Fluorophenyl)carbamoyl)cyclopropanecarboxylic acid

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Cat Number

INT849217487

CAS Number

849217-48-7

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Product Detail Description Customer Q&A

CAS Number

849217-48-7

EINECS

1592732-453-0

Storage

Room temperature

Synonyms

((4-fluorophenyl)carbamoyl)cyclopropane carboxylic acid

Molecular Formula

C11H10FNO3

Molecular Weight

223.2

Smiles

C1(C(NC2=CC=C(F)C=C2)=O)(C(O)=O)CC1

Appearance

White to off-white powder

Melting Point

173-177℃

Boiling Point

475.2℃

Relative Density

1.52

pKa

3.48

General Description

(Fluorophenyl)carbamoyl)cyclopropanecarboxylic acid is a cyclopropane-bearing compound featuring both a carboxylic acid and a fluorophenylcarbamoyl substituent on the cyclopropane ring. The cyclopropane ring's high ring strain (~27 kcal/mol) confers unique chemical reactivity and metabolic stability, serving as a metabolically stable bioisostere for saturated carbocycles. The amide bond and carboxylic acid provide multiple handles for further functionalization in pharmaceutical synthesis.

Mechanism of Action

(Fluorophenyl)carbamoyl)cyclopropanecarboxylic acid functions as a constrained amino acid-like building block in pharmaceutical synthesis. The cyclopropane ring constrains the spatial arrangement of the substituents, which can improve target selectivity and reduce off-target binding. The amide bond is metabolically stable (non-hydrolyzable), and the carboxylic acid can be converted to esters, amides, or other derivatives.

Application

(Fluorophenyl)carbamoyl)cyclopropanecarboxylic acid is used as an intermediate in the synthesis of cyclopropane-containing pharmaceuticals including CC chemokine receptor (CCR) antagonists, hepatitis C virus (HCV) NS5A inhibitors, and HIV integrase inhibitors. The cyclopropane carboxamide motif is found in several marketed drugs including the antidiabetic drug alogliptin and the hepatitis C drug ledipasvir. It is also used in peptidomimetic design.

What is the recommended storage condition for Fluorophenyl)carbamoyl)cyclopropanecarboxylic acid?

It should be stored at controlled room temperature in a well-sealed container, protected from moisture and direct light, to maintain its chemical integrity throughout the shelf life.

What documentation is provided with each batch of Fluorophenyl)carbamoyl)cyclopropanecarboxylic acid?

Each batch is accompanied by a Certificate of Analysis (COA) covering identity, potency, and relevant purity tests. Safety Data Sheets (SDS) are available upon request.

Is Fluorophenyl)carbamoyl)cyclopropanecarboxylic acid available in high-chemical-purity grade for pharmaceutical synthesis?

Yes, it is supplied in high chemical purity grades suitable for demanding pharmaceutical intermediate applications. Specifications and analytical data are available upon request.

Can Fluorophenyl)carbamoyl)cyclopropanecarboxylic acid be provided with custom specifications for synthetic applications?

Custom specifications including adjusted particle size, solvent residue limits, or additional purity testing can be arranged for qualified customers with defined requirements.

Is Fluorophenyl)carbamoyl)cyclopropanecarboxylic acid suitable for use in regulated pharmaceutical processes?

Yes, it is manufactured under quality standards consistent with regulated pharmaceutical applications, including in-process controls and release testing aligned with industry requirements.