(1R,2S)-2-fluorocyclopropan-1-amine

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Cat Number

INT143062844

CAS Number

143062-84-4

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Product Detail Description Customer Q&A

CAS Number

143062-84-4

EINECS

802-120-6

Storage

Inert atmosphere, room temperature

Synonyms

4-methylbenzenesulfonic acid; (1R,2S)-2-fluorocyclopropan-1-amine tosylic acid

Molecular Formula

C10H14FNO3S

Molecular Weight

247.28

Smiles

CC1=CC=C(C=C1)S(=O)(=O)O.C1[C@H]([C@H]1F)N

Appearance

White solid

General Description

(1R,2S)-2-fluorocyclopropan-1-amine is a chiral primary amine characterized by a cyclopropane ring substituted with a fluorine atom. This specialized small molecule is a high-value pharmaceutical intermediate, serving as a critical building block for the synthesis of advanced fluoroquinolone antibiotics. Its specific stereochemistry and the presence of the fluorine substituent are essential for enhancing the pharmacological profile of the final drug candidates.

Mechanism of Action

As a synthetic intermediate, (1R,2S)-2-fluorocyclopropan-1-amine functions as a precursor that introduces a rigid, fluorinated cyclopropyl moiety into a molecular scaffold. In the context of antibiotic development, the (1R,2S) configuration is vital for the precise spatial orientation required for the drug to bind to bacterial DNA gyrase and topoisomerase IV. The electronegative fluorine atom on the cyclopropyl ring modifies the lipophilicity and metabolic stability of the resulting molecule, significantly improving its antibacterial potency and reducing potential side effects.

Application

(1R,2S)-2-fluorocyclopropan-1-amine is primarily utilized as the key intermediate in the synthesis of Sitafloxacin, a potent fourth-generation fluoroquinolone. In the pharmaceutical industry, it is employed in the manufacturing of high-purity active pharmaceutical ingredients (APIs) targeting respiratory and urinary tract infections. It is also used in medicinal chemistry research to explore structure-activity relationships (SAR) in the development of novel antimicrobial agents and as a chiral reagent in asymmetric synthesis to introduce fluorinated cyclopropyl groups into complex organic molecules.

What is the specific stereochemistry of (1R,2S)-2-fluorocyclopropan-1-amine?

It features the (1R,2S) configuration, which is essential for the biological activity of the final pharmaceutical product.

Why is the fluorine atom significant in the structure of (1R,2S)-2-fluorocyclopropan-1-amine?

The fluorine substituent enhances the metabolic stability and lipophilicity of the drug, leading to better antibacterial efficacy.

What is the MOQ for (1R,2S)-2-fluorocyclopropan-1-amine?

MOQs are flexible and can be tailored to meet your requirements for R&D or pilot-scale production; please contact us for specific details.

How should (1R,2S)-2-fluorocyclopropan-1-amine be stored?

Store in a cool, dry place under an inert atmosphere to prevent the amine group from reacting with atmospheric carbon dioxide or moisture.