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Ethyl chrysanthemumate

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Ethyl chrysanthemumate Basic information

Product Name:
Ethyl chrysanthemumate
Synonyms:
  • (1R,3S)-2,2-dimethyl-3-(2-methylprop-1-enyl)-1-cyclopropanecarboxylic acid ethyl ester
  • 2,2-DIMETHYL-3-(2-METHYL-1-PROPENYL)CYCLOPROPANE CARBOXYLIC ACID ETHYL ESTER
  • 2,2-DIMETHYL-3-(1-ISOBUTENYL)CYCLOPROPANE-1-CARBOXYLIC ACID ETHYL ESTER
  • ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate
  • CHRYSANTHEMUM MONOCARBOXYLIC ACID ETHYL ESTER
  • CHRYSANTHEMYLMONOCARBOXYLIC ACID ETHYL ESTER
  • ETHYL CHRYSANTHEMATE
  • ETHYL CHRYSANTHEMUMATE
CAS:
97-41-6
MF:
C12H20O2
MW:
196.29
EINECS:
202-579-7
Product Categories:
  • Cyclopropanes
  • Simple 3-Membered Ring Compounds
  • Pharmaceutical Intermediates
  • 3
Mol File:
97-41-6.mol
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Ethyl chrysanthemumate Chemical Properties

Boiling point:
112 °C10 mm Hg(lit.)
Density 
0.906 g/mL at 25 °C(lit.)
refractive index 
n20/D 1.461(lit.)
Flash point:
184 °F
storage temp. 
2-8°C
solubility 
Chloroform (Slightly), Methanol (Slightly)
form 
Liquid
color 
Yellow
Odor
at 10.00 % in dipropylene glycol. herbal wine fruity everlasting flower chrysanthemum sweet
Odor Type
herbal
BRN 
2045740
LogP
4.181 (est)
CAS DataBase Reference
97-41-6(CAS DataBase Reference)
NIST Chemistry Reference
Ethyl chrysanthemate(97-41-6)
EPA Substance Registry System
Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, ethyl ester (97-41-6)
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Safety Information

Safety Statements 
24/25
WGK Germany 
2
RTECS 
GZ1727000
TSCA 
Yes
HS Code 
29162090

MSDS

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Ethyl chrysanthemumate Usage And Synthesis

Chemical Properties

clear colorless to yellow liquid. Very slightly soluble in water, soluble in alcohol and oils. Powerful, winey-herbaccous, sweet and ethereal, very pleasant odor of intriguing complexity, and with a powerfully lifting minty undertone. The spicy-hcrbaccous, warm and almost green-floral notes resemble certain notes in the Jasmin complex.

Uses

Ethyl Chrysanthemate is an organic building block used in the synthesis of various chemical compounds, such as insecticide, Resmethrin (R144685). It is used in the preparation of trans-norchrysanthemates and trans-norpyrethrates, having insecticidal activity.

Synthesis Reference(s)

Tetrahedron Letters, 22, p. 1783, 1981 DOI: 10.1016/S0040-4039(01)90438-1
Synthesis, p. 600, 1976 DOI: 10.1055/s-1976-24132

Purification Methods

Purify the ester by vacuum distillation. The free trans-acid has m 54o (from EtOAc), and the free cis-acid has m 113-116o (from EtOAc). The 4-nitrophenyl ester has m 44-45o (from pet ether) [Campbell & Harper J Chem Soc 283 1945, IR: Allen et al. J Org Chem 22 1291 1957]. [Beilstein 9 II 45.]

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