12)17-14)21-10-5-3-2-4-6-10/h2-9H,1H3,(H2,16,17,18,19)

43210-67-9 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Sigma-Aldrich (35032)  Fenbendazole  VETRANAL, analytical standard 43210-67-9 35032-100MG 360.36CNY Detail
USP (1269403)  Fenbendazole  United States Pharmacopeia (USP) Reference Standard 43210-67-9 1269403-100MG 14,578.20CNY Detail
Sigma-Aldrich (F0040000)  Fenbendazole  European Pharmacopoeia (EP) Reference Standard 43210-67-9 F0040000 1,880.19CNY Detail
Aldrich (F5396)  Fenbendazole  ≥98% 43210-67-9 F5396-100G 4,210.83CNY Detail
Aldrich (F5396)  Fenbendazole  ≥98% 43210-67-9 F5396-5G 809.64CNY Detail
TCI America (F0812)  Fenbendazole  >98.0%(HPLC)(N) 43210-67-9 25g 790.00CNY Detail

43210-67-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name fenbendazole

1.2 Other means of identification

Product number -
Other names Fenbendazole

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:43210-67-9 SDS

43210-67-9Synthetic route

1,2-diamino-4-phenylthiobenzene
43156-48-5

1,2-diamino-4-phenylthiobenzene

S-Methylisothiourea sulfate
867-44-7

S-Methylisothiourea sulfate

methyl chloroformate
79-22-1

methyl chloroformate

Fenbendazole
43210-67-9

Fenbendazole

Conditions
ConditionsYield
Stage #1: S-Methylisothiourea sulfate; methyl chloroformate With sodium hydroxide In water at 3 - 6℃; for 0.666667h;
Stage #2: 1,2-diamino-4-phenylthiobenzene With acetic acid In ethanol; water at 95℃; for 24h;
88%
2-nitro-5-phenylthioaniline
43156-47-4

2-nitro-5-phenylthioaniline

Fenbendazole
43210-67-9

Fenbendazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: H2 / Pd/C / ethanol / 20 °C / 3102.89 Torr
2.1: NaOH / H2O / 0.67 h / 3 - 6 °C
2.2: 88 percent / AcOH / H2O; ethanol / 24 h / 95 °C
View Scheme
5-chloro-2-nitroaniline
1635-61-6

5-chloro-2-nitroaniline

Fenbendazole
43210-67-9

Fenbendazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: K2CO3 / dimethylformamide / 6 h / Heating
2.1: H2 / Pd/C / ethanol / 20 °C / 3102.89 Torr
3.1: NaOH / H2O / 0.67 h / 3 - 6 °C
3.2: 88 percent / AcOH / H2O; ethanol / 24 h / 95 °C
View Scheme
thiophenol
108-98-5

thiophenol

Fenbendazole
43210-67-9

Fenbendazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: K2CO3 / dimethylformamide / 6 h / Heating
2.1: H2 / Pd/C / ethanol / 20 °C / 3102.89 Torr
3.1: NaOH / H2O / 0.67 h / 3 - 6 °C
3.2: 88 percent / AcOH / H2O; ethanol / 24 h / 95 °C
View Scheme
(5-phenylsulfanyl-1-phosphonooxymethyl-1H-benzoimidazol-2-yl)carbamic acid methyl ester disodium salt; (6-phenylsulfanyl-1-phosphonooxymethyl-1H-benzoimidazol-2-yl)carbamic acid methyl ester disodium salt; mixture of

(5-phenylsulfanyl-1-phosphonooxymethyl-1H-benzoimidazol-2-yl)carbamic acid methyl ester disodium salt; (6-phenylsulfanyl-1-phosphonooxymethyl-1H-benzoimidazol-2-yl)carbamic acid methyl ester disodium salt; mixture of

