Icaridin

Base Information

• Chemical Name: Icaridin
• CAS No.: 119515-38-7
• Deprecated CAS: 658051-75-3
• Molecular Formula: C12H23NO3
• Molecular Weight: 229.32
• European Community (EC) Number: 423-210-8,842-492-7
• UNII: N51GQX0837
• DSSTox Substance ID: DTXSID0034227
• Nikkaji Number: J806.232C
• Wikipedia: Icaridin
• Wikidata: Q418792
• NCI Thesaurus Code: C83777
• Metabolomics Workbench ID: 154779
• ChEMBL ID: CHEMBL2104314
• Mol file: 119515-38-7.mol

Synonyms:1-(1-methylpropoxycarbonyl)-2-(2-hydroxyethyl)piperidine;2-(2-hydroxyethyl)-1-piperidinecarboxylic acid 1-methylpropyl ester;Bayrepel;icaridin;KBR 3023;picaridin;Saltidin;sec-butyl 2-(2-hydroxyethyl)piperidine-1-carboxylate

Chemical Property of Icaridin

Chemical Property:

• Appearance/Colour: Colourless liquid
• Vapor Pressure: 1.18E-05mmHg at 25°C
• Melting Point: <-170°
• Refractive Index: 1.477
• Boiling Point: 330.9 °C at 760 mmHg
• PKA: 15.15±0.10(Predicted)
• Flash Point: 153.9 °C
• PSA: 49.77000
• Density: 1.041 g/cm³
• LogP: 2.09630
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 229.16779360
• Heavy Atom Count: 16
• Complexity: 220

Purity/Quality:

99% ^*data from raw suppliers

Picaridin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Insect Repellents
• Canonical SMILES: CCC(C)OC(=O)N1CCCCC1CCO
• Description: Picaridin is an insect repellent. It inhibits A. aegypti odorant receptor 2 (AaOR2) or AaOR8 in the presence of their odorant activators, indole and octenol, respectively, expressed in Xenopus oocytes (IC50s = 1,452 and 1,911 μM, respectively). Picaridin reduces the number of entries into a food chamber by female D. melanogaster in an olfactory-based choice assay. It acts synergistically with the non-pyrethroid insecticide pyrimiphos methyl to increase mortality of A. gambiae and reduce blood feeding when used at a concentration of 10 g/m2 on nets surrounding guinea pig cages. Formulations containing picaridin have been used as insect repellents against flies, mosquitoes, chiggers, ticks, and fleas.
• Uses: Acts on certain olfactory receptor cell types to reduce the activating or attracting effect of odor sources. Insect repellent Insect repellent. Acts on certain olfactory receptor cell types to reduce the activating or attracting effect of odor sources.Insect repellent.

Technology Process of Icaridin

There total 1 articles about Icaridin 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:

sec-butyl 2-(2-(((2R,3S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-oxotetrahydro-2H-pyran-2-yl)oxy)ethyl)piperidine-1-carboxylate → icaridin (119515-38-7)

Guidance literature:

With water-d2; In aq. buffer; at 32 ℃; for 50h; pH=4; pH-value;

Reference yield: 84.0%

bromobenzene (108-86-1,52753-63-6) + icaridin (119515-38-7) → C18H27NO2

Guidance literature:

With N-ethyl-N,N-diisopropylamine; triphenylphosphine; 4,4'-di-tert-butyl-2,2'-bipyridine; lithium bromide; nickel dibromide; In 1-methyl-pyrrolidin-2-one; at 20 ℃; for 14h; Glovebox; Electrolysis;

DOI:10.1021/jacs.0c13093

Reference yield: 66.0%

bromodifluoroacetic acid (354-08-5) + icaridin (119515-38-7) → C14H22BrF2NO4

Guidance literature:

With oxalyl dichloride; triethylamine; N,N-dimethyl-formamide; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.1c03076

Refernces