Glutarimide , >98.0%(HPLC) , 1121-89-7

Synonym(s):
2,6-Piperidinedione;NSC 58190

CAS NO.：1121-89-7

Empirical Formula: C5H7NO2

Molecular Weight: 113.11

MDL number: MFCD00006670

EINECS: 214-340-4

PRODUCT Properties

• Melting point: 155-157 °C (lit.)
• Boiling point: 211.82°C (rough estimate)
• Density: 1.2416 (rough estimate)
• refractive index: 1.4200 (estimate)
• storage temp.: Inert atmosphere,Room Temperature
• solubility: soluble in Chloroform, DCM
• form: Crystals or Crystalline Flakes
• pka: pKa 11.4 (Uncertain)
• color: White
• Water Solubility: Soluble in water, hot ethanol and boiling benzene. Insoluble in ether.
• BRN: 110052
• InChI: InChI=1S/C5H7NO2/c7-4-2-1-3-5(8)6-4/h1-3H2,(H,6,7,8)
• InChIKey: KNCYXPMJDCCGSJ-UHFFFAOYSA-N
• SMILES: N1C(=O)CCCC1=O
• CAS DataBase Reference: 1121-89-7(CAS DataBase Reference)
• EPA Substance Registry System: Glutarimide (1121-89-7)

Description and Uses

Glutarimide, also known as Piperidine-2,6-dione or 2,6-Piperidinedione, is a versatile and commonly used organic reagent, classified in pharmacology as a protein synthesis inhibitor compound. It is also an important component of the anti-cancer drug thalidomide. The study reported the synthesis of triazoloquinoxaline derivative (Compound 15), a new potent anticancer drug containing a glutarimide molecule, based on the CRBN binding property of the glutarimide molecule in thalidomide molecule and the cytotoxic activity of triazole-quinoxaline. The IC50s were 9.81 ± 0.7, 15.49 ± 1.2 and 10.09 ± 0.9 μM for hepatocellular carcinoma (HepG2), prostate cancer (PC3) and breast cancer (MCF-7), respectively. It was superior to thalidomide in decreasing NF-κB P65 levels in HepG-2 cells^[1].

Glutarimide acts as an inhibitor of protein synthesis. Further, it is used as a reactant for thionations and biocatalytic asymmetric synthesis of sitagliptin production. It is also employed in the generation of beta-adrenoceptor ligands, enantioselective synthesis of securinega alkaloids and alfa-fluoro-alfa amino amides. In addition to this, it is used in intramolecular amidocyclopropanation reactions.

Safety

• Symbol(GHS): GHS07
• Signal word: Warning
• Hazard statements: H302-H315-H319-H335
• Precautionary statements: P261-P301+P312-P302+P352-P304+P340-P305+P351+P338
• Hazard Codes: Xi
• Risk Statements: 36
• Safety Statements: 37/39-26
• WGK Germany: 3
• RTECS: MA4000000
• HS Code: 29251995