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Methyl 3-aminocrotonate

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Name

Methyl 3-aminocrotonate

EINECS 238-056-5
CAS No. 14205-39-1 Density 1.031 g/cm3
PSA 52.32000 LogP 0.72220
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 N/A Appearance yellowish-white crystals
Safety 37/39-26 Risk Codes 22-36/37/38
Molecular Structure Molecular Structure of 14205-39-1 (Methyl 3-aminocrotonate) Hazard Symbols HarmfulXn
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;

Article Data 42

Methyl 3-aminocrotonate Synthetic route

105-45-3

acetoacetic acid methyl ester

14205-39-1

methyl 3-aminocrotonate

Conditions
ConditionsYield
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
ConditionsYield
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
6372-01-6

(E)-methyl 3-chloro-2-butenoate

14205-39-1

methyl 3-aminocrotonate

Conditions
ConditionsYield
With ammonia at 100℃;
105-45-3

acetoacetic acid methyl ester

A

5977-14-0

acetoacetamido

B

14205-39-1

methyl 3-aminocrotonate

Conditions
ConditionsYield
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
ConditionsYield
With ammonia
7664-41-7

ammonia

105-45-3

acetoacetic acid methyl ester

14205-39-1

methyl 3-aminocrotonate

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

C11H7Cl3O4

14205-39-1

methyl 3-aminocrotonate

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

Conditions
ConditionsYield
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
ConditionsYield
In ethanol at 100℃;98.2%
104-15-4

toluene-4-sulfonic acid

14205-39-1

methyl 3-aminocrotonate

650602-19-0

methyl 3-aminocrotonate p-toluenesulfonate

Conditions
ConditionsYield
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%

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,

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