METHYL CARBAMOYLACETATE

METHYL CARBAMOYLACETATE Property

Melting point:

39-44 °C

Boiling point:

263.7±23.0 °C(Predicted)

Density 

1.184±0.06 g/cm3(Predicted)

storage temp. 

Store at room temperature

pka

13.51±0.46(Predicted)

form 

solid

Appearance

White to off-white Solid

BRN 

2237801

InChI

InChI=1S/C4H7NO3/c1-8-4(7)2-3(5)6/h2H2,1H3,(H2,5,6)

InChIKey

LSNSJCKGQREPDW-UHFFFAOYSA-N

SMILES

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

Safety

Safety Statements 

22-24/25

WGK Germany 

3

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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.

METHYL CARBAMOYLACETATE Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of methylmalonamide from methyl 3-aminopropionate hydrochloride and diethyl chlorophosphate is as follows: Example 10: Synthesis of 2-methoxycarbonyl ethylamides of monoacetic acid A 1. Monic acid A (1.72 g; 5 mM) was dissolved in THF (40 ml). 2. Triethylamine (0.7 ml; 5 mM) and diethyl chlorophosphate (0.85 g; 5 mM) were added and the reaction was stirred under argon protection for 3 hours. 3. The resulting triethylamine hydrochloride precipitate was removed by filtration. 4. To the filtrate, aqueous THF solution (50%; 40 ml) of β-alanine methyl ester hydrochloride (0.7 g; 5 mM) and triethylamine (0.7 ml) were added and the reaction was stirred at room temperature overnight. 5. After completion of the reaction, the reaction solution was evaporated to dryness. 6. The residue was dissolved in water (20 ml), washed with saturated brine and extracted with ethyl acetate (5 x 40 ml). 7. The ethyl acetate extracts were combined, dried with anhydrous MgSO4 and evaporated to dryness to give an oil. 8. Purification by silica gel column chromatography (Type 60, 30 g) gave the target product as an oil (0.335 g; 16% yield). The characterization data of the product were as follows: νmax (CDCl3) 3420, 3000, 1730, 1665, 1635 cm-1; λmax (EtOH) 222 nm (εm 14,790). δH (CDCl3) 6.47 (1H, t, NH), 5.65 (1H, s, C2-H), 3.67 (3H, s, -CO2CH3), 2.11 (3H, s, C15-CH3), 1.20 (3H, d, C14-CH3), 0.91 (3H, d, C17-CH3). δC (CDCl3) 173.0 (C1'), 167.6 (C1), 151.3 (C3), 120.0 (C2), 75.1 (C5), 70.8 (C13), 70.5 (C7), 69.0 (C6), 65.4 (C16), 60.9 (C11), 55.7 (C10), 51.8 (OMe), 42.7 (C4, C12), 39.8 (C8), 34.9 (C3'), 34.0 (C2'), 31.8 (C9), 20.7 (C7), 18.8 (C15), 12.5 (C17).

References

[1] Patent: US4200635, 1980, A