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ETHYL CHRYSANTHEMUMATE
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Name

ETHYL CHRYSANTHEMUMATE

 EINECS 202-579-7
CAS No. 97-41-6 Density 0.991 g/cm3
PSA 26.30000 LogP 2.78790
Solubility N/A Melting Point 0oC
Formula C12H20O2 Boiling Point 240.8 °C at 760 mmHg
Molecular Weight 196.29 Flash Point 84.4 °C
Transport Information N/A Appearance clear colorless to yellow liquid
Safety 24/25 Risk Codes N/A
Molecular Structure Molecular Structure of 97-41-6 (Ethyl chrysanthemumate) Hazard Symbols N/A
Synonyms

NSC 10819;Ethylchrysanthemate;Chrysanthemumic acid ethyl ester;Ethyl2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate;Chrysanthemic acid ethyl ester;Chrysanthemummonocarboxylicacid, ethyl ester (6CI);Cyclopropanecarboxylic acid,2,2-dimethyl-3-(2-methyl-1-propenyl)-, ethyl ester (9CI);

Article Data 55

ETHYL CHRYSANTHEMUMATE Synthetic route

764-13-6

2,5-Dimethyl-2,4-hexadiene

459-73-4

GlyOEt*HCl

97-41-6

ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

Conditions
ConditionsYield
Stage #1: GlyOEt*HCl With acetic acid; carbonic acid dimethyl ester at 20 - 28℃; pH=3.5 - 4.53; Large scale;
Stage #2: 2,5-Dimethyl-2,4-hexadiene With copper(l) chloride at 90 - 95℃; Large scale;		92%
623-73-4

diazoacetic acid ethyl ester

764-13-6

2,5-Dimethyl-2,4-hexadiene

A

97-41-6

ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

B

623-91-6

diethyl Fumarate

C

141-05-9

Diethyl maleate

Conditions
ConditionsYield
hexarhodium hexadecacarbonyl at 60℃; for 7h;A 91%
B n/a
C n/a
623-73-4

diazoacetic acid ethyl ester

764-13-6

2,5-Dimethyl-2,4-hexadiene

97-41-6

ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

Conditions
ConditionsYield
K-PFIEP[SO3 H] In dichloromethane89.6%
Stage #1: 2,5-Dimethyl-2,4-hexadiene With dirhodium tetraacetate In dichloromethane for 0.5h;
Stage #2: diazoacetic acid ethyl ester In dichloromethane at 20℃; for 24h; Reagent/catalyst;		80%
dirhodium tetraacetate at 25℃; Yield given;
623-73-4

diazoacetic acid ethyl ester

764-13-6

2,5-Dimethyl-2,4-hexadiene

A

97-41-6

ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

B

41641-25-2

ethyl 2,2-dimethyl-3-(2-methylpropenyl)-cyclopropanecarboxylate

C

41641-27-4

ethyl 2,2-dimethyl-3-(2-methylpropenyl)-cyclopropanecarboxylate

Conditions
ConditionsYield
Stage #1: 2,5-Dimethyl-2,4-hexadiene With C30H27FeN2P; 2Cu(1+)*2CF3O3S(1-)*0.5C6H6 In 1,2-dichloro-ethane at 60℃; for 0.5h; Inert atmosphere; Molecular sieve; Industrial scale;
Stage #2: diazoacetic acid ethyl ester In 1,2-dichloro-ethane for 18h; Reagent/catalyst; Inert atmosphere; Molecular sieve; Industrial scale; enantioselective reaction;		A n/a
B 80%
C n/a
167690-92-8

ethyl oxido-chrysanthemate

97-41-6

ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

Conditions
ConditionsYield
With pyridine; carbon disulfide; phosphorous triiodide for 4h; Heating;77%
167690-92-8

ethyl oxido-chrysanthemate

A

(E)-6-Hydroxy-3,3,6-trimethyl-hept-4-enoic acid ethyl ester

B

97-41-6

ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

Conditions
ConditionsYield
With samarium diiodide; tert-butyl alcohol In tetrahydrofuran at 20℃; for 2h;A 70%
B 12%
764-13-6

