1214-54-6

Basic information

• Product Name: 2,2-DIMETHYL-5-(PHENYLMETHYLENE)-1,3-DIOXANE-4,6-DIONE
• Synonyms: 2,2-DIMETHYL-5-(PHENYLMETHYLENE)-1,3-DIOXANE-4,6-DIONE;2-Benzylidenemalonic acid isopropylidene ester;5-Benzylidene-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS NO: 1214-54-6
• Molecular Formula: C₁₃H₁₂O₄
• Molecular Weight: 232.23
• Mol File: 1214-54-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,2-DIMETHYL-5-(PHENYLMETHYLENE)-1,3-DIOXANE-4,6-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-DIMETHYL-5-(PHENYLMETHYLENE)-1,3-DIOXANE-4,6-DIONE(1214-54-6)
• EPA Substance Registry System: 2,2-DIMETHYL-5-(PHENYLMETHYLENE)-1,3-DIOXANE-4,6-DIONE(1214-54-6)

Safety Data

• Hazardous Substances Data: 1214-54-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Fine Chemical Synthesis:
2,2-DIMETHYL-5-(PHENYLMETHYLENE)-1,3-DIOXANE-4,6-DIONE is used as a building block for the synthesis of pharmaceuticals and fine chemicals due to its reactivity and stability in forming intermediates that are crucial in the production of these compounds.
Used in the Food Industry:
In the food industry, 2,2-DIMETHYL-5-(PHENYLMETHYLENE)-1,3-DIOXANE-4,6-DIONE is used as a flavoring agent, leveraging its aromatic properties to enhance the taste and aroma of various food products.
Used in Fragrance and Perfume Preparation:
2,2-DIMETHYL-5-(PHENYLMETHYLENE)-1,3-DIOXANE-4,6-DIONE is used as a component in the preparation of fragrances and perfumes, where its unique aromatic characteristics contribute to the creation of distinct and appealing scents.

Upstream product

• 2033-24-1 cycl-isopropylidene malonate 
• 100-52-7 benzaldehyde 
• 631-61-8 ammonium acetate 
• 126-81-8 dimedone 
• 75039-60-0 5-[(dimethylamino)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 15568-85-1 5-methoxymethylene-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 110-86-1 pyridine 
• 105-36-2 ethyl bromoacetate 
• 70-11-1 α-bromoacetophenone 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 102-04-5 1,3-Diphenylpropanone 
• 579-43-1 (1S,2R)-1,2-diphenylethane-1,2-diol 
• 3709-27-1 5-benzyl-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 1137-96-8 N-(benzylidene)aniline N-oxide 

Downstream Products

• 41274-87-7 2,2,6,6-tetramethyl-7-morpholin-4-yl-5-phenyl-6,7-dihydro-5H-pyrano[2,3-d][1,3]dioxin-4-one 
• 41274-82-2 2,2-dimethyl-9a-morpholin-4-yl-5-phenyl-5a,6,7,8,9,9a-hexahydro-5H-[1,3]dioxino[4,5-b]chromen-4-one 
• 53990-81-1 2,4-Bis(benzyliden)cyclobutan-1,3-dion 
• 3056-73-3 N-phenylcinnamamide 
• 3709-33-9 1-benzyl-6,6-dimethyl-5,7-dioxaspiro[2.5]octane-4,8-dione 
• 3709-32-8 6,6-dimethyl-1-phenyl-5,7-dioxaspiro[2.5]octane-4,8-dione 
• 103150-39-6 C₁₈H₂₂NO₄^(1-) 
• 73372-66-4 C₁₈H₂₂NO₄^(1-)*H⁽¹⁺⁾ 
• 12256-88-1 Meldrum's acid anion 
• 100-52-7 benzaldehyde 
• 75804-53-4 2,2-Dimethyl-5-(1-phenylethyl)-1,3-dioxane-4,6-dione 
• 131447-60-4 1,7,7-Trimethyl-4-phenyl-4,6,7,8-tetrahydro-1H,3H-quinoline-2,5-dione 
• 132599-92-9 7,7-dimethyl-1,4-diphenyl-3,4,7,8-tetrahydroquinoline-2,5(1H,6H)-dione 
• 132600-14-7 1,4-diphenyl-3,4,7,8-tetrahydroquinoline-2,5(1H,6H)-dione 

