2,2-Dimethyl-1,3-dioxane-4,6-dione

Base Information

• Chemical Name: 2,2-Dimethyl-1,3-dioxane-4,6-dione
• CAS No.: 2033-24-1
• Deprecated CAS: 2550393-68-3
• Molecular Formula: C6H8O4
• Molecular Weight: 144.127
• Hs Code.: 29322090
• European Community (EC) Number: 217-992-8
• NSC Number: 688343,71902
• UNII: DD139RP1SC
• DSSTox Substance ID: DTXSID7051846
• Nikkaji Number: J7.852B
• Wikipedia: Meldrum%27s_acid,Meldrum's_acid
• Wikidata: Q421283
• Mol file: 2033-24-1.mol

Synonyms:2,2-dimethyl-1,3-dioxane-4,6-dione;cyclic isopropylidene malonate;Meldrum's acid

Chemical Property of 2,2-Dimethyl-1,3-dioxane-4,6-dione

Chemical Property:

• Appearance/Colour: white to beige crystals
• Vapor Pressure: 1.89E-05mmHg at 25°C
• Melting Point: 92-96 °C(lit.)
• Refractive Index: 1.571
• Boiling Point: 356.7 °C at 760 mmHg
• PKA: 5.1(at 25℃)
• Flash Point: 195.1 °C
• PSA: 52.60000
• Density: 1.201 g/cm³
• LogP: 0.21260
• Storage Temp.: 0-6°C
• Solubility.: dioxane: soluble5%, clear to very slightly hazy, colorless to fa
• Water Solubility.: 2.5 g/100 mL (20 ºC)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 144.04225873
• Heavy Atom Count: 10
• Complexity: 164

Purity/Quality:

98.0%min ^*data from raw suppliers

Meldrum’sAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, T
• Hazard Codes: Xi,T
• Statements: 36/37/38-45
• Safety Statements: 37/39-24/25-53-45-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Other Organic Compounds
• Canonical SMILES: CC1(OC(=O)CC(=O)O1)C
• Uses: Meldrum`s acid is an intermediate for different organic syntheses. For typical reactions please consult the Meldrum`s acid brochure, which you can order. Contact us. Product Data Sheet An antimicrobial agent In organic synthesis as a substitute for acyclic malonic esters and generally as a C3O2 synthon. 2,2-Dimethyl-1,3-dioxane-4,6-dione was used in the synthesis of:macrocyclic β-keto lactone4-pyridyl-substituted heterocycles2-substituted indolesisofraxidin.

Technology Process of 2,2-Dimethyl-1,3-dioxane-4,6-dione

There total 61 articles about 2,2-Dimethyl-1,3-dioxane-4,6-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

5-(bis(4-tert-phenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione → cycl-isopropylidene malonate (2033-24-1) + 1,1-bis(4-t-butylphenyl)methane (19099-48-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 24h; under 760.051 Torr;

DOI:10.1002/adsc.201600535

Reference yield: 98.0%

5-((2-methoxyphenyl)(phenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione → cycl-isopropylidene malonate (2033-24-1) + o-benzyl anisole (883-90-9)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 24h; under 760.051 Torr;

DOI:10.1002/adsc.201600535

Reference yield: 96.0%

5-(bis(4-methoxyphenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione (1190929-81-7) → cycl-isopropylidene malonate (2033-24-1) + 4,4'-dianisylmethane (726-18-1)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 24h; under 760.051 Torr;

DOI:10.1002/adsc.201600535

upstream raw materials:

2-chloro-2-nitro-propane

sodium diethylmalonate

malonic acid

isopropenyl-malonic acid diethyl ester

Downstream raw materials:

2,2-dimethyl-5-(piperidin-2-ylidene)-1,3-dioxane-4,6-dione

5-(furan-2-ylmethyl)-2,2-dimethyl[1,3]dioxane-4,6-dione

5-furfurylidene-2,2-dimethyl-[1,3]dioxane-4,6-dione

2,2-dimethyl-5-thiophen-2-ylmethylene-[1,3]dioxane-4,6-dione

Refernces

• 1、 Shevchenko,Khimich,Platz,Nikolaev. "Chemistry of diazocarbonyl compounds: XXVII. Thermolysis and photolysis of diazirines, derivatives of 1,3-dioxane-4,6-dione". . p. 1213 - 1219. Retrieved 2006.
• 2、 Bogdanova, Aneta,Popik, Vladimir V.. "Experimental and Theoretical Investigation of Reversible Interconversion, Thermal Reactions, and Wavelength-Dependent Photochemistry of Diazo Meldrum's Acid and Its Diazirine Isomer, 6,6-Dimethyl-5,7-dioxa-1,2-diaza-spiro[2,5]oct-1-ene-4,8-dione". . p. 14153 - 14162. Retrieved 2003.
• 3、 Tong, Fei,Chen, Shaolong,Li, Zhiwei,Liu, Mingyue,Al-Kaysi, Rabih O.,Mohideen, Umar,Yin, Yadong,Bardeen, Christopher J.. "Crystal-to-Gel Transformation Stimulated by a Solid-State E→Z Photoisomerization". . p. 15429 - 15434. Retrieved 2019.
• 4、 Abramovitch. "-". . p. 361. Retrieved 1959.
• 5、 Ferreira, Natasha L.,de Cordova, Letícia M.,Schramm, Adriana D.S.,Nicoleti, Celso R.,Machado, Vanderlei G.. "Chromogenic and fluorogenic chemodosimeter derived from Meldrum's acid detects cyanide and sulfide in aqueous medium". . p. 142 - 153. Retrieved 2019.
• 6、 -. "Method for synthesizing coumarin-3-carboxylic acid compounds by one-pot two-step method". Paragraph 0053; 0055-0056; 0079; 0081-0083. . Retrieved 2021/06/12.
• 7、 Sabahi-Agabager, Leila,Eskandari, Habibollah,Nasiri, Farough,Shamkhali, Amir Nