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97-41-6 Usage

Chemical Properties

clear colorless to yellow liquid

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)90438-1Synthesis, 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.]

Check Digit Verification of cas no

The CAS Registry Mumber 97-41-6 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 7 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 97-41:
(4*9)+(3*7)+(2*4)+(1*1)=66
66 % 10 = 6
So 97-41-6 is a valid CAS Registry Number.
InChI:InChI=1/C12H20O2/c1-6-14-11(13)10-9(7-8(2)3)12(10,4)5/h7,9-10H,6H2,1-5H3/t9-,10-/m0/s1

97-41-6 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • TCI America

  • (D2112)  Ethyl 2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropane-1-carboxylate  >95.0%(GC)

  • 97-41-6

  • 25g

  • 310.00CNY

  • Detail
  • TCI America

  • (D2112)  Ethyl 2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropane-1-carboxylate  >95.0%(GC)

  • 97-41-6

  • 100g

  • 860.00CNY

  • Detail
  • Alfa Aesar

  • (H59589)  Ethyl chrysanthemate, 95%   

  • 97-41-6

  • 25g

  • 258.0CNY

  • Detail
  • Alfa Aesar

  • (H59589)  Ethyl chrysanthemate, 95%   

  • 97-41-6

  • 100g

  • 714.0CNY

  • Detail

97-41-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Ethyl chrysanthemumate

1.2 Other means of identification

Product number -
Other names chrysanthemicacidethylester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:97-41-6 SDS

97-41-6Synthetic route

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

2,5-Dimethyl-2,4-hexadiene

GlyOEt*HCl
459-73-4

GlyOEt*HCl

ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate
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%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

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

2,5-Dimethyl-2,4-hexadiene

A

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

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

B

diethyl Fumarate
623-91-6

diethyl Fumarate

C

Diethyl maleate
141-05-9

Diethyl maleate

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

diazoacetic acid ethyl ester

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

2,5-Dimethyl-2,4-hexadiene

ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate
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;
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

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

2,5-Dimethyl-2,4-hexadiene

A

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

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

B

ethyl 2,2-dimethyl-3-(2-methylpropenyl)-cyclopropanecarboxylate
41641-25-2

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

C

ethyl 2,2-dimethyl-3-(2-methylpropenyl)-cyclopropanecarboxylate
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
ethyl oxido-chrysanthemate
167690-92-8

ethyl oxido-chrysanthemate

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

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

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

ethyl oxido-chrysanthemate

A

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

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

B

ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate
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%
2,5-Dimethyl-2,4-hexadiene
764-13-6

2,5-Dimethyl-2,4-hexadiene

glycine ethyl ester hydrochloride
623-33-6

glycine ethyl ester hydrochloride

ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate
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%
ethyl 3-methylbut-2-enoate
638-10-8

ethyl 3-methylbut-2-enoate

(3-Methyl-2-butenyl)(nonafluorbutyl)sulfon
77600-82-9

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

ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate
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%
ethyl 3-methylbut-2-enoate
638-10-8

ethyl 3-methylbut-2-enoate

prenyl tolyl sulfone
15543-64-3

prenyl tolyl sulfone

sodium methylate
124-41-4

sodium methylate

A

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

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

B

chrysanthemumic acid methyl ester
5460-63-9

chrysanthemumic acid methyl ester

C

methyl 2,4,4-trimethyl-6-oxo-1-cyclohexene-1-carboxylate
75100-65-1

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

D

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

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

Conditions
ConditionsYield
In N,N-dimethyl-formamide
ethyl 3-methylbut-2-enoate
638-10-8

ethyl 3-methylbut-2-enoate

prenyl tolyl sulfone
15543-64-3

prenyl tolyl sulfone

A

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

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

B

chrysanthemumic acid methyl ester
5460-63-9

chrysanthemumic acid methyl ester

C

methyl 2,4,4-trimethyl-6-oxo-1-cyclohexene-1-carboxylate
75100-65-1

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

D

methyl 3,3,6-trimethyl-4,6-heptadienoate
72410-97-0

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

E

ethyl 3,3,6-trimethyl-4,6-heptadienoate
80348-48-7

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

F

ethyl 2,2,4-trimethyl-6-oxo-1-cyclohexene-1-carboxylate
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;
ethyl 3-methylbut-2-enoate
638-10-8

ethyl 3-methylbut-2-enoate

prenyl tolyl sulfone
15543-64-3

prenyl tolyl sulfone

A

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

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

B

chrysanthemumic acid methyl ester
5460-63-9

chrysanthemumic acid methyl ester

C

methyl 2,4,4-trimethyl-6-oxo-1-cyclohexene-1-carboxylate
75100-65-1

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

D

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

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

Conditions
ConditionsYield
With sodium methylate In N,N-dimethyl-formamide
Benzoic acid (E)-5-ethoxycarbonyl-1,1,4,4-tetramethyl-pent-2-enyl ester
86297-03-2

