(1S,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid

Base Information

• Chemical Name: (1S,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid
• CAS No.: 59042-50-1
• Molecular Formula: C₈H₁₀Cl₂O₂
• Molecular Weight: 209.072
• European Community (EC) Number: 611-302-2
• Nikkaji Number: J323.238G
• Wikidata: Q27131993
• Metabolomics Workbench ID: 62267
• Mol file: 59042-50-1.mol

Synonyms:3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid;3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid, calcium salt;3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid, monosodium salt;CDCCA compound;cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid;CL2CA;TDCCA compound;trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid

Chemical Property of (1S,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid

Chemical Property:

• Melting Point: 95-96.5 °C
• Boiling Point: 290.6±30.0 °C(Predicted)
• PKA: 4.09±0.33(Predicted)
• PSA: 37.30000
• Density: 1.433±0.06 g/cm3(Predicted)
• LogP: 2.66220
• Storage Temp.: Amber Vial, -20°C Freezer
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 208.0057849
• Heavy Atom Count: 12
• Complexity: 241

Purity/Quality:

98%Min ^*data from raw suppliers

rac-trans-PermethrinicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(C1C(=O)O)C=C(Cl)Cl)C
• Isomeric SMILES: CC1([C@H]([C@@H]1C(=O)O)C=C(Cl)Cl)C
• Uses: trans-Permethrinic acid is a potent insecticide used in the agricultural industry to eliminate unwanted pests from crops. trans-Permethrinic acid is also metabolite of pyrethroid compounds, a group of pesticides that are relatively low toxicity (to organisms that are not intended to be targeted) and biodegradable.

Technology Process of (1S,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid

There total 26 articles about (1S,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid 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: 95.0%

methyl trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate (59897-93-7,59897-94-8,61898-95-1,61976-30-5,61976-31-6,63805-74-3,74561-29-8,84984-65-6,84984-66-7) → trans-permethrin acid (55667-40-8,55701-03-6,55701-05-8,55701-06-9,55701-07-0,55701-08-1,55701-09-2,59042-49-8,59042-50-1)

Guidance literature:

With sodium hydroxide; In methanol; at 40 ℃; for 8h;

Reference yield:

cis,trans methyl 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropanecarboxylate (61898-95-1) → trans-permethrin acid (55667-40-8,55701-03-6,55701-05-8,55701-06-9,55701-07-0,55701-08-1,55701-09-2,59042-49-8,59042-50-1) + cis-permethrinic acid (59042-49-8)

Guidance literature:

With sodium hydroxide; In ethanol; water; Heating;

DOI:10.1021/jf970408o

Reference yield:

cis-2-Chlor-4-(2',2',2'-trichloraethyl)-3,3-dimethylcyclobutanon → trans-permethrin acid (55667-40-8,55701-03-6,55701-05-8,55701-06-9,55701-07-0,55701-08-1,55701-09-2,59042-49-8,59042-50-1) + cis-permethrinic acid (59042-49-8)

Guidance literature:

With sodium hydroxide; In water; 1.) -7 deg C, 24 h; 2.) 100 deg C, 8 h;

DOI:10.1002/hlca.19830660421

upstream raw materials:

diazoacetic acid ethyl ester

1,1-dichloro-4-methyl-penta-1,3-diene

cis,trans methyl 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropanecarboxylate

ethyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate

Downstream raw materials:

(+)-trans-(1R,3S)-2,2-dimethyl-3-(2',2'-dichlorovinyl)cyclpropanecarboxylic acid

(-)-trans-(1S,3R)-2,2-dimethyl-3-(2',2'-dichlorovinyl)cyclpropanecarboxylic acid

(1R,3S)-3-(2,2-Dichloro-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid benzyl ester

(1R,3S)-3-(2,2-Dichloro-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid phenylamide

Refernces

• 1、 Liang, Wei Q.,Wang, Zhuo Y.,Li, He,Wu, Pei C.,Hu, Ji M.,Luo, Na,Cao, Li X.,Liu, Yu H.. "Purification and characterization of a novel pyrethroid hydrolase from Aspergillus niger ZD11". . p. 7415 - 7420. Retrieved 2007/10/03.
• 2、 Kumar,Chakravarthy, P.Pawan,Shesha Rao,Reddy, P.Sunder Ram,Yadav. "Free radical addition of haloalkanes to polymer bound olefins and its application to the solid-phase synthesis of pyrethroids". . p. 7817 - 7819. Retrieved 2007/10/03.