Chrysanthemic acid

Base Information

• Chemical Name: Chrysanthemic acid
• CAS No.: 10453-89-1
• Deprecated CAS: 30636-83-0,497-68-7
• Molecular Formula: C10H16 O2
• Molecular Weight: 168.236
• Hs Code.: 2916209090
• European Community (EC) Number: 233-941-2
• NSC Number: 11779
• DSSTox Substance ID: DTXSID30871866
• Nikkaji Number: J10.459K
• Wikipedia: Chrysanthemic_acid
• Wikidata: Q56122646
• ChEMBL ID: CHEMBL1437285
• Mol file: 10453-89-1.mol

Synonyms:chrysanthemic acid;chrysanthemic acid, (+,-);chrysanthemic acid, (cis)-(+-)-isomer;chrysanthemic acid, (cis)-(S)-isomer;chrysanthemic acid, (cis)-isomer;chrysanthemic acid, (trans)-(+-)-isomer;chrysanthemic acid, (trans)-(R)-isomer;chrysanthemic acid, (trans)-(S)-isomer;chrysanthemic acid, (trans)-isomer;chrysanthemumdicarboxylic acid;chrysanthemummonocarboxylic acid

Chemical Property of Chrysanthemic acid

Chemical Property:

• Vapor Pressure: 0.0088mmHg at 25°C
• Melting Point: 50-51 °C
• Refractive Index: 1.546
• Boiling Point: 246.4oC at 760 mmHg
• PKA: 4.90±0.33(Predicted)
• Flash Point: 119oC
• PSA: 37.30000
• Density: 1.077g/cm3
• LogP: 2.30940
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 168.115029749
• Heavy Atom Count: 12
• Complexity: 234

Purity/Quality:

99% ^*data from raw suppliers

2,2-Dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC1C(C1(C)C)C(=O)O)C
• Uses: Chrysanthemic Acid is an intermediate in the synthesis of Chrysanthemic Acid (C903440); Dimethrin is a pesticide, a pyrethroid insecticide. An acaricide for agricultural purposes.

Technology Process of Chrysanthemic acid

There total 65 articles about Chrysanthemic 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: 86.0%

ethyl trans-(+/-)-chrysanthemate (97-41-6,1802-02-4,7377-84-6,15543-65-4,16642-27-6,34909-55-2,41641-25-2,41641-26-3,41641-27-4) → trans-chrysanthemic acid (827-90-7,2259-14-5,2935-23-1,4638-92-0,10453-89-1,15259-78-6,26771-06-2,26771-11-9,705-16-8)

Guidance literature:

With potassium hydroxide; In ethanol; water; for 3h;

DOI:10.1021/acs.joc.9b02767

Reference yield: 73.0%

tert-amyl trans-chrysanthemate (78715-54-5) → trans-chrysanthemic acid (827-90-7,2259-14-5,2935-23-1,4638-92-0,10453-89-1,15259-78-6,26771-06-2,26771-11-9,705-16-8)

Guidance literature:

With potassium hydroxide; In ethanol; for 24h; Heating;

DOI:10.1021/jo00335a002

Reference yield: 63.0%

N-[trans-2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarbonyloxy]-5-(4-methoxyphenyl)-4-methylthiazole-2(3H)-thione → trans-chrysanthemic acid (827-90-7,2259-14-5,2935-23-1,4638-92-0,10453-89-1,15259-78-6,26771-06-2,26771-11-9,705-16-8)

Guidance literature:

With cyclohexa-1,4-diene; In benzene; at 20 ℃; for 7.5h; Photolysis;

DOI:10.1055/s-0029-1217102

upstream raw materials:

2,5-Dimethyl-2,4-hexadiene

(+/-)-3t-(β-chloro-isobutyl)-2,2-dimethyl-cyclopropane-r-carboxylic acid

(+/-)-trans-2,2-dimethyl-3-(2',2'-dimethylvinyl)cyclopropanecarbonitrile

(+/-)-cis-2,2-dimethyl-3-(2',2'-dimethylvinyl)cyclopropanecarboxamide

Downstream raw materials:

(1S,3S)-trans-chrysanthemic acid

(1R,3R)-trans-chrysanthemic acid

(+/-)-trans-Homochrysanthemsaeure

(+/-)-trans-(E)-pyrethricsaeure

Refernces

• 1、 Armesto, Diego,Gallego, Mar G.,Horspool, William M.,Agarrabeitia, Antonia R.. "A New Photochemical Synthesis of Cyclopropanecarboxylic Acids Present in Pyrethroids by the Aza-di-?-methane Rearrangement". . p. 9223 - 9240. Retrieved 1995.
• 2、 Rudashevskaya,Nesmeyanova. "". . . Retrieved 1979.
• 3、 Brady, William T.,Norton, Scott J.,Ko, Jinren. "A Versatile New Synthesis of Pyrethroid Acids". . p. 1002 - 1005. Retrieved 1983.
• 4、 Bhaskar Rao,Rehman,Krishnakumari,Yadav. "Lipase catalysed kinetic resolution of racemic (±)2,2-dimethyl-3-(2-methyl-1-propenyl)-cyclopropane carboxyl esters". . p. 2611 - 2614. Retrieved 1994.
• 5、 Corey,Jautelat. "-". . p. 3912. Retrieved 1967.
• 6、 Tappin, Nicholas D. C.,Michalska, Weronika,Rohrbach, Simon,Renaud, Philippe. "Cyclopropanation of Terminal Alkenes through Sequential Atom-Transfer Radical Addition/1,3-Elimination". supporting information. p. 14240 - 14244. Retrieved 2019/08/26.
• 7、 Krief, Alain,Jeanmart, Stéphane,Gondal, Humaira Y.,Kremer, Adrian. "Syntheses of racemic and scalemic cis-chrysanthemic acid from β,γ-unsaturated cyclohexanol". . p. 2123 - 2167. Retrieved 2013/02/23.