626-34-6

Basic information

• Product Name: ETHYL 3-AMINOCROTONATE
• Synonyms: Ethyl (2Z)-3-amino-2-butenoate;(Z)-ETHYL 3-AMINOBUT-2-ENOATE;3-AMINOCROTONIC ACIDETHYL ESTER;AURORA KA-7376;Ethyl 3-aminocrotonate, 98+%;2-Butenoic acid, 3-amino-, ethyl ester, (2Z)-;trans-3-amino-but-2-enoic acid ethyl ester;(2Z)-3-Amino-2-butenoic acid ethyl ester
• CAS NO: 626-34-6
• Molecular Formula: C₆H₁₁NO₂
• Molecular Weight: 129.16
• EINECS: 230-782-0
• Product Categories: Starting Raw Materials & Intermediates;Organic acids;C6 to C7;Carbonyl Compounds;Esters
• Mol File: 626-34-6.mol
• Article Data: 65

Chemical Properties

• Melting Point: 33-35 °C(lit.)
• Boiling Point: 210-215 °C(lit.)
• Flash Point: 207 °F
• Appearance: liquid
• Density: 1.022 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.173mmHg at 25°C
• Refractive Index: 1.4990
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 5.32±0.70(Predicted)
• Water Solubility: Soluble in water (26 g/L) (25°C).
• Sensitive: Air & Moisture Sensitive & Hygro
• BRN: 471284
• CAS DataBase Reference: ETHYL 3-AMINOCROTONATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 3-AMINOCROTONATE(626-34-6)
• EPA Substance Registry System: ETHYL 3-AMINOCROTONATE(626-34-6)

Safety Data

• Hazard Codes: C
• Statements: 34-36/37
• Safety Statements: 26-27-28-36/37/39-45
• RIDADR: UN 3263 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 626-34-6(Hazardous Substances Data)

Usage

Uses

Ethyl 3-aminocrotonate, is used as an intermediate in organic synthesis. It is also used as an active ingredient in pharmaceutical synthesis and feed auxiliary agent. It is also used as an active pharmaceutical intermediate.

InChI:InChI=1/C6H11NO2/c1-3-9-6(8)4-5(2)7/h4H,3,7H2,1-2H3/b5-4-

Synthetic route

ethyl acetoacetate (141-97-9) → ethyl 3-aminobut-2-enoate (626-34-6)

Conditions	Yield
With ammonium carbamate In methanol at 20℃; for 1.5h;	100%
With ammonia; silica gel at 20℃; for 4h;	99%
With ammonium hydroxide; montmorillonite K-10 for 24h; Ambient temperature;	90%

2-Acetyl-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-3-oxo-nonanoic acid ethyl ester (115479-07-7) → tridecafluoroheptamide (2358-22-7) + ethyl 3-aminobut-2-enoate (626-34-6)

Conditions	Yield
With ammonia In water at -20 - 20℃; for 3h;	A 95% B n/a

2-Acetyl-4,4,5,5-tetrafluoro-3-oxo-pentanoic acid ethyl ester (116206-91-8) → 3-hydro-2,2,3,3-tetrafluoropropionamide (2069-86-5) + ethyl 3-aminobut-2-enoate (626-34-6)

Conditions	Yield
With ammonia In water at -20 - 20℃; for 3h;	A 83% B n/a

ethyl acetoacetate (141-97-9) + methylamine (74-89-5) → ethyl 3-aminobut-2-enoate (626-34-6)

Conditions	Yield
at 20℃;	76%

ethyl bromoacetate (105-36-2) + acetonitrile (75-05-8) → ethyl 3-aminobut-2-enoate (626-34-6)

Conditions	Yield
With zinc(II) oxide; zinc In tetrahydrofuran for 2h; Irradiation; sonochemical reaction;	67%

ethyl acetoacetate (141-97-9) + dimethyl sulfoxide (67-68-5) → diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (1149-23-1) + 2,6-dimethyl-pyridine-3,5-dicarboxylic acid diethyl ester (1149-24-2) + ethyl 3-aminobut-2-enoate (626-34-6)

