ChemicalBook--->CAS DataBase List--->1121-89-7

1121-89-7

1121-89-7 Structure

1121-89-7 Structure
IdentificationMore
[Name]

Glutarimide
[CAS]

1121-89-7
[Synonyms]

2,6-DIKETOPIPERIDINE
2,6-PIPERIDINEDIONE
GLUTARIMIDE
PIPERIDINE-2,6-DIONE
Glutarimide98%
2,6-Dioxopiperidine
[EINECS(EC#)]

214-340-4
[Molecular Formula]

C5H7NO2
[MDL Number]

MFCD00006670
[Molecular Weight]

113.11
[MOL File]

1121-89-7.mol
Chemical PropertiesBack Directory
[Appearance]

white crystalline powder
[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]

1121-89-7(EPA Substance)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

R36:Irritating to the eyes.
[Safety Statements ]

S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
[WGK Germany ]

3
[RTECS ]

MA4000000
[HS Code ]

29251995
Raw materials And Preparation ProductsBack Directory
[Preparation Products]

Buspirone-->2-Piperidinone,6-ethoxy-1-(4-pentenyl)-(9CI)-->1-phenylpiperidine-2,6-dione
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

Glutarimide(1121-89-7).msds
Hazard InformationBack Directory
[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.
[Definition]

ChEBI: A dicarboximide that is piperidine which is substituted by oxo groups at positions 2 and 6.
[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.
Preparation of Glutarimide
[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.
Spectrum DetailBack Directory
[Spectrum Detail]

Glutarimide(1121-89-7)1HNMR
Glutarimide(1121-89-7)FT-IR
Glutarimide(1121-89-7)Raman
Glutarimide(1121-89-7)IR
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

Glutarimide, 98%(1121-89-7)
[Alfa Aesar]

Glutarimide, 98%(1121-89-7)
[Sigma Aldrich]

1121-89-7(sigmaaldrich)
[TCI AMERICA]

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