CAS Number: 161596-47-0
Chemical Name: (S)-(+)-Glycidyl Phthalimide
IUPAC Name: (S)-2-(Oxiran-2-ylmethyl)isoindoline-1,3-dione
Synonyms:
(S)-Glycidyl phthalimide;
(S)-2-(Glycidyloxy)phthalimide;
(S)-2-(2,3-Epoxypropyl)isoindoline-1,3-dione;
Chiral glycidyl phthalimide
Molecular Formula: C₁₁H₉NO₃
Molecular Weight: ~203.19 g/mol
Appearance: White to off-white crystalline powder
Physical State: Solid
Melting Point: Typically reported in the range of 80–95 °C (may vary depending on purity)
Boiling Point: Not applicable (may decompose at elevated temperatures)
Solubility:
Soluble in common organic solvents such as methanol, ethanol, dichloromethane, acetone, and DMSO; limited solubility in water
Stability:
Stable under normal laboratory conditions; sensitive to strong acids, bases, and moisture due to the epoxide ring
Functional Groups:
Epoxide (oxirane) ring
Imide group (phthalimide moiety)
Aromatic benzene ring
Chiral center at the glycidyl carbon
Chemical Class:
Chiral epoxide / Imide derivative / Heterocyclic organic compound
SMILES (representative):
O=C1NC(=O)c2ccccc12C[C@H]3CO3
InChI Key (representative):
(Varies by database; available from chemical registries)
161596-47-0 is widely used as a chiral building block in organic synthesis. The presence of an optically active epoxide makes it valuable for:
Enantioselective synthesis
Ring-opening reactions
Formation of β-hydroxy amines and alcohol derivatives
Preparation of chiral pharmaceutical intermediates
The epoxide functionality allows regio- and stereoselective nucleophilic attack, enabling controlled synthesis of complex molecules.
Intermediate in the synthesis of active pharmaceutical ingredients (APIs)
Precursor for chiral amine derivatives
Building block for heterocyclic and nitrogen-containing compounds
Used in medicinal chemistry research programs
Its phthalimide group can serve as a protected amine functionality, which can be selectively removed in multi-step synthesis.
Commonly employed in:
Asymmetric synthesis studies
Development of chiral catalysts and ligands
Structure–activity relationship (SAR) investigations
Advanced academic and industrial research
The combination of chirality and reactive epoxide functionality enhances its synthetic versatility.
GHS Classification (typical for similar compounds):
Harmful if swallowed
Causes skin and eye irritation
May cause respiratory irritation
Common Hazard Statements:
H302: Harmful if swallowed
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
Precautionary Statements:
P261: Avoid breathing dust
P280: Wear protective gloves and eye protection
P305 + P351 + P338: IF IN EYES, rinse cautiously with water and remove contact lenses
P301 + P312: IF SWALLOWED, call a doctor if you feel unwell
Handle in a well-ventilated area using appropriate personal protective equipment (PPE).
Typical Purity: 97–99% (Research and Industrial Grade)
Storage Conditions:
Store in a tightly sealed container
Keep in a cool, dry, and well-ventilated area
Protect from moisture and direct sunlight
Keep away from strong acids and bases
Commercial Use:
Available from specialty chemical manufacturers for research and industrial applications.
Not intended for direct pharmaceutical, food, or diagnostic use without proper regulatory compliance.
161596-47-0 ((S)-(+)-Glycidyl Phthalimide) is an important chiral epoxide intermediate widely used in enantioselective organic synthesis. Its unique combination of a reactive epoxide ring and protected imide functionality makes it highly valuable in pharmaceutical development, fine chemical production, and advanced research applications.
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