trans-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid

Base Information

• Chemical Name: trans-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid
• CAS No.: 55701-03-6
• Molecular Formula: C8H10Cl2O2
• Molecular Weight: 209.072
• Hs Code.: 2902900000
• European Community (EC) Number: 611-302-2
• DSSTox Substance ID: DTXSID9052717
• Nikkaji Number: J323.239E
• Mol file: 55701-03-6.mol

Synonyms:59042-50-1;(1R,3S)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid;55701-03-6;trans-Permethemic acid;55701-07-0;trans-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid;(1R,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid;trans-Permethrinic Acid;trans-Permethric acid;(1R,3S)-3-(2,2-DICHLOROETHENYL)-2,2-DIMETHYL-CYCLOPROPANE-1-CARBOXYLIC ACID;C8-H10-Cl2-O2;trans-Permethrinic acid 100 microg/mL in Acetonitrile;rac-trans-Permethrinic Acid;1R-trans-Permethrinic Acid;SCHEMBL586158;Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, trans-;DTXSID9052717;trans-3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid;trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid;(1R,3S)-trans-Permethric acid;AKOS015951326;W-105551;(1R,3S)-3-(2,2-Dichloroethenyl)-2,2-dimethyl-cyclopropanecarboxylic Acid;(1r)-trans-2,2-dimethyl-3-(2,2-dichloroethenyl) cyclopropanecarboxylic acid;Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (1R,3S)-;Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (1R,3S)-rel-;Trans 3-(2, 2 dichlorovinyl)-2, 2-dimethyl cyclopropane-1, carboxylic acid

Chemical Property of trans-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid

Chemical Property:

• Vapor Pressure: 0.000512mmHg at 25°C
• Melting Point: 70-71 °C
• Refractive Index: 1.6
• Boiling Point: 290.6 °C at 760 mmHg
• PKA: 4.09±0.33(Predicted)
• Flash Point: 129.6 °C
• PSA: 37.30000
• Density: 1.433 g/cm³
• LogP: 2.66220
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Dichloromethane (Slightly), 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%,99%, ^*data from raw suppliers

1R-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: 1R-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 trans-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid

There total 36 articles about trans-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: 93.0%

(1R,3S)-[(R)-2'-ethoxy-1,1'-binaphth-2-yl]-3-(2',2'-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate → (+)-trans-(1R,3S)-2,2-dimethyl-3-(2',2'-dichlorovinyl)cyclpropanecarboxylic acid (55701-03-6)

Guidance literature:

(1R,3S)-[(R)-2'-ethoxy-1,1'-binaphth-2-yl]-3-(2',2'-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate; With potassium hydroxide; water; In tetrahydrofuran; methanol; at 60 - 65 ℃; for 2h;

With hydrogenchloride; water; pH=1; optical yield given as %ee;

DOI:10.1016/j.tetasy.2009.02.060

Reference yield: 48.0%

3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid (55701-05-8) → (-)-cis-(1S,3S)-2,2-dimethyl-3-(2',2'-dichlorovinyl)cyclopropanecarboxylic acid (55701-08-1) + (+)-trans-(1R,3S)-2,2-dimethyl-3-(2',2'-dichlorovinyl)cyclpropanecarboxylic acid (55701-03-6) + 1(R)-cis-permethrinic acid (55667-40-8) + (-)-trans-(1S,3R)-2,2-dimethyl-3-(2',2'-dichlorovinyl)cyclpropanecarboxylic acid (55701-09-2)

Guidance literature:

3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid; With Tentagel resin;

With lipase enzyme; In tetrahydrofuran; tert-butyl alcohol; at 30 ℃; for 8h; pH=7.8;

DOI:10.1016/S0040-4039(99)01127-2

upstream raw materials:

trans-permethrin acid

3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid

(+/-)-trans-2-(2,2-dichloroethenyl)-3,3-dimethylcyclopropanecarboxylic acid chloride

diazoacetic acid ethyl ester

Downstream raw materials:

3t-(2,2-dichloro-vinyl)-2,2-dimethyl-cyclopropane-r-carboxylic acid-(3-allyl-2-methyl-4-oxo-cyclopent-2-enyl ester)

(+/-)-trans-2-(2,2-dichloroethenyl)-3,3-dimethylcyclopropanecarboxylic acid chloride

(1R)-trans-3-(2,2-dichloro-1-ethenyl)-2,2-dimethylcyclopropanecarboxylic acid chloride

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

Refernces

• 1、 Bicker, Wolfgang,Kacprzak, Karol,Kwit, Marcin,Laemmerhofer, Michael,Gawronski, Jacek,Lindner, Wolfgang. "Assignment of absolute configurations of permethrin and its synthon 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid by electronic circular dichroism, optical rotation, and X-ray crystallography". experimental part. p. 1027 - 1035. Retrieved 2009/10/10.
• 2、 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.