Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)-
2,2-DIMETHYL-3-(2-METHYLPROP-1-ENYL)CYCLOPROPANECARBOXYLIC ACID
CAS: 10453-89-1
Molecular Formula: C10H16O2
Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)- - Names and Identifiers
Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)- - Physico-chemical Properties
| Molecular Formula | C10H16O2 |
| Molar Mass | 168.23 |
| Density | 0.9812 (rough estimate) |
| Melting Point | 50-51 °C |
| Boling Point | 257.18°C (rough estimate) |
| pKa | 4.90±0.33(Predicted) |
| Refractive Index | 1.4890 (estimate) |
| Physical and Chemical Properties | The first chemical property chrysanthemum acid is a white crystal or light yellow solid, containing cis-trans isomers. due to the different content of cis-trans isomers, its melting point is not fixed. (+) trans chrysanthemum acid m.p.54 ~ 55 ℃,(+) cis chrysanthemum acid m.p.114 ~ 115 ℃, B. p.109 ℃/133Pa, chrysanthemum acid is insoluble in water and soluble in organic solvents. |
| Use | Uses the first chrysanthemum acid referred to as the chrysanthemum acid, chemical name is (±)cis -2,2-dimethyl-3-(2-methylpropenyl) cyclopropane carboxylic acid [(±)cis,trans-2,2-dimethyl-3-(2-methyl-1-probenyl) cyclopropane carbolic acid], is an important intermediate of pyrethroid, can be used to synthesize Allyl, promethrin, furthrin, amithrin, methylethrin, furenthrin, pyrethroids such as fenfurothrin, fenthrin, fenvalerate and cyhalothrin. |
Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)- - Upstream Downstream Industry
| Raw Materials | ISOBUTYLENE 1-Hexene Isobutyryl chloride Ethyl chrysanthemumate 3-Methyl-1-butene diazoacetic acid ESTRONE(RG) 1-HEPTENE orthoacetic acid |
| Downstream Products | Empenthrin |
Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)- - Reference Information
| chemical properties | the first chrysanthemum acid is a white crystal or light yellow solid, containing cis-trans isomer. due to the different content of cis-trans isomer, the melting point is not fixed, (+) trans chrysanthemum acid m.p.54 ~ 55 ℃,(+) cis chrysanthemum acid m.p.114 ~ 115 ℃, B. p.109 ℃/133Pa, chrysanthemum acid is insoluble in water, soluble in ethanol, benzene, ether and other organic solvents. |
| Use | The first chrysanthemum acid is abbreviated as chrysanthemum acid, and the chemical name is (±)cis-trans-2,2-dimethyl-3-(2-Methylpropyl) cyclopropane carboxylic acid [(±)cis,trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropane carboxylic acid], is an important intermediate of pyrethroids, it can be used to synthesize pyrethroid, pyrethrin, permethrin, pyrethrin, methrin, ethenthrin, methenthrin, methenthrin, phenetherin, pyrethrin, pyrethrin, cypermethrin and other pyrethroids. |
| Production method | There are many synthetic methods for the first chrysanthemum acid, but the current industrial production mainly includes diazoacetate method (also known as Harper and Campbell method) and Isopentenyl sulfone method (also known as Martel method). The reaction equations are described below. Diazoacetate method isopentenyl sulfone method (Martel method) The ethyl chrysanthemum acid (methyl ester) obtained by the above method is hydrolyzed in the alcohol solution in the presence of alkali, and then acidified to obtain chrysanthemum acid. Later, Jacqueline and others reported that the first chrysanthemum acid can also be synthesized by the orthoacetate method. The isobutylene and isobutyryl chloride are condensed under the catalysis of AlCl3 to obtain 2, 5-dimethylhexene-2-keto-3, which is then reduced by NaBH4 and reacted with orthoacetate to obtain 3,3, 6-trimethylhepten-4-acid ethyl ester, which is then added with chlorine gas, and then dehydrochlorinated and cyclized to obtain (±) cis-trans-first pyrethrate ethyl ester, and is mainly trans isomer. Add ethyl chrysanthemum acid (methyl ester) lye and ethanol (or methanol) to the reaction bottle respectively, refluxing under heating and stirring for 4~6h, and recover ethanol (methanol) under normal pressure. The recovered alcohol can be applied. The dealcohol reaction liquid is acidified with hydrochloric acid, then toluene or benzene is added for extraction, and the organic layer is separated. Chrysanthemum acid is obtained by washing, drying and desolution, which is a waxy or solid substance, the yield is 96% ~ 97%. |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
Last Update：2024-04-10 22:29:15
Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)- - Production method
There are many methods for the synthesis of the first chrysanthemum acid, but the current industrial production mainly includes diazoacetate method (also known as Harper and Campbell method) and isopentenyl sulfone method (also known as Martel method). The reaction equations are described below.
Diazoacetate method
Isopentenyl sulfone method (Martel method)
The ethyl chrysanthemum acid (methyl ester) obtained by the above method is hydrolyzed in the alcohol solution in the presence of alkali, and then acidified to obtain chrysanthemum acid.
Later, Jacqueline and others reported that the first chrysanthemum acid can also be synthesized by the orthoacetate method. The isobutylene and isobutyryl chloride are condensed under the catalysis of AlCl3 to obtain 2, 5-dimethylhexene-2-keto-3, which is then reduced by NaBH4 and reacted with orthoacetate to obtain 3,3, 6-trimethylhepten-4-acetate, and then added with chlorine gas to react, and then dehydrochlorination and cyclization to obtain (±) cis-trans-first pyrethrate.
Add ethyl chrysanthemum acid (methyl ester) lye and ethanol (or methanol) into the reaction bottle respectively, refluxed under heating and stirring for 4~6h, and recover ethanol (methanol) under normal pressure. The recovered alcohol can be applied. The reaction liquid to remove alcohol is acidified with hydrochloric acid, then toluene or benzene is added for extraction, and the organic layer is separated, and the chrysanthemum acid is obtained by washing, drying and dissolving with water, the yield was 96% ~ 97%.
Last Update：2024-04-10 22:29:15
Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)- - Nature
| EPA chemical information | Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)- (10453-89-1) |
Last Update：2024-04-09 19:04:55
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Raw Materials for Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)-
Downstream Products for Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)-