Spirodiclofen

Base Information

• Chemical Name: Spirodiclofen
• CAS No.: 148477-71-8
• Molecular Formula: C21H24Cl2O4
• Molecular Weight: 411.325
• European Community (EC) Number: 604-636-5
• UNII: 3X7G31F5MX
• DSSTox Substance ID: DTXSID6034928
• Nikkaji Number: J1.571.716E
• Wikipedia: Spirodiclofen
• Wikidata: Q425807
• Metabolomics Workbench ID: 55947
• ChEMBL ID: CHEMBL2227839
• Mol file: 148477-71-8.mol

Synonyms:spirodiclofen

Chemical Property of Spirodiclofen

Chemical Property:

• Appearance/Colour: white power
• Vapor Pressure: 3.73E-12mmHg at 25°C
• Melting Point: 94.8oC
• Refractive Index: 1.57
• Boiling Point: 561.1 °C at 760 mmHg
• Flash Point: 199.8 °C
• PSA: 52.60000
• Density: 1.28 g/cm³
• LogP: 5.94360
• Storage Temp.: 0-6°C
• Solubility.: Chloroform (Slightly), DMSO, Methanol (Sparingly)
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 410.1051646
• Heavy Atom Count: 27
• Complexity: 634

Purity/Quality:

99% ^*data from raw suppliers

Spirodiclofen ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, Xn, F
• Hazard Codes: Xi,Xn,F
• Statements: 43-67-65-63-48/20-38-11
• Safety Statements: 36/37-62

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC(C)(C)C(=O)OC1=C(C(=O)OC12CCCCC2)C3=C(C=C(C=C3)Cl)Cl
• Description: Spirodiclofen is a new selective, non systemic acaricide belonging to the chemical group of the spirocyclic tetronic acid derivatives. It acts by interfering with mite development, thereby controlling such pests as Panonychus spp., Phyllocoptruta spp., Brevipalpus spp., and Aculus and Tetranychus species. Spirodiclofen is active by contact to mite eggs, all nymphal stages, and adult females (adult males are not effected). Spirodiclofen is structurally similar to spiromesifen, which is also a tetronic acid insecticide. Spirodiclofen is registered worldwide for use on a variety of crops including citrus, pome fruits, stone fruits, grapes and ornamentals.
• Uses: Spirodiclofen is a tetronic acid acaricide fungicide used in controlling red mites. Spirodiclofen is used in cannabis testing kits as a component of pesticide mixes (P698240).

Technology Process of Spirodiclofen

There total 12 articles about Spirodiclofen 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: 97.8%

2,2-dimethylbutanoyl chloride (5856-77-9) + 3-(2,4-dichlorophenyl)-4-hydroxy-1-oxaspiro[4.5]dec-3-en-2-one (148476-22-6) → spirodiclofen (148477-71-8)

Guidance literature:

With sodium carbonate; sodium hydroxide; In tetrahydrofuran; at 10 - 20 ℃; for 2h; Solvent; Reagent/catalyst; Large scale;

Reference yield:

1-hydroxy-1-cyclohexanecarbonitrile (931-97-5) → spirodiclofen (148477-71-8)

Guidance literature:

Multi-step reaction with 5 steps

1: aq. HCl

2: p-TsOH

3: KOtBu

With hydrogenchloride; potassium tert-butylate; toluene-4-sulfonic acid;

DOI:10.2533/000942903777678588

Reference yield:

ethyl 1-hydroxycyclohexanecarboxylate (1127-01-1) → spirodiclofen (148477-71-8)

Guidance literature:

Multi-step reaction with 3 steps

1: KOtBu

With potassium tert-butylate;

DOI:10.2533/000942903777678588

upstream raw materials:

2,2-dimethylbutanoyl chloride

3-(2,4-dichlorophenyl)-4-hydroxy-1-oxaspiro[4.5]dec-3-en-2-one

1-hydroxy-cyclohexanecarboxylic acid

1-hydroxy-1-cyclohexanecarbonitrile

Refernces

• 1、 -. "Production process of high-purity and high-yield spirodiclofen". Paragraph 0050; 0058; 0068. . Retrieved 2019/03/08.
• 2、 -. "NOVEL FORM OF SPIRODICLOFEN, A PROCESS FOR ITS PREPARATION AND USE THE SAME". Paragraph 0076; 0077. . Retrieved 2017/07/06.