Relevant articles and documents

Ionic liquid-mediated knoevenagel condensation of Meldrum's acid and aldehydes

A simple, efficient, and green protocol for Knoevenagel condensation of Meldrum's acid and aldehydes in ionic liquid at room temperature without any catalyst is described. The reaction has been performed in different ionic liquids. The enhancement in the

An Adverse Effect of Higher Catalyst Loading and Longer Reaction Time on Enantioselectivity in an Organocatalytic Multicomponent Reaction

An enantioselective organocatalytic multicomponent reaction of aldehydes, ketones, and Meldrum's acid has been developed. A cinchona-based primary amine (1 mol %) catalyses the multicomponent reaction via the formation of the Knoevenagel product and a chiral enamine to form enantiopure δ-keto Meldrum's acids in a tandem catalytic pathway. An adverse effect of higher catalyst loading and longer reaction time on enantioselectivity was studied. This mild protocol provides an easy access to enantiopure carboxylic acids, esters and amides and the method is scalable on a gram quantity. DFT calculations were carried out on the proposed reaction mechanism and they were in close agreement with the experimental results.

Organocatalysed multicomponent synthesis of pyrazolidinones: Meldrum's acid approach

We discovered a novel organocatalysed multicomponent domino Knoevenagel-aza-Michael-cyclocondensation reaction leading to an unprecedented straightforward synthesis of 1,5-diazabicyclo[3.3.0]octane-2,6-diones. The specific capability of the (DHQ)2PHAL organocatalyst in this process was also highlighted to eventually furnish the corresponding bicyclopyrazolidinones with up to 96:4 er. This journal is the Partner Organisations 2014.

An alternative, practical, and ecological protocol for synthesis of arylidene analogues of Meldrum’s acid as useful intermediates

This paper presents an ecological protocol for Knoevenagel condensation using a catalytic amount of 4,4′-trimethylenedipiperidine as a versatile, efficient, safe, commercially available, inexpensive, and recyclable organocatalyst by a ball-milling process

GaCl3-catalyzed insertion of diazene derivatives into the cyclopropane ring

(Chemical Equation Presented) GaCl3 has been found to efficiently catalyze the formal cycloadditions of diazene derivatives 6 onto 2-arylcyclopropane-1,1-dicarboxylates 5, giving rise to the pyrazolidine derivatives 7. The insertion into the cy

One Pot Synthesis of Monoalkylated and Mixed, Dialkylated Meldrum's Acid Derivatives

A simple one pot method, involving sequential Knoevenagel condensation of Meldrum's acid with aromatic aldehydes, conjugate reduction of ylidene Meldrum's acid using sodium borohydride followed by alkylation, to prepare mixed dialkylated derivatives of Meldrum's acid is described.

Knoevenagel condensation of aldehydes with cyclic active methylene compounds in water

A new route of Knoevenagel condensation of aromatic aldehydes with Meldrum's acid, barbituric acid and dimedone in the presence of cetyltrimethyl ammonium bromide at room temperature in water is described.

Multicomponent self-sorting of a Pd7 molecular boat and its use in catalytic Knoevenagel condensation

Unique three-component self-assembly of a cis-blocked 90° Pd(ii) acceptor with a mixture of tri- and tetra-imidazole donors led to the self-sorting of a Pd7 molecular boat with an internal nanocavity, which catalyses the Knoevenagel condensation of a series of aromatic aldehydes with 1,3-dimethylbarbituric acid and Meldrum's acid in aqueous media.

Difluoromethylene phosphabetaine as an equivalent of difluoromethyl carbanion

A method for nucleophilic difluoromethylation of reactive Michael acceptors, aldehydes, and azomethines is described. The reaction is performed using the readily available and air-stable reagent difluoromethylene phosphabetaine. The process involves inter

Three Resorcin[4]arene-Based Two-Dimensional Zn(II) Supramolecular Isomers Synthesized via a Structure-Directing Strategy for Knoevenagel Condensation

Herein, in the presence of three structure-directing agents (SDAs), a family of imidazole-functionalized resorcin[4]arene-based coordination polymers (CPs), [Zn(TIC4R)(HCOO)]·HCOO·0.5DMF·1.5H2O (1), [Zn(TIC4R)(CN)]·HCOO·DMF·2.5H2O (2), and [Zn(TIC4R)(H2O)