2,5-Dimethyl-2,4-hexadiene

623-33-6

glycine ethyl ester hydrochloride

97-41-6

ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

Conditions
ConditionsYield
With sulfuric acid; sodium nitrite; iodo(5,10,15,20-tetraphenylporphyrinato-κ4N)rhodium(III) In dichloromethane; water at 20℃; for 96h;52%
638-10-8

ethyl 3-methylbut-2-enoate

77600-82-9

(3-Methyl-2-butenyl)(nonafluorbutyl)sulfon

97-41-6

ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

Conditions
ConditionsYield
With sodium hydroxide; tertamethylammonium iodide In N,N-dimethyl-formamide 1.) -15 deg C, 3 d; 2.) 0 deg C, 3 d; 3.) 10 deg C, 3 d; 4.) room temperature, 120 d;50%
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at -10 - 20℃; for 1200h; Product distribution; other PT-catalysts, bases, temperatures, times and catalyst/reactant ratios;35%
638-10-8

ethyl 3-methylbut-2-enoate

15543-64-3

prenyl tolyl sulfone

124-41-4

sodium methylate

A

97-41-6

ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

B

5460-63-9

chrysanthemumic acid methyl ester

C

75100-65-1

methyl 2,4,4-trimethyl-6-oxo-1-cyclohexene-1-carboxylate

D

80348-45-4

ethyl 2,2,4-trimethyl-6-oxo-1-cyclohexene-1-carboxylate

Conditions
ConditionsYield
In N,N-dimethyl-formamide
...Expand
638-10-8

ethyl 3-methylbut-2-enoate

15543-64-3

prenyl tolyl sulfone

A

97-41-6

ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

B

5460-63-9

chrysanthemumic acid methyl ester

C

75100-65-1

methyl 2,4,4-trimethyl-6-oxo-1-cyclohexene-1-carboxylate

D

72410-97-0

methyl 3,3,6-trimethyl-4,6-heptadienoate

E

80348-48-7

ethyl 3,3,6-trimethyl-4,6-heptadienoate

F

80348-45-4

ethyl 2,2,4-trimethyl-6-oxo-1-cyclohexene-1-carboxylate

Conditions
ConditionsYield
With sodium methylate In N,N-dimethyl-formamide Product distribution; different ratio of sodium methoxide to the title compounds;
...Expand

ETHYL CHRYSANTHEMUMATE Chemical Properties

Ethyl chrysanthemumate(97-41-6)'s molecular formula is C12H20O2 and its formula weight is 196.29.
The density of ethyl chrysanthemumate(97-41-6) is 0.906 g/mL at 25 °C(lit.) and it has a   boiling point of 112 °C 10 mm Hg(lit.). The refractive index is about 1.461(lit.). Its flash point is 184 °F.
Ethyl chrysanthemumate(97-41-6) has the property of being dissolved in ethanol, methanol, acetone, benzene, toluene. It is not soluble in  water.
The molecular structure of ethyl chrysanthemumate(97-41-6):

ETHYL CHRYSANTHEMUMATE Uses

Ethyl chrysanthemumate(97-41-6) is mainly used as the key intermediate of pesticides such as propylene permethrin, tetramethrin, phenothrin, prallethrin , etc.

ETHYL CHRYSANTHEMUMATE Toxicity Data With Reference

1.   

mrc-smc 1 pph

   NTIS**    National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) PB85-193761 .
2.   

orl-rat LD50:2600 mg/kg

   GISAAA    Gigiena i Sanitariya. 51 (1)(1986),16. GTPZAB    Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 31 (7)(1987),53.
3.   

orl-mus LD50:2600 mg/kg

   GISAAA    Gigiena i Sanitariya. 51 (1)(1986),16.
4.   

skn-mus LD50:>5 g/kg

   GISAAA    Gigiena i Sanitariya. 51 (1)(1986),16.
5.   

orl-gpg LD50:1900 mg/kg

   GISAAA    Gigiena i Sanitariya. 51 (1)(1986),16.

ETHYL CHRYSANTHEMUMATE Consensus Reports

Reported in EPA TSCA Inventory.

ETHYL CHRYSANTHEMUMATE Safety Profile

Moderately toxic by ingestion. Mildly toxic by skin contact. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating vapors.

ETHYL CHRYSANTHEMUMATE Specification

Handling: Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation. 
Storage: Store in a cool, dry place. Keep container closed when not in use. 
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