61193-04-2

Basic information

• Product Name: 4,4-Dimethyl-2,6-dioxopiperidine-3,5-dicarbonitrile
• Synonyms: 4,4-Dimethyl-2,6-dioxopiperidine-3,5-dicarbonitrile;3-(R,S),5-(R,S)-3,5-dicyano-4,4-dimethyl-2,6-dioxopiperidine
• CAS NO: 61193-04-2
• Molecular Formula: C₉H₉N₃O₂
• Molecular Weight: 191.18666
• Mol File: 61193-04-2.mol

Chemical Properties

• Melting Point: 212 °C
• Boiling Point: 484.8°C at 760 mmHg
• Flash Point: 247°C
• Appearance: /
• Density: 1.27g/cm³
• Vapor Pressure: 1.49E-09mmHg at 25°C
• Refractive Index: 1.516
• PKA: 16.75±0.70(Predicted)
• CAS DataBase Reference: 4,4-Dimethyl-2,6-dioxopiperidine-3,5-dicarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4-Dimethyl-2,6-dioxopiperidine-3,5-dicarbonitrile(61193-04-2)
• EPA Substance Registry System: 4,4-Dimethyl-2,6-dioxopiperidine-3,5-dicarbonitrile(61193-04-2)

Safety Data

• Hazardous Substances Data: 61193-04-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4,4-Dimethyl-2,6-dioxopiperidine-3,5-dicarbonitrile is utilized as a building block in the synthesis of various organic compounds, playing a crucial role in the development of new pharmaceutical products.
Used in Agrochemical Production:
4,4-Dimethyl-2,6-dioxopiperidine-3,5-dicarbonitrile serves as an intermediate in the production of agrochemicals, contributing to the creation of substances that are vital for agricultural applications.
Used in Specialty Chemicals:
4,4-Dimethyl-2,6-dioxopiperidine-3,5-dicarbonitrile is also employed in the production of specialty chemicals, which are tailored for specific industries and applications.
Used in Medicinal Chemistry:
With its potential applications in medicinal chemistry, 4,4-Dimethyl-2,6-dioxopiperidine-3,5-dicarbonitrile is instrumental in the research and development of innovative drugs, enhancing the scope of treatment options available in the medical field.

InChI:InChI=1/C9H9N3O2/c1-9(2)5(3-10)7(13)12-8(14)6(9)4-11/h5-6H,1-2H3,(H,12,13,14)

Upstream product

• 110-89-4 piperidine 
• 67-64-1 acetone 
• 107-91-5 cyanoacetic acid amide 
• 759-58-0 ethyl isopropylidenecyanoacetate 
• 105-56-6 ethyl 2-cyanoacetate 
• 7732-18-5 water 

Downstream Products

• 5512-95-8 6,6-dimethyl-2,4-dioxo-3-aza-bicyclo[3.1.0]hexane-1,5-dicarbonitrile 
• 4839-46-7 3,3-Dimethylglutaric acid 
• 90961-84-5 3,7-Dibutyl-9,9-dimethyl-3,7-diaza-bicyclo[3.3.1]nonane-2,4,6,8-tetraone 
• 90961-45-8 N,N-di-n-butyl-9,9-dimethyl-3,7-diaza bicyclo-(3,3,1)-nonane 
• 17804-59-0 diethyl 3,3-dimethylglutarate 
• 22748-16-9 4,4-dimethylcyclopent-2-ene-1-one 
• 100620-05-1 2,2,4-trimethyl-cyclohexane-1,1,3,3-tetracarboxylic acid 
• 90868-50-1 2,4-Dioxo-5-carboxamido-6,6-dimethyl-3-azabicyclo<3.1.0>hexan-1-carbonsaeure 
• 91004-47-6 2,4-Dioxo-6,6-dimethyl-3-azabicyclo<3.1.0>hexan-1,5-dicarbonsaeure 
• 53120-74-4 3,3-dimethylpent-1,5-diol 
• 4160-82-1 3,3-dimethylglutaric anhydride 
• 22791-80-6 4,4-dimethyl-tetrahydro-pyran-2-one 

Relevant articles and documents

The development of a new class of inhibitors for betaine-homocysteine S-methyltransferase

Betaine-homocysteine S-methyltransferase (BHMT) is an important zinc-dependent methyltransferase that uses betaine as the methyl donor for the remethylation of homocysteine to form methionine. In the liver, BHMT performs to half of the homocysteine remethylation. In this study, we systematically investigated the tolerance of the enzyme for modifications at the "homocysteine" part of the previously reported potent inhibitor (R,S)-5-(3-amino-3-carboxy-propylsulfanyl)-pentanoic acid (1). In the new compounds, which are S-alkylated homocysteine derivatives, we replaced the carboxylic group in the "homocysteine" part of inhibitor 1 with different isosteric moieties (tetrazole and oxadiazolone); we suppressed the carboxylic negative charge by amidations; we enhanced acidity by replacing the carboxylate with phosphonic or phosphinic acids; and we introduced pyrrolidine steric constraints. Some of these compounds display high affinity toward human BHMT and may be useful for further pharmacological studies of this enzyme. Although none of the new compounds were more potent inhibitors than the reference inhibitor 1, this study helped to completely defi ne the structural requirements of the active site of BHMT and revealed the remarkable selectivity of the enzyme for homocysteine.

Synthesis of 4-substituted 3,5-dicyano-2,6-piperidinediones using lithium nitride as a convenient source of ammonia

A simple and efficient one-pot synthesis of 4-substituted-3,5-dicyano-2,6-piperidinediones was achieved in good yields via the three-component reaction of aldehyde or ketone, ethyl cyanoacetate, lithium nitride (Li3N) as a convenient source of ammonia in MeOH.