Methyl 3-aminocrotonate supplier

Name
Methyl 3-aminocrotonate
EINECS 238-056-5
CAS No. 14205-39-1
Article Data42
CAS DataBase
Density 1.031 g/cm³
Solubility insoluble in water
Melting Point 81-83 °C(lit.)
Formula C₅H₉NO₂
Boiling Point 194.1 °C at 760 mmHg
Molecular Weight 115.132
Flash Point 65.3 °C
Transport Information
Appearance yellowish-white crystals
Safety 37/39-26
Risk Codes 22-36/37/38
Molecular Structure
Hazard Symbols Xn
Synonyms Crotonicacid, 3-amino-, methyl ester (7CI,8CI);3-Aminocrotonic acid methyl ester;Methyl 3-amino-2-butenenoate;β-Aminocrotonic acid methyl ester;Crotonic acid, β-amino-, methyl ester;
PSA 52.32000
LogP 0.72220

Synthetic route

: 105-45-3
acetoacetic acid methyl ester

: 14205-39-1
methyl 3-aminocrotonate

Conditions

Conditions	Yield
With ammonium hydroxide In methanol; water for 16h; Heating;	96%
With ammonia; acetic acid Product distribution / selectivity;	94%
With ammonia In methanol at 0 - 10℃; for 4h; Large scale;	85%

: (-)-methyl (2S,3R)-2-(indol-3-yl)-1-(2-hydroxyethyl)piperidine-3-carboxylate

: 57570-85-1
lithium enolate of methyl acetate

A: (-)-methyl 3-((2S,3R)-1-(2-hydroxyethyl)-2-(indol-3-yl)piperidin-3-yl)-3-oxopropanoate

B: 14205-39-1
methyl 3-aminocrotonate

Conditions

Conditions	Yield
Stage #1: (-)-methyl (2S,3R)-2-(indol-3-yl)-1-(2-hydroxyethyl)piperidine-3-carboxylate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.333333h; Claisen Condensation; Stage #2: lithium enolate of methyl acetate at -78 - 20℃; for 20.0833h; Claisen Condensation;	A 72% B 102 mg

...Expand

: 6372-01-6
(E)-methyl 3-chloro-2-butenoate

: 14205-39-1
methyl 3-aminocrotonate

Conditions

Conditions	Yield
With ammonia at 100℃;

: 105-45-3
acetoacetic acid methyl ester

A: 5977-14-0
acetoacetamido

B: 14205-39-1
methyl 3-aminocrotonate

Conditions

Conditions	Yield
With ammonia

β--crotonic acid methyl ester: β--crotonic acid methyl ester

A: 541-35-5
butanamide

B: 14205-39-1
methyl 3-aminocrotonate

Conditions

Conditions	Yield
With ammonia

: 7664-41-7
ammonia

: 105-45-3
acetoacetic acid methyl ester

: 14205-39-1
methyl 3-aminocrotonate

Conditions

Conditions	Yield
With iron(III) chloride In dichloromethane at 20℃; for 6h;

: 3240-34-4
[bis(acetoxy)iodo]benzene

: 64-19-7
acetic acid

: 14205-39-1
methyl 3-aminocrotonate

: C13H16INO4

Conditions

Conditions	Yield
In 2,2,2-trifluoroethanol at 20℃; for 0.0833333h;	100%

...Expand

: C11H7Cl3O4

: 14205-39-1
methyl 3-aminocrotonate

: dimethyl (S)-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3,4-dicarboxylate

Conditions

Conditions	Yield
With (+)-(R,S)-Fused-BTM; diphenyl-phosphinic acid In tetrahydrofuran at 25℃; for 24h; Schlenk technique; Inert atmosphere; enantioselective reaction;	99%

: 141-97-9
ethyl acetoacetate

: 75-07-0
acetaldehyde

: 14205-39-1
methyl 3-aminocrotonate

: 53632-38-5
2,4,6-Trimethyl-3-ethoxycarbonyl-5-methoxycarbonyl-1,4-dihydropyridine

