60512-08-5

Basic information

• Product Name: (3R,4R)-3,4-dimethylpyrrolidine-2,5-dione
• Synonyms: (3R,4R)-3,4-Dimethylpyrrolidine-2,5-dione; 2,5-pyrrolidinedione, 3,4-dimethyl-, (3R,4R)-
• CAS NO: 60512-08-5
• Molecular Formula: C₆H₉NO₂
• Molecular Weight: 127.1412
• Mol File: 60512-08-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 261.1°C at 760 mmHg
• Flash Point: 129°C
• Density: 1.079g/cm³
• Vapor Pressure: 0.0118mmHg at 25°C
• Refractive Index: 1.447
• CAS DataBase Reference: (3R,4R)-3,4-dimethylpyrrolidine-2,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4R)-3,4-dimethylpyrrolidine-2,5-dione(60512-08-5)
• EPA Substance Registry System: (3R,4R)-3,4-dimethylpyrrolidine-2,5-dione(60512-08-5)

Safety Data

• Hazardous Substances Data: 60512-08-5(Hazardous Substances Data)

Usage

General Description

(3R,4R)-3,4-dimethylpyrrolidine-2,5-dione, also known as (R,R)-pipecolic acid, is a cyclic amino acid with a pyrrolidine ring structure. It is a white crystalline powder with a molecular formula of C7H11NO2 and a molecular weight of 141.17 g/mol. It is naturally occurring in the human body and is an intermediate in the biosynthesis of the neurotransmitter, gamma-aminobutyric acid (GABA). Additionally, (R,R)-pipecolic acid has been found to have potential pharmacological properties and may be useful in the treatment of inflammatory and autoimmune diseases due to its ability to modulate the immune response. It also has applications in the synthesis of pharmaceuticals and agrochemicals.

Upstream product

• 13545-04-5 2,3-dimethylsuccinic acid 
• 82621-78-1 2,3-dimethyl-N-bromosuccinimide 
• 5615-90-7 3-methylsuccinimide 
• 124-38-9 carbon dioxide 
• 74-88-4 methyl iodide 
• 17825-86-4 3,4-dimethylmaleimide 
• 766-39-2 2,3-Dimethylmaleic anhydride 

Downstream Products

• 344407-17-6 methyl 3-((methoxycarbonyl)amino)-2-methylbutanoate 
• 5309-82-0 trans-3,4-dimethylpyrrolidine 

Relevant articles and documents

Chemo- And diastereoselectivities in the electrochemical reduction of maleimides

The electrochemical cathodic reduction of cyclic imides (maleimides) to succinimides can be achieved chemoselectively in the presence of alkene, alkyne, and benzyl groups. The efficiency of the system was demonstrated by using a 3D electrode in a continuous flow reactor. The reduction of 3,4-dimethylmaleimides to the corresponding succinimides proceeds with a 3:2 diastereomeric ratio, which is independent of the nitrogen substituent and electrode surface area. The stereoselectivity of the process was rationalized by using DFT calculations, involving an acid-catalyzed tautomerization of a half-enol occurring through a double hydrogen-transfer mechanism.

PYRIMIDINE COMPOUNDS AND PESTS CONTROLLING COMPOSITION CONTAINING THE SAME

The present invention relates to a pyrimidine compound of the formula (I):wherein R?1? represents a hydrogen atom, halogen atom or C1-C4 alkyl; R?2? represents C3-C7 alkynyloxy; R?3? represents a hydrogen atom, halogen atom or C1-C3 alkyl; X represents C4

Excited-State ? Succimidyl and Glutarimidyl Radicals: Reversible Ring Opening

The free-radical isomerization of N-bromosuccinimide to β-bromopropionyl isocyanate has been examined.Of the two varieties of succinimidyl radical (S? or S?), only the ? excited state undergoes the ring opening to the β propionyl isocyanatyl radical.The conversion optimally takes place in >95percent yield.The dependence of NBS concentration along with results obtained from deuterium labeling studies indicate that the ring opening of S? is a reversible process.This explains the failure of N-chlorosuccinimide to produce β-chloropropionyl isocyanate, as well as the increase in ring-opened product for N-bromosuccinimides upon methyl substitution at the 2- and/or 3-position of the succinimidyl ring, since the open-chain radical intermediates are more stable.In the N-bromoglutarimide system, methyl groups on the 2-position are required for the glutarimidyl radicals to undergo the isomerization, ultimately producing isocyanates.The radical-chain nature of these systems is confirmed.