Diethyl 1,1-cyclopropanedicarboxylate Chemical Properties

Melting point:

134-136 °C(lit.)

Boiling point:

94-96 °C/10 mmHg (lit.)

Density 

1.055 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.433(lit.)

Flash point:

188 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

Acetone (Slightly), Chlorform (Slightly), Methanol (Slightly)

form 

Liquid

color 

Clear colorless

BRN 

2049509

CAS DataBase Reference

1559-02-0(CAS DataBase Reference)

NIST Chemistry Reference

Diethyl 1,1-cyclopropanedicarboxylate(1559-02-0)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25-23

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29172090

MSDS

• Language:English Provider:Diethyl 1,1-cyclopropanedicarboxylate
• Language:English Provider:SigmaAldrich
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Diethyl 1,1-cyclopropanedicarboxylate Usage And Synthesis

Chemical Properties

clear colorless liquid

Uses

Diethyl 1,1-Cyclopropanedicarboxylate (cas# 1559-02-0) is a compound useful in organic synthesis.

Synthesis Reference(s)

Synthesis, p. 690, 1980 DOI: 10.1055/s-1980-29171

General Description

Diethyl cyclopropane-1,1-dicarboxylate participates in ring-opening addition reactions with various nucleophilic reagents.

Synthesis

Step 1: Diethyl malonate (300 g, 1.87 mol) and 1,2-dibromoethane (634.5 g, 3.38 mol) were dissolved in DMSO (1.5 L) in a 5 L four-necked round bottom flask. To this solution was added K2CO3 (1020 g, 7.39 mol) and Bu4NBr (6.4 g, 19 mmol). The reaction mixture was stirred at room temperature for 48 hours. After completion of the reaction, the reaction was quenched by adding 2 L of water and extracted with EtOAc (1.5 L, 3 times). The organic phases were combined, dried with Na2SO4 and concentrated under reduced pressure. The residue was distilled under vacuum at 5-10 mmHg at 64-65°C to give diethyl cyclopropane-1,1-dicarboxylate 400 g (90% yield) as an oil.

Purification Methods

If it is free from OH bands in the IR, then fractionally distil the ester and redistil the middle fraction. Otherwise shake it with aqueous NaHCO3, dry it (MgSO4), filter and distil as before or re-esterify it. [As synthon see Danishefsky Acc Chem Res 12 66 1979, Beilstein 9 I 314, 9 II 512, 9 III 3595, 9 IV 2786.]

References

[1] Tetrahedron, 2010, vol. 66, # 51, p. 9733 - 9737
[2] Tetrahedron Letters, 2005, vol. 46, # 4, p. 635 - 638
[3] Journal of Fluorine Chemistry, 2000, vol. 102, # 1-2, p. 141 - 146
[4] Mendeleev Communications, 2014, vol. 24, # 6, p. 345 - 345
[5] Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 474 - 480

Diethyl 1,1-cyclopropanedicarboxylate(1559-02-0)Related Product Information

• Diethyl malonate
• 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
• Diethyl sulfate
• Diethyl phosphite
• Diethyl carbonate
• Diethyl oxalate
• Diethyl 1,3-acetonedicarboxylate
• Mefenpyr-diethyl
• Diethyl phthalate
• Cyclopropyl methyl ketone
• Ethylene glycol diethyl ether
• Celiprolol
• n-propyl dioxepene
• 1,1-Cyclopropanedicarboxylic acid
• Cyclopropane
• Diethyl ether
• DIETHYL 2-PHENYL-1,1-CYCLOPROPANEDICARBOXYLATE
• 2-VINYLCYCLOPROPANE-1,1-DICARBOXYLIC ACID DIETHYL ESTER