ETHYL CHRYSANTHEMUMATE supplier

Name
Ethyl chrysanthemumate
EINECS 202-579-7
CAS No. 97-41-6
Article Data55
CAS DataBase
Density 0.991 g/cm³
Solubility
Melting Point 0oC
Formula C₁₂H₂₀O₂
Boiling Point 240.8 °C at 760 mmHg
Molecular Weight 196.29
Flash Point 84.4 °C
Transport Information
Appearance clear colorless to yellow liquid
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols
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);
PSA 26.30000
LogP 2.78790

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

Conditions	Yield
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

Conditions	Yield
hexarhodium hexadecacarbonyl at 60℃; for 7h;	A 91% B n/a C n/a

...Expand

: 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

Conditions	Yield
K-PFIEP[SO3 H] In dichloromethane	89.6%
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

Conditions	Yield
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

...Expand

: 167690-92-8
ethyl oxido-chrysanthemate

: 97-41-6
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

...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: 80348-45-4
ethyl 2,2,4-trimethyl-6-oxo-1-cyclohexene-1-carboxylate

Conditions

Conditions	Yield
With sodium methylate In N,N-dimethyl-formamide

...Expand

: 86297-03-2
Benzoic acid (E)-5-ethoxycarbonyl-1,1,4,4-tetramethyl-pent-2-enyl ester

: 97-41-6
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

Conditions

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran for 0.0833333h; from -78 degC to room temp.;

: 121950-30-9
5-hydroxy-2,5-dimethyl-2-acetyloxy-3-hexene

: 97-41-6
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

Conditions

Conditions	Yield
Ficini's reaction;

: 64-17-5
ethanol

semicarbazone of pyrethrin I: semicarbazone of pyrethrin I

: 97-41-6
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

Conditions

Conditions	Yield
With sodium hydroxide at 0℃; dann bei 20grad; d-trans-chrysanthemum-oic acid ethyl ester;

: 6227-48-1
chrysanthemumic acid-(2-methyl-3-penta-2,4-dienyl-4-semicarbazono-cyclopent-2-enyl ester)

ethanolic NaOH-solution: ethanolic NaOH-solution

A: 97-41-6
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

B: 10453-89-1
chrysanthemumic acid

C pyrethrolone semicarbazone: pyrethrolone semicarbazone

Conditions

Conditions	Yield
semicarbazone of pyrethrin I;

...Expand

: 870-63-3
prenyl bromide

sodium-compound of 5,7-dihydroxy-2-methyl-chromen-4-one: sodium-compound of 5,7-dihydroxy-2-methyl-chromen-4-one

: 97-41-6
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 70 percent / Bu4NI / dimethylformamide / 2 h / 70 °C 2: 35 percent / NaOH, Bu4NI / dimethylformamide / 1200 h / -10 - 20 °C / other PT-catalysts, bases, temperatures, times and catalyst/reactant ratios View Scheme

: 78-79-5
isoprene

: 97-41-6
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / petroleum ether / 0 °C 2: 35 percent / NaOH, Bu4NI / dimethylformamide / 1200 h / -10 - 20 °C / other PT-catalysts, bases, temperatures, times and catalyst/reactant ratios View Scheme

: 623-73-4
diazoacetic acid ethyl ester

: 764-13-6
2,5-Dimethyl-2,4-hexadiene

: 34946-82-2
copper(II) bis(trifluoromethanesulfonate)

: 107-06-2
1,2-dichloro-ethane

: 97-41-6
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

Conditions

Conditions	Yield
In nitrogen

...Expand

: 623-73-4
diazoacetic acid ethyl ester

: 220578-26-7
2,2'-methylenebis[(4R)-4-phenyl-5,5-diphenyl-2-oxazoline]

: 109-69-3
n-Butyl chloride

: 764-13-6
2,5-Dimethyl-2,4-hexadiene

: 34946-82-2, 42152-44-3, 109572-99-8
copper(I) triflate

: 97-41-6
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

Conditions

Conditions	Yield
In nitrogen

...Expand

: 352015-01-1
(R)-(N-5-nitrosalicylidene)-2-amino-1,1-di(2-methoxyphenyl)-1-propanol