Conditions

Conditions	Yield
In ethanol at 100℃;	98.2%

...Expand

: 104-15-4
toluene-4-sulfonic acid

: 14205-39-1
methyl 3-aminocrotonate

: 650602-19-0
methyl 3-aminocrotonate p-toluenesulfonate

Conditions

Conditions	Yield
Stage #1: toluene-4-sulfonic acid In toluene for 2h; Heating / reflux; Stage #2: methyl 3-aminocrotonate In toluene at 5 - 20℃; for 1.5h;	98.2%

: 99-61-6
3-nitro-benzaldehyde

: 105-45-3
acetoacetic acid methyl ester

: 14205-39-1
methyl 3-aminocrotonate

: 21881-77-6
m-nifedipine

Conditions

Conditions	Yield
With sodium tosylate In water for 0.3h; Reagent/catalyst; Time; Hantzsch Dihydropyridine Synthesis; Microwave irradiation; Reflux; Green chemistry;	98%
for 7h; microwave irradiation;	59.4%
In ethanol at 90℃; Hantzsch condensation reaction;	20%

...Expand

: 3-[1-Ethoxycarbonyloxy-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid ethyl ester

: 14205-39-1
methyl 3-aminocrotonate

: 3-(3-amino-2-methoxycarbonyl-but-2-enylidene)-2-oxo-2,3-dihydro-indole-1-carboxylic acid ethyl ester

Conditions

Conditions	Yield
In tetrahydrofuran for 2.5h; Heating;	98%

: 79-04-9
chloroacetyl chloride

: 14205-39-1
methyl 3-aminocrotonate

: methyl (Z)-3-amino-2-(2-chloroacetyl)but-2-enoate

Conditions

Conditions	Yield
With pyridine In diethyl ether at -25 - 0℃; for 4.75h;	98%

: C12H9Cl3O4

: 14205-39-1
methyl 3-aminocrotonate

: 4-ethyl 3-methyl (S)-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3,4-dicarboxylate

Conditions

Conditions	Yield
With (+)-(R,S)-Fused-BTM; diphenyl-phosphinic acid In tetrahydrofuran at 25℃; for 24h; Schlenk technique; Inert atmosphere; enantioselective reaction;	98%

: 620-02-0
5-Methylfurfural

: 105-45-3
acetoacetic acid methyl ester

: 14205-39-1
methyl 3-aminocrotonate

: 296266-88-1
1,4-dihydro-2,6-dimethyl-4-(5'-methyl-furan-2'-yl)pyridine-3,5-dicarboxylic acid dimethyl ester

Conditions

Conditions	Yield
With ZnNO3 supported on MCM-41 In ethanol at 20℃; for 2h; Hantzsch Dihydropyridine Synthesis;	97%

...Expand

: 104-87-0
4-methyl-benzaldehyde

: 126-81-8
dimedone

: 14205-39-1
methyl 3-aminocrotonate

: methyl 2,7,7-trimethyl-5-oxo-4-p-tolyl-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

Conditions

Conditions	Yield
With ZnNO3 supported on MCM-41 In ethanol at 20℃; for 1h; Hantzsch Dihydropyridine Synthesis;	96%
With Fe(1+)HO4S(1-)12H2O*H3N In ethanol at 20℃; for 4.5h; Hantzsch reaction;	92%

...Expand

: 105-45-3
acetoacetic acid methyl ester

: 147959-19-1
(4S)-2,2-dimethyl-3-(t-butoxycarbonyl)-4-(formylmethyl)-1,3-oxazolidine

: 14205-39-1
methyl 3-aminocrotonate

: 596828-11-4
(4''S)-4-(3''-tert-butoxycarbonyl-2'',2''-dimethyloxazolidin-4''-ylmethyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester

Conditions

Conditions	Yield
With 4 A molecular sieve In methanol at 90℃; for 24h; Hantzsch cyclocondensation;	95%