Conditions	Yield
With ammonium acetate at 115℃; for 10h; Sealed tube;	A 17% B 12% C 50%

ethyl aminocrotonate (626-34-6, 7318-00-5, 41867-20-3) → ethyl 3-aminobut-2-enoate (626-34-6)

Conditions	Yield
With ammonium acetate In ethanol at 20℃; for 60h; Inert atmosphere; Schlenk technique;

1-(4-methylphenyl)prop-2-yn-1-one (14377-18-5) + ethyl 3-aminobut-2-enoate (626-34-6) → ethyl 2-methyl-6-(4-tolyl)pyridine-3-carboxylate (271597-75-2)

Conditions	Yield
Stage #1: 1-(4-methylphenyl)prop-2-yn-1-one; ethyl 3-aminobut-2-enoate In ethanol at 50℃; Addition; Stage #2: at 125℃; for 1h; Cyclization; Further stages.;	100%

ethyl 3-aminobut-2-enoate (626-34-6) + phenyl propargyl ketone (3623-15-2) → ethyl 2-methyl-6-phenylnicotinate (1702-14-3)

Conditions	Yield
In acetic acid; toluene at 170℃; for 0.166667h; Product distribution; Further Variations:; Solvents; microwave irradiation; Bohlmann-Rahtz synthesis;	98%

methyl 3,3,3-trifluoropyruvate (13089-11-7) + ethyl 3-aminobut-2-enoate (626-34-6) → 1-ethyl 6-methyl 3-amino-5-hydroxy-5-(trifluoromethyl)-2-hexendicarboxylate

Conditions	Yield
at 20℃; for 2h; Neat (no solvent);	98%

methyl 3,3,3-trifluoropyruvate (13089-11-7) + ethyl 3-aminobut-2-enoate (626-34-6) → ethyl [4-hydroxy-5-oxo-4-(trifluoromethyl)pyrrolidin-2-ylidene]acetate (1225583-56-1)

Conditions	Yield
at 20℃; for 2h; Neat (no solvent);	98%

ethyl 3-aminobut-2-enoate (626-34-6) + 1-(2-thiazolyl)propynone (271597-73-0) → ethyl 2-methyl-6-(thiazol-2-yl)pyridine-3-carboxylate

Conditions	Yield
Stage #1: ethyl 3-aminobut-2-enoate; 1-(2-thiazolyl)propynone In ethanol at 50℃; Addition; Stage #2: at 125℃; for 1h; Cyclization; Further stages.;	97%

ethyl (2Z)-3-phenyl-3-(phenylamino)prop-2-enoate (3556-76-1, 124413-92-9, 53256-22-7) + ethyl 3-aminobut-2-enoate (626-34-6) → 3,4-diethoxycarbonyl-2-methyl-1,5-diphenylpyrrole

Conditions	Yield
With tetrabutylammonium hexanitratocerate(IV) In chloroform	96%

ethyl acetoacetate (141-97-9) + ethyl 3-aminobut-2-enoate (626-34-6) + (2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)methanal (140397-46-2) → diethyl 4-(2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)-1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate (421554-00-9)

Conditions	Yield
With ytterbium(III) triflate In tetrahydrofuran at 90℃; for 12h; Hantzsch cyclocondensation;	95%

maleic anhydride (108-31-6) + ethyl 3-aminobut-2-enoate (626-34-6) → 2-(4-(ethoxycarbonyl)-5-methyl-2-oxo-2,3-dihydro-1H-pyrrol-3-yl)acetic acid (54585-20-5)

Conditions	Yield
In acetonitrile at 20℃; for 0.5h;	95%

ethyl 3-aminobut-2-enoate (626-34-6) + acetoacetic acid methyl ester (105-45-3) + 2,3-dichlorobenzylaldehyde (6334-18-5) → ethyl methyl 1,4-dihydro-2,6-dimethyl-4(2,3-dichlorophenyl)-3,5-pyridinedicarboxylate (72509-76-3)

Conditions	Yield
Stage #1: ethyl 3-aminobut-2-enoate; acetoacetic acid methyl ester; 2,3-dichlorobenzylaldehyde With piperidine; pyridine In neat (no solvent) at 75 - 80℃; for 9h; Stage #2: With ethanol for 1h; Reagent/catalyst; Solvent; Reflux;	94.3%

4-hydroxy-6-methylquinolin-2(1H)-one (1677-44-7) + ethyl 3-aminobut-2-enoate (626-34-6) → 4,9-Dimethyl-6H-pyrano[3,2-c]quinoline-2,5-dione (79359-45-8)

Conditions	Yield
In nitrobenzene at 200℃; for 1h;	94%

3-hexyn-2-one (1679-36-3) + ethyl 3-aminobut-2-enoate (626-34-6) → Ethyl 2,6-dimethyl-4-ethylpyridine-3-carboxylate

Conditions	Yield
In dimethyl sulfoxide at 170℃; for 0.333333h; Bohlmann-Rahtz reaction; microwave irradiation;	94%

ethyl 3-aminobut-2-enoate (626-34-6) + (Z)-ethyl 3-((4-bromophenyl)amino)-3-phenylacrylate (66283-07-6) → 1-(p-bromophenyl)-3,4-diethoxycarbonyl-2-methyl-5-phenylpyrrole

Conditions	Yield
With tetrabutylammonium hexanitratocerate(IV) In chloroform	94%

ethyl 3-aminobut-2-enoate (626-34-6) + propynoic acid methyl ester (922-67-8) → (2E,4Z)-5-ethyl 1-methyl 4-(1-aminoethylidene)pent-2-enedioate (53256-25-0)

Conditions	Yield
at 110℃; for 10h;	93%
at 108℃; for 3h; Inert atmosphere; Neat (no solvent);	72%
In benzene
In toluene for 36h; Reflux; Inert atmosphere;
In toluene for 16h; Inert atmosphere; Reflux;

ethyl (Z)-3-amino-3-phenylacrylate (53256-19-2) + ethyl 3-aminobut-2-enoate (626-34-6) → diethyl 2-methyl-5-phenyl-1H-pyrrole-3,4-dicarboxylate (69640-22-8)

Conditions	Yield
With tetrabutylammonium hexanitratocerate(IV) In acetonitrile at 20℃; for 1h;	92%

ethyl 3-aminobut-2-enoate (626-34-6) + (Z)-ethyl 3-((4-chlorophenyl)amino)-3-phenylacrylate (86397-94-6) → 1-(p-chlorophenyl)-3,4-diethoxycarbonyl-2-methyl-5-phenylpyrrole

Conditions	Yield
With tetrabutylammonium hexanitratocerate(IV) In methanol at 20℃;	92%

4-hydroxy-1-methyl-2(1H)-quinolone (1677-46-9) + ethyl 3-aminobut-2-enoate (626-34-6) → 4,6-dimethyl-5,6-dihydro-2H-pyrano[3,2-c]quinoline-2,5-dione (79359-49-2)

Conditions	Yield
In nitrobenzene at 200℃; for 1h;	91%

ethyl 3-aminobut-2-enoate (626-34-6) + 3-chloro-3-(4-nitrophenyl)-prop-2-en-1-ylidenedimethyliminium perchlorate → 4-[(Z)-2-Chloro-2-(4-nitro-phenyl)-vinyl]-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester

Conditions	Yield
In acetic acid for 0.25h; Heating;	91%

ethyl 3-aminobut-2-enoate (626-34-6) + (Z)-ethyl 4-(3-ethoxy-3-oxo-1-phenylprop-1-enylamino)benzoate → 3,4-diethoxycarbonyl-1-(p-ethoxycarbonylphenyl)-2-methyl-5-phenylpyrrole

Conditions	Yield
With tetrabutylammonium hexanitratocerate(IV) In chloroform	91%

ethyl 3-aminobut-2-enoate (626-34-6) + 3,4,6-tri-O-benzyl-1,2-dideoxy-2-nitro-D-arabino-hex-1-enopyranose (117136-22-8) → (Z)-ethyl 2-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-glucopyranosyl)-3-aminobut-2-enoate (1256092-82-6)

Conditions	Yield
at 95℃; for 6h; Michael type addition; neat (no solvent); stereoselective reaction;	91%

tetrahydro-1,3-oxazine (14558-49-7) + ethyl 3-aminobut-2-enoate (626-34-6) → diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (1149-23-1)