Fenbendazole
43210-67-9

Fenbendazole

Conditions
ConditionsYield
With chicken alkaline phosphatase In water at 39℃; pH=6.5 - 9.0; Enzyme kinetics;
With porcine alkaline phosphatase In water at 37℃; pH=6.5 - 9.0; Enzyme kinetics;
Conditions
ConditionsYield
With dihydrogen peroxide; sodium sulfite In methanol; water98.8%
With urea hydrogen peroxide adduct In formic acid; water at 25 - 45℃; for 5.5h; Temperature; Concentration;98%
Fenbendazole
43210-67-9

Fenbendazole

5-(phenylthio)-1H-benzo[d]imidazol-2-amine
53065-28-4

5-(phenylthio)-1H-benzo[d]imidazol-2-amine

Conditions
ConditionsYield
With potassium hydroxide In methanol; water for 48h; Heating;98%
In N,N-dimethyl-formamide for 12h; Heating;50%
chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

Fenbendazole
43210-67-9

Fenbendazole

A

2-Methoxycarbonylamino-5-phenylsulfanyl-benzoimidazole-1-carboxylic acid ethyl ester
58521-88-3

2-Methoxycarbonylamino-5-phenylsulfanyl-benzoimidazole-1-carboxylic acid ethyl ester

B

2-Methoxycarbonylamino-6-phenylsulfanyl-benzoimidazole-1-carboxylic acid ethyl ester
58522-05-7

2-Methoxycarbonylamino-6-phenylsulfanyl-benzoimidazole-1-carboxylic acid ethyl ester

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane Ambient temperature;
methyl chloroformate
79-22-1

methyl chloroformate

Fenbendazole
43210-67-9

Fenbendazole

A

methyl 1-methoxycarbonyl-5-phenylthiobenzimidazole-2-carbamate
58521-87-2

methyl 1-methoxycarbonyl-5-phenylthiobenzimidazole-2-carbamate

B

2-Methoxycarbonylamino-6-phenylsulfanyl-benzoimidazole-1-carboxylic acid methyl ester
58522-04-6

2-Methoxycarbonylamino-6-phenylsulfanyl-benzoimidazole-1-carboxylic acid methyl ester

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane for 20h; Ambient temperature;A 12 g
B 8 g
Fenbendazole
43210-67-9

Fenbendazole

Ethyl chlorothioformate
2941-64-2

Ethyl chlorothioformate

A

2-Methoxycarbonylamino-5-phenylsulfanyl-benzoimidazole-1-carbothioic acid S-ethyl ester
104663-11-8

2-Methoxycarbonylamino-5-phenylsulfanyl-benzoimidazole-1-carbothioic acid S-ethyl ester

B

2-Oxo-5-phenylsulfanyl-benzoimidazole-1,3-dicarbothioic acid di-S-ethyl ester
104663-33-4

2-Oxo-5-phenylsulfanyl-benzoimidazole-1,3-dicarbothioic acid di-S-ethyl ester

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane Ambient temperature;
Fenbendazole
43210-67-9

Fenbendazole

methyl iodide
74-88-4

methyl iodide

Methyl-(1-methyl-5-phenylsulfanyl-1H-benzoimidazol-2-yl)-carbamic acid methyl ester

Methyl-(1-methyl-5-phenylsulfanyl-1H-benzoimidazol-2-yl)-carbamic acid methyl ester

Conditions
ConditionsYield
With AG-MP1 anion exchange resin In carbon dioxide at 80℃; under 150012 Torr; for 0.333333h; Product distribution; further conditions: CH3CN, room temperature, 1 h;
Fenbendazole
43210-67-9

Fenbendazole

6-Benzenesulfinyl-2-methoxycarbonylamino-benzoimidazole-1-carboxylic acid methyl ester
104663-22-1

6-Benzenesulfinyl-2-methoxycarbonylamino-benzoimidazole-1-carboxylic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 8 g / 1N aq sodium hydroxide / CH2Cl2 / 20 h / Ambient temperature
2: m-chloroperbenzoic acid / CH2Cl2
View Scheme
Fenbendazole
43210-67-9

