Isopropyl 3-aminocrotonate Chemical Properties

Melting point:

19-23°C

Boiling point:

80°C/1mmHg(lit.)

Density 

0.987±0.06 g/cm3(Predicted)

refractive index 

1.4870 to 1.4910

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

Chloroform, Ethyl Acetate, Methanol

form 

Colourless Liquid

pka

5.36±0.70(Predicted)

color 

Colorless to Light yellow

InChI

InChI=1S/C7H13NO2/c1-5(2)10-7(9)4-6(3)8/h4-5H,8H2,1-3H3

InChIKey

YCKAGGHNUHZKCL-UHFFFAOYSA-N

SMILES

C(OC(C)C)(=O)C=C(N)C

CAS DataBase Reference

14205-46-0(CAS DataBase Reference)

Safety Information

RTECS 

EM9095000

HazardClass 

IRRITANT

HS Code 

2922498590

Isopropyl 3-aminocrotonate Usage And Synthesis

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.

Synthesis

The general procedure for the synthesis of isopropyl 3-amino-2-butenoate from isopropyl acetoacetate was as follows: 2.0 g (~20.83 mmol) of isopropyl acetoacetate was accurately weighed and dissolved in 15 mL of anhydrous ethanol. Subsequently, 1.6 g of ammonium acetate was added and the reaction mixture was heated to reflux at 90°C in an oil bath. The reaction progress was monitored by thin layer chromatography (TLC). After 24 hours of reaction, the heating was stopped and the reaction mixture was evaporated to dryness at low temperature. Finally, the reaction solution was distilled under reduced pressure to afford the target compound isopropyl 3-amino-2-butenoate (compound Sf) in 100% yield.

References

[1] Patent: CN102464608, 2016, B. Location in patent: Paragraph 0153; 0154
[2] Patent: CN108101798, 2018, A. Location in patent: Paragraph 0022; 0024; 0026; 0028; 0030-0032; 0034; 0036
[3] Patent: CN105461691, 2016, A. Location in patent: Paragraph 0016
[4] Chemical and Pharmaceutical Bulletin, 1979, vol. 27, # 6, p. 1426 - 1440
[5] Chemical and Pharmaceutical Bulletin, 1989, vol. 37, # 8, p. 2117 - 2121

Isopropyl 3-aminocrotonate(14205-46-0)Related Product Information

• Dimethyl succinate
• Tris(trimethylsilyl)phosphate
• Methyl acrylate
• Crotonic acid
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• Diisopropyl malonate
• 2,2-Dimethyl-1,3-dioxane-4,6-dione
• Methyl 3-aminocrotonate
• ISOPROPYL LAURATE
• 3-Aminocrotononitrile
• Isopropyl alcohol
• BUTYL OLEATE
• Isopropyl palmitate
• 4-Benzofurazancarboxaldehyde
• 4-METHYL-BENZO(1,2,5)OXADIAZOLE
• 5-(BROMOMETHYL)-2,1,3-BENZOXADIAZOLE
• ETHYL 3-AMINOCROTONATE
• 4-Methylbenzofurazan 3-oxid