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14205-46-0

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14205-46-0 Usage

Chemical Properties

Colourless Liquid

Uses

Isopropyl 3-Aminocrotonate (cas# 14205-46-0) is a compound useful in organic synthesis.

Hazard

Moderately toxic by ingestion. Low toxicity by inhalation. A mild skin and eye irritant.

Check Digit Verification of cas no

The CAS Registry Mumber 14205-46-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,2,0 and 5 respectively; the second part has 2 digits, 4 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 14205-46:
(7*1)+(6*4)+(5*2)+(4*0)+(3*5)+(2*4)+(1*6)=70
70 % 10 = 0
So 14205-46-0 is a valid CAS Registry Number.
InChI:InChI=1/C7H13NO2/c1-5(2)10-7(9)4-6(3)8/h4-5H,8H2,1-3H3/b6-4-

14205-46-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Isopropyl 3-aminocrotonate

1.2 Other means of identification

Product number -
Other names Isopropyl 3-Aminocrotonate

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:14205-46-0 SDS

14205-46-0Synthetic route

isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

Conditions
ConditionsYield
With ammonium acetate In ethanol for 24h; Reflux;100%
With ammonia In water at 25℃; for 3h; Temperature; Reagent/catalyst;91.7%
With ammonium hydroxide; ammonium acetate at -5 - 5℃; for 18h;86%
isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

2-cyanoethylacetoacetate
65193-87-5

2-cyanoethylacetoacetate

3-(2-cyanoethyl) 5-isopropyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate
74936-70-2

3-(2-cyanoethyl) 5-isopropyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate

Conditions
ConditionsYield
In isopropyl alcohol Inert atmosphere; Reflux;95%
isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

C26H23N3O5

C26H23N3O5

azelnidipine
123524-52-7

azelnidipine

Conditions
ConditionsYield
With sodium methylate In ethanol for 6h; Reflux;89%
isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

4-(4-chlorophenyl)-1,1,1-trifluorobut-3-yn-2-one
77063-21-9

4-(4-chlorophenyl)-1,1,1-trifluorobut-3-yn-2-one

isopropyl 4-(4-chlorophenyl)-2-methyl-6-(trifluoromethyl)nicotinate

isopropyl 4-(4-chlorophenyl)-2-methyl-6-(trifluoromethyl)nicotinate

Conditions
ConditionsYield
With zinc dibromide In toluene at 110℃; for 8h; Bohlmann-Rahtz Pyridine Synthesis;82%
isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

methyl vinyl ketone
78-94-4

methyl vinyl ketone

2-propyl 2,6-dimethylpyridine-3-carboxylate

2-propyl 2,6-dimethylpyridine-3-carboxylate

Conditions
ConditionsYield
In toluene at 120℃; for 3h; Sealed tube;81%
isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

ammonium thiocyanate
1147550-11-5

ammonium thiocyanate

(E)-isopropyl 3-amino-2-thiocyanatobut-2-enoate

(E)-isopropyl 3-amino-2-thiocyanatobut-2-enoate

Conditions
ConditionsYield
With dihydrogen peroxide In water at 20℃;81%
isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

2-[1-(2-Fluoro-phenyl)-meth-(Z)-ylidene]-3-oxo-butyric acid methyl ester
39561-90-5

2-[1-(2-Fluoro-phenyl)-meth-(Z)-ylidene]-3-oxo-butyric acid methyl ester

1,4-dihydro-4-(2-fluorophenyl)-2,6-dimethyl-3-methoxycarbonyl-5-isopropoxycarbonylpyridine

1,4-dihydro-4-(2-fluorophenyl)-2,6-dimethyl-3-methoxycarbonyl-5-isopropoxycarbonylpyridine

Conditions
ConditionsYield
In ethanol Heating;80%
pyridine-2-carbaldehyde
1121-60-4

pyridine-2-carbaldehyde

1-nitro-2-propanone
10230-68-9

1-nitro-2-propanone

isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

1,4-dihydro-2,6-dimethyl-3-nitro-4-(pyridine-2-yl)-5-pyridinecarboxylic acid isopropyl ester

1,4-dihydro-2,6-dimethyl-3-nitro-4-(pyridine-2-yl)-5-pyridinecarboxylic acid isopropyl ester

Conditions
ConditionsYield
In ethanol for 12h; Heating;79%
4-(4-methylphenyl)-1,1,1-trifluorobut-3-yn-2-one

4-(4-methylphenyl)-1,1,1-trifluorobut-3-yn-2-one

isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

isopropyl 2-methyl-4-(p-tolyl)-6-(trifluoromethyl)nicotinate

isopropyl 2-methyl-4-(p-tolyl)-6-(trifluoromethyl)nicotinate

Conditions
ConditionsYield
With zinc dibromide In toluene at 110℃; for 8h; Bohlmann-Rahtz Pyridine Synthesis;79%
5-(2-nitrophenyl)-2-furaldehyde
20000-96-8

