DIETHYL (BOC-AMINO)MALONATE

DIETHYL (BOC-AMINO)MALONATE Property

Boiling point:

218 °C (lit.)

Density 

1.079 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.438(lit.)

Flash point:

>230 °F

storage temp. 

Sealed in dry,2-8°C

solubility 

Chloroform, Ethyl Acetate, Methanol

form 

Oil

pka

9.97±0.46(Predicted)

color 

Colourless

BRN 

5055305

Stability:

Below-40C

InChI

InChI=1S/C12H21NO6/c1-6-17-9(14)8(10(15)18-7-2)13-11(16)19-12(3,4)5/h8H,6-7H2,1-5H3,(H,13,16)

InChIKey

ULRLHEXGRUWQLQ-UHFFFAOYSA-N

SMILES

C(OCC)(=O)C(NC(OC(C)(C)C)=O)C(OCC)=O

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2917198090

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.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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

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

DIETHYL (BOC-AMINO)MALONATE Chemical Properties,Usage,Production

Chemical Properties

Colourless Oil

Uses

Diethyl (Boc-amino)malonate (cas# 102831-44-7) is a compound useful in organic synthesis.

Synthesis

Diethyl aminomalonate (17.5 g, 0.1 mol) and triethylamine (20 g, 0.2 mol) were dissolved in 250 mL of dichloromethane in a three-necked flask under ice bath conditions. Subsequently, di-tert-butyl dicarbonate (26 g, 0.12 mol) was slowly added. The reaction mixture was gradually brought to room temperature and stirred continuously at this temperature and the progress of the reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was extracted with dichloromethane (200 mL × 3). The organic phases were combined, dried with anhydrous magnesium sulfate, and concentrated to give 27 g of the colorless oily product diethyl 2-Boc-aminomalonate in 98% yield.

References

[1] Journal of Organic Chemistry, 1986, vol. 51, # 15, p. 2910 - 2913
[2] Patent: CN106946724, 2017, A. Location in patent: Paragraph 0027; 0028; 0034; 0040
[3] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 12, p. 3973 - 3979
[4] Journal of Medicinal Chemistry, 2009, vol. 52, # 9, p. 2909 - 2922
[5] Patent: US2003/65176, 2003, A1