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623-70-1

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623-70-1 Usage

Chemical properties

It appears as colorless to pale yellow liquid with the boiling point of 136 ° C and flash point of 22 ° C. It exhibits strong acid coke and fruit aroma with the incense of rum and ether. The natural products exist in apples, papaya, strawberries, rums, wines and cocoa.

Application

It as allowable food spices. Mainly used for the preparation of fruit wine flavor. Used as the intermediate of organic synthesis, solvents, paint softener.

Production

It is obtained from the esterification of crotonic acid and ethanol in the presence of concentrated sulfuric acid.

Chemical Properties

colourless liquid

Uses

Different sources of media describe the Uses of 623-70-1 differently. You can refer to the following data:
1. Ethyl crotonate is used as a solvent for cellulose esters as well as a plasticizer for acrylic resins.
2. Ethyl Crotonate is a synthetic flavoring agent that is a moderately stable, colorless to light yellow liquid of sharp winey note. it should be stored in glass, tin, or resin-lined containers. it is used in fruit flavors for application in baked goods, beverages, and candy at 2–7 ppm.
3. Solvent and softening agent, lacquers, organic synthesis.

General Description

Ethyl trans-2-butenoate is a volatile flavor compound found in fruits such as cashew apple, African star apple, naranjilla fruit and sweet passion fruit.

Safety Profile

Moderately toxic by ingestion and probably by inhalation. A skin , mucous membrane, and severe eye irritant. Very dangerous fire hazard when exposed to heat or flame; can react vigorously with oxidizing materials. To fight fire, use foam, CO2, or dry chemical. See also ESTERS. When heated to decomposition it emits acrid smoke and fumes.

Purification Methods

Wash it with aqueous 5% Na2CO3, then with saturated aqueous CaCl2, dry it with CaCl2 and distil it. [Beilstein 2 IV 1500.]

Check Digit Verification of cas no

The CAS Registry Mumber 623-70-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,2 and 3 respectively; the second part has 2 digits, 7 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 623-70:
(5*6)+(4*2)+(3*3)+(2*7)+(1*0)=61
61 % 10 = 1
So 623-70-1 is a valid CAS Registry Number.
InChI:InChI=1/C6H10O2/c1-3-5-6(7)8-4-2/h3,5H,4H2,1-2H3/b5-3+

623-70-1 Well-known Company Product Price

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  • Alfa Aesar

  • (A12529)  Ethyl crotonate, 98%   

  • 623-70-1

  • 100g

  • 331.0CNY

  • Detail
  • Alfa Aesar

  • (A12529)  Ethyl crotonate, 98%   

  • 623-70-1

  • 500g

  • 956.0CNY

  • Detail
  • Alfa Aesar

  • (A12529)  Ethyl crotonate, 98%   

  • 623-70-1

  • 2500g

  • 4153.0CNY

  • Detail

623-70-1SDS

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 trans-2-butenoate

1.2 Other means of identification

Product number -
Other names Ethyl crotonate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
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:623-70-1 SDS

623-70-1Synthetic route

3-(ethylthio)-butanoic acid, ethyl ester
90201-28-8

3-(ethylthio)-butanoic acid, ethyl ester

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
With tetrabutylammomium bromide In ethanol electrolysis;98%
ethyl trans-2-methylthiirane carboxylate
107467-99-2

ethyl trans-2-methylthiirane carboxylate

CO

CO

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
di(rhodium)tetracarbonyl dichloride In benzene under 20685.9 Torr; for 18h; Ambient temperature;97%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

acetaldehyde
75-07-0

acetaldehyde

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
With potassium carbonate In 1,4-dioxane at 25℃; for 2.2h;95%
With sodium hydride In tetrahydrofuran 1.) r.t., 1 h; 2.) -70 deg C then up to 0 deg C over 2 h;90%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.5h;
Stage #2: acetaldehyde In tetrahydrofuran; mineral oil at 0 - 20℃;
fac-tricarbonyl{1-ethoxy-1-oxo-2-butenyl-C(3),O}(triphenylphosphine)rhenium

fac-tricarbonyl{1-ethoxy-1-oxo-2-butenyl-C(3),O}(triphenylphosphine)rhenium

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
With CF3CO2H In benzene-d6 React. at 25°C, 10 h.; Monitored by (1)H-NMR.;95%
ethyl α-bromo-α-trimethylsilylacetate
86294-63-5

