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Glutarimide

CAS No.1121-89-7
Chemical Name:Glutarimide
CBNumber:CB2221090
Molecular Formula:C5H7NO2
Formula Weight:113.11
MOL File:1121-89-7.mol

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)
EWG's Food Scores 1-3
FDA UNII MV728O9612
EPA Substance Registry System Glutarimide (1121-89-7)
UNSPSC Code 12352100
NACRES NA.22

Safety

Hazard Codes :Xi
Risk Statements :36
Safety Statements :37/39-26
WGK Germany :3
RTECS :MA4000000
HS Code :29251995

NFPA 704:

	1
1		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Hazard statements
Precautionary statements

Glutarimide Price More Price(3)

Brand: Sigma-Aldrich(India)
Product number: 178098
Product name : Glutarimide
Purity: 98%
Packaging: 5G
Price: ₹2460
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 178098
Product name : Glutarimide
Purity: 98%
Packaging: 25G
Price: ₹7300
Updated: 2022/06/14
Buy: Buy

Brand: TCI Chemicals (India)
Product number: G0269
Product name : Glutarimide
Purity:
Packaging: 5G
Price: ₹5600
Updated: 2022/05/26
Buy: Buy

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.