15014-25-2 | Dibenzyl malonate

Packsize	Purity	Availability	Price	Discounted Price
5g	97%	in stock	$9.00	$6.00
10g	97%	in stock	$15.00	$10.00
25g	97%	in stock	$32.00	$22.00
100g	97%	in stock	$122.00	$85.00

Description

• Catalog Number: AA75457
• Chemical Name: Dibenzyl malonate
• CAS Number: 15014-25-2
• Molecular Formula: C17H16O4
• Molecular Weight: 284.3065
• MDL Number: MFCD00004779
• SMILES: O=C(CC(=O)OCc1ccccc1)OCc1ccccc1
• NSC Number: 101027

Computed Properties

• Complexity: 296
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 21
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• XLogP3: 3.1

Upstream Synthesis Route

Dibenzyl malonate is a versatile compound commonly used in chemical synthesis as a key building block for the preparation of various organic molecules. Its unique structure and reactivity make it particularly valuable in the formation of complex organic compounds through a variety of reactions.One prominent application of dibenzyl malonate is its role as a precursor in the Claisen condensation reaction. This reaction allows for the formation of β-keto esters, which are important intermediates in the synthesis of numerous pharmaceuticals, agrochemicals, and natural products. By undergoing a Claisen condensation with appropriate reagents, dibenzyl malonate can yield β-keto esters that can further be transformed into diverse organic compounds.Additionally, dibenzyl malonate can participate in decarboxylative reactions, where the carboxyl group is removed, leading to the formation of substituted benzyl compounds. This type of transformation is widely utilized in the synthesis of aromatic compounds with specific functional groups.Furthermore, dibenzyl malonate can serve as a masked form of malonic acid, providing a protected version of the malonate functionality in organic reactions. By strategically deprotecting the dibenzyl malonate group under certain conditions, chemists can access the reactive malonate moiety for subsequent transformations, enabling the synthesis of intricate organic molecules.Overall, the versatility and reactivity of dibenzyl malonate make it a valuable reagent in organic synthesis, allowing chemists to access a wide array of functionalized compounds with diverse applications in the fields of pharmaceuticals, materials science, and agrochemicals.

Literature

• Inhibition of Escherichia coli glycosyltransferase MurG and Mycobacterium tuberculosis Gal transferase by uridine-linked transition state mimics.

  Bioorganic & medicinal chemistry 20100401

• Microsphere-based protease assays and screening application for lethal factor and factor Xa.

  Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

• Polymer-supported bisBINOL ligands for the immobilization of multicomponent asymmetric catalysts.

  Organic letters 20030724

• Catalysis of the Michael addition reaction by late transition metal complexes of BINOL-derived salens.

  The Journal of organic chemistry 20030307

• BINOL-salen metal catalysts incorporating a bifunctional design.

  Organic letters 20010531