ethyl α-bromo-α-trimethylsilylacetate

acetaldehyde
75-07-0

acetaldehyde

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
silver-graphite; zinc In tetrahydrofuran at -78℃; for 0.166667h;79%
ethanol
64-17-5

ethanol

(E)-but-2-enoic acid
107-93-7

(E)-but-2-enoic acid

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
With sulfuric acid In benzene Heating;78.5%
With sulfuric acid; magnesium sulfate In benzene Heating; Yield given;
With phosphorus pentoxide 1.) 0-5 deg C, 2.) reflux, 3 h; Yield given. Multistep reaction;
With bis(2,2,2-trifluoroethoxy)diphenylsulfurane 1.) THF, -78 deg C, 2.) THF, -78 deg C; Yield given. Multistep reaction;
4-bromoethylbutanoate
2969-81-5

4-bromoethylbutanoate

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
With bis(triphenylphosphine)nickel(II) chloride; n-butyllithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine In tetrahydrofuran; hexane Ambient temperature;77%
diethyl sulphite
623-81-4

diethyl sulphite

(E)-but-2-enoic acid
107-93-7

(E)-but-2-enoic acid

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
sulfuric acid In ethanol for 2h; Heating;73%
carbon monoxide
201230-82-2

carbon monoxide

sodium ethanolate
141-52-6

sodium ethanolate

allyl bromide
106-95-6

allyl bromide

A

ethyl 3-butenoate
1617-18-1

ethyl 3-butenoate

B

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
Na2PdCl4-dppe In ethanol at 50℃; for 2h;A 17%
B 72%
(E)-but-2-enoic acid
107-93-7

(E)-but-2-enoic acid

Fe(ClO4)3(CH3CH2OH)6/SiO2

Fe(ClO4)3(CH3CH2OH)6/SiO2

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
for 2h; Solid phase reaction; esterification;69%
(E)-crotonaldehyde diethyl acetal
63511-92-2

(E)-crotonaldehyde diethyl acetal

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
With tert.-butylhydroperoxide; dipyridinium dichromate In dichloromethane for 7h; Ambient temperature;67%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
C-200 (barium hydroxide) In tetrahydrofuran; water for 0.166667h; Ambient temperature; sonication;61%
Vinyl bromide
593-60-2

Vinyl bromide

bromo(2-ethoxy-2-oxoethyl)zinc
5764-82-9

bromo(2-ethoxy-2-oxoethyl)zinc

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
With tetrakis(triphenylphosphine)nickel(0) In N,N,N,N,N,N-hexamethylphosphoric triamide for 3h; Heating;55%
3-aminobutanoic acid ethyl ester
5303-65-1

3-aminobutanoic acid ethyl ester

4-chloro-2,2-dimethyl-2H-benzo[e][1,3]oxazine
74405-07-5

4-chloro-2,2-dimethyl-2H-benzo[e][1,3]oxazine

A

2,4-bis(2-hydroxyphenyl)-6-methylpyrimidine
82507-91-3

2,4-bis(2-hydroxyphenyl)-6-methylpyrimidine

B

ethyl 3-(2,2-dimethyl-2H-1,3-benzoxazin-4-ylamino)butylate

ethyl 3-(2,2-dimethyl-2H-1,3-benzoxazin-4-ylamino)butylate

C

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
at 150 - 160℃; for 4h;A 38%
B 10%
C n/a
at 150 - 160℃; for 4h; Product distribution; Mechanism;A 38%
B 10%
C n/a
(E)-but-2-enoic acid
107-93-7

(E)-but-2-enoic acid

(2,2-diethoxyvinylidene)triphenylphosphorane
21882-77-9, 53472-13-2

(2,2-diethoxyvinylidene)triphenylphosphorane

A

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

B

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

Conditions
ConditionsYield
In tetrahydrofuran for 3h; Ambient temperature;A 33%
B n/a
ethanol
64-17-5

ethanol

carbon monoxide
201230-82-2

carbon monoxide

3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

A

ethyl 3-butenoate
1617-18-1

ethyl 3-butenoate

B

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
carbonylchlorobis(triethylphosphine)rhodium(I) at 120℃; under 30002.4 Torr; for 4h;A 28%
B 12 % Turnov.
3-aminobutanoic acid ethyl ester
5303-65-1