Fenbendazole

1-carbomethoxy-2-carbomethoxyamino-5-phenylsulfinylbenzimidazole
104663-01-6

1-carbomethoxy-2-carbomethoxyamino-5-phenylsulfinylbenzimidazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 12 g / 1N aq sodium hydroxide / CH2Cl2 / 20 h / Ambient temperature
2: 8 g / m-chloroperbenzoic acid / CH2Cl2 / 16 h / 15 - 20 °C
View Scheme
Fenbendazole
43210-67-9

Fenbendazole

1-carbomethoxy-2-carbomethoxyamino-5-phenylsulfonylbenzimidazole
104663-08-3

1-carbomethoxy-2-carbomethoxyamino-5-phenylsulfonylbenzimidazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 12 g / 1N aq sodium hydroxide / CH2Cl2 / 20 h / Ambient temperature
2: 1.5 g / m-chloroperbenzoic acid / CH2Cl2
View Scheme
Fenbendazole
43210-67-9

Fenbendazole

6-Benzenesulfonyl-2-methoxycarbonylamino-benzoimidazole-1-carboxylic acid methyl ester
104663-29-8

6-Benzenesulfonyl-2-methoxycarbonylamino-benzoimidazole-1-carboxylic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 8 g / 1N aq sodium hydroxide / CH2Cl2 / 20 h / Ambient temperature
2: m-chloroperbenzoic acid / CH2Cl2
View Scheme
Fenbendazole
43210-67-9

Fenbendazole

5-Benzenesulfinyl-2-methoxycarbonylamino-benzoimidazole-1-carboxylic acid ethyl ester
104663-02-7

5-Benzenesulfinyl-2-methoxycarbonylamino-benzoimidazole-1-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1N aq sodium hydroxide / CH2Cl2 / Ambient temperature
2: m-chloroperbenzoic acid / CH2Cl2
View Scheme
Fenbendazole
43210-67-9

Fenbendazole

5-Benzenesulfinyl-2-methoxycarbonylamino-benzoimidazole-1-carbothioic acid S-ethyl ester
104663-12-9

5-Benzenesulfinyl-2-methoxycarbonylamino-benzoimidazole-1-carbothioic acid S-ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1N aq sodium hydroxide / CH2Cl2 / Ambient temperature
2: m-chloroperbenzoic acid / CH2Cl2
View Scheme
Fenbendazole
43210-67-9

Fenbendazole

6-Benzenesulfinyl-2-methoxycarbonylamino-benzoimidazole-1-carboxylic acid ethyl ester
104663-23-2

6-Benzenesulfinyl-2-methoxycarbonylamino-benzoimidazole-1-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1N aq sodium hydroxide / CH2Cl2 / Ambient temperature
2: m-chloroperbenzoic acid / CH2Cl2
View Scheme
Fenbendazole
43210-67-9

Fenbendazole

2-amino-5(6)-benzenesulfonylbenzimidazole
59530-20-0

2-amino-5(6)-benzenesulfonylbenzimidazole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 98 percent / KOH / methanol; H2O / 48 h / Heating
2: 82 percent / pyridine / 1 h / Heating
3: 82.6 percent / KMnO4 / acetic acid / 2 h / Ambient temperature
4: 73.5 percent / aq. NaOH / ethanol / 2 h / Ambient temperature
View Scheme
Fenbendazole
43210-67-9

Fenbendazole

2-Acetamido-5(6)-phenylthiobenzimidazole
125422-34-6

2-Acetamido-5(6)-phenylthiobenzimidazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 98 percent / KOH / methanol; H2O / 48 h / Heating
2: 82 percent / pyridine / 1 h / Heating
View Scheme
Fenbendazole
43210-67-9

Fenbendazole

5(6)-Phenylthio-2-(carboxamidomethylamino)-benzimidazole
125422-38-0

5(6)-Phenylthio-2-(carboxamidomethylamino)-benzimidazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 98 percent / KOH / methanol; H2O / 48 h / Heating
2: 50 percent / triethylamine / acetone / 12 h / Heating
View Scheme
Fenbendazole
43210-67-9

