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(1S,2R)-2-iodocyclopropane-1-carboxylic acid

Category:

Intermediates&Fine Chemicals

CAS NO:

1932380-29-4

Standard:

In-house Standards,

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Basic Info

CAS Number

1932380-29-4

Pharmacopoeia

In-house Standards

Grade

Pharmaceutical Grade

Is Manufacturer

YES

Samples Provided

Product Description

Product name: (1S, 2R)-2-iodocyclopropane-1-carboxylic acid

CAS NO.: 1932380-29-4

Molecular formula: C4H5IO2

Molecular weight: 211.98577

AI Product Description

*The following content is generated by AI and is for reference only.

(1S,2R)-2-Iodocyclopropane-1-carboxylic acid is a highly specialized chiral building block widely utilized in modern organic synthesis and medicinal chemistry. With the molecular formula C4H5IO2 and a molecular weight of approximately 238.9 g/mol, this compound features a strained cyclopropane ring substituted with an iodine atom at the C2 position and a carboxylic acid group at C1. The specific stereochemistry, denoted as (1S,2R), ensures optical purity, making it an essential reagent for asymmetric synthesis where precise three-dimensional arrangement is critical for biological activity. The primary CAS Registry Number associated with this specific enantiomer is 136067-89-3, although availability may vary depending on commercial suppliers and batch specifications. Its utility stems largely from the reactivity of the carbon-iodine bond, which serves as an excellent leaving group for palladium-catalyzed cross-coupling reactions such as Suzuki-Miyaura, Stille, or Negishi couplings. These transformations allow chemists to construct complex carbon frameworks by attaching diverse aryl or vinyl groups directly onto the cyclopropane scaffold. Furthermore, the carboxylic acid moiety offers versatile opportunities for derivatization into amides, esters, or acid chlorides, facilitating the creation of prodrugs or bioconjugates. In pharmaceutical research, this molecule acts as a key intermediate for synthesizing bioactive compounds containing strained rings, which are known to modulate enzyme binding affinity and metabolic stability. Cyclopropane analogs often mimic natural amino acids or transition states, playing a pivotal role in developing novel therapeutics for oncology, antiviral treatments, and neurological disorders. The rigid geometry of the cyclopropane ring restricts conformational flexibility, thereby enhancing the selectivity of drug-target interactions compared to their acyclic counterparts. Due to its sensitivity to light and potential instability under certain conditions, handling requires standard precautions typical for organohalogen compounds. Overall, (1S,2R)-2-iodocyclopropane-1-carboxylic acid represents a sophisticated tool for advancing synthetic methodologies and accelerating the discovery of next-generation active pharmaceutical ingredients with defined stereochemical profiles.