Vinclozolin

Base Information

• Chemical Name: Vinclozolin
• CAS No.: 50471-44-8
• Molecular Formula: C₁₂H₉Cl₂NO₃
• Molecular Weight: 286.114
• Hs Code.: 2934999039
• European Community (EC) Number: 256-599-6
• UN Number: 3077,2588
• UNII: JJ258EZN1I
• DSSTox Substance ID: DTXSID4022361
• Nikkaji Number: J1.897J
• Wikipedia: Vinclozolin
• Wikidata: Q412907
• Metabolomics Workbench ID: 67731
• ChEMBL ID: CHEMBL513221
• Mol file: 50471-44-8.mol

Synonyms:3-(3,5-dichlorophenyl)-5-methyl-5-vinyl-1,3-oxazolidine-2,4-dione;Ronilan;vinclozolin

Chemical Property of Vinclozolin

Chemical Property:

• Appearance/Colour: Vinclozolin is a colorless crystal with a slight aromatic odor
• Vapor Pressure: 1.15E-05mmHg at 25°C
• Melting Point: 108 ºC
• Refractive Index: 1.6100 (estimate)
• Boiling Point: 369.9 °C at 760 mmHg
• PKA: -3.43±0.40(Predicted)
• Flash Point: 177.5 °C
• PSA: 46.61000
• Density: 1.496 g/cm³
• LogP: 3.48630
• Storage Temp.: APPROX 4°C
• Water Solubility.: 3.4 mg l-1 (20 °C)
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 284.9959485
• Heavy Atom Count: 18
• Complexity: 391
• Transport DOT Label: Class 9

Purity/Quality:

99% ^*data from raw suppliers

Vinclozolin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N,Xn,F
• Hazard Codes: T,N,Xn,F
• Statements: 60-61-40-43-51/53-36-20/21/22-11
• Safety Statements: 53-45-61-36-26-16-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Fungicides
• Canonical SMILES: CC1(C(=O)N(C(=O)O1)C2=CC(=CC(=C2)Cl)Cl)C=C
• General Description: Vinclozolin is a fungicide that undergoes rapid photodegradation under UV light (254 nm), with half-lives of 1.01 minutes in water and 2.0 minutes in methanol-water solutions. Its photolysis primarily involves the cleavage of the 2,4-oxazolidine-dione ring, yielding 3,5-dichlorophenyl isocyanate and 3,5-dichloroaniline as major degradation products, along with dechlorination and the loss of the vinyl group (-CH=CH2). This indicates its instability in aquatic environments under UV exposure.

Technology Process of Vinclozolin

There total 7 articles about Vinclozolin 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: 85.0%

isobutyl 2-hydroxy-2-vinylpropionate (72531-53-4) + bis-(3,5-dichlorophenyl)-urea → 3-(3,5-dichlorophenyl)-5-methyl-5-vinyloxazolidine-2,4-dione (152723-53-0,152723-54-1,50471-44-8)

Guidance literature:

In methanol; 2-methyl-propan-1-ol;

Reference yield:

ethyl vinyl lactate + 3,4-dichlorophenyl isocyanate (34893-92-0) → 3-(3,5-dichlorophenyl)-5-methyl-5-vinyloxazolidine-2,4-dione (152723-53-0,152723-54-1,50471-44-8)

Guidance literature:

With triethylamine; In benzene;

Reference yield:

isobutyl 2-hydroxy-2-vinylpropionate (72531-53-4) + 3,5-dichlorophenyl-carbamic acid isobutyl ester (25216-51-7) → 3-(3,5-dichlorophenyl)-5-methyl-5-vinyloxazolidine-2,4-dione (152723-53-0,152723-54-1,50471-44-8)

Guidance literature:

With tributyl-amine; In methanol;

upstream raw materials:

3,4-dichlorophenyl isocyanate

isobutyl 2-hydroxy-2-vinylpropionate

1-(3,5-Dichlorophenyl)urea

3,5-dichlorophenyl-carbamic acid isobutyl ester

Downstream raw materials:

N-(3,5-Dichlorophenyl)-2-hydroxy-2-methylbut-3-enanilide

Refernces

Photochemistry of vinclozolin in water and methanol-water solution

10.1002/(SICI)1096-9063(199911)55:11<1116::AID-PS65>3.0.CO;2-Y

The research aims to investigate the photodegradation of the fungicide vinclozolin in aqueous and methanol-water solutions. The study exposed vinclozolin to UV light at 254nm, resulting in significant substrate transformation within 10 minutes, with less than 90% and ≤95% transformation in water and methanol-water solutions, respectively. The half-lives for dissipation of vinclozolin in these environments were calculated to be 1.01 and 2.0 minutes, respectively. The research concluded that photolysis leads to the opening of the 2,4-oxazolidine-dione ring, forming 3,5-dichlorophenyl isocyanate and 3,5-dichloroaniline, along with dechlorination and the elimination of the -CH=CH2 moiety.