Triethyl methanetricarboxylate

• CAS: 6279-86-3
• Catalog Number: ACM6279863
• Category: Main Products
• Molecular Weight: 232.23
• Molecular Formula: C10H16O6
• Synonyms: tris(carboethoxy)methane
• Boiling Point: 253 °C
• Melting Point: 25-26 °C
• Flash Point: 113 °C
• Density: 1.095 g/mL
• Appearance: Colorless or White Liquid or Solid

Case Study

Triethyl Methanetricarboxylate for the Palladium-Catalyzed Allylation Reaction

Cravotto G, et al. Tetrahedron, 1998, 54(8), 1639-1646.

This study highlights the synthetic utility of TEMT in palladium-mediated C-C bond formation, offering a valuable approach for generating densely functionalized ester compounds under practical laboratory conditions.
Triethyl methanetricarboxylate (TEMT) was employed as a nucleophilic substrate in a palladium-catalyzed allylation reaction with allyl carbonates, demonstrating its high reactivity under mild conditions. The transformation was facilitated by catalytic amounts of a Pd(0) complex in the presence of an appropriate ancillary ligand, allowing for efficient C-C bond formation. The reaction proceeded rapidly at ambient temperature, producing the corresponding allylated derivatives of TEMT in excellent yields. Notably, the use of allyl carbonates as electrophilic partners enabled regioselective allylic substitution with minimal byproduct formation. The reaction conditions underscore the mildness and efficiency of the catalytic system, making it highly suitable for constructing functionalized triester scaffolds.

Triethyl Methanetricarboxylate for the Alkylation of Alcohols via Mitsunobu Reaction

Cravotto G, et al. Tetrahedron, 1996, 52(40), 13007-13016.

Triethyl methanetricarboxylate (TEMT) has been successfully employed as a reactive methylene surrogate in Mitsunobu alkylation reactions, enabling the efficient dehydrative alkylation of various alcohols. Under classical Mitsunobu conditions-typically involving triphenylphosphine (PPh₃) and diethyl azodicarboxylate (DEAD) in anhydrous tetrahydrofuran (THF)-TEMT undergoes substitution with primary, benzylic, and allylic alcohols to furnish the corresponding alkylated products in fair to good yields.
The procedure begins by dissolving TEMT and the target alcohol in dry THF under an inert nitrogen atmosphere. Equimolar amounts of PPh₃ and DEAD are then added at 0 °C, followed by stirring at room temperature for several hours. The Mitsunobu reaction proceeds via the formation of an alkoxyphosphonium intermediate, which is displaced by the nucleophilic enolate-like center of TEMT, resulting in C-C bond formation and elimination of the corresponding hydrazine and phosphine oxide byproducts.

Custom Q&A

What is the molecular formula of Triethyl methanetricarboxylate?

The molecular formula of Triethyl methanetricarboxylate is C10H16O6.

What are the synonyms for Triethyl methanetricarboxylate?

The synonyms for Triethyl methanetricarboxylate are Tricarbethoxymethane and Methanetricarboxylic acid, triethyl ester.

What is the computed molecular weight of Triethyl methanetricarboxylate?

The computed molecular weight of Triethyl methanetricarboxylate is 232.23 g/mol.

When was Triethyl methanetricarboxylate created?

Triethyl methanetricarboxylate was created on March 26, 2005.

What is the IUPAC name of Triethyl methanetricarboxylate?

The IUPAC name of Triethyl methanetricarboxylate is triethyl methanetricarboxylate.

What is the InChI of Triethyl methanetricarboxylate?

The InChI of Triethyl methanetricarboxylate is InChI=1S/C10H16O6/c1-4-14-8(11)7(9(12)15-5-2)10(13)16-6-3/h7H,4-6H2,1-3H3.

What is the InChIKey of Triethyl methanetricarboxylate?

The InChIKey of Triethyl methanetricarboxylate is AGZPNUZBDCYTBB-UHFFFAOYSA-N.

What is the canonical SMILES of Triethyl methanetricarboxylate?

The canonical SMILES of Triethyl methanetricarboxylate is CCOC(=O)C(C(=O)OCC)C(=O)OCC.

What is the CAS number of Triethyl methanetricarboxylate?

The CAS number of Triethyl methanetricarboxylate is 6279-86-3.

What is the hydrogen bond acceptor count of Triethyl methanetricarboxylate?

The hydrogen bond acceptor count of Triethyl methanetricarboxylate is 6.