5-(2-nitrophenyl)-2-furaldehyde

isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

dimedone
126-81-8

dimedone

2,7,7-Trimethyl-4-[5-(2-nitro-phenyl)-furan-2-yl]-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid isopropyl ester
111400-15-8

2,7,7-Trimethyl-4-[5-(2-nitro-phenyl)-furan-2-yl]-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid isopropyl ester

Conditions
ConditionsYield
In methanol; acetic acid for 2h; Heating;77%
isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

1,1-difluoro-4-phenyl-3-butyn-2-one
117710-72-2

1,1-difluoro-4-phenyl-3-butyn-2-one

iso-propyl 6-(difluoromethyl)-2-methyl-4-phenylnicotinate

iso-propyl 6-(difluoromethyl)-2-methyl-4-phenylnicotinate

Conditions
ConditionsYield
With zinc dibromide In toluene at 110℃; for 6h;75%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

1-nitro-2-propanone
10230-68-9

1-nitro-2-propanone

isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

2',6'-Dimethyl-5'-nitro-1',4'-dihydro-[3,4']bipyridinyl-3'-carboxylic acid isopropyl ester

2',6'-Dimethyl-5'-nitro-1',4'-dihydro-[3,4']bipyridinyl-3'-carboxylic acid isopropyl ester

Conditions
ConditionsYield
In ethanol for 12h; Heating;71%
1-nitro-2-propanone
10230-68-9

1-nitro-2-propanone

6-chloropyridine-2-carboxaldehyde
54087-03-5

6-chloropyridine-2-carboxaldehyde

isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

6-chloro-2',6'-dimethyl-5'-nitro-1',4'-dihydro-[2,4']bipyridinyl-3'-carboxylic acid isopropyl ester

6-chloro-2',6'-dimethyl-5'-nitro-1',4'-dihydro-[2,4']bipyridinyl-3'-carboxylic acid isopropyl ester

Conditions
ConditionsYield
In ethanol a) 25 deg C, 1 h, b) reflux, 16 h;71%
acetoxy-acetic acid ethyl ester
623-86-9

acetoxy-acetic acid ethyl ester

isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

3-ethyl 5-isopropyl 4-(2-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

3-ethyl 5-isopropyl 4-(2-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Conditions
ConditionsYield
Hantzsch Dihydropyridine Synthesis; Darkness; Reflux;71%
isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

1,1,1-trifluoro-4-phenylbut-3-yn-2-one
58518-08-4

1,1,1-trifluoro-4-phenylbut-3-yn-2-one

isopropyl 2-methyl-4-phenyl-6-(trifluoromethyl)nicotinate

isopropyl 2-methyl-4-phenyl-6-(trifluoromethyl)nicotinate

Conditions
ConditionsYield
With zinc dibromide In toluene at 110℃; for 8h; Bohlmann-Rahtz Pyridine Synthesis;68%
5-(3-nitrophenyl)furfural
13148-43-1

5-(3-nitrophenyl)furfural

isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

dimedone
126-81-8

dimedone

2,7,7-Trimethyl-4-[5-(3-nitro-phenyl)-furan-2-yl]-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid isopropyl ester
111400-16-9

2,7,7-Trimethyl-4-[5-(3-nitro-phenyl)-furan-2-yl]-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid isopropyl ester

Conditions
ConditionsYield
In methanol; acetic acid for 2h; Heating;65%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

1-nitro-2-propanone
10230-68-9

1-nitro-2-propanone

isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

2,6-Dimethyl-5-nitro-1,4-dihydro-[4,4']bipyridinyl-3-carboxylic acid isopropyl ester

2,6-Dimethyl-5-nitro-1,4-dihydro-[4,4']bipyridinyl-3-carboxylic acid isopropyl ester

Conditions
ConditionsYield
In ethanol for 12h; Heating;64%
acetyl acetic acid-3-[N-(1,2-benzisothiazolyl-3(2H)one-1,1-dioxide)]-propylester

acetyl acetic acid-3-[N-(1,2-benzisothiazolyl-3(2H)one-1,1-dioxide)]-propylester

isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

2,6-Dimethyl-5-isopropoxycarbonyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid-3-[N-(1,2-benzisothiazolyl-3(2H)one-1,1-dioxide)]-propylester
136941-66-7

2,6-Dimethyl-5-isopropoxycarbonyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid-3-[N-(1,2-benzisothiazolyl-3(2H)one-1,1-dioxide)]-propylester

Conditions
ConditionsYield
In ethanol64%
isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