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

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

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

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran for 0.0833333h; from -78 degC to room temp.;
5-hydroxy-2,5-dimethyl-2-acetyloxy-3-hexene
121950-30-9

5-hydroxy-2,5-dimethyl-2-acetyloxy-3-hexene

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

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

Conditions
ConditionsYield
Ficini's reaction;
ethanol
64-17-5

ethanol

semicarbazone of pyrethrin I

semicarbazone of pyrethrin I

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

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

Conditions
ConditionsYield
With sodium hydroxide at 0℃; dann bei 20grad; d-trans-chrysanthemum-oic acid ethyl ester;
chrysanthemumic acid-(2-methyl-3-penta-2,4-dienyl-4-semicarbazono-cyclopent-2-enyl 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

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

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

B

chrysanthemumic acid
10453-89-1

chrysanthemumic acid

C

pyrethrolone semicarbazone

pyrethrolone semicarbazone

Conditions
ConditionsYield
semicarbazone of pyrethrin I;
prenyl bromide
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

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

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

Conditions
ConditionsYield
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
isoprene
78-79-5

isoprene

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

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

Conditions
ConditionsYield
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
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

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

2,5-Dimethyl-2,4-hexadiene

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

copper(II) bis(trifluoromethanesulfonate)

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

1,2-dichloro-ethane

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

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

Conditions
ConditionsYield
In nitrogen
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

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

2,2'-methylenebis[(4R)-4-phenyl-5,5-diphenyl-2-oxazoline]

n-Butyl chloride
109-69-3

n-Butyl chloride

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

2,5-Dimethyl-2,4-hexadiene

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

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

Conditions
ConditionsYield
In nitrogen
(R)-(N-5-nitrosalicylidene)-2-amino-1,1-di(2-methoxyphenyl)-1-propanol
352015-01-1

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

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

titanium(IV) isopropylate
546-68-9

titanium(IV) isopropylate

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

2,5-Dimethyl-2,4-hexadiene

copper(II) acetate monohydrate
6046-93-1

copper(II) acetate monohydrate

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

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

Conditions
ConditionsYield
With nitrogen; phenylhydrazine; copper In ethyl acetate
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

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

2,5-Dimethyl-2,4-hexadiene

aluminum ethoxide
555-75-9

aluminum ethoxide

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

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

Conditions
ConditionsYield
With phenylhydrazine; copper In ethyl acetate
With phenylhydrazine; copper In ethyl acetate
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate
97-41-6

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

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

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

C16H29BO3

C16H29BO3

Conditions
ConditionsYield
With ToMMgMe at 24.84℃;99%
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate
97-41-6

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

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

(1R,3R)-trans-chrysanthemic acid

Conditions
ConditionsYield
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;
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate
97-41-6

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

chrysanthemol
5617-92-5

chrysanthemol

Conditions
ConditionsYield
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%
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate
97-41-6

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

ethyl oxido-chrysanthemate
167690-92-8

ethyl oxido-chrysanthemate

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane93%
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;
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate
97-41-6

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

Conditions
ConditionsYield
With sodium hydride In mineral oil for 3h; Inert atmosphere;93%
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate
97-41-6

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

chrysanthemumic acid
10453-89-1

chrysanthemumic acid

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

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

ethyl chrysanthemumate diol
74481-30-4

ethyl chrysanthemumate diol

Conditions
ConditionsYield
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%
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate
97-41-6

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

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

ethyl 3-formyl-2,2-dimethylcyclopropanecarboxylate

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

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

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

2-Benzyl-3-furanylmethylacetat

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

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

Conditions
ConditionsYield
With sodium ethanolate In toluene for 4h; Heating;80%
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate
97-41-6

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

p-nitrobenzenesulfonamide
6325-93-5

p-nitrobenzenesulfonamide

C18H24N2O6S

C18H24N2O6S

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; 1,3-dimethyl-imidazoline-2-selone In dichloromethane Inert atmosphere; diastereoselective reaction;79%
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate
97-41-6

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

C12H21NO8S

C12H21NO8S

C24H39NO10S

C24H39NO10S

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; 1,3-dimethyl-imidazoline-2-selone In dichloromethane Inert atmosphere;72%
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate
97-41-6