: 623-73-4
diazoacetic acid ethyl ester

: 546-68-9
titanium(IV) isopropylate

: 764-13-6
2,5-Dimethyl-2,4-hexadiene

: 6046-93-1
copper(II) acetate monohydrate

: 97-41-6
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

Conditions

Conditions	Yield
With nitrogen; phenylhydrazine; copper In ethyl acetate

...Expand

: 623-73-4
diazoacetic acid ethyl ester

: 764-13-6
2,5-Dimethyl-2,4-hexadiene

: 555-75-9
aluminum ethoxide

: 97-41-6
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

Conditions

Conditions	Yield
With phenylhydrazine; copper In ethyl acetate
With phenylhydrazine; copper In ethyl acetate

...Expand

: 97-41-6
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

: 25015-63-8
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

: C16H29BO3

Conditions

Conditions	Yield
With ToMMgMe at 24.84℃;	99%

: 97-41-6
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

: 4638-92-0
(1R,3R)-trans-chrysanthemic acid

Conditions

Conditions	Yield
With water; sodium hydroxide In ethanol for 2h; Reagent/catalyst; Solvent; Reflux;	98.3%
With glycine-NaOH buffer In ethanol; water at 45℃; Arthrobacter globiformis carboxylesterase;
With glycine-NaOH buffer In ethanol; water at 45℃; stereoselective hydrolysis with Arthrobacter globiformis esterase;

: 97-41-6
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

: 5617-92-5
chrysanthemol

Conditions

Conditions	Yield
With C39H53ClN2P2Ru; potassium methanolate; hydrogen In tetrahydrofuran at 20℃; under 3800.26 Torr; Glovebox; Autoclave; chemoselective reaction;	98%
With n-butyllithium; poly(methylhydrosiloxane); bis(cyclopentadienyl)titanium dichloride In tetrahydrofuran; hexane for 1h; Ambient temperature;	90%
With HN(CH2CH2C3H3N2Mes)2Cl2; potassium tert-butylate; hydrogen; cobalt(II) chloride In tetrahydrofuran at 100℃; under 22502.3 Torr; for 16h; Autoclave; Glovebox;	79%

: 97-41-6
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

: 167690-92-8
ethyl oxido-chrysanthemate

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane	93%
With dihydrogen peroxide; formamide In methanol; water at 50℃; for 3h;	69%
With manganese(II) sulfate; sodium hydrogencarbonate In N,N-dimethyl-formamide pH=8;
With manganese(II) sulfate; dihydrogen peroxide; sodium hydrogencarbonate In N,N-dimethyl-formamide pH=8.0;

: 97-41-6
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

: 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
ethyl trans-(+/-)-chrysanthemate

Conditions

Conditions	Yield
With sodium hydride In mineral oil for 3h; Inert atmosphere;	93%

: 97-41-6
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

: 10453-89-1
chrysanthemumic acid

Conditions

Conditions	Yield
With water; sodium hydroxide In tetrahydrofuran; methanol at 80℃; Inert atmosphere;	91%
Stage #1: ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate With sodium hydroxide; water In tetrahydrofuran; methanol at 80℃; for 4h; Stage #2: With hydrogenchloride In water	90%
Stage #1: ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate With sodium hydroxide; water In tetrahydrofuran; methanol at 80℃; for 4h; Stage #2: With hydrogenchloride In water	90%
alkaline hydrolysis;
With sodium hydroxide In diethyl ether; ethanol; water

: 97-41-6
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

: 74481-30-4
ethyl chrysanthemumate diol

Conditions

Conditions	Yield
With pyridine; trimethylamine-N-oxide; osmium(VIII) oxide In water; tert-butyl alcohol for 24h; Heating;	91%
With osmium(VIII) oxide; trimethylamine-N-oxide In pyridine; water; tert-butyl alcohol for 24h; Heating;	91%

