(R)-4-(Oxiran-2-ylmethyl)isoindoline-1,3-dione, CAS No. 181140-34-1

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181140-34-1

Catalog No. EBD248911

CAS 181140-34-1

Name (R)-4-(Oxiran-2-ylmethyl)isoindoline-1,3-dione

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Basic Information

Synonyms: 2-((2r)-oxiranylmethyl)-1h-isoindole-1,3(2h)-dione (r)-2-oxiranylmethyl-isoindole-1,3-dione (r)-(-)-glycidylphthalimide (r)-glycidylphthalimide (r)-(-)-n-(2,3-epoxypropyl)phthalimide (r)-n-glycidylphthalimide 2-[(2r)-2-oxiranylmethyl]-1h-isoindol-1,3(2h)-dione (r)-2-(oxiran-2-ylmethyl)isoindoline-1,3-dione 2-[(2R)-Oxiran-2-Ylmethyl]-1H-Isoindole-1,3(2H)-Dione (R)-4-(Oxiran-2-ylmethyl)isoindoline-1,3-dione

Molecular Formula: C11H9NO3

Molecular Weight: 203.19

MDL Number: MFCD04973349

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Chiral Intermediates Synthetic Chemistry > Organic Building Blocks > Amines

Product Description:

(R)-N-Glycidylphthalimide is a chiral epoxide derivative featuring a phthalimide protecting group. It is a white to off-white crystalline solid with a molecular formula of C11H9NO3. This compound is characterized by its (R)-configuration at the epoxide ring, making it a valuable chiral building block. Its primary and most significant application is as a key chiral intermediate in the synthesis of active pharmaceutical ingredients (APIs). Specifically, it serves as a crucial precursor for the production of (R)-(-)-Carnitine and its derivatives, such as (R)-(-)-Acetylcarnitine. These compounds are important nutraceuticals and pharmaceuticals used in the treatment of various metabolic and neurological disorders. The chiral epoxide moiety allows for the stereoselective introduction of the desired (R)-configuration into the target molecule. As a versatile chiral synthon, it is also employed in other asymmetric synthesis routes. The phthalimide group can be readily removed under mild conditions (e.g., hydrazinolysis), revealing the primary amine functionality for further transformations. This reactivity profile makes it a useful reagent in medicinal chemistry and fine chemical synthesis beyond its primary role in carnitine production.

Physical Properties

Melting Point: 100-102 °C

Boiling Point: 347.4 °C at 760 mmHg

Flash Point: 163.9 °C

Density: 1.446 g/cm3