Captafol

Base Information

• Chemical Name: Captafol
• CAS No.: 2425-06-1
• Deprecated CAS: 30017-05-1,61913-12-0
• Molecular Formula: C10H9 Cl4 N O2 S
• Molecular Weight: 349.065
• Hs Code.: 29305000
• European Community (EC) Number: 219-363-3
• ICSC Number: 0119
• DSSTox Substance ID: DTXSID4020242
• Nikkaji Number: J3.026K
• Wikipedia: Captafol
• Wikidata: Q63088167
• NCI Thesaurus Code: C77381
• Metabolomics Workbench ID: 45028
• ChEMBL ID: CHEMBL1893263
• Mol file: 2425-06-1.mol

Synonyms:captafol;captafol, (cis)-isomer;captefol;captofol;Difolatan;merpafol;N-(tetrachloroethylthio)tetrahydrophthalimide

Chemical Property of Captafol

Chemical Property:

• Vapor Pressure: 1.54E-05mmHg at 25°C
• Melting Point: 160-161°
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 365.7°C at 760 mmHg
• PKA: -2.67±0.20(Predicted)
• Flash Point: >100 °C
• PSA: 62.68000
• Density: 1.64g/cm³
• LogP: 3.45880
• Storage Temp.: 0-6°C
• Water Solubility.: 1.4 mg l-1 (20 °C)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 348.907860
• Heavy Atom Count: 18
• Complexity: 387

Purity/Quality:

Captafol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Absorbed by skin. TLV: 0.1 mg/m³; not classifiable as a human carcinogen.
• Hazard Codes: T,N
• Statements: 45-43-50/53
• Safety Statements: 53-45-60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Fungicides
• Canonical SMILES: C1C=CCC2C1C(=O)N(C2=O)SC(C(Cl)Cl)(Cl)Cl
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis. Repeated or prolonged contact may cause skin sensitization and allergic conjunctivities. Repeated or prolonged inhalation may cause asthma. This substance is probably carcinogenic to humans.
• Description: Captafol appears as white, colourless to pale yellow, or tan (technical-grade) crystals or as a crystalline solid or powder, with a slight characteristic pungent odour. It is practically insoluble in water but is soluble or slightly soluble in most organic solvents. Captafol reacts with bases, acids, acid vapours, and strong oxidisers. Captafol is a broad-spectrum nonsystemic fungicide that is categorised as a phthalimide fungicide based on its tetrahydrophthalimide chemical ring structure (other phthalimide fungicides include captan and folpet). It hydrolyses slowly in aqueous emulsions or suspensions but rapidly in acidic and basic aqueous alkaline media. Captafol will not burn, but when heated to decomposition, it emits toxic fumes, including nitrogen oxides, sulphur oxides, phosgene, and chlorine. Captafol is effective for the control of almost all fungal diseases of plants except powdery mildews and is widely used outside the United States for the control foliage and fruit disease on apples, citrus, tomato, cranberry, potato, coffee, pineapple, peanut, onion, stone fruit, cucumber, blueberry, prune, watermelon, sweet corn, wheat, barley, oilseed rape, leek, and strawberry. It is also used as a seed protectant in cotton, peanuts, and rice. Captafol is also used in the lumber and timber industries to reduce losses from wood rot fungi in logs and wood products. Formulations of captafol include dusts, flowables, wettables, water dispersibles, and aqueous suspensions. Mixed formulations include (captafol +) triadimefon, ethirimol, folpet, halacrinate, propiconazole, and pyrazophos. Captafol is compatible with most plant-protection products, with the exception of alkaline preparations and formulating material.
• Uses: Captafol is used to control a wide range of fungal diseases on many crops. Agricultural fungicide, especially for potatoes. Captafol is a pesticide, belonging to thiophtalimide group. Occupational contact dermatitis was reported in an agricultural worker who had multiple sensitizations.

Technology Process of Captafol

There total 1 articles about Captafol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ captafol (2425-06-1,2939-80-2)

Guidance literature:

entspr. Phthalimid, Cl3C-CH(Cl)-S-Cl;

Refernces

N-(heteroarenesulfonyl)prolinamides-catalyzed aldol reaction between acetone and aryl trihalomethyl ketones

10.1021/ol2001039

The research focuses on the development of a highly enantioselective method for constructing a quaternary carbon center by catalytic enantioselective cross-aldol reactions between acetone and aryl trihalomethyl ketones, using N-(heteroarenesulfonyl)prolinamides as organocatalysts. The experiments involved the reaction of various trihalomethyl ketones (both trifluoromethyl and trichloromethyl) with acetone, utilizing N-(8-quinolinesulfonyl)prolinamide as the catalyst of choice, which was found to be highly efficient. The reactants included different aryl trifluoromethyl ketones and trichloromethyl ketones, along with acetone, and the products were analyzed for yield and enantioselectivity using high-performance liquid chromatography (HPLC) and X-ray crystallography to determine the absolute configuration of certain products. The study also employed molecular orbital calculations to elucidate the role of hydrogen bonding in exerting enantioselectivity, revealing that the interaction between the sulfonimide proton and the 8-quinolyl nitrogen atom is crucial for the reaction's selectivity.