3-aminobutanoic acid ethyl ester

4-chloro-2-methyl-2-methoxycarbonylmethyl-2H-1,3-benzoxazine
82507-98-0

4-chloro-2-methyl-2-methoxycarbonylmethyl-2H-1,3-benzoxazine

A

2-(2-hydroxyphenyl)-6-methyl-4(3H)-pyrimidinone
76467-22-6

2-(2-hydroxyphenyl)-6-methyl-4(3H)-pyrimidinone

B

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
at 170 - 180℃; for 3h;A 26%
B n/a
(Z)-2-{Methylsulfanyl-[(2,2,2-trifluoro-acetyl)-hydrazono]-methylsulfanyl}-but-2-enoic acid ethyl ester

(Z)-2-{Methylsulfanyl-[(2,2,2-trifluoro-acetyl)-hydrazono]-methylsulfanyl}-but-2-enoic acid ethyl ester

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
With aluminium amalgam In diethyl ether; ethanol Ambient temperature;18%
2-butenoic acid
3724-65-0

2-butenoic acid

ethanol
64-17-5

ethanol

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
With sulfuric acid
With sulfuric acid
ethyl 3-hydroxybutyrate
5405-41-4

ethyl 3-hydroxybutyrate

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
With aluminum oxide at 325 - 350℃;
ethanol
64-17-5

ethanol

trans-chrotonyl chloride
625-35-4, 3488-22-0, 10487-71-5

trans-chrotonyl chloride

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

ethanol
64-17-5

ethanol

3-chloro-butyric acid ethyl ester
7425-48-1

3-chloro-butyric acid ethyl ester

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
With sodium hydroxide at 0 - 5℃;
3-chloro-butyric acid ethyl ester
7425-48-1

3-chloro-butyric acid ethyl ester

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
With ethanol; ammonia
3-methyl-1,4-diphenyl-1,2,3,4-tetrahydro-1,4-epoxido-naphthalene-2-carboxylic acid ethyl ester
872297-31-9

3-methyl-1,4-diphenyl-1,2,3,4-tetrahydro-1,4-epoxido-naphthalene-2-carboxylic acid ethyl ester

A

1,3-diphenylisobenzofuran
5471-63-6

1,3-diphenylisobenzofuran

B

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

ethyl 3-hydroxybutyrate
5405-41-4

ethyl 3-hydroxybutyrate

acetic anhydride
108-24-7

acetic anhydride

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
und Erhitzen des Reaktionsprodukts mit Kaliumacetat;
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

acetaldehyde
75-07-0

acetaldehyde

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
With piperidine; pyridine
diethyl ether
60-29-7

diethyl ether

2-methyl-butane-1,3,3-tricarboxylic acid triethyl ester
854462-99-0

2-methyl-butane-1,3,3-tricarboxylic acid triethyl ester

sodium ethanolate
141-52-6

sodium ethanolate

methyl iodide
74-88-4

methyl iodide

A

2,2-dimethylmalonic acid diethyl ester
1619-62-1

2,2-dimethylmalonic acid diethyl ester

B

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
unter Kuehlung;
2-bromobutyric acid ethyl ester
533-68-6

2-bromobutyric acid ethyl ester

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
With N,N-diethylaniline
ethyl 3-butenoate
1617-18-1

ethyl 3-butenoate

A

ethyl (Z)-crotonate
6776-19-8

ethyl (Z)-crotonate

B

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
With (isomerization); diethylamine In diethyl ether at 40℃; Kinetics; other catalysts;
ethyl iodide
75-03-6

ethyl iodide

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
With 18-crown-6 ether; potassium naphthalenide 1) THF, 20 deg C, 10 min; Yield given. Multistep reaction;
ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

1-nitrocyclohexane
1122-60-7

1-nitrocyclohexane

3-(1-nitro-cyclohexyl)-butyric acid ethyl ester

3-(1-nitro-cyclohexyl)-butyric acid ethyl ester

Conditions
ConditionsYield
With 2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane 2,8,9-tris(1-methylethyl) In various solvent(s) at 20℃; for 4h; Michael addition;100%
ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

