Diethyl 1,1-cyclobutanedicarboxylate Chemical Properties

Boiling point:

104-105 °C12 mm Hg(lit.)

Density 

1.05 g/mL at 20 °C(lit.)

refractive index 

1.4360

Flash point:

89°C

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform, Dichloromethane, Methanol,

form 

Oil

Specific Gravity

1.05

color 

Colourless

Water Solubility 

Insoluble in water.

BRN 

2050195

InChI

InChI=1S/C10H16O4/c1-3-13-8(11)10(6-5-7-10)9(12)14-4-2/h3-7H2,1-2H3

InChIKey

JPNJEJSZSMXWSV-UHFFFAOYSA-N

SMILES

C1(CCC1)(C(=O)OCC)C(=O)OCC

CAS DataBase Reference

3779-29-1(CAS DataBase Reference)

NIST Chemistry Reference

Diethyl 1,1-cyclobutanedicarboxylate(3779-29-1)

EPA Substance Registry System

1,1-Cyclobutanedicarboxylic acid, diethyl ester (3779-29-1)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

23-24/25

WGK Germany 

3

TSCA 

Yes

HS Code 

38220090

MSDS

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

Diethyl 1,1-cyclobutanedicarboxylate Usage And Synthesis

Chemical Properties

Colourless Oil

Uses

Diethyl 1,1-cyclobutanedicarboxylate is used as a pharmaceutical intermediate. Used as intermediate in the production of Carboplatin.

Uses

Diethyl cyclobutane-1,1-dicarboxylate may be used in chemical synthesis studies.

Preparation

The preparation of diethyl 1,1-cyclobutanedicarboxylate is as follows:The major product is tetraethy1 1,1,5,5-pentanetetra-carboxylate II with diethyl malonate. To eliminate this side reaction, II was independently prepared by the addition of hydrogen bromide to diethyl allylmalonate (I) and then cyclized to II by treatment with sodium ethylate. The over-all yield from I is about 50%.

Synthesis

GENERAL METHOD: Diethyl malonate (2.53 mL, 17 mmol), 1,3-dibromopropane (22 mmol), potassium carbonate (K2CO3, 5.7 g, 42 mmol) and tetrabutylammonium bromide (TBAB, 0.27 g, 0.08 mmol) were added to dry N,N-dimethylformamide (DMF). The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the solvent was removed by rotary evaporator and the residue was extracted three times with ethyl acetate (100 mL). The organic layers were combined, washed with water and then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated to give diethyl cyclobutyl-1,1-dicarboxylate as a colorless oil (89% yield).

References

[1] Molecules, 2016, vol. 21, # 5,
[2] Journal of Organic Chemistry, 1993, vol. 58, # 27, p. 7709 - 7717
[3] Journal of Fluorine Chemistry, 2000, vol. 102, # 1-2, p. 141 - 146
[4] Journal of Organic Chemistry, 1949, vol. 14, p. 1036
[5] Journal of the Chemical Society, 1887, vol. 51, p. 2

Diethyl 1,1-cyclobutanedicarboxylate (3779-29-1)Related Product Information

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