Ethyl 4-cyclopropyl-2,4-dioxobutanoate

Name: Ethyl 4-cyclopropyl-2,4-dioxobutanoate
Brand: ChemScene
Availability: InStock
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CAS No. 21080-80-8
Cat. No. CS-0144059
Purity≥98%
MDL No.MFCD09052462

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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Ethyl 4-cyclopropyl-2,4-dioxobutanoate|CS-0144059

Structure of 21080-80-8

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General Information

CAS No. 21080-80-8
Cat. No. CS-0144059
Purity ≥98%
MDL No. MFCD09052462
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₁₂O₄
Molecular Weight 184.19
Synonym(s) thyl 4-cyclopropyl-2,4-dioxobutanoate
SMILES O=C(OCC)C(CC(C1CC1)=O)=O

Description

Ethyl 4-cyclopropyl-2,4-dioxobutanoate features a reactive 1,3-dicarbonyl scaffold flanked by a cyclopropyl substituent, enabling efficient enolization and nucleophilic addition. This bench-stable reagent integrates readily into multicomponent condensations and heterocycle syntheses, delivering high functional group tolerance under standard conditions.

Application

Ethyl 4-cyclopropyl-2,4-dioxobutanoate serves as a versatile synthon in heterocyclic synthesis, enabling efficient access to substituted pyrrolidines and other nitrogen-containing scaffolds via Michael addition or cyclocondensation reactions. Its α,β-unsaturated β-ketoester functionality exhibits excellent functional group tolerance and bench stability, facilitating straightforward purification and integration into multi-step sequences. The cyclopropyl substituent imparts distinct stereochemical control in cyclization processes, enhancing its utility in medicinal chemistry lead optimization.

Synthesis

Route1
- 765-43-5
- 95-92-1
- ~92%
- In-stock
  
  21080-80-8
References
- GRUeNENTHAL GMBH; FRANK, Robert; CHRISTOPH, Thomas; FRORMANN, Sven Patent: WO2012/62463 A1, 2012 ; Location in patent: Page/Page column 87-88 ;
Route2
- 95-92-1
- ~%
- In-stock
  
  21080-80-8
References
- Tschelinzew Zhurnal Obshchei Khimii, 1944 , vol. 14, p. 1070 Chem.Abstr., 1947 , p. 101

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 60.44
LogP 0.4878
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 5

Other Classifications

Building Blocks Functional Group Ketone

Building Blocks Functional Group Ester

Building Blocks Skeleton Fatty ring compounds Cyclopropane compounds

Key Words

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Ethyl 4-cyclopropyl-2,4-dioxobutanoate

CAS No. 21080-80-8

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