Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (1R,3R)-

Base Information

• Chemical Name: Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (1R,3R)-
• CAS No.: 55667-40-8
• Molecular Formula: C8H10 Cl2 O2
• Molecular Weight: 209.072
• DSSTox Substance ID: DTXSID3041823
• Nikkaji Number: J490.847C
• Mol file: 55667-40-8.mol

Synonyms:55667-40-8;cis-DCCA;cis-trans-Permethric acid;Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (1R,3R)-;cis-DL-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylicacid;cis-(+-)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid;Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, cis-(+-)-;55701-06-9;1R-cis-Permethrinicacid;C8-H10-Cl2-O2;(1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid;starbld0016568;SCHEMBL192770;DTXSID3041823;(1R,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropane-1-carboxylic acid;(1R,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid;(1R-cis)-3-(2,2-Dichioroethenyl)-2,2-dimethyl-cyclopropane carboxylic acid

Chemical Property of Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (1R,3R)-

Chemical Property:

• Vapor Pressure: 0.000512mmHg at 25°C
• Boiling Point: 290.6°Cat760mmHg
• PKA: 4.66±0.42(Predicted)
• Flash Point: 129.6°C
• PSA: 37.30000
• Density: 1.433g/cm³
• LogP: 2.66220
• Storage Temp.: Amber Vial, -20°C Freezer
• Solubility.: Chloroform (Slightly), Dichloromethane (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

(+)-cis-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: (+)-cis-Permethrinic Acid is an enantiomer of rac-trans-Permethrinic Acid (P287705), a potent insecticide used in the agricultural industry to eliminate unwanted pests from crops.

Technology Process of Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (1R,3R)-

There total 28 articles about Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (1R,3R)- 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: 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

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

upstream raw materials:

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

ethyl (+/-)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate

diazoacetic acid ethyl ester

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

Downstream raw materials:

permethrin

2,2-dimethyl-3R-(2',2'-dibromovinyl)-cyclopropane-1R-carboxylic acid

(+)-(S)-α-cyano-3-phenoxybenzyl (1R)-cis-3-(2,2-dichlorovinyl)-2, 2-dimethylcyclopropanecarboxylate

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

Refernces

• 1、 Martin, Pierre. "Dependence of the Stereoselectivity on the Leaving Group, the Temperature and the Solvent in the Favoskii-Reaction of Enolisable Cyclobutanones". . p. 1189 - 1199. Retrieved 1983.
• 2、 Kallam, Srinivasa Reddy,Eda, Vishnuvardhan Reddy,Sen, Saikat,Datrika, Rajender,Rapolu, Rajesh Kumar,Khobare, Sandip,Gajare, Vikas,Banda, Malavika,Khan, Rashid Abdul Rehman,Singh, Manpreet,Lloyd, Michael,Kandagatla, Bhaskar,Janagili, Moses Babu,Tadikonda, Veerabhadra Pratap,Vidavalur, Siddaiah,Iqbal, Javed,Fox, Martin E.,Dahanukar, Vilas H.,Oruganti, Srinivas. "A diastereoselective synthesis of boceprevir's gem-dimethyl bicyclic [3.1.0] proline intermediate from an insecticide ingredient cis-cypermethric acid". supporting information. p. 4285 - 4294. Retrieved 2017/07/03.
• 3、 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.