Glutarimide

Base Information

• Chemical Name: Glutarimide
• CAS No.: 1121-89-7
• Molecular Formula: C5H7NO2
• Molecular Weight: 113.116
• Hs Code.: 29251995
• European Community (EC) Number: 214-340-4
• NSC Number: 58190
• UNII: MV728O9612
• DSSTox Substance ID: DTXSID7074452
• Nikkaji Number: J137.949F
• Wikipedia: Glutarimide
• Wikidata: Q3109315
• Metabolomics Workbench ID: 53204
• ChEMBL ID: CHEMBL3763941
• Mol file: 1121-89-7.mol

Synonyms:2,6-piperidinedione;glutarimide;glutarimide calcium salt

Chemical Property of Glutarimide

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0.0024mmHg at 25°C
• Melting Point: 155-157 °C(lit.)
• Refractive Index: 1.47
• Boiling Point: 287.979 °C at 760 mmHg
• PKA: pKa 11.4 (Uncertain)
• Flash Point: 152.298 °C
• PSA: 46.17000
• Density: 1.185 g/cm³
• LogP: 0.14190
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility.: Soluble in water, hot ethanol and boiling benzene. Insoluble in ether.
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 113.047678466
• Heavy Atom Count: 8
• Complexity: 116

Purity/Quality:

99%, ^*data from raw suppliers

Glutarimide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC(=O)NC(=O)C1
• 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.

Technology Process of Glutarimide

There total 53 articles about Glutarimide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

piperidin-2-one (675-20-7) → piperidine-2,6-dione (1121-89-7)

Guidance literature:

With 3,3-dimethyldioxirane; In acetone; at 0 - 25 ℃; for 48h;

DOI:10.1002/chem.201604507

Reference yield: 92.0%

Glutaronitrile (544-13-8) + 2-cyclohexyl-2-phenylacetic acid (3894-09-5,51019-55-7) → piperidine-2,6-dione (1121-89-7) + cyclohexyl phenyl acetonitrile (3893-23-0)

Guidance literature:

With aluminum (III) chloride; at 200 ℃; for 2.5h; Temperature; Sealed tube;

DOI:10.1055/s-0033-1341227

Reference yield: 92.0%

glutaric anhydride, (108-55-4) → piperidine-2,6-dione (1121-89-7)

Guidance literature:

With ammonium acetate; for 0.00416667h; microwave heating;

upstream raw materials:

piperidine

glutaric anhydride,

1,5-pentanedioic acid

4-cyanobutyric acid

Downstream raw materials:

N-methyladipinimide

N-[5-(4-nitro-phenoxy)-pentyl]-glutaramic acid ethyl ester

pyridine

2,3,6-tribromopyridine

Refernces

N-Acyl-glutarimides: Effect of Glutarimide Ring on the Structures of Fully Perpendicular Twisted Amides and N-C Bond Cross-Coupling

10.1021/acs.joc.0c00227

The study reports the synthesis and characterization of five new N-acyl-glutarimides:1-Benzoylpiperidine-2,6-dione, 1-Benzoyl-4,4-dimethylpiperidine-2,6-dione, 8-Benzoyl-8-azaspiro[4.5]decane-7,9-dione, 3-Benzoyl-3-azaspiro[5.5]undecane-2,4-dione, 1-Benzoyl-4-phenylpiperidine-2,6-dione, demonstrating their extreme twist angles close to 90 degrees, which significantly enhances their reactivity in N–C(O) bond cross-coupling reactions. The compounds were found to be highly reactive in both metal-catalyzed Suzuki–Miyaura cross-coupling and transition-metal-free transamidation reactions. Computational studies revealed high rotational barriers around the N–C(O) axis, indicating a strong preference for the twisted conformation. This work expands the toolkit of N-acyl-glutarimides for developing new N–C(O) bond activation reactions, highlighting their potential in synthetic chemistry.

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