ETHYL 3-AMINOCROTONATE Chemical Properties

Melting point:

33-35 °C (lit.)

Boiling point:

210-215 °C (lit.)

Density 

1.022 g/mL at 25 °C (lit.)

refractive index 

1.4990

Flash point:

207 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

5.32±0.70(Predicted)

Appearance

Off-white to light yellow <33°C Solid,>35°C Liquid

Water Solubility 

Soluble in water (26 g/L) (25°C).

Sensitive 

Air & Moisture Sensitive & Hygroscopic

BRN 

471284

InChI

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

InChIKey

YPMPTULBFPFSEQ-PLNGDYQASA-N

SMILES

C(OCC)(=O)/C=C(\N)/C

LogP

0.390 (est)

CAS DataBase Reference

626-34-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk 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

HS Code 

29224999

ETHYL 3-AMINOCROTONATE Usage And Synthesis

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.

Synthesis

Example 9: Preparation of ethyl 3-aminocrotonate was carried out using continuous flow experiments. The experiments were carried out in a 1.58 mm OD SS316 tubular reactor. By using a simple T-mixer and a 1 m long reactor, ethyl acetoacetate was mixed with ammonia (25% solution) in a ratio of 1:3 with a residence time of 22 min. The yield of the product ethyl 3-aminocrotonate was 94% at 50 °C.

References

[1] Comptes Rendus Chimie, 2011, vol. 14, # 5, p. 511 - 515
[2] Patent: WO2012/147103, 2012, A2. Location in patent: Page/Page column 7
[3] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1986, vol. 35, p. 1438 - 1442
[4] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1986, # 7, p. 1586 - 1592
[5] European Journal of Medicinal Chemistry, 2018, vol. 155, p. 946 - 960

ETHYL 3-AMINOCROTONATE(626-34-6)Related Product Information

• Isopropyl 3-aminocrotonate
• Methyl 3-aminocrotonate
• 3-Aminocrotononitrile
• Ethyl 2-amino-1-cyclopentene-1-carboxylate
• Ethyl 3-amino-4,4,4-trifluorocrotonate
• tert-Butyl cyanoacetate
• Ethyl crotonate
• 3-Amino-2-butenoic acid ethyl ester
• Crotonic acid
• Crotonic acid
• 2,2-DIMETHYL-5-(2-HEXAHYDROAZEPINYLIDENE)-1,3-DIOXAN-4,6-DIONE
• 2,2-DIMETHYL-5-(2-TETRAHYDROPYRROLYLIDENE)-1,3-DIOXANE-4,6-DIONE
• 5-[1-AMINO-2-(4-CHLOROPHENYL)ETHYLIDENE]-2,2-DIMETHYL-1,3-DIOXANE-4,6-DIONE
• ETHYL 2-(3-OXO-2-PIPERAZINYLIDENE)ACETATE
• 2,2-Dimethyl-5-(2-piperidinylidene)-1,3-dioxane-4,6-dione
• thiodiethane-1,2-diyl bis(3-aminobut-2-enoate)
• 3-MORPHOLIN-4-YL-BUT-2-ENOIC ACID ETHYL ESTER
• AURORA KA-3294