thiabendazole
Conditions | Yield |
---|---|
With sodium hypochlorite; sodium carbonate In methanol; water at 0 - 65℃; for 1.5h; pH=9 - 10; | 97.82% |
Stage #1: C10H9N3S*ClH With sodium carbonate In methanol; water at 0 - 5℃; for 0.333333h; Stage #2: With sodium hypochlorite In methanol; water at 5 - 65℃; for 2h; |
thiazole-4-carbonitrile
1,2-diamino-benzene
ascorbic acid
thiabendazole
Conditions | Yield |
---|---|
With hydrogenchloride; ethylenediaminetetraacetic acid In water | 92.7% |
thiazole-4-carbonitrile
o-phenylenediamine hydrochloride
1,2-diamino-benzene
ascorbic acid
thiabendazole
Conditions | Yield |
---|---|
With hydrogenchloride; ethylenediaminetetraacetic acid In methanol; water | 91.7% |
With hydrogenchloride; ethylenediaminetetraacetic acid In water |
Conditions | Yield |
---|---|
Stage #1: 1,2-diamino-benzene With polyphosphoric acid at 150℃; Inert atmosphere; Stage #2: Thiazole-4-carboxylic acid at 230℃; for 2h; Reagent/catalyst; Temperature; Inert atmosphere; | 88% |
With polyphosphoric acid for 3h; Reflux; |
thiazole-4-carbonitrile
1,2-diamino-benzene
ascorbic acid
butan-1-ol
thiabendazole
Conditions | Yield |
---|---|
With methanesulfonic acid In water | 87.1% |
With acetic acid In water | 75.4% |
Conditions | Yield |
---|---|
With sodium metabisulfite In N,N-dimethyl-formamide at 120℃; | 85% |
Stage #1: 1,3-thiazole-4-carbaldehyde; 1,2-diamino-benzene In N,N-dimethyl-formamide for 0.0833333h; Inert atmosphere; Stage #2: With sodium metabisulfite In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | |
With sodium disulfite In N,N-dimethyl-formamide at 20℃; for 8h; | |
With sodium metabisulfite In N,N-dimethyl-formamide at 120℃; | |
With sodium metabisulfite In N,N-dimethyl-formamide for 6h; |
thiazole-4-carbonitrile
aminosulfonic acid
1,2-diamino-benzene
ascorbic acid
butan-1-ol
thiabendazole
Conditions | Yield |
---|---|
In water | 75.7% |
thiazole-4-carbonitrile
1,2-diamino-benzene
ascorbic acid
butan-1-ol
thiabendazole
Conditions | Yield |
---|---|
In water | 74.5% |
thiabendazole
Conditions | Yield |
---|---|
With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate In tert-butyl methyl ether at 20℃; for 36h; Schlenk technique; Sealed tube; Inert atmosphere; | 40% |
thiabendazole
Conditions | Yield |
---|---|
With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate In tert-butyl methyl ether at 20℃; for 36h; Schlenk technique; Sealed tube; | 40% |
Conditions | Yield |
---|---|
With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); copper diacetate; potassium carbonate In tert-Amyl alcohol; N,N-dimethyl-formamide at 100℃; for 16h; Inert atmosphere; | 15% |
Conditions | Yield |
---|---|
In water |
diisopropyl malonate
di-tert-butyl dicarbonate
1,2-dihydroisoquinoline
thiabendazole
Conditions | Yield |
---|---|
In dichloromethane; ethyl acetate |
Conditions | Yield |
---|---|
With tetraphosphorus decasulfide In ethyl acetate at 45℃; for 2h; |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: hydrogenchloride / water / 3 h / 100 °C 2: sulfuric acid; potassium permanganate / acetone / 1.5 h / 35 - 40 °C 3: bromine; acetic acid / 1 h / 90 °C 4: tetraphosphorus decasulfide / ethyl acetate / 2 h / 45 °C View Scheme | |
Multi-step reaction with 4 steps 1: hydrogenchloride / water / 0.03 h 2: sulfuric acid; potassium permanganate / acetone 3: acetic acid; bromine 4: tetraphosphorus decasulfide / ethyl acetate / 0.03 h View Scheme | |
Multi-step reaction with 4 steps 1: hydrogenchloride / water 2: sulfuric acid; potassium permanganate / acetone 3: bromine; acetic acid 4: tetraphosphorus decasulfide / ethyl acetate View Scheme |
1-benzimidazol-2-ylethanol
thiabendazole
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sulfuric acid; potassium permanganate / acetone / 1.5 h / 35 - 40 °C 2: bromine; acetic acid / 1 h / 90 °C 3: tetraphosphorus decasulfide / ethyl acetate / 2 h / 45 °C View Scheme | |
Multi-step reaction with 3 steps 1: sulfuric acid; potassium permanganate / acetone 2: acetic acid; bromine 3: tetraphosphorus decasulfide / ethyl acetate / 0.03 h View Scheme | |
Multi-step reaction with 3 steps 1: sulfuric acid; potassium permanganate / acetone 2: bromine; acetic acid 3: tetraphosphorus decasulfide / ethyl acetate View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: hydrogenchloride / 1,2-dichloro-benzene / 3 h / 135 °C 2.1: sodium carbonate / water; methanol / 0.33 h / 0 - 5 °C 2.2: 2 h / 5 - 65 °C View Scheme |
thiabendazole
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 1 h / 0 °C 2: [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate / tert-butyl methyl ether / 36 h / 20 °C / Schlenk technique; Sealed tube; Inert atmosphere View Scheme |
formamide
thiabendazole
Conditions | Yield |
---|---|
With tetraphosphorus decasulfide In ethyl acetate for 0.0333333h; | |
With tetraphosphorus decasulfide In ethyl acetate |
thiabendazole