Conditions	Yield
With acetic acid In acetonitrile for 0.1h; Ambient temperature;	90%

ethyl 3-aminobut-2-enoate (626-34-6) + 5-amino-2,4-dihydro-4-<(phenylamino)methylene>-2-phenyl-3H-pyrazole-3-one (93020-68-9) → 3-<<1,5-dihydro-5-oxo-4-<(phenylamino)methylene>-1-phenyl-4H-pyrazole-3-yl>amino>-2-butenoate d'ethyle (107183-70-0)

Conditions	Yield
In acetic acid at 20℃;	90%

ethyl 3-aminobut-2-enoate (626-34-6) + p-benzoquinone (106-51-4) → ethyl 5-hydroxy-2-methylindole-3-carboxylate (7598-91-6)

Conditions	Yield
With acetic acid at 15 - 40℃; for 2.5h; Nenitzescu indole synthesis;	90%

C21H18N2O6 + ethyl 3-aminobut-2-enoate (626-34-6) → C27H27N3O7

Conditions	Yield
With ammonium acetate In ethanol at 85℃; for 2h;	89.2%

2-amino-5,5-dimethyl-3-cyano-4,5-dihydro-7H-thieno<2,3-c>pyran (65413-45-8) + ethyl 3-aminobut-2-enoate (626-34-6) → ethyl (2E)-3-[(3-cyano-5,5-dimethyl-4,7-dihydro-5H-thieno[2,3-c]pyran-2-yl)amino]but-2-enoate

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 16h; Reflux;	89%

2-chloro-3,4-dihydro-3-oxo-2H-1,4-benzothiazine (55043-49-7) + ethyl 3-aminobut-2-enoate (626-34-6) → ethyl 3-amino-2-(3-oxo-3,4-dihydro-2H-1,4-benzothiazin-2-yl)but-2-enoate (1030608-86-6)

Conditions	Yield
With triethylamine In dichloromethane for 4h; Heating;	87%

1,1-Dioxo-5-N-formyl-2,3,4,5-tetrahydro-[1,5]-benzothiazepine-3-one (140217-86-3) + ethyl 3-aminobut-2-enoate (626-34-6) + 2,3-dichlorobenzylaldehyde (6334-18-5) → Ethyl 4-(2,3-dichlorophenyl)-5,5-dioxo-10-formyl-2-methyl-1,4,10,11-tetrahydropyrido[3,2-b][1,5]-benzothiazepine-3-carboxylate (140217-75-0)

Conditions	Yield
In ethanol	86%

malonic acid bis-(2,4,6-trichloro-phenyl) ester (15781-70-1) + ethyl 3-aminobut-2-enoate (626-34-6) → 4,6-dihydroxy-2-methyl nicotinic acid ethyl ester (3950-10-5, 70254-48-7, 70254-49-8)

Conditions	Yield
for 0.833333h; Time; Reflux;	86%

C15H20O4S + ethyl acetoacetate (141-97-9) + ethyl 3-aminobut-2-enoate (626-34-6) → diethyl 2,6-dimethyl-4-(4-((tosyloxy)methyl)cyclohexyl)-1,4-dihydropyridine-3,5-dicarboxylate

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate In ethylene glycol at 85℃; for 4h; Inert atmosphere;	86%

Upstream product

• 4341-76-8 Ethyl 2-butynoate 
• 141-97-9 ethyl acetoacetate 
• 6127-92-0 E-Ethyl β-chlorocrotonate 
• 128001-87-6 ethyl 3-(bromoacetamido)crotonate 
• 105-56-6 ethyl 2-cyanoacetate 
• 7664-41-7 ammonia 
• 141-78-6 ethyl acetate 
• 412321-15-4 4-cyano-3-methyl-pentenedioic acid diethyl ester 
• 91558-49-5 2,3-dicyano-3-methyl-glutaric acid diethyl ester 
• 73758-52-8 3-amino-3-ureido-butyric acid ethyl ester 
• 56294-09-8 ethyl 5-methoxycarbonyl-3-oxopentanoate 
• 123-11-5 4-methoxy-benzaldehyde 
• 105-36-2 ethyl bromoacetate 
• 75-05-8 acetonitrile 

