6342-79-6

Basic information

• Product Name: 1,2-di(morpholin-4-yl)ethane-1,2-dione
• Synonyms: 1,2-Di-morpholin-4-yl-ethane-1,2-dione; 1,2-ethanedione, 1,2-di-4-morpholinyl-
• CAS NO: 6342-79-6
• Molecular Formula: C₁₀H₁₆N₂O₄
• Molecular Weight: 228.245
• Mol File: 6342-79-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 371.3°C at 760 mmHg
• Flash Point: 178.4°C
• Density: 1.281g/cm³
• Vapor Pressure: 1.04E-05mmHg at 25°C
• Refractive Index: 1.522
• CAS DataBase Reference: 1,2-di(morpholin-4-yl)ethane-1,2-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-di(morpholin-4-yl)ethane-1,2-dione(6342-79-6)
• EPA Substance Registry System: 1,2-di(morpholin-4-yl)ethane-1,2-dione(6342-79-6)

Safety Data

• Hazardous Substances Data: 6342-79-6(Hazardous Substances Data)

Usage

General Description

1,2-di(morpholin-4-yl)ethane-1,2-dione is a chemical compound with the molecular formula C10H16N2O4. It is also known as DMPU (N,N'-Dimethylpropyleneurea) and is a polar aprotic solvent that is used in various organic reactions and as a co-solvent in lithium-ion battery electrolytes. DMPU is a colorless liquid with a high boiling point and a low vapor pressure, making it useful for reactions requiring high temperatures. It is also used as a reagent in the synthesis of pharmaceuticals and agrochemicals. DMPU is considered to be a versatile and efficient solvent for a variety of reactions and applications in organic chemistry.

Upstream product

• 15159-40-7 4-morpholinocarbonyl chloride 
• 917-54-4 methyllithium 
• 598-30-1 sec.-butyllithium 
• 110-91-8 morpholine 
• 201230-82-2 carbon monoxide 
• 31268-20-9 bromomethyl phenyl sulfoxide 

Downstream Products

• 471-46-5 Oxalamide 
• 622-40-2 2-(morpholin-4-yl)ethanol 
• 51068-78-1 2-hydroxy-1-(morpholin-4-yl)ethan-1-one 
• 107-21-1 ethylene glycol 

Relevant articles and documents

Switchable palladium-catalyst reaction of bromomethyl sulfoxides, CO, and N-nucleophiles: Aminocarbonylation at Csp3 versus oxidative carbonylation of amines

The palladium-catalyzed reaction of α-bromomethyl sulfoxides, carbon monoxide, and N-nucleophiles follows different reaction pathways according to the catalytic system and the reaction conditions. The Pd-xantphos catalyst affords high yields of α-sulfinyl amides by an aminocarbonylation process and is the first example of this type of transformation for a nonbenzylic sp3-hybridized carbon. On the other hand, the oxidative carbonylation of amines occurs with α-bromomethyl sulfoxides, carbon monoxide, and catalytic Pd(PPh3)4 under aerobic conditions, yielding ureas and oxalamides from either primary or secondary amines. The reaction with ambident nucleophiles such as amino alcohols was highly selective and took place exclusively at the amino group despite the presence of the alcohol functionality. In parallel to the reaction paths for simple amines, amino alcohols were converted into hydroxy sulfinyl amides when the reaction was catalyzed by Pd-xantphos, while Pd(PPh3)4 catalyst afforded cyclic carbamates. The alkoxycarbonylation reaction of bromomethyl sulfoxides with simple alcohols and CO leading to the corresponding sulfinyl esters is also described.

Preparation of tertiary amides from carbamoyl chlorides and organocuprates

(Chemical Equation Presented) Reaction of carbamoyl chlorides with cyano-Gilman cuprates affords tertiary amides in good to excellent yields. The reaction is general due to the possibility of using reagents made either from organolithium or from Grignard compounds. The characterization of the main side products allowed for the suggestion of a possible mechanism.