C26H38N2O4
810671-46-6

C26H38N2O4

C32H48N2O6
810671-55-7

C32H48N2O6

Conditions
ConditionsYield
Stage #1: C26H38N2O4 With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1h;
Stage #2: ethyl (E)-crotonate In tetrahydrofuran at -78 - -20℃; for 2h; Michael addition;
100%
anthracen-9(10H)-one
90-44-8

anthracen-9(10H)-one

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

3-(10-oxo-9,10-dihydro-anthracen-9-yl)-butyric acid ethyl ester

3-(10-oxo-9,10-dihydro-anthracen-9-yl)-butyric acid ethyl ester

Conditions
ConditionsYield
With lithium perchlorate; triethylamine In diethyl ether for 16h; Michael addition;100%
lithium hydroxide monohydrate

lithium hydroxide monohydrate

Methyl thioglycolate
2365-48-2

Methyl thioglycolate

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

4-ethoxycarbonyl-2-methylthiolan-3-one
80289-37-8

4-ethoxycarbonyl-2-methylthiolan-3-one

Conditions
ConditionsYield
In ethyl acetate; N,N-dimethyl-formamide100%
N-((1S)-1-phenylethyl)hydroxylamine
53933-47-4

N-((1S)-1-phenylethyl)hydroxylamine

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

C14H21NO3
912650-23-8

C14H21NO3

Conditions
ConditionsYield
In tetrahydrofuran100%
nitromethane
75-52-5

nitromethane

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

3-methyl-4-nitrobutyric acid ethyl ester
2985-50-4

3-methyl-4-nitrobutyric acid ethyl ester

Conditions
ConditionsYield
With 2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane 2,8,9-tris(1-methylethyl) In various solvent(s) at -63℃; for 0.15h; Michael addition;99%
With N,N,N',N'-tetramethylguanidine for 18h;99.2%
With N,N,N',N'-tetramethylguanidine at 20℃; for 24h; Michael addition;91%
With N,N,N',N'-tetramethylguanidine at 20℃; for 24h; Inert atmosphere;82%
dimethyl amine
124-40-3

dimethyl amine

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

3-Dimethylamino-buttersaeureethylester
85118-28-1

3-Dimethylamino-buttersaeureethylester

Conditions
ConditionsYield
With carbon dioxide for 1h; Ambient temperature;99%
p-methoxybenzyl chloride
824-94-2

p-methoxybenzyl chloride

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

ethyl 4-(4-methoxyphenyl)-3-methylbutanoate
183134-81-8

ethyl 4-(4-methoxyphenyl)-3-methylbutanoate

Conditions
ConditionsYield
Stage #1: p-methoxybenzyl chloride With iodine; magnesium In tetrahydrofuran for 2h;
Stage #2: With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78℃; for 0.833333h;
Stage #3: ethyl (E)-crotonate With chloro-trimethyl-silane In tetrahydrofuran at -30℃; for 18h;
99%
With copper(l) iodide; chloro-trimethyl-silane; N,N,N,N,-tetramethylethylenediamine; iodine; magnesium Yield given. Multistep reaction;
ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

thioacetic acid
507-09-5

thioacetic acid

ethyl 3-(acetylthio)butanoate
92065-74-2

ethyl 3-(acetylthio)butanoate

Conditions
ConditionsYield
With indium(III) chloride In 1,2-dichloro-ethane at 60℃; for 18h; Inert atmosphere;99%
2-aminophenylboronic acid
5570-18-3

2-aminophenylboronic acid

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

4-methyl-3,4-dihydroquinolin-2(1H)-one
30696-28-7

4-methyl-3,4-dihydroquinolin-2(1H)-one

Conditions
ConditionsYield
With [Rh(OH)(cod)]2; potassium carbonate In water at 50℃; for 5h; Inert atmosphere;99%
ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

ethyl 2,3-dibromobutyrate
609-11-0

ethyl 2,3-dibromobutyrate

Conditions
ConditionsYield
With bromine In tetrachloromethane for 2h; Heating;98%
With bromine In tetrachloromethane for 24h; Heating;78%
With N-Bromosuccinimide In 1,4-dioxane; water
butyraldehyde
123-72-8

butyraldehyde

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

3-methyl-4-oxo-heptanoic acid ethyl ester
67893-05-4

3-methyl-4-oxo-heptanoic acid ethyl ester

Conditions
ConditionsYield
With triisopropylsilanethiol; trans-di-O-tert-butyl hyponitrite In 1,4-dioxane at 60℃; for 3.5h;98%
trimethyl(4-mercaptomethylphenyl)silane
57337-85-6

trimethyl(4-mercaptomethylphenyl)silane

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

3-(4-trimethylsilanyl-benzylsulfanyl)-butyric acid ethyl ester
497181-03-0

3-(4-trimethylsilanyl-benzylsulfanyl)-butyric acid ethyl ester

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.5h; Michael addition;98%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.5h; Michael addition;98%
N-(diphenylmethylene)glycine tert-butyl ester
81477-94-3