...Expand

: 1003-29-8
2-pyrrole aldehyde

: 71-23-8
propan-1-ol

: 5394-63-8
2,2,6-trimethyl-4H-1,3-dioxin-4-one

: 14205-39-1
methyl 3-aminocrotonate

: C17H22N2O4

Conditions

Conditions	Yield
Stage #1: propan-1-ol; 2,2,6-trimethyl-4H-1,3-dioxin-4-one With N,N-dimethyl-formamide In 5,5-dimethyl-1,3-cyclohexadiene at 60 - 143℃; for 8h; Stage #2: 2-pyrrole aldehyde; methyl 3-aminocrotonate In 5,5-dimethyl-1,3-cyclohexadiene at 85 - 320℃; for 6h; Stage #3: With cinchonidine In 5,5-dimethyl-1,3-cyclohexadiene at 80 - 142℃; for 10h; Temperature; Reagent/catalyst;	95%

...Expand

: 100-52-7
benzaldehyde

: 126-81-8
dimedone

: 14205-39-1
methyl 3-aminocrotonate

: methyl 1,4,5,6,7,8-hexahydro-2,7,7-trimethyl-5-oxo-4-phenylquinoline-3-carboxylate

Conditions

Conditions	Yield
With Fe(1+)HO4S(1-)12H2O*H3N In ethanol at 20℃; for 4.5h; Hantzsch reaction;	94%

...Expand

: 141-97-9
ethyl acetoacetate

: 99-61-6
3-nitro-benzaldehyde

: 14205-39-1
methyl 3-aminocrotonate

: 39562-70-4
1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridine-dicarboxylic acid ethyl methyl ester

Conditions

Conditions	Yield
With sodium tosylate In water for 0.4h; Reagent/catalyst; Time; Hantzsch Dihydropyridine Synthesis; Microwave irradiation; Reflux; Green chemistry;	94%
With C21H38N(1+)Mo11O40PV(4-)3H(1+) In ethanol at 78℃; for 8h; Catalytic behavior; Hantzsch Pyridine Synthesis; Green chemistry;	78%
Hantzsch Dihydropyridine Synthesis; Darkness; Reflux;	59%

...Expand

: C10H4Cl3F3O2

: 14205-39-1
methyl 3-aminocrotonate

: methyl (S)-2-methyl-6-oxo-4-(trifluoromethyl)-1,4,5,6-tetrahydropyridine-3-carboxylate

Conditions

Conditions	Yield
With (+)-(R,S)-Fused-BTM; diphenyl-phosphinic acid In tetrahydrofuran at 25℃; for 24h; Schlenk technique; Inert atmosphere; enantioselective reaction;	94%

: 126-81-8
dimedone

: 591-31-1
3-methoxy-benzaldehyde

: 14205-39-1
methyl 3-aminocrotonate

: methyl 1,4,5,6,7,8‐hexahydro‐4‐(3‐methoxyphenyl)‐2,7,7‐trimethyl‐5‐oxoquinoline‐3‐carboxylate

Conditions

Conditions	Yield
With Fe(1+)HO4S(1-)12H2O*H3N In ethanol at 20℃; for 4.5h; Hantzsch reaction;	93%

...Expand

: 3471-13-4
dimedone

: 104-88-1
4-chlorobenzaldehyde

: 14205-39-1
methyl 3-aminocrotonate

: methyl 4‐(4‐chlorophenyl)‐1,4,5,6,7,8‐hexahydro‐2,7,7‐trimethyl‐5‐oxoquinoline‐3‐carboxylate

Conditions

Conditions	Yield
With ammonium acetate In water at 45℃; for 2h; Green chemistry;	93%

...Expand

: 126-81-8
dimedone

: 6630-33-7
ortho-bromobenzaldehyde

: 14205-39-1
methyl 3-aminocrotonate

: 312585-92-5
methyl 4-(2-bromophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

Conditions

Conditions	Yield
With ZnNO3 supported on MCM-41 In ethanol at 20℃; for 2h; Hantzsch Dihydropyridine Synthesis;	93%

