1121-89-7

Basic information

• Product Name: Glutarimide
• Synonyms: PIPERIDINE-2,6-DIONE;GLUTARIMIDE;2,6-PIPERIDINEDIONE;2,6-DIKETOPIPERIDINE;Glutarimide98%;2,6-Dioxopiperidine;GlutariMide, 98% 25GR;2,6-Diketopiperidine 2,6-Piperidinedione
• CAS NO: 1121-89-7
• Molecular Formula: C₅H₇NO₂
• Molecular Weight: 113.11
• EINECS: 214-340-4
• Product Categories: Miscellaneous Biochemicals;organic intermediate;Building Blocks;Heterocyclic Building Blocks;Piperidines
• Mol File: 1121-89-7.mol

Chemical Properties

• Melting Point: 155-157 °C(lit.)
• Boiling Point: 211.82°C (rough estimate)
• Flash Point: 152.298 °C
• Appearance: White/Crystals or Crystalline Flakes
• Density: 1.2416 (rough estimate)
• Vapor Pressure: 0.0024mmHg at 25°C
• Refractive Index: 1.4200 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: pKa 11.4 (Uncertain)
• Water Solubility: Soluble in water, hot ethanol and boiling benzene. Insoluble in ether.
• BRN: 110052
• CAS DataBase Reference: Glutarimide(CAS DataBase Reference)
• NIST Chemistry Reference: Glutarimide(1121-89-7)
• EPA Substance Registry System: Glutarimide(1121-89-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 37/39-26
• WGK Germany: 3
• RTECS: MA4000000
• Hazardous Substances Data: 1121-89-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Glutarimide is used as an inhibitor of protein synthesis for its antiviral, antitumor, and antifungal properties. The expression is: Glutarimide is used as a protein synthesis inhibitor for its antiviral, antitumor, and antifungal activities.
Used in Chemical Synthesis:
Glutarimide is used as a reactant for thionations and biocatalytic asymmetric synthesis of sitagliptin production. The expression is: Glutarimide is used as a reactant for thionations and biocatalytic asymmetric synthesis of sitagliptin production.
Used in Medicinal Chemistry:
Glutarimide is employed in the generation of beta-adrenoceptor ligands, enantioselective synthesis of securinega alkaloids, and alfa-fluoro-alfa amino amides. The expression is: Glutarimide is used in the generation of beta-adrenoceptor ligands, enantioselective synthesis of securinega alkaloids, and alfa-fluoro-alfa amino amides.
Used in Organic Chemistry:
Glutarimide is used in intramolecular amidocyclopropanation reactions. The expression is: Glutarimide is used in intramolecular amidocyclopropanation reactions for its unique chemical properties.

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 pro-duct 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.

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.]

InChI:InChI=1/C5H7NO2/c7-4-2-1-3-5(8)6-4/h1-3H2,(H,6,7,8)

Upstream product

• 110-89-4 piperidine 
• 108-55-4 glutaric anhydride, 
• 110-94-1 1,5-pentanedioic acid 
• 39201-33-7 4-cyanobutyric acid 
• 544-13-8 Glutaronitrile 
• 25335-74-4 glutaramic acid 
• 64-18-6 formic acid 
• 77287-34-4 formamide 
• 75-05-8 acetonitrile 
• 675-20-7 piperidin-2-one 
• 1119-40-0 Dimethyl glutarate 
• 89003-34-9 N-(piperidin-1-ylmethyl)glutarimide 
• 89003-36-1 N-(morpholin-4-ylmethyl)glutarimide 
• 89003-35-0 N-(1,2,5,6-tetrahydropyridin-1-ylmethyl)glutarimide 

Downstream Products

• 25077-25-2 N-methyladipinimide 
• 101715-90-6 N-[5-(4-nitro-phenoxy)-pentyl]-glutaramic acid ethyl ester 
• 110-86-1 pyridine 
• 2402-92-8 2,3,6-tribromopyridine 
• 2766-64-5 2,3,5,6-tetrabromopyridine 
• 3699-18-1 N-bromoglutarimide 
• 93538-08-0 DL-3-(2,6-Dioxo-piperidinomethyl)-4-methyl-5-phenyl-oxazolidin 
• 80696-76-0 N-(1-phenylbut-3-en-1-yl)glutarimide 
• 73157-68-3 6-hydroxy-(1-phenylbut-3-en-1-yl)-2-piperidinone 
• 115881-08-8 N-<1-(3,4-dimethoxyphenyl)but-3-en-1-yl>glutarimide 
• 132416-67-2 1-(2-azidobenzoyl)piperidine-2,6-dione 
• 58804-91-4 1-(but-3-yn-1-yl)piperidine-2,6-dione 
• 6271-50-7 2,2',4,4'-tetrachlorostilbene 
• 124482-63-9 3-(2,4-Dichloro-benzyl)-piperidine-2,6-dione 

