42472-93-5

Basic information

• Product Name: 1-Methyl-3-(1,3-dioxoisoindolin-2-yl)-2,6-piperidinedione
• Synonyms: 1-Methyl-3-(1,3-dioxoisoindolin-2-yl)-2,6-piperidinedione;WU-313
• CAS NO: 42472-93-5
• Molecular Formula: C₁₄H₁₂N₂O₄
• Molecular Weight: 272.28
• Mol File: 42472-93-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 415.31°C (rough estimate)
• Flash Point: 232°C
• Appearance: /
• Density: 1.2499 (rough estimate)
• Vapor Pressure: 2.9E-09mmHg at 25°C
• Refractive Index: 1.6180 (estimate)
• CAS DataBase Reference: 1-Methyl-3-(1,3-dioxoisoindolin-2-yl)-2,6-piperidinedione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-3-(1,3-dioxoisoindolin-2-yl)-2,6-piperidinedione(42472-93-5)
• EPA Substance Registry System: 1-Methyl-3-(1,3-dioxoisoindolin-2-yl)-2,6-piperidinedione(42472-93-5)

Safety Data

• Hazardous Substances Data: 42472-93-5(Hazardous Substances Data)

Usage

Molecular structure

A complex structure consisting of a piperidinedione ring with a methyl group and a 1,3-dioxoisoindolin-2-yl group attached.

Natural occurrence

Not naturally occurring.

Synthesis

Typically synthesized in a laboratory setting.

Potential applications

May have applications in pharmaceutical research and organic synthesis.

Research status

Further research is needed to fully understand its properties and potential uses.

InChI:InChI=1/C14H12N2O4/c1-15-11(17)7-6-10(14(15)20)16-12(18)8-4-2-3-5-9(8)13(16)19/h2-5,10H,6-7H2,1H3

Upstream product

• 50-35-1 thalidomide 
• 74-88-4 methyl iodide 
• 85-44-9 phthalic anhydride 
• 31140-42-8 (RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester 
• 67-56-1 methanol 
• 373-68-2 tetramethylammonium fluoride 
• 74-89-5 methylamine 
• 3343-28-0 N-phthaloylglutamic acid anhydride 

Relevant articles and documents

Physicochemical characterization and solubility analysis of thalidomide and its N-alkyl analogs

Purpose. The present study was primarily aimed at exploring the feasibility of improving percutaneous delivery via chemical manipulation of the thalidomide molecule to form analogs with improved physicochemical properties. N-Alkyl analogs were synthesized with the belief that these would be suitably hydrophobic and far less crystalline than the reference compound. This article presents their physicochemical properties. Methods. Thalidomide and three of its N-alkyl analogs were synthesized. Identification and levels of purity (>96%) were assured through element analysis, fast atom-bombardment mass spectrometry, nuclear magnetic resonance spectroscopy, and high-performance liquid chromatography. N-Octanol/water partition cohigh efficients were determined at pH 6.4. Solubilities in water and a series of n-alkanols were obtained. Best-fit solubility parameters were determined from the solubilities of the respective compounds in London solvents and were also calculated from respective hexane solubilities, melting points and heats of fusion. Results. Methylation of the thalidomide molecule at its acidic nitrogen led to an aqueous solubility about 6-fold higher than thalidomide but, because the alkyl chain length was further extended from methyl to pentyl, aqueous solubilities decreased essentially exponentially. The destabilization of the crystalline structure with increasing alkyl chain length led to an increased solubility in nonpolar media. The log partition coefficient increased linearly with increasing alkyl chain length and the solubility parameters declined systematically through this series. By adding a methyl group to the thalidomide structure, the melting point dropped by more than 100°C. Adding to the alkyl chain length led to further, more modest decreases. Heats of fusion decreased dramatically upon thalidomide's alkylation as well. Conclusion. Alkylation of the thalidomide molecule resulted in compounds with physicochemical properties that appear to be markedly better suited for percutaneous delivery.

Selective Methylation of Amides, N-Heterocycles, Thiols, and Alcohols with Tetramethylammonium Fluoride

We herein disclose the use of tetramethylammonium fluoride (TMAF) as a direct and selective methylating agent of a variety of amides, indoles, pyrroles, imidazoles, alcohols, and thiols. The method is characterized by operational simplicity, wide scope, and ease of purification. Our computational studies suggest a concerted methylation-deprotonation as the preferred reaction pathway.

AMINE-LINKED C3-GLUTARIMIDE DEGRONIMERS FOR TARGET PROTEIN DEGRADATION

This invention provides amine-linked C3-glutarimide Degronimers and Degrons for therapeutic applications as described further herein, and methods of use and compositions thereof as well as methods for their preparation.