Diethyl iminodiacetate Chemical Properties

Boiling point:

208 °C (lit.)

Density 

1.056 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.435(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

4.92±0.20(Predicted)

form 

Viscous Liquid

color 

Clear light yellow to yellow

Water Solubility 

Moderately soluble in water.

InChI

InChI=1S/C8H15NO4/c1-3-12-7(10)5-9-6-8(11)13-4-2/h9H,3-6H2,1-2H3

InChIKey

LJDNMOCAQVXVKY-UHFFFAOYSA-N

SMILES

C(OCC)(=O)CNCC(OCC)=O

CAS DataBase Reference

6290-05-7(CAS DataBase Reference)

EPA Substance Registry System

Glycine, N-(2-ethoxy-2-oxoethyl)-, ethyl ester (6290-05-7)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

RIDADR 

1993

WGK Germany 

3

TSCA 

Yes

HazardClass 

3.2

PackingGroup 

III

HS Code 

29252900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Diethyl iminodiacetate Usage And Synthesis

Chemical Properties

clear colorless to slightly yellow liquid

Uses

It is mainly used for the manufacture of N-(Phosphonomethyl) iminodiacetic acid and glyphosate. Used as raw material for ion exchange resin; for rubbers, electroplating and food additives.

Synthesis

Ethanol was placed in a reaction flask at 0°C and stirred, thionyl chloride was added slowly and dropwise, and stirring was maintained until the temperature of the reaction mixture was raised to room temperature (about 30 min). Subsequently, iminodiacetic acid (3.33 g, 25 mmol) was added to the reaction system and the temperature of the reaction was raised to reflux and the reaction was continued overnight. Upon completion of the reaction, the mixture was cooled to room temperature and the reaction was quenched with saturated sodium bicarbonate solution (20 mL) and the pH was adjusted to neutral by adding solid sodium bicarbonate. After distillation under reduced pressure to remove most of the ethanol, the mixture was extracted three times with ethyl acetate (3 x 20 mL). The organic phases were combined, washed once with brine, dried through magnesium sulfate and filtered. Finally, the target product diethyl iminodiacetate (4.15 g, 88% yield) was obtained by distillation under reduced pressure (recovery of organic solvent).

References

[1] Journal of Organic Chemistry, 1988, vol. 53, # 9, p. 1966 - 1969
[2] Journal of the American Chemical Society, 2000, vol. 122, # 26, p. 6169 - 6174
[3] Patent: CN105949080, 2016, A. Location in patent: Paragraph 0018
[4] Tetrahedron Letters, 2008, vol. 49, # 36, p. 5293 - 5296
[5] Helvetica Chimica Acta, 1993, vol. 76, # 2, p. 893 - 899

Diethyl iminodiacetate(6290-05-7)Related Product Information

• Iminodiacetonitrile
• Iminodiacetic acid
• Diethyl malonate
• Glycine
• Ethyl bromoacetate
• Ethyl 3-aminopropanoate hydrochloride
• Ethyl bromodifluoroacetate
• Ethyl phenylacetate
• IMINODIACETIC ACID DISODIUM SALT
• IMINODIACETIC ACID DISODIUM SALT HYDRATE
• Ethyl chloroacetate
• Ethyl acetate
• Diethyl oxalacetate
• DI-TERT-BUTYL IMINODIACETATE
• Tetrasodium Iminidisuccinate
• TETRAETHYL METHYLENEDIPHOSPHONATE
• Di-tert-butyl iminodicarboxylate
• DIETHYL IMINODIACETATE