Glutarimide

Glutarimide Property

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)

Safety

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

37/39-26

WGK Germany 

3

RTECS 

MA4000000

HS Code 

29251995

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Glutarimide Chemical Properties,Usage,Production

Description

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].

Chemical Properties

white crystalline powder

Uses

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.

Preparation

To a flask containing 70 gm (0.53 mole) of glutaric acid is added 150 ml (2.2 mole) of 28% aqueous ammonia. The mixture is set for distillation and heated for 7 hr as the temperature of the mixture rises from 90° to 180°C. The temperature is held at 170-180°C for \\ hr or until the evolution of ammonia ceases. The reaction mixture solidifies on cooling and the pro­duct is recrystallized from acetone to afford 37.4 gm (63%), m.p. 145-146°C.
t may be advantageous to preform the ammonium salt of dicarboxylic acids prior to the application of enough heat to form the imide. The preparation of succinimide is a case in point.

Definition

ChEBI: Glutarimide (Piperidine-2,6-dione) is a dicarboximide that is piperidine which is substituted by oxo groups at positions 2 and 6. It is a member of piperidones and a dicarboximide.

General Description

A glutarimide antibiotic, 9-methylstreptimidone, shows antiviral, antitumor and antifungal activities.

Purification Methods

Purify it by dissolving 75g in 200mL of H2O, boil for 30minutes with 2g of charcoal, filter, evaporate to dryness and recystallise the residue from 125mL of 95% EtOH to give 70g of white crystals, m 152-154o. It also crystallises from Me2CO (m 163-165o) or EtOH (m 153-154o). The N-bromo derivative (a brominating agent) crystallises from H2O with m 180-185o. [Paris et al. Org Synth Coll Vol IV 496 1963, Beilstein 21 H 382, 21 I 331, 21 II 307, 21 III/IV 4582.]

References

[1] MAGED MOHAMMED SALEH AL WARD . Design, synthesis and biological evaluation of newly triazolo-quinoxaline based potential immunomodulatory anticancer molecules[J]. Journal of Molecular Structure, 2023. DOI:10.1016/j.molstruc.2023.137041.