CAS 22882-43-5

rel-(1R,2R)-2-Nitrocyclopropanecarboxylic acid

Description:

Rel-(1R,2R)-2-Nitrocyclopropanecarboxylic acid is a chemical compound characterized by its cyclopropane structure, which features a nitro group and a carboxylic acid functional group. The "rel" designation indicates that the compound has a specific stereochemistry, with both the 1R and 2R configurations contributing to its chiral nature. This compound is typically a solid at room temperature and is soluble in polar solvents due to the presence of the carboxylic acid group. The nitro group introduces significant reactivity, making it a useful intermediate in organic synthesis, particularly in the development of pharmaceuticals and agrochemicals. Its unique structure allows for various chemical transformations, including reduction and substitution reactions. Additionally, the compound's stereochemistry can influence its biological activity and interactions, making it of interest in medicinal chemistry. Safety data should be consulted for handling and storage, as nitro compounds can be sensitive to heat and shock.

Formula: C₄H₅NO₄

InChI: InChI=1/C4H5NO4/c6-4(7)2-1-3(2)5(8)9/h2-3H,1H2,(H,6,7)

InChI key: InChIKey=ZWYGYMZMGJZSMM-MZTXYVAJNA-N

SMILES: C(O)(=O)[C@H]1[C@H](N(=O)=O)C1

Synonyms:

• Cyclopropanecarboxylic acid, 2-nitro-, trans-
• rel-(1R,2R)-2-Nitrocyclopropanecarboxylic acid
• Cyclopropanecarboxylic acid, 2-nitro-, (1R,2R)-rel-
• Cyclopropanecarboxylic acid, 2-nitro-, (1R,2R)-rel- (9CI)
• (1S,2S)-2-Nitrocyclopropanecarboxylic acid

(1S,2S)-2-Nitrocyclopropanecarboxylic acid

CAS: 22882-43-5

(1S,2S)-2-Nitrocyclopropanecarboxylic acid is a β-unsaturated carboxylic acid that catalyzes the cyclopropanation of 1,3-dienes. It is used as a catalyst to produce synlett products by asymmetric addition to α,β-unsaturated carbonyls with thiourea. (1S,2S)-2-Nitrocyclopropanecarboxylic acid has been shown to be an effective organocatalyst for asymmetric synthesis of chiral compounds.

Formula: C₄H₅NO₄

Purity: Min. 95%

Molecular weight: 131.09 g/mol

Ref: 3D-XAA88243