1196086-79-9

Basic information

• Product Name: TetrabutylphosphoniuM Malonate
• Synonyms: TetrabutylphosphoniuM Malonate
• CAS NO: 1196086-79-9
• Molecular Formula: C35H74O4P2
• Molecular Weight: 620.907182
• Mol File: 1196086-79-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 112-122°C
• Appearance: /
• CAS DataBase Reference: TetrabutylphosphoniuM Malonate(CAS DataBase Reference)
• NIST Chemistry Reference: TetrabutylphosphoniuM Malonate(1196086-79-9)
• EPA Substance Registry System: TetrabutylphosphoniuM Malonate(1196086-79-9)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3263 8 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 1196086-79-9(Hazardous Substances Data)

Upstream product

• 141-82-2 malonic acid 
• 14518-69-5 tetra-n-butylphosphonium hydroxide 

Relevant articles and documents

New Insights into the Reaction Capabilities of Ionic Organic Bases in Cu-Catalyzed Amination

The application of ionic organic bases in the copper-catalyzed amination reaction (Ullmann reaction) has been studied at room temperature, with sub-mol-% catalyst loadings, and with more challenging amines at elevated temperatures. The cation present in the base has been shown to have little effect on the reaction at standard catalyst and ancillary ligand loadings, whereas the choice of anion is crucial for good reactivity. A substrate scope carried out at room temperature with the best performing bases, TBAM and TBPM, showed both bases to be highly effective under these mild reaction conditions. Moreover, under sub-mol % catalyst loadings and room temperature conditions, TBPM gave good to excellent yields for a number of different amines and functionalized aryl iodides (14 examples). However, reactions involving more challenging amines gave little or no yield. By using more forceful conditions (120 °C) moderate to excellent yields of cross-coupled products containing more challenging amines was achievable using TBPM and to a lesser extent with TBAM. As part of this work a study on the stability of the organic bases at 120 °C was undertaken. TBAM is shown to decompose to give nBu3N and mono-butylmalonate at higher temperatures, and this can be correlated to a decrease in performance in the coupling reaction. The phosphonium cations in TBPM did not undergo analogous reactivity but were shown instead to experience some degree of deprotonation at the α-CH2 to generate phosphonium ylides. This however did not lead to a significantly degradation in the activity of the TBPM in the cross-coupling reaction.

Room-temperature copper-catalyzed carbon-nitrogen coupling of aryl iodides and bromides promoted by organic ionic bases

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