ChemicalBook > CAS DataBase List > Glutarimide

Glutarimide

Product Name
Glutarimide
CAS No.
1121-89-7
Chemical Name
Glutarimide
Synonyms
PIPERIDINE-2,6-DIONE;NSC 58190;NSC 168666;GLUTARIMIDE;Glutarimide98%;Glutarimide>2,6-Dioxopiperidine;2,6-PIPERIDINEDIONE;2,6-DIKETOPIPERIDINE;GlutariMide, 98% 25GR
CBNumber
CB2221090
Molecular Formula
C5H7NO2
Formula Weight
113.11
MOL File
1121-89-7.mol
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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)
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Safety

Hazard Codes 
Xi
Risk Statements 
36
Safety Statements 
37/39-26
WGK Germany 
3
RTECS 
MA4000000
HS Code 
29251995
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
178098
Product name
Glutarimide
Purity
98%
Packaging
5g
Price
$121
Updated
2024/03/01
Sigma-Aldrich
Product number
178098
Product name
Glutarimide
Purity
98%
Packaging
25g
Price
$240
Updated
2024/03/01
TCI Chemical
Product number
G0269
Product name
Glutarimide
Purity
>98.0%(N)
Packaging
5g
Price
$111
Updated
2024/03/01
Alfa Aesar
Product number
L00968
Product name
Glutarimide, 98%
Packaging
5g
Price
$54.65
Updated
2024/03/01
Alfa Aesar
Product number
L00968
Product name
Glutarimide, 98%
Packaging
25g
Price
$162
Updated
2024/03/01
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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.

Glutarimide Preparation Products And Raw materials

Raw materials

Preparation Products

Buspirone
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Glutarimide Suppliers

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View Lastest Price from Glutarimide manufacturers

Hebei Weibang Biotechnology Co., Ltd
Product
Glutarimide 1121-89-7
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
500000kg
Release date
2024-11-04
Hebei Mojin Biotechnology Co., Ltd
Product
Glutarimide 1121-89-7
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
50000KG/month
Release date
2023-10-16
Hong Kong Tiansheng New Material Trading Co., Ltd
Product
Glutarimide 1121-89-7
Price
US $8.99/KG
Min. Order
1KG
Purity
99%
Supply Ability
100KG
Release date
2021-12-24

1121-89-7, GlutarimideRelated Search:

O-Phthalimide Succinimide Bismaleimide Glutacondianil hydrochloride ethyl pentanimidate hydrochloride Diethyl glutarate MONO-METHYL GLUTARATE 3-(cyanomethylene)glutaric acid dimethyl ester Glutaric anhydride Glutaric acid Dimethyl Glutarate ETHYL HYDROGEN GLUTARATE GLUTARIC ACID-2-METHYLAMINO-5-NITROMONOANILIDE DIALIFOS Buspirone hydrochloride BMY 7378 DIHYDROCHLORIDE BENZETIMIDE Glutarimide, 2-(p-aminophenyl)-2-ethyl-,(RS)-2-ETHYL-2-(4-AMINO-PHENYL)-GLUTARIMIDE

  • PIPERIDINE-2,6-DIONE
  • GLUTARIMIDE
  • 2,6-PIPERIDINEDIONE
  • 2,6-DIKETOPIPERIDINE
  • Glutarimide98%
  • 2,6-Dioxopiperidine
  • GlutariMide, 98% 25GR
  • 2,6-Diketopiperidine 2,6-Piperidinedione
  • AcetylglycinaMide IMpurity B
  • NSC 58190
  • NSC 168666
  • Acetylglycinamide Impurity 2
  • Glutarimide&gt
  • 1121-89-7
  • Heterocyclic Building Blocks
  • Piperidines
  • Building Blocks
  • Building Blocks
  • Heterocyclic Building Blocks
  • Piperidines
  • Miscellaneous Biochemicals
  • organic intermediate