Downstream Products

• 52199-37-8 2,4-dimethyl-1,4-dihydro-pyridine-3-carboxylic acid ethyl ester 
• 23652-67-7 ethyl (Z)-β-acetylaminobut-2-enoate 
• 23652-67-7 methyl (E)-3-acetamido-2-butenoate 
• 78120-37-3 (E)-ethyl 2-acetyl-3-aminobut-2-enoate 
• 23125-28-2 2',6'-dimethyl-1',4'-dihydro-[2,4']bipyridinyl-3',5'-dicarboxylic acid diethyl ester 
• 1693-94-3 2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one 
• 1569-15-9 7-amino-4-methyl-1,8-naphthyridin-2(1H)-one 
• 53274-27-4 diethyl 1,4-dihydro-2,6-dimethyl-4-(4-quinolinyl)pyridine-3,5-dicarboxylate 
• 23429-92-7 2-methyl-4H-benzo[4,5]thiazolo[3,2-a]pyrimidin-4-one 
• 50290-51-2 2-methylpyrimido[1,2-a]benzimidazol-4(1H)-one 
• 2199-54-4 2,4,5-trimethyl-3-ethoxycarbonylpyrrole 
• 35929-79-4 4-(4-chloro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester 
• 21881-54-9 2,6-dimethyl-4-(4-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester 
• 34014-60-3 diethyl 1,4-dihydro-2,6-dimethyl-4-(4-methoxyphenyl)pyridine-3,5-dicarboxylate 

Relevant articles and documents

Efficient synthesis of decahydroacridine-1,8-diones and polyhydroquinolines using the step-wise method

Various symmetrical and unsymmetrical decahydroacridine-1,8-dione and polyhydroquinoline derivatives were synthesized via two-step cyclocondensation reactions. The advantages of this step-wise addition of reactants in comparison with other one-pot reactions are avoiding the formation of 2 or 3 undesired by-products, therefore allowing cleaner work up of reaction. The important factor of this effective cyclocondensation method is that the prepared β-enaminone component was added dropwise to the solution, in which the Knoevenagel condensation product is slowly being formed by reaction of aldehyde molecule and 1,3-dicarbonyl compounds. The results of the proposed step-wise method are compared and discussed with those obtained in the one-pot reactions.

HISTONE ACETYLTRANSFERASE (HAT) INHIBITOR AND USE THEREOF

The present invention relates to a histone acetyltransferase (HAT) inhibitor. Provided are a compound represented by general formula I, a pharmaceutically acceptable salt, a stereoisomer, an enantiomer, a diastereomer, an atropisomer, a racemate, a polymorph, a solvate or an isotope-labeled compound (including deuterium substitution) thereof, a preparation method therefor, a pharmaceutical composition comprising the same, and use thereof in the treatment of various HAT-related diseases or conditions.

Synthesis and Biological Activities of Nicotinaldehyde Based 1,4-Dihydropyridinedicarboxylates

Abstract: 1,4-Dihydropyridinecarboxylates were prepared by the reaction of nicotinaldehydes with aminocrotonoates in the presence of p-TsOH at room temperature. The prepared compounds were evaluated for their anti-microbial, free-radical scavenging and α-glucosidase inhibitory activities. Compounds diethyl 2,6-diphenyl-4-(pyridin-3-yl)-1,4-dihydropyridine-3,5-dicarboxylate and diethyl 4-(2-chloro-5-(4-fluorophenyl)pyridin-3-yl)-2,6-diphenyl-1,4-dihydropyridine-3,5-dicarboxylate were identified as potent anti-fungal agents. The compounds diethyl 2,6-dimethyl-4-(pyridin-3-yl)-1,4-dihydropyridine-3,5-dicarboxylate, dimethyl 4-(2-chloropyridin-3-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate and diethyl 2,6-dimethyl-4-(pyridin-4-yl)-1,4-dihydropyridine-3,5-dicarboxylate were identified as ABT?+ free radical scavengers. The compounds diethyl 4-(2-chloro-5-phenylpyridin-3-yl)-2,6-diphenyl-1,4-dihydropyridine-3,5-dicarboxylate and diethyl 4-(2-chloro-5-phenylpyridin-3-yl)-2,6-diphenyl-1,4-dihydropyridine-3,5-dicarboxylate denoted α-glucosidase inhibitory activity.