Related news

Synthesis of actiketal, a Glutarimide (cas 1121-89-7) antibiotic09/30/2019

The first synthesis of actiketal (RK-441S), an antibiotic from Streptomyces pulveraceus subsp. epiderstagenes, was achieved from 5,7-dimethylbenzofuran and dimethyl glutaconate via palladium-assisted coupling reaction as a key step.detailed

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The reintroduction of thalidomide in the pharmacotherapy greatly stimulated the interest in the synthesis and pharmacological evaluation of phthalimide analogs with new and improved activities and also greater safety. In the present study, we evaluated the activities of two phthalimide analogs d...detailed

Relevant articles and documents

Synthesis and Antimicrobial Evaluation of Fire Ant Venom Alkaloid Based 2-Methyl-6-alkyl-Δ1,6-piperideines

The first synthesis of 2-methyl-6-pentadecyl-Δ1,6-piperideine (1), a major alkaloid of the piperideine chemotype in fire ant venoms, and its analogues, 2-methyl-6-tetradecyl-Δ1,6-piperideine (2) and 2-methyl-6-hexadecyl-Δ1,6-piperideine (3), was achieved by a facile synthetic method starting with glutaric acid (4) and urea (5). Compound 1 showed in vitro antifungal activity against Cryptococcus neoformans and Candida albicans with IC50 values of 6.6 and 12.4 μg/mL, respectively, and antibacterial activity against vancomycin-resistant Enterococcus faecium with an IC50 value of 19.4 μg/mL, while compounds 2 and 3 were less active against these pathogens. All three compounds strongly inhibited the parasites Leishmania donovani promastigotes and Trypanosoma brucei with IC50 values in the range of 5.0-6.7 and 2.7-4.0 μg/mL, respectively.

The synthesis of unsubstituted cyclic imides using hydroxylamine under microwave irradiation

Unsubstituted cyclic imides were synthesized from a series of cyclic anhydrides, hydroxylamine hydrochloride (NH2OH·HCl), and 4-N,N-dimethylamino-pyridine (DMAP, base catalyst) under microwave irradiation in monomode and multimode microwaves. This novel microwave synthesis produced high yields of the unsubstituted cyclic imides for both the monomode (61-81%) and multimode (84-97%) microwaves.

Preparation method of glutaryl imide derivative

The invention discloses a preparation method of a glutaryl imide derivative, which comprises the following steps: in a negative pressure state, dropwise adding acetic anhydride into molten 1, 1-cyclohexyl diacetic acid, and reacting to obtain 1, 1-cyclohexyl diacetic anhydride; adding ammonia water into an ammoniation kettle, dropwise adding 1, 1-cyclohexanediacetic anhydride to carry out ammoniation reaction, and adding hydrochloric acid to adjust the pH value, so as to obtain precipitated crystals, namely pentane valeric acid; adding pentane valeric acid, a toluene solvent and glacial aceticacid into the reaction kettle, heating, stirring, reacting, cooling, and carrying out suction filtration to obtain a filter cake; and adding the filter cake into ammonia water for soaking and stirring, carrying out suction filtration again, leaching with deionized water, and drying to obtain glutaryl imide. According to the preparation method of a glutaryl imide derivative, acetic anhydride and 1, 1-cyclohexyldiacetic acid are used as raw materials, so that the reaction efficiency is effectively improved, the product yield is increased, the production cost of the product is reduced, and producing benefits are improved.

Synthesis of N-unsubstituted cyclic imides from anhydride with urea in deep eutectic solvent (DES) choline chloride/urea

N-Unsubstituted cyclic imides were readily synthesized in deep eutectic solvent (DES) choline chloride (ChCl)/urea from anhydrides with urea. Urea serves as both a DES component and a nitrogen source, which endows the protocol with advantages of smooth reaction, easy separation of products, simple recovery and recycling of ChCl/urea.