4,4-Dimethoxy-3-oxo-2-[1-(2-trifluoromethyl-phenyl)-meth-(E)-ylidene]-butyric acid methyl ester
75530-13-1, 75571-91-4

4,4-Dimethoxy-3-oxo-2-[1-(2-trifluoromethyl-phenyl)-meth-(E)-ylidene]-butyric acid methyl ester

2-Dimethoxymethyl-6-methyl-4-(2-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 5-isopropyl ester 3-methyl ester
75530-35-7

2-Dimethoxymethyl-6-methyl-4-(2-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 5-isopropyl ester 3-methyl ester

Conditions
ConditionsYield
at 95 - 120℃; for 8.5h;63.2%
isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

2-(2-difluoromethoxybenzylidene)indandione-1,3

2-(2-difluoromethoxybenzylidene)indandione-1,3

4-(2-Difluoromethoxy-phenyl)-2-methyl-5-oxo-4,5-dihydro-1H-indeno[1,2-b]pyridine-3-carboxylic acid isopropyl ester

4-(2-Difluoromethoxy-phenyl)-2-methyl-5-oxo-4,5-dihydro-1H-indeno[1,2-b]pyridine-3-carboxylic acid isopropyl ester

Conditions
ConditionsYield
With acetic acid for 0.0833333h; Heating;63.2%
C16H14ClNO2S

C16H14ClNO2S

isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

C23H23ClN2O3S
1076202-66-8

C23H23ClN2O3S

Conditions
ConditionsYield
In methanol modified Hantzsch synthesis; Reflux; Darkness;63%
isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

o-Difluoromethylthiobenzaldehyde
79676-69-0

o-Difluoromethylthiobenzaldehyde

2,6-Dimethyl-3,5-di(isopropoxycarbonyl)-4-(o-difluoromethylthiophenyl)-1,4-dihydropyridine
110525-41-2

2,6-Dimethyl-3,5-di(isopropoxycarbonyl)-4-(o-difluoromethylthiophenyl)-1,4-dihydropyridine

Conditions
ConditionsYield
In isopropyl alcohol for 10h; Heating;62%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

5-(2-Oxopropyl)-1H-tetrazole
13616-38-1

5-(2-Oxopropyl)-1H-tetrazole

isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

Isopropyl 1,4-dihydro-2,6-dimethyl-4-(3-pyridinyl)-5-(1H-tetrazol-5-yl)-3-pyridinecarboxylate

Isopropyl 1,4-dihydro-2,6-dimethyl-4-(3-pyridinyl)-5-(1H-tetrazol-5-yl)-3-pyridinecarboxylate

Conditions
ConditionsYield
In ethanol for 14h; Heating;62%
isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

3-aminoindazole
874-05-5

3-aminoindazole

isopropyl 1-amino-3-methylisoquinoline-4-carboxylate

isopropyl 1-amino-3-methylisoquinoline-4-carboxylate

Conditions
ConditionsYield
With tert.-butylhydroperoxide; copper diacetate; caesium carbonate In decane; acetonitrile at 60℃; for 20h; Sealed tube; Inert atmosphere;61%
isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

2-[1-(2-Chloro-phenyl)-meth-(E)-ylidene]-4,4-dimethoxy-3-oxo-butyric acid methyl ester
75530-09-5, 75530-10-8

2-[1-(2-Chloro-phenyl)-meth-(E)-ylidene]-4,4-dimethoxy-3-oxo-butyric acid methyl ester

4-(2-Chloro-phenyl)-2-dimethoxymethyl-6-methyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 5-isopropyl ester 3-methyl ester
75530-34-6

4-(2-Chloro-phenyl)-2-dimethoxymethyl-6-methyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 5-isopropyl ester 3-methyl ester

Conditions
ConditionsYield
at 95 - 120℃; for 8.5h;59.3%
pyridine-2-carbaldehyde
1121-60-4

pyridine-2-carbaldehyde

5-(2-Oxopropyl)-1H-tetrazole
13616-38-1

5-(2-Oxopropyl)-1H-tetrazole

isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

Isopropyl 1,4-dihydro-2,6-dimethyl-4-(2-pyridinyl)-5-(1H-tetrazol-5-yl)-3-pyridinecarboxylate

Isopropyl 1,4-dihydro-2,6-dimethyl-4-(2-pyridinyl)-5-(1H-tetrazol-5-yl)-3-pyridinecarboxylate

Conditions
ConditionsYield
In ethanol for 14h; Heating;59%
C16H14ClNO2S

C16H14ClNO2S

isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

C23H23ClN2O3S
1076202-60-2

C23H23ClN2O3S

Conditions
ConditionsYield
In methanol modified Hantzsch synthesis; Reflux; Darkness;58%
isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

