Methyl 4,4,4-trifluoroacetoacetate

CAS No. 83643-84-9
Cat. No. CS-0121468
Purity≥98%
MDL No.MFCD00041004

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Methyl 4,4,4-trifluoroacetoacetate|CS-0121468

Structure of 83643-84-9

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Description

Methyl 4,4,4-trifluoroacetoacetate features a trifluoromethyl group flanking a β-keto ester moiety, enabling facile enolization and nucleophilic reactivity. This electron-deficient acetyl unit integrates readily into synthetic sequences requiring stabilized enolates or fluorinated building blocks. The compound exhibits enhanced stability under standard conditions and serves as a key intermediate in the construction of fluorinated heterocycles and bioactive molecules.

Application

Methyl 4,4,4-trifluoroacetoacetate serves as a versatile building block in synthetic organic chemistry, enabling the efficient construction of fluorinated heterocycles and carbonyl-containing scaffolds. Its electron-deficient β-keto ester functionality facilitates aldol condensations, Michael additions, and cyclizations under mild conditions. The trifluoromethyl group enhances metabolic stability and modulates lipophilicity, making it valuable for medicinal chemistry applications. Bench-stable and readily purified by distillation or chromatography, it functions reliably in multi-step syntheses.

General Information

CAS No. 83643-84-9
Cat. No. CS-0121468
Purity ≥98%
MDL No. MFCD00041004
Storage RT, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₅H₅F₃O₃
Molecular Weight None
Synonym(s) Methyl 4,4,4-trifluoro-3-oxobutanoate
SMILES O=C(C(F)(F)F)CC(OC)=O

Computational Chemistry Data

TPSA 43.37
LogP 0.6809
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 2

Safety Information

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GHS Pictogram :	GHS No : GHS02,GHS07
Signal Word : Danger	UN#: 3272
Class : 3	Packing Group : Ⅲ
Hazard Statements : H226-H315-H319
Precautionary Statements : P210-P233-P240-P241-P243-P264-P280-P302+P352-P362-P501

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Other Classifications

Building Blocks Functional Group Ketone

Building Blocks Functional Group Ester

Building Blocks Skeleton Fatty chain compounds

Key Words

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Methyl 4,4,4-trifluoroacetoacetate

CAS No. 83643-84-9

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