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

C12H21FO2

C12H21FO2

Conditions
ConditionsYield
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%
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate
97-41-6

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

ethyl 3,3-dimethyl-2-carboxycyclopropanecarboxylate

ethyl 3,3-dimethyl-2-carboxycyclopropanecarboxylate

Conditions
ConditionsYield
With potassium permanganate; sulfuric acid; sodium sulfite for 4h;30%
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate
97-41-6

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

C12H22N4O2

C12H22N4O2

Conditions
ConditionsYield
With iron(II) triflate; sodium azide; O-pivaloylhydroxylamine trifluoromethanesulfonate salt In methanol at 20℃; for 16h; regioselective reaction;23%
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate
97-41-6

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

trans-chrysanthemic acid

trans-chrysanthemic acid

cis-Chrysanthemic acid
2935-23-1

cis-Chrysanthemic acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol Reflux;A n/a
B 7%
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate
97-41-6

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

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

(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

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

Conditions
ConditionsYield
With sodium ethanolate In ethanol
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate
97-41-6

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

sodium tert-pentoxide
14593-46-5

sodium tert-pentoxide

tert-amyl trans-chrysanthemate
78715-54-5

tert-amyl trans-chrysanthemate

Conditions
ConditionsYield
In toluene for 0.75h; Heating;
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate
97-41-6

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

2-(2-Methyl-1-propenyl)-4-furanylmethylacetat
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

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

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

97-41-6Relevant articles and documents

Asymmetric cyclopropanation method of copper-catalyzed olefin and application of asymmetric cyclopropanation method

-

Paragraph 0082-0086, (2021/05/22)

The invention discloses an asymmetric cyclopropanation method of copper-catalyzed olefin and application thereof. The copper catalyst adopted by the method is generated in situ from a metal copper precursor and a chiral P, N, N-ligand in a reaction medium. The method has the characteristics of cheap catalyst, simple ligand preparation, high activity, high selectivity, mild reaction conditions, simple operation and the like, can realize continuous operation, and is suitable for large-scale industrial production. The method is also suitable for asymmetric synthesis of chiral first chrysanthemic acid which is an important intermediate of pyrethroid pesticides, the yield can reach 80%, the enantioselectivity can reach 85%, and the method can be applied to industrial preparation.

Cycloaddition Reactions of Alkene Radical Cations using Iron(III)-Phenanthroline Complex

Cho, Yong Hyun,Kim, Jae Hyung,An, Hyeju,Ahn, Kwang-Hyun,Kang, Eun Joo

supporting information, p. 2183 - 2188 (2020/04/29)

Single electron oxidation of electron-rich alkenes using the iron(III)-phenanthroline complex produced electrophilic alkene radical cations, which promoted efficient radical cation [2+1] cycloaddition reactions with diazo compounds. Subsequent chain propagation afforded tri- and tetra-substituted cyclopropanes. This methodology was also expanded to [3+2] cycloaddition reactions with vinyl diazoesters, validating this sustainable, first-row transition metal iron system for the single electron redox reactions. (Figure presented.).

High-yield ethyl chrysanthemate preparation method

-

Paragraph 0037-0080, (2020/12/08)

The invention belongs to the technical field of chemical processes, and specifically relates to a high-yield ethyl chrysanthemate preparation method. The high-yield ethyl chrysanthemate preparation method comprises the following steps: (1) diazotization: a step of adding water, glycine ethyl ester acid salt, glacial acetic acid and dimethyl carbonate as solvents into a diazotization kettle, dropwisely adding a sodium nitrite aqueous solution into the diazotization kettle, and carrying out a reaction so as to a diazo liquid; (2) cyclization: a step of putting 2,5-dimethyl-2,4-hexadiene into a cyclization kettle, and carrying out a reaction with cuprous chloride as a catalyst so as to obtain a cyclized solution; (3) desolventizing: a step of sending the cyclized solution into a high-yield desolventizing tower to remove the solvents so as to obtain a crude ethyl chrysanthemate product; and (4) distillation: a step of putting the crude ethyl chrysanthemate product into a distillation kettle, and carrying out vacuum distillation so as to obtain the high-purity ethyl chrysanthemate. The high-yield ethyl chrysanthemate preparation method provided by the invention has the following beneficial effects: when the dimethyl carbonate is used as a solvent, a diazotization reaction can be carried out more completely, so the loss of raw materials is reduced; and meanwhile, the yield of ethyl chrysanthemate in the subsequent cyclization reaction can be improved.

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