(1R-cis)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane carboxylic acid
(1R-cis)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane carboxylic acid
CAS: 53179-78-5
Molecular Formula: C8H10Br2O2
(1R-cis)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane carboxylic acid - Names and Identifiers
(1R-cis)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane carboxylic acid - Physico-chemical Properties
| Molecular Formula | C8H10Br2O2 |
| Molar Mass | 297.97 |
| Density | 1.993±0.06 g/cm3(Predicted) |
| Boling Point | 326.4±32.0 °C(Predicted) |
| Storage Condition | 2-8℃ |
| Physical and Chemical Properties | Chemical quality This product is white crystal, m.p.128 ~ 129 ℃,[α]= 25.98 (2.1% DMF), insoluble in water, soluble in benzene, toluene and other organic solvents. |
| Use | Use 1R 3R-er xiu ju suan is efficient insecticide deltamethrin of important intermediates |
(1R-cis)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane carboxylic acid - Upstream Downstream Industry
(1R-cis)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane carboxylic acid - Production method
The preparation method can be prepared with first chrysanthemum acid or cis-dichlorochrysanthemum acid as raw materials. The (±) trans-chrysanthemum acid synthesized by Martel method was resolved by L-(+)-Su-type p-nitrophenyl-2-N, N-dimethyl-1, 3-propanediol or α-methylbenzylamine to obtain (+) trans-chrysanthemum acid and (-) trans-chrysanthemum acid, respectively. () Trans-chrysanthemum acid is 1R, 3R-chrysanthemum acid, which is esterified with methanol to obtain methyl dextrotrans-chrysanthemum acid, and further ozonation reaction, and the temperature is kept at -10~12 ℃ to obtain methyl dextrotrans-carbonic acid. The ester is then epimerized and reacted in a methanol solution of sodium methoxide. The temperature is below 10 ℃, the material is fed under nitrogen protection, and then, after the reaction is over for 3h, the methanol is removed, and the acetal lactone is obtained after post-treatment. The lactone is treated with dioxane, water and a small amount of acetic acid, and then recrystallized into hemiacetal lactone. The lactone opens the ring to obtain 1R, 3S-caruronic acid, and then undergoes Wittig reaction with triphenylmethylene dibromoporous to obtain 1R.
(-) Trans-chrysanthemum acid, I .e. 1S,3S-chrysanthemum acid, generates 2,2-dimethyl (2 & prime;-hydroxy -2 & prime;-methylpropanyl) cyclopropane carboxylic acid, in the presence of potassium tert-butoxide, carries out C1 epimerism to obtain bicyclolactone, then carries out acid hydrolysis to obtain 1R,3S-chrysanthemum acid, and then, 3S-cardoxic acid, which also reacts with triphenylmethylene phosphorus dibromide to obtain 1R, 3R-dibromophoric acid.
It is also possible to react 1R, 3S-carylic acid with tribromomethane to obtain tribromobicyclolactone compounds, and then perform the elimination reaction in tetrahydrofuran with zinc powder to obtain 1R, 3R-dibromopranic acid.
It is also possible to react 1R, 3R-dichlorochrysanthemum with AlBr3 to obtain 1R, 3R-dibromothrin.
Using cis-dichlorochrysanthemum acid as raw material to prepare 1R, 3R-dibromothrin acid is to split (±) cis-dichlorochrysanthemum acid to obtain () cis-dichlorochrysanthemum acid. After ozonation and Wittig reaction, 1R, 3R-dibromothrin acid can also be obtained.
Last Update：2024-04-10 22:29:15
(1R-cis)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane carboxylic acid - Nature
| acidity coefficient (pKa) | 3.94±0.42(Predicted) |
Last Update：2024-04-09 01:59:50
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CAS: 53179-78-5
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CAS: 53179-78-5
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View History
Raw Materials for (1R-cis)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane carboxylic acid
Potassium tert-butoxide
Permethric acid
Acetal
Cyclopropanecarboxylic acid
Ozone
Bromoform
methyl(±)cis,trans-2,2-dimethyl-3-(2-methyl-1-propenyl cyclopropane carboxylate)
Dibromomethane
1R-trans-methyl caronaldehydate
Permethric acid
Acetal
Cyclopropanecarboxylic acid
Ozone
Bromoform
methyl(±)cis,trans-2,2-dimethyl-3-(2-methyl-1-propenyl cyclopropane carboxylate)
Dibromomethane
1R-trans-methyl caronaldehydate