| Identification | More | [Name]
Diethyl 1,1-cyclopropanedicarboxylate | [CAS]
1559-02-0 | [Synonyms]
1,1-CYCLOPROPANEDICARBOXYLIC ACID
1,1-CYCLOPROPANEDICARBOXYLIC ACID DIETHYL ESTER
CYCLOPROPANE-1,1-DICARBOXYLIC ACID
CYCLOPROPANE-1,1-DICARBOXYLIC ACID DIETHYL ESTER
DIETHYL 1,1-CYCLOPROPANEDICARBOXYLATE
DIETHYL CYCLOPROPANE-1,1-DICARBOXYLATE
RARECHEM AL BO 0836
DIETHYL 1,1-CYCLOPROPANEDICARBOXYLATE, 9 7%
DiethyldifluoroMalonate96%
DIETHYL 1,1-CYCLOPROPANE-DICARBONYLATE
1,1-Cyclopropanedicarboxylic acid, 1,1-diethyl ester
1,1-Bis(ethoxycarbonyl)cyclopropane
Ethyl 1,1-cyclopropanedicarboxylate | [EINECS(EC#)]
209-917-2 | [Molecular Formula]
C9H14O4 | [MDL Number]
MFCD00013727 | [Molecular Weight]
186.21 | [MOL File]
1559-02-0.mol |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S24/25:Avoid contact with skin and eyes .
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) . | [RIDADR ]
UN 3261 8/PG 2
| [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29172090 |
| Hazard Information | Back Directory | [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 |
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