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: trifluoroacetic acid / dichloromethane 2: chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); copper diacetate; potassium carbonate / N,N-dimethyl-formamide; tert-Amyl alcohol / 16 h / 100 °C / Inert atmosphere View Scheme |
thiabendazole
(2-(4'-thiazolyl)benzimidazole)-dichloro-copper(II)
Conditions | Yield |
---|---|
In ethanol mixing of solns. (molar ratio metal:ligand 1:1), boiling (1-3 h); filtration, washing (EtOH), drying (air); elem. anal.; | 98% |
Conditions | Yield |
---|---|
In ethanol molar ratio Hg : ligand = 1 : 1, stirring, boiling (1 h, pptn.); filtration off, washing (EtOH), drying (in air); elem. anal.; | 98% |
Conditions | Yield |
---|---|
With Amberlite IRA-400 (Cl(1-)form) resin In methanol | 96% |
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 23℃; for 12h; Inert atmosphere; | 95% |
thiabendazole
Conditions | Yield |
---|---|
With Amberlite IRA-400 (Cl(1-)form) resin In methanol | 94% |
thiabendazole
Conditions | Yield |
---|---|
With Amberlite IRA-400 (Cl(1-)form) resin In methanol | 94% |
thiabendazole
(2-(4'-thiazolyl)benzimidazole)-dichloro-manganese(II)
Conditions | Yield |
---|---|
In ethanol mixing of solns. (molar ratio metal:ligand 1:1), boiling (1-3 h); filtration, washing (EtOH), drying (air); elem. anal.; | 94% |
benzyl bromide
thiabendazole
4-(1-benzyl-1H-benzo[d]imidazol-2-yl)thiazole
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 60℃; Inert atmosphere; | 94% |
With sodium hydride In N,N-dimethyl-formamide at 20℃; | 87% |
Stage #1: thiabendazole With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 4h; Schlenk technique; Inert atmosphere; | 65% |
bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]
thiabendazole
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 20h; Inert atmosphere; Schlenk technique; | 94% |
Conditions | Yield |
---|---|
With Amberlite IRA-400 (Cl(1-)form) resin In methanol | 93% |
Conditions | Yield |
---|---|
With Amberlite IRA-400 (Cl(1-)form) resin In methanol | 93% |
thiabendazole
zinc(II) chloride
(2-(4'-thiazolyl)benzimidazole)-dichloro-zinc
Conditions | Yield |
---|---|
In ethanol mixing of solns. (molar ratio metal:ligand 1:1), boiling (1-3 h); filtration, washing (EtOH), drying (air); elem. anal.; | 93% |
thiabendazole
Conditions | Yield |
---|---|
With Amberlite IRA-400 (Cl(1-)form) resin In methanol | 92% |
Conditions | Yield |
---|---|
With Amberlite IRA-400 (Cl(1-)form) resin In methanol | 92% |
thiabendazole
N-propyl-2-(4-thiazolyl)benzimidazole
Conditions | Yield |
---|---|
With Amberlite IRA-400 (Cl(1-)form) resin In methanol | 92% |
thiabendazole
4-(1-benzyl-1H-benzo[d]imidazol-2-yl)thiazole
Conditions | Yield |
---|---|
With Amberlite IRA-400 (Cl(1-)form) resin In methanol | 91% |
With sodium hydride In N,N-dimethyl-formamide at 20℃; |
Conditions | Yield |
---|---|
Stage #1: thiabendazole With hydrogenchloride In water at 20℃; for 1h; Stage #2: sodium docusate In water; acetone at 20℃; Product distribution / selectivity; | 91% |
thiabendazole
methyl iodide
4-(1-methyl-1H-benzo[d]imidazol-2-yl)thiazole
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 20℃; | 90% |
Stage #1: thiabendazole With sodium hydride In N,N-dimethyl-formamide; benzene for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide; benzene for 1h; Heating; | 79% |
Stage #1: thiabendazole With caesium carbonate In dimethyl sulfoxide at 80℃; for 1.5h; Inert atmosphere; Schlenk technique; Stage #2: methyl iodide In dimethyl sulfoxide at 20℃; for 20h; Inert atmosphere; Schlenk technique; | 71% |
With sodium hydride; N,N-dimethyl-formamide In benzene Heating; | |
With sodium hydride In N,N-dimethyl-formamide |
Conditions | Yield |
---|---|
With Amberlite IRA-400 (Cl(1-)form) resin In methanol | 90% |
thiabendazole
Conditions | Yield |
---|---|
With Amberlite IRA-400 (Cl(1-)form) resin In methanol | 90% |
thiabendazole
4-(1-methyl-1H-benzo[d]imidazol-2-yl)thiazole
Conditions | Yield |
---|---|
With Amberlite IRA-400 (Cl(1-)form) resin In methanol | 90% |
With sodium hydride In N,N-dimethyl-formamide at 20℃; |
Conditions | Yield |
---|---|
In ethanol mixing of solns. (molar ratio metal:ligand 1:2), boiling (1-3 h); filtration, washing (EtOH), drying (air); elem. anal.; | 90% |
thiabendazole
Conditions | Yield |
---|---|
In ethanol addn. of a soln. of metal salt in ethanol to a soln. of ligand in ethanol, standing for 1 wk; elem. anal.; | 89% |
Conditions | Yield |
---|---|
Stage #1: aqueous cadmium chloride; diphenic acid; water; thiabendazole With sodium hydroxide In methanol; N,N-dimethyl-formamide for 0.5h; pH=6; Stage #2: In methanol; N,N-dimethyl-formamide at 130℃; for 72h; Sealed tube; | 88% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 8h; | 88% |
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 20℃; | 88% |
EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.