...Expand

: 459-45-0
4-fluorobenzenediazonium tetrafluoroborate

: 14205-39-1
methyl 3-aminocrotonate

: methyl 2-(4-fluorophenyl)-5-methyl-2H-1,2,3-triazole-4-carboxylate

Conditions

Conditions	Yield
With caesium carbonate; copper dichloride In acetonitrile at 20℃; for 0.5h;	93%

: C16H14ClNO2S

: 14205-39-1
methyl 3-aminocrotonate

: 1076202-58-8
methyl 4-[2-(2-chlorophenylthiazol)-2-yl]-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

Conditions

Conditions	Yield
In methanol modified Hantzsch synthesis; Reflux; Darkness;	92%

: 555-16-8
4-nitrobenzaldehdye

: 126-81-8
dimedone

: 14205-39-1
methyl 3-aminocrotonate

: 2,7,7-trimethyl-5-oxo-4-(4-nitrophenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid methyl ester

Conditions

Conditions	Yield
With Fe(1+)HO4S(1-)12H2O*H3N In ethanol at 20℃; for 4.5h; Hantzsch reaction;	92%

...Expand

: 3471-13-4
dimedone

: 89-98-5
2-chloro-benzaldehyde

: 14205-39-1
methyl 3-aminocrotonate

: methyl 4-(2‐chlorophenyl)‐1,4,5,6,7,8‐hexahydro‐2,7,7‐trimethyl‐5‐oxoquinoline‐3‐carboxylate

Conditions

Conditions	Yield
With ammonium acetate In water at 45℃; for 2.5h; Green chemistry;	92%

...Expand

: 70-11-1
α-bromoacetophenone

: 14205-39-1
methyl 3-aminocrotonate

: 28168-20-9
2-methyl-5-phenyl-1H-pyrrole-3-carboxylic acid methyl ester

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 130℃; for 0.166667h; Reagent/catalyst; Solvent; Microwave irradiation;	92%

: 126-81-8
dimedone

: 552-89-6
2-nitro-benzaldehyde

: 14205-39-1
methyl 3-aminocrotonate

: 126412-02-0
1,4,5,6,7,8-Hexahydro-2,7,7-trimethyl-4-(2-nitrophenyl)-5-oxo-chinolin-3-methylat

Conditions

Conditions	Yield
With ZnNO3 supported on MCM-41 In ethanol at 20℃; for 2h; Hantzsch Dihydropyridine Synthesis;	92%

...Expand

: 102993-38-4
2-cyanoethyl 2-(3-nitrobenzylidene)-3-oxobutanoate

: 14205-39-1
methyl 3-aminocrotonate

: 75130-24-4
2,6-dimethyl-4-(3-nitrophenyl)-5-methoxycarbonyl-1,4-dihydropyridine-3-carboxylic acid 2-cyanoethyl ester

Conditions

Conditions	Yield
In methanol for 2h; Reflux;	91.1%

: 107-02-8
acrolein

: 14205-39-1
methyl 3-aminocrotonate

: 65719-09-7
methyl 2-methylnicotinate

Conditions

Conditions	Yield
In toluene at 120℃; for 3h; Solvent; Temperature; Sealed tube;	91%
With piperidine; sulfuric acid; nitric acid 1.) ethanol, 24 h, reflux, 2.) water, 10 min, water bath; Yield given. Multistep reaction;

: 845267-78-9
tert-butyl 2,4-dioxopiperidine-1-carboxylate

: 591-31-1
3-methoxy-benzaldehyde

: 14205-39-1
methyl 3-aminocrotonate

: 6-tert-butyl 3-methyl 4-(3-methoxyphenyl)-7,8-dihydro-2-methyl-5-oxo-1,6-naphthy-ridine-3,6(1H,4H,5H)-dicarboxylate

Conditions

Conditions	Yield
at 80℃; for 8h; Ionic liquid; Green chemistry;	91%

...Expand

: 51490-01-8
1-(3,4,5-trimethoxyphenyl)-2-bromoethanone

: 14205-39-1
methyl 3-aminocrotonate

: 1419101-66-8
methyl 2-methyl-5-(3,4,5-trimethoxyphenyl)-1H-pyrrol-3-carboxylate

