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Glutarimide

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CAS:1121-89-7
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Glutarimide Basic information
Product Name:Glutarimide
Synonyms:GLUTARIMIDE;2,6-PIPERIDINEDIONE;2,6-DIKETOPIPERIDINE;Glutarimide98%;2,6-Dioxopiperidine;GlutariMide, 98% 25GR;2,6-Diketopiperidine 2,6-Piperidinedione;AcetylglycinaMide IMpurity B
CAS:1121-89-7
MF:C5H7NO2
MW:113.11
EINECS:214-340-4
Product Categories:Building Blocks;Heterocyclic Building Blocks;Piperidines;Miscellaneous Biochemicals;organic intermediate
Mol File:1121-89-7.mol
Glutarimide Structure
Glutarimide Chemical 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
pkapKa 11.4 (Uncertain)
color White
Water Solubility Soluble in water, hot ethanol and boiling benzene. Insoluble in ether.
BRN 110052
InChIInChI=1S/C5H7NO2/c7-4-2-1-3-5(8)6-4/h1-3H2,(H,6,7,8)
InChIKeyKNCYXPMJDCCGSJ-UHFFFAOYSA-N
SMILESN1C(=O)CCCC1=O
CAS DataBase Reference1121-89-7(CAS DataBase Reference)
EPA Substance Registry SystemGlutarimide (1121-89-7)
Safety Information
Hazard Codes Xi
Risk Statements 36
Safety Statements 37/39-26
WGK Germany 3
RTECS MA4000000
HS Code 29251995
MSDS Information
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Glutarimide Usage And Synthesis
Chemical Propertieswhite crystalline powder
UsesGlutarimide 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.
PreparationTo 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
DefinitionChEBI: A dicarboximide that is piperidine which is substituted by oxo groups at positions 2 and 6.
General DescriptionA glutarimide antibiotic, 9-methylstreptimidone, shows antiviral, antitumor and antifungal activities.
Purification MethodsPurify 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.]
Glutarimide Preparation Products And Raw materials
Preparation ProductsBuspirone-->2-Piperidinone,6-ethoxy-1-(4-pentenyl)-(9CI)-->1-phenylpiperidine-2,6-dione
Tag:Glutarimide(1121-89-7) Related Product Information
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