Triethyl 1,1,2-ethanetricarboxylate Chemical Properties

Boiling point:

99 °C/0.5 mmHg (lit.)

Density 

1.074 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.429(lit.)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform, Ethyl Acetate

form 

Liquid

pka

11.78±0.59(Predicted)

Specific Gravity

1.074

color 

Clear colorless

BRN 

1796294

Dielectric constant

6.5（19.0℃）

InChI

InChI=1S/C11H18O6/c1-4-15-9(12)7-8(10(13)16-5-2)11(14)17-6-3/h8H,4-7H2,1-3H3

InChIKey

TVWZLLYAJDSSCJ-UHFFFAOYSA-N

SMILES

C(C(=O)OCC)(C(=O)OCC)CC(=O)OCC

CAS DataBase Reference

7459-46-3(CAS DataBase Reference)

NIST Chemistry Reference

1,1,2-Ethanetricarboxylic acid, triethyl ester(7459-46-3)

Safety Information

Safety Statements 

23-24/25

WGK Germany 

3

HS Code 

29420000

MSDS

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

Triethyl 1,1,2-ethanetricarboxylate Usage And Synthesis

Description

Triethyl 1,1,2-ethanetricarboxylate is a carboxylic acid ester compound that can be used in nanomaterials, pharmaceutical intermediates, organic synthesis and other fields.

Chemical Properties

CLEAR COLOURLESS LIQUID

Uses

1,1,2-Ethanetricarboxylic Acid 1,1,2-Triethyl Ester is a useful synthetic intermediate. It can be used to prepare Isobutylsuccinic Acid (I780660) which was used to synthesize succinimide derivatives as inhibitors of human leukocyte elastase, cathepsin G and proteinase 3.

Synthesis

Step a): Sodium metal (23 g, 1 mole) was slowly added to anhydrous ethanol (500 mL) under stirring conditions until completely dissolved. Subsequently, diethyl malonate (160 g, 1 mole) was added dropwise over 30 min. After cooling the reaction mixture to 15°C, ethyl chloroacetate (117 g, 0.095 mol) was added dropwise over the same time. After the dropwise addition, the reaction mixture was refluxed for 6 hours. After completion of the reaction, the mixture was poured into 2 liters of water and the organic phase was extracted with dichloromethane (500 mL each time, three times). The organic extracts were combined, dried with anhydrous sodium sulfate, filtered and the solvent was evaporated to give an oily crude product. Finally, purification by vacuum distillation afforded triethyl ethyl-1,1,2-tricarboxylate (220 g, 89% yield).

References

[1] Patent: WO2013/29767, 2013, A1. Location in patent: Page/Page column 16; 17
[2] Patent: CN105566111, 2016, A. Location in patent: Paragraph 0029-30
[3] Liebigs Annalen der Chemie, 1983, # 1, p. 112 - 136
[4] Patent: WO2012/92880, 2012, A1. Location in patent: Page/Page column 45-46
[5] Justus Liebigs Annalen der Chemie, 1882, vol. 214, p. 38

Triethyl 1,1,2-ethanetricarboxylate(7459-46-3)Related Product Information

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