METHYL 3-METHYLAMINOCROTONATE

METHYL 3-METHYLAMINOCROTONATE Property

Melting point:

62-68 °C

Boiling point:

187.5±23.0 °C(Predicted)

Density 

0.969±0.06 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

5.73±0.70(Predicted)

Appearance

White to off-white Solid

Water Solubility 

Soluble in water at (54 g/L) (25°C), Calc.

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26

HS Code 

29224985

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

METHYL 3-METHYLAMINOCROTONATE Chemical Properties,Usage,Production

Chemical Properties

white crystalline powder

Uses

It is employed as an intermediate in the synthesis of an analogue to amlodipine, bearing a short amino polyethylene glycol chain.

Synthesis

1.2 g of silica gel was added to 11.6 g (100 mmol, 1 eq.) of methyl acetoacetate. To this was added 9.25 g (120 mmol, 1.2 eq.) of methylamine solution (40% aqueous solution) and the mixture was stirred overnight. The reaction mixture was extracted with dichloromethane (DCM), dried with anhydrous magnesium sulfate (MgSO?), filtered and the solvent was evaporated to give the yellow oily product methyl 3-(methylamino)but-2-enoate in 12.21 g, 95% yield.1H-NMR (CDCl?, δ/ppm): 8.47 (s, NH, 1H), 4.47 (s, CH, 1H). 3.61 (s, OCH?, 3H), 2.91 (d, NHCH?, J = 5.22 Hz, 3H), 1.92 (s, CH?, 3H).

References

[1] RSC Advances, 2015, vol. 5, # 49, p. 39193 - 39204
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 8, p. 1944 - 1947
[3] Patent: WO2013/25733, 2013, A1. Location in patent: Paragraph 0402
[4] Chemical and Pharmaceutical Bulletin, 1987, vol. 35, # 12, p. 4819 - 4828
[5] Bulletin de la Societe Chimique de France, 1923, vol. <4> 33, p. 1108