: 97-41-6
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

: 66692-75-9
ethyl 3-formyl-2,2-dimethylcyclopropanecarboxylate

Conditions

Conditions	Yield
Stage #1: ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate In dichloromethane at -78℃; for 2h; ozonolysis; Stage #2: With triphenylphosphine In dichloromethane at -78 - 20℃; Reduction;	90%
Stage #1: ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; Stage #2: With periodic acid In diethyl ether at 0 - 20℃;	58%
With ozone

: 97-41-6
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

: 39856-65-0
2-Benzyl-3-furanylmethylacetat

: 39856-62-7
2,2-Dimethyl-3-(2-methyl-propenyl)-cyclopropanecarboxylic acid 2-benzyl-furan-3-ylmethyl ester

Conditions

Conditions	Yield
With sodium ethanolate In toluene for 4h; Heating;	80%

: 97-41-6
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

: 6325-93-5
p-nitrobenzenesulfonamide

: C18H24N2O6S

Conditions

Conditions	Yield
With [bis(acetoxy)iodo]benzene; 1,3-dimethyl-imidazoline-2-selone In dichloromethane Inert atmosphere; diastereoselective reaction;	79%

: 97-41-6
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

: C12H21NO8S

: C24H39NO10S

Conditions

Conditions	Yield
With [bis(acetoxy)iodo]benzene; 1,3-dimethyl-imidazoline-2-selone In dichloromethane Inert atmosphere;	72%

: 97-41-6
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

: C12H21FO2

Conditions

Conditions	Yield
With HO4S(1-)K(1+)13FH In 1,2-dichloro-ethane at 0 - 20℃; for 2h; regioselective reaction;	61%
With HSO4- exchanged Amberlyst A26 resin-supported hydrogen fluoride In 1,2-dichloro-ethane at 20℃; for 15h;	57%

: 97-41-6
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

: ethyl 3,3-dimethyl-2-carboxycyclopropanecarboxylate

Conditions

Conditions	Yield
With potassium permanganate; sulfuric acid; sodium sulfite for 4h;	30%

: 97-41-6
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

: C12H22N4O2

Conditions

Conditions	Yield
With iron(II) triflate; sodium azide; O-pivaloylhydroxylamine trifluoromethanesulfonate salt In methanol at 20℃; for 16h; regioselective reaction;	23%

: 97-41-6
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

: trans-chrysanthemic acid

: 2935-23-1
cis-Chrysanthemic acid

Conditions

Conditions	Yield
With potassium hydroxide In ethanol Reflux;	A n/a B 7%

: 97-41-6
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

: (E)-4-(3-Methoxy-phenyl)-but-2-en-1-ol

: 2,2-Dimethyl-3-(2-methyl-propenyl)-cyclopropanecarboxylic acid (E)-4-(3-methoxy-phenyl)-but-2-enyl ester

Conditions

Conditions	Yield
With sodium ethanolate In ethanol

: 97-41-6
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

: 14593-46-5
sodium tert-pentoxide

: 78715-54-5
tert-amyl trans-chrysanthemate

Conditions

Conditions	Yield
In toluene for 0.75h; Heating;

: 97-41-6
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

: 78520-06-6
2-(2-Methyl-1-propenyl)-4-furanylmethylacetat

: 2,2-Dimethyl-3-(2-methyl-propenyl)-cyclopropanecarboxylic acid 5-(2-methyl-propenyl)-furan-3-ylmethyl ester

Conditions

Conditions	Yield
With sodium ethanolate In toluene for 4h; Heating;	39 % Turnov.

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.

Product Name

Ethyl chrysanthemumate

Synthetic route

ETHYL CHRYSANTHEMUMATE Chemical Properties

ETHYL CHRYSANTHEMUMATE Uses

ETHYL CHRYSANTHEMUMATE Toxicity Data With Reference

ETHYL CHRYSANTHEMUMATE Consensus Reports

ETHYL CHRYSANTHEMUMATE Safety Profile

ETHYL CHRYSANTHEMUMATE Specification

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