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 130℃; for 0.233333h; Microwave irradiation;	91%

: 555-16-8
4-nitrobenzaldehdye

: 126-81-8
dimedone

: 14205-39-1
methyl 3-aminocrotonate

A: methyl 2,7,7-trimethyl-4-(4-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

B: 40588-46-3
9-(4-nitrophenyl)-3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8-octahydroxanthene-1,8-dione

Conditions

Conditions	Yield
With C22H25F6N5S; ammonium acetate In dichloromethane at 20℃; for 1h; Reagent/catalyst; Hantzsch Dihydropyridine Synthesis;	A 91% B 3%

...Expand

Methyl 3-aminocrotonate Standards and Recommendations

APPEARANCE of methyl 3-aminocrotonate: yellowish semi-solid
ASSAY: 99.0% min

Methyl 3-aminocrotonate Specification

The 2-Butenoicacid, 3-amino-, methyl ester, with the CAS registry number 14205-39-1 and EINECS registry number 238-056-5, has the systematic name and IUPAC name of methyl 3-aminobut-2-enoate. It is a kind of yellowish-white crystals, and belongs to the product category of API intermediates. It is also hygroscopic, and insoluble in water. And the molecular formula of this chemical is C₅H₉NO₂.

The physical properties of 2-Butenoicacid, 3-amino-, methyl ester are as following: (1)ACD/LogP: -0.14; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.34; (4)ACD/LogD (pH 7.4): -0.14; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 12.64; (8)ACD/KOC (pH 7.4): 19.83; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 29.54 Å²; (13)Index of Refraction: 1.457; (14)Molar Refractivity: 30.42 cm³; (15)Molar Volume: 111.6 cm³; (16)Polarizability: 12.06×10^-24cm³; (17)Surface Tension: 33.3 dyne/cm; (18)Density: 1.031 g/cm³; (19)Flash Point: 65.3 °C; (20)Enthalpy of Vaporization: 43.03 kJ/mol; (21)Boiling Point: 194.1 °C at 760 mmHg; (22)Vapour Pressure: 0.449 mmHg at 25°C.

Uses of 2-Butenoicacid, 3-amino-, methyl ester: It can react with pyridine-2-carbaldehyde and acetoacetic acid methyl ester to produce 2',6'-dimethyl-1',4'-dihydro-[2,4']bipyridinyl-3',5'-dicarboxylic acid dimethyl ester. This reaction will need solvent ethanol. The reaction time is 16 hours with heating, and the yield is about 77%.

2-Butenoicacid, 3-amino-, methyl ester can react with pyridine-2-carbaldehyde and acetoacetic acid methyl ester to produce 2',6'-dimethyl-1',4'-dihydro-[2,4']bipyridinyl-3',5'-dicarboxylic acid dimethyl ester

You should be cautious while dealing with this chemical. It irritates eyes, respiratory system and skin, and it is also harmful if swallowed. Therefore, you had better take the following instructions: Wear suitable gloves and eye/face protection, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC)C=C(N)C
(2)InChI: InChI=1/C5H9NO2/c1-4(6)3-5(7)8-2/h3H,6H2,1-2H3
(3)InChIKey: XKORCTIIRYKLLG-UHFFFAOYAV

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LC50	inhalation	> 23mg/m³/4H (23mg/m³)		International Journal of Toxicology. Vol. 16(Suppl,
rat	LD50	oral	1760mg/kg (1760mg/kg)	BEHAVIORAL: GENERAL ANESTHETIC LUNGS, THORAX, OR RESPIRATION: DYSPNEA GASTROINTESTINAL: OTHER CHANGES	International Journal of Toxicology. Vol. 16(Suppl,

Product Name

Methyl 3-aminocrotonate

Synthetic route

Methyl 3-aminocrotonate Standards and Recommendations

Methyl 3-aminocrotonate Specification

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