4,4-Dimethoxy-2-[1-(2-nitro-phenyl)-meth-(E)-ylidene]-3-oxo-butyric acid methyl ester
67448-12-8

4,4-Dimethoxy-2-[1-(2-nitro-phenyl)-meth-(E)-ylidene]-3-oxo-butyric acid methyl ester

isopropyl 2-dimethoxymethyl-3-methoxycarbonyl-6-methyl-4-(2-nitrophenyl)-1,4-dihydropyridine-5-carboxylate
67448-14-0

isopropyl 2-dimethoxymethyl-3-methoxycarbonyl-6-methyl-4-(2-nitrophenyl)-1,4-dihydropyridine-5-carboxylate

Conditions
ConditionsYield
at 95 - 120℃; for 8.5h;56.8%
1,4-dioxoquinoxaline-2-carboxaldehyde
17626-51-6

1,4-dioxoquinoxaline-2-carboxaldehyde

isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

4-(1,4-Dioxy-quinoxalin-2-yl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-isopropyl ester 5-methyl ester
138970-01-1

4-(1,4-Dioxy-quinoxalin-2-yl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-isopropyl ester 5-methyl ester

Conditions
ConditionsYield
In methanol for 3h; Heating;55%
isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

methyl 4-fluoro-3-oxo-butanoate
95399-93-2

methyl 4-fluoro-3-oxo-butanoate

3-methyl 5-(1-methylethyl) 2-(fluoromethyl)-1,4-dihydro-6-methyl-4-(4-nitrophenyl)pyridine-3,5-dicarboxylate
117772-23-3

3-methyl 5-(1-methylethyl) 2-(fluoromethyl)-1,4-dihydro-6-methyl-4-(4-nitrophenyl)pyridine-3,5-dicarboxylate

Conditions
ConditionsYield
In tert-butyl alcohol at 60℃; for 72h;55%

14205-46-0Upstream product

14205-46-0Relevant articles and documents

Nimodipine impurity IV reference substance as well as preparation method and application thereof

-

Page/Page column 0051; 0053-0054, (2020/11/22)

The invention discloses a nimodipine impurity IV reference substance and a preparation method thereof. The method includes the steps that diketene, ethyl alcohol and triethylamine are taken and addedinto a container to be heated and cooled, reaction liquid is washed with water, washing liquid is discarded, anhydrous sodium sulfate is added and placed overnight, filtrate is obtained after filtration, ammonia gas is introduced into the filtrate until the filtrate is saturated, and the nimodipine impurity IV reference substance is obtained; and after the reaction is finished, m-nitrobenzaldehyde, methoxyethyl acetoacetate and ethanol are added, heating refulx is performed, the mixture is cooled and filtered, the solvent is removed through volatilization in a water bath to obtain a yellow viscous liquid, and recrystallization is carried out to obtain a yellow acicular crystal, namely the nimodipine impurity IV reference substance. The invention also discloses an application of the nimodipine impurity IV reference substance in nimodipine tablet consistency evaluation. According to the preparation method, the impurity IV can be prepared in a general analysis laboratory, special preparation equipment is not needed, the operation is simple, the purity of the obtained impurity reference substance can reach 98.4%, the purity requirement of the reference substance is met, and the preparation method can be used for consistency evaluation of the variety.

Synthesis method of isopropyl 3-aminocrotonate

-

Paragraph 0022; 0024; 0026; 0028; 0030-0032; 0034; 0036, (2018/06/26)

Isopropyl 3-aminocrotonate is an important chemical intermediate and has excellent industrial production value; however, methods in the prior art have problems of incomplete raw material conversion, difficulty of raw material removal, low product content and low yield; the method in the invention includes steps of with isopropyl acetoacetate and ammonium salt as raw materials, mixing the raw materials and performing a heating reaction, and when the isopropyl acetoacetate is reacted completely, separating the product to prepare the isopropyl 3-aminocrotonate. The method has simple operation, more completely converts the raw materials, and is high in product purity.

Preparation method of azelnidipine

-

Paragraph 0016, (2017/03/08)

The invention relates to a preparation method of azelnidipine, which comprises the following steps: carrying out Knoevenagel reaction on cyanoacetic acid and m-nitrobenzaldehyde used as starting materials to generate a compound 1; hydrolyzing cyano group of the compound 1 to generate a compound 2; carrying out esterification on the compound 2 and 1-diphenylmethyl-3-azetidin-ol under the action of DCC (N,N'-dicyclohexylcarbodiimide) to generate a compound 3; carrying out Hantzsch cyclization on the compound 3 and isopropyl 3-aminocrotonate under alkaline conditions to generate an azelnidipine crude product; and refining the crude product to obtain the azelnidipine fine product. The method is simple to operate and suitable for industrial production; and the reaction product is easy to separate.

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