Thiabendazole, with the IUPAC Name of 4-(1H-Benzimidazol-2-yl)-1,3-thiazole, is one kind of light yellow powder. This chemical belongs to the Product Categories which include Xanthones; Heterocyclic Compounds; FUNGICIDE; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals; Sulfur & Selenium Compounds; API's. With the CAS NO. 148-79-8, Thiabendazole is a systemic benzimidazole fungicide.
Physical properties about Thiabendazole are: (1)ACD/LogP: 2.47; (2)ACD/LogD (pH 5.5): 2.46; (3)ACD/LogD (pH 7.4): 2.47; (4)ACD/BCF (pH 5.5): 43.36; (5)ACD/BCF (pH 7.4): 44.36; (6)ACD/KOC (pH 5.5): 513.56; (7)ACD/KOC (pH 7.4): 525.39; (8)#H bond acceptors: 3; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Index of Refraction: 1.74; (12)Molar Refractivity: 57.687 cm3; (13)Molar Volume: 143.083 cm3; (14)Polarizability: 22.869 10-24cm3; (15)Surface Tension: 71.1259994506836 dyne/cm; (16)Density: 1.407 g/cm3; (17)Flash Point: 226.212 °C ; (18)Enthalpy of Vaporization: 70.403 kJ/mol; (19)Boiling Point: 445.951 °C at 760 mmHg
Uses of Thiabendazole: Thiabendazole is used primarily to control mold, blight, and other fungally caused diseases in fruits (e.g. oranges) and vegetables; it is also used as a prophylactic treatment for Dutch Elm disease and used in treatment of Aspergillus has been reported.As an antiparasitic, it is able to control roundworms, hookworms, and other helminth species which attack wild animals, livestock and humans.Medicinally, Thiabendazole is also a chelating agent, which means that it is used medicinally to bind metals in cases of metal poisoning, such as lead poisoning, mercury poisoning or antimony poisoning. In dogs and cats thiabendazole is also used to treat ear infections. Thiabendazole is also used as a food additive, a preservative with E number E233. For example, it is applied to bananas to ensure freshness, and is a common ingredient in the waxes applied to the skin of citrus fruits.
When you are using this chemical, please be cautious about it as the following:
1. This material and/or its container must be disposed of as hazardous waste;
2. Avoid release to the environment. Refer to special instructions safety data sheet;
3. Wear suitable protective clothing;
4. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
You can still convert the following datas into molecular structure:
(1)InChI=1S/C10H7N3S/c1-2-4-8-7(3-1)12-10(13-8)9-5-14-6-11-9/h1-6H,(H,12,13);
(2)InChIKey=WJCNZQLZVWNLKY-UHFFFAOYSA-N;
(3)Smilesc1(c2cscn2)[nH]c2ccccc2n1;
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
chicken | LD50 | oral | 4gm/kg (4000mg/kg) | Veterinarno-Meditsinski Nauki. Veterinary Science. Vol. 19(3), Pg. 99, 1982. | |
domestic animals - goat/sheep | LD50 | oral | 400mg/kg (400mg/kg) | Veterinarno-Meditsinski Nauki. Veterinary Science. Vol. 19(3), Pg. 99, 1982. | |
man | TDLo | oral | 47619ug/kg/1D (47.619mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Journal of Pediatrics. Vol. 102, Pg. 317, 1983. |
mouse | LD50 | oral | 1300mg/kg (1300mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 55(10), Pg. 28, 1990. | |
rabbit | LD50 | oral | 3850mg/kg (3850mg/kg) | "Wirksubstanzen der Pflanzenschutz und Schadlingsbekampfungsmittel," Perkow, W., Berlin, Verlag Paul Parey, 1971-1976Vol. -, Pg. -, 1971/1976. | |
rat | LD50 | oral | 2080mg/kg (2080mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA | Science Reports of the Research Institutes, Tohoku University, Series C: Medicine. Vol. 36(1-4), Pg. 10, 1989. |
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