Fenbendazole

5(6)-Phenylthio-2-chloroacetamidobenzimidazole
125422-41-5

5(6)-Phenylthio-2-chloroacetamidobenzimidazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 98 percent / KOH / methanol; H2O / 48 h / Heating
2: 88 percent / triethylamine / acetone / 3 h / Ambient temperature
View Scheme
Fenbendazole
43210-67-9

Fenbendazole

2-Acetamido-5(6)-phenylsulphonobenzimidazole
125422-35-7

2-Acetamido-5(6)-phenylsulphonobenzimidazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 98 percent / KOH / methanol; H2O / 48 h / Heating
2: 82 percent / pyridine / 1 h / Heating
3: 82.6 percent / KMnO4 / acetic acid / 2 h / Ambient temperature
View Scheme
Fenbendazole
43210-67-9

Fenbendazole

(5-Phenylsulfanyl-1H-benzoimidazol-2-ylamino)-acetic acid methyl ester
125422-37-9

(5-Phenylsulfanyl-1H-benzoimidazol-2-ylamino)-acetic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 98 percent / KOH / methanol; H2O / 48 h / Heating
2: 64 percent / triethylamine
View Scheme
Fenbendazole
43210-67-9

Fenbendazole

2-(Carbethoxymethylamino)-5(6)-phenylthiobenzimidazole
125443-69-8

2-(Carbethoxymethylamino)-5(6)-phenylthiobenzimidazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 98 percent / KOH / methanol; H2O / 48 h / Heating
2: 55 percent / triethylamine / acetone / 12 h / Heating
View Scheme
Fenbendazole
43210-67-9

Fenbendazole

2,2,2-Trifluoro-N-(5-phenylsulfanyl-1H-benzoimidazol-2-yl)-acetamide
125443-68-7

2,2,2-Trifluoro-N-(5-phenylsulfanyl-1H-benzoimidazol-2-yl)-acetamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 98 percent / KOH / methanol; H2O / 48 h / Heating
2: 71 percent / 3 h / Heating
View Scheme
Fenbendazole
43210-67-9

Fenbendazole

2-Chloroacetamido-5(6)-phenylsulphonobenzimidazole
125422-49-3

2-Chloroacetamido-5(6)-phenylsulphonobenzimidazole

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 98 percent / KOH / methanol; H2O / 48 h / Heating
2: 82 percent / pyridine / 1 h / Heating
3: 82.6 percent / KMnO4 / acetic acid / 2 h / Ambient temperature
4: 73.5 percent / aq. NaOH / ethanol / 2 h / Ambient temperature
5: 80 percent / triethylamine / tetrahydrofuran / 3 h / Ambient temperature
View Scheme
Fenbendazole
43210-67-9

Fenbendazole

2-(5-Phenylsulfanyl-1H-benzoimidazol-2-ylamino)-1-piperidin-1-yl-ethanone
125422-39-1

2-(5-Phenylsulfanyl-1H-benzoimidazol-2-ylamino)-1-piperidin-1-yl-ethanone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 98 percent / KOH / methanol; H2O / 48 h / Heating
2: 56 percent / triethylamine
View Scheme
Fenbendazole
43210-67-9

Fenbendazole

2-(1-Pyrrolidinoacetylamino)-5(6)-phenylthiobenzimidazole
125422-42-6

2-(1-Pyrrolidinoacetylamino)-5(6)-phenylthiobenzimidazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 98 percent / KOH / methanol; H2O / 48 h / Heating
2: 88 percent / triethylamine / acetone / 3 h / Ambient temperature
3: 64 percent / triethylamine / acetone / 12 h / Heating
View Scheme
Fenbendazole
43210-67-9

Fenbendazole

N-(5-Phenylsulfanyl-1H-benzoimidazol-2-yl)-2-piperidin-1-yl-acetamide
125422-43-7

N-(5-Phenylsulfanyl-1H-benzoimidazol-2-yl)-2-piperidin-1-yl-acetamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 98 percent / KOH / methanol; H2O / 48 h / Heating
2: 88 percent / triethylamine / acetone / 3 h / Ambient temperature
3: 67 percent / triethylamine
View Scheme

43210-67-9Downstream Products

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