N-(diphenylmethylene)glycine tert-butyl ester

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

2-tert-butyl 4-ethyl 3-methyl-5,5-diphenylpyrrolidine-2,4-dicarboxylate

2-tert-butyl 4-ethyl 3-methyl-5,5-diphenylpyrrolidine-2,4-dicarboxylate

Conditions
ConditionsYield
With 4 A molecular sieve; calcium bis-iso-propoxide; 2,2'-methylene bis((4S)-4-phenyl-2-oxazoline) In tetrahydrofuran at -30℃; for 12h; Michael addition;98%
4-bromo-N-cyclohexyl-N-isobutyl-2-nitroaniline

4-bromo-N-cyclohexyl-N-isobutyl-2-nitroaniline

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

ethyl (E)-3-(4-(cyclohexyI(isobutyI)arnino)-3-nitrophenyl)but-2-enoate

ethyl (E)-3-(4-(cyclohexyI(isobutyI)arnino)-3-nitrophenyl)but-2-enoate

Conditions
ConditionsYield
With dichlorobis(tri-O-tolylphosphine)palladium; tetrabutylammomium bromide; triethylamine In N,N-dimethyl-formamide at 110℃; Inert atmosphere;98%
With tetrakis(tris(2-methyl)phenyl)phosphinepalladium; tetrabutylammomium bromide; triethylamine In N,N-dimethyl-formamide at 110℃; Inert atmosphere;81%
ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

benzylamine
100-46-9

benzylamine

ethyl 3-(benzylamino)butanoate
6335-80-4

ethyl 3-(benzylamino)butanoate

Conditions
ConditionsYield
With ytterbium(III) triflate In tetrahydrofuran for 6h; Ambient temperature;97%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 20h; Kinetics; Solvent; Temperature; Time; Michael Addition; Reflux;86%
In ethanol at 20℃; for 38h;84.3%
BuMnCl
88626-90-8

BuMnCl

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

3-methyl-heptanoic acid ethyl ester
37492-08-3

3-methyl-heptanoic acid ethyl ester

Conditions
ConditionsYield
With chloro-trimethyl-silane; copper(l) chloride In tetrahydrofuran for 1h; 0 to 20 deg C;97%
ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

((R)-1-Phenyl-ethyl)-(3-trimethylsilanyl-prop-2-ynyl)-amine
192655-92-8

((R)-1-Phenyl-ethyl)-(3-trimethylsilanyl-prop-2-ynyl)-amine

(R)-3-[((R)-1-Phenyl-ethyl)-(3-trimethylsilanyl-prop-2-ynyl)-amino]-butyric acid ethyl ester
192655-84-8

(R)-3-[((R)-1-Phenyl-ethyl)-(3-trimethylsilanyl-prop-2-ynyl)-amino]-butyric acid ethyl ester

Conditions
ConditionsYield
97%
2-(4-(benzyloxy)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

2-(4-(benzyloxy)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

ethyl 3-(2-(4-(benzyloxy)phenyl)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)butanoate

ethyl 3-(2-(4-(benzyloxy)phenyl)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)butanoate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1-methyl-pyrrolidin-2-one at 140℃; for 1h; Michael Addition;97%
piperidin-2-one
675-20-7

piperidin-2-one

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

3-(2-Oxo-piperidin-1-yl)-butyric acid ethyl ester

3-(2-Oxo-piperidin-1-yl)-butyric acid ethyl ester

Conditions
ConditionsYield
With tetraethoxy orthosilicate; cesium fluoride In neat (no solvent) at 25℃; for 0.166667h;96%
Ethyl propionate
105-37-3

Ethyl propionate

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

Diethyl 2,3-dimethylpentanedioate
344883-66-5

Diethyl 2,3-dimethylpentanedioate

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 1h;96%
C3H7ClMn
105486-13-3

C3H7ClMn

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

ethyl 3,4-dimethylpentanoate
6570-83-8

ethyl 3,4-dimethylpentanoate

Conditions
ConditionsYield
With chloro-trimethyl-silane; copper(l) chloride In tetrahydrofuran 0 to 20 deg C, 0.5-1.5 h; other α,β-ethylenic ester, other organomanganese chlorides;96%
With chloro-trimethyl-silane; copper(l) chloride In tetrahydrofuran 0 to 20 deg C, 0.5-1.5 h;96%
ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

3-azidobutyric acid ethyl ester
189870-35-7

3-azidobutyric acid ethyl ester

Conditions
ConditionsYield
With tris-(2-chloro-ethyl)-amine; triethylamine In benzene at 80℃; for 24h;96%
para-iodoanisole
696-62-8

para-iodoanisole

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

(E)-ethyl 3-(4-methoxyphenyl)but-2-enoate
7706-82-3

(E)-ethyl 3-(4-methoxyphenyl)but-2-enoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h; Heck Reaction; Inert atmosphere;96%
With potassium carbonate; triphenylphosphine; palladium diacetate In N,N-dimethyl-formamide for 0.15h; Heck reaction; microwave irradiation;87%
ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

(2S,3R)-ethyl 2,3-dihydroxybutanoate
139165-59-6

(2S,3R)-ethyl 2,3-dihydroxybutanoate

Conditions
ConditionsYield
With methanesulfonamide In water; tert-butyl alcohol at 0 - 24℃; Sharpless dihydroxylation;96%
N-methoxylamine hydrochloride
593-56-6

N-methoxylamine hydrochloride

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

(2E)-N-methoxybut-2-enamide
1569096-25-8

(2E)-N-methoxybut-2-enamide

Conditions
ConditionsYield
Stage #1: N-methoxylamine hydrochloride With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1h;
Stage #2: ethyl (E)-crotonate In tetrahydrofuran
96%
(2S,3S)-3-benzyloxy-2-(p-methoxybenzyloxymethyl)-3,4-dihydro-2H-pyrrole-1-oxide

(2S,3S)-3-benzyloxy-2-(p-methoxybenzyloxymethyl)-3,4-dihydro-2H-pyrrole-1-oxide

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

ethyl (2R,3S,3aR,5S,6S)-5-(benzyloxy)-6-(p-methoxybenzyloxymethyl)-2-methylhexahydro-pyrrolo[1,2-b]isoxazole-3-carboxylate

ethyl (2R,3S,3aR,5S,6S)-5-(benzyloxy)-6-(p-methoxybenzyloxymethyl)-2-methylhexahydro-pyrrolo[1,2-b]isoxazole-3-carboxylate

Conditions
ConditionsYield
In toluene at 40℃; for 24h; Inert atmosphere;96%
N-(4-bromo-2-nitrophenyl)-N-isobutylspiro[3.3]heptan-2-amine

N-(4-bromo-2-nitrophenyl)-N-isobutylspiro[3.3]heptan-2-amine

ethyl (E)-crotonate
623-70-1

ethyl (E)-crotonate

(E)-ethyl 3-(4-(isobutyl(spiro[3.3]heptan-2-yl)amino)-3-nitrophenyl)but-2-enoate

(E)-ethyl 3-(4-(isobutyl(spiro[3.3]heptan-2-yl)amino)-3-nitrophenyl)but-2-enoate

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In N,N-dimethyl-formamide at 110℃; for 4h; Inert atmosphere;96%

623-70-1Relevant articles and documents

-

Shimamura et al.

, p. 221 (1954)

-

Visible-Light-Promoted Intramolecular α-Allylation of Aldehydes in the Absence of Sacrificial Hydrogen Acceptors

Liu, Feng,Liu, Jia-Li,tu, Jia-Lin

supporting information, p. 7369 - 7372 (2020/10/05)

We report herein an unprecedented protocol for radical cyclization of aldehydes with pendant alkenes via synergistic photoredox, cobaloxime, and amine catalysis. The transformation was achieved in the absence of external oxidants, providing a variety of 5-, 6-, and 7-membered ring products with alkene transposition in satisfactory yields. The reaction exhibits wide functional group compatibility and occurs under mild conditions with extrusion of H2.

MONOMER, POLYMER, RESIST COMPOSITION, AND PATTERNING PROCESS

-

, (2014/03/21)

A polymer comprising recurring units derived from a (meth)acrylate monomer of tertiary ester type having branched alkyl on alicycle is used to form a resist composition. When subjected to exposure, PEB and organic solvent development, the resist composition is improved in dissolution contrast.

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