Method for catalytically oxidizing amine to be synthesized into amide through dipyridyl-type manganese catalyst

The invention discloses a methodfor catalytically oxidizing amine to be synthesized into amide througha dipyridyl-type manganese catalyst. According to the method, a dipyridyl manganese complex formedafter coordination of a dipyridyl-type complex and cheap metal manganese serves as the catalyst, clean and environment-friendly hydrogen peroxide serves as an oxidizing agent, oxidation of N ortho-position sp3 C-H bonds catalyzed by the cheap metal manganese is achieved, and the amine is directly oxidized to obtain the amide. Compared with existing methods, the method has the advantages that theadopted catalyst is low in price, the preparing method is simple, raw materials are easy to obtain, the use level of the catalyst is low, the substrate range is wide, the reaction condition is mild, the operation is simple and environmentally friendly, the reaction time is short, the yield is high, the selectivity is high, and the industrialization cost is low.

Visible-Light-Driven Oxidation of N -Alkylamides to Imides Using Oxone/H 2 O and Catalytic KBr

Imides are prepared conveniently by visible-light-driven oxidations of various N -alkylamides under mild conditions. The majority of the reactions proceed efficiently by using Oxone as the oxidant in the presence of a catalytic amount of KBr in H 2 O/CH 2 Cl 2 under irradiation by an 8 W white LED at room temperature. Experimental studies suggest that an imine, obtained from the substrate amide via a radical process, is the key intermediate.

Heterolytic (2 e) vs Homolytic (1 e) Oxidation Reactivity: N?H versus C?H Switch in the Oxidation of Lactams by Dioxirans

Dioxiranes are powerful oxidants that can act via two different mechanisms: 1) homolytic (H abstraction and oxygen rebound) and 2) heterolytic (electrophilic oxidation). So far, it has been reported that the nature of the substrate dictates the reaction mode independently from the dioxirane employed. Herein, we report an unprecedented case in which the nature of the dioxirane rules the oxidation chemoselectivity. In particular, a switch from C?H to N?H oxidation is observed in the oxidation of lactams moving from dimethyl dioxirane (DDO) to methyl(trifluoromethyl)dioxirane (TFDO). A physical organic chemistry study, which combines the oxidation with two other dioxiranes methyl(fluoromethyl)dioxirane, MFDO, and methyl(difluoromethyl)dioxirane, DFDO, with computational studies, points to a diverse ability of the dioxiranes to either stabilize the homo or the heterolytic pathway.

Strong influence of intramolecular Si?O proximity on reactivity: Systematic molecular structure, solvolysis, and mechanistic study of cyclic N-trimethylsilyl carboxamide derivatives

A comparative alcoholysis study of N-silylated derivatives of simple heterocyclic carboxamides (lactams, imides, ureas) is presented. The second-order rate constant values span a range as wide as three orders of magnitude. On the basis of DFT calculations, a good correlation between reactivity and the Si?O distance was found within each family of compounds. The viability of two different reaction pathways was evaluated using a detailed computational mechanistic study of the methanolysis of cyclic urea homologues. Peculiarities in the single-crystal X-ray diffraction structures of the trimethylsilyl and trimethylsiloxy phthalimides are also discussed.

Nitrile synthesis through catalyzed cascades involving acid-nitrile exchange

Irreversible acid-nitrile exchange reactions using both glutaronitrile and (phenylsulfonyl)acetonitrile may be catalyzed by Lewis acids. Whereas a cyclization towards imides displaces the equilibria in the reaction with dinitriles, a decarboxylation step is involved when using the (phenylsulfonyl)acetonitrile. Georg Thieme Verlag Stuttgart New York.

Method for producing compounds comprising nitrile functions

The present invention concerns the production of compounds comprising nitrite functions and cyclic imide compounds. More specifically, the invention relates to the production of compounds comprising nitrile functions from compounds comprising carboxylic functions, advantageously of natural and renewable origin, and from methyl-2 glutaronitrile (MGN) or a mixture N of dinitriles comprising methyl-2 glutaronitrile (MGN), ethyl-2 succinonitrile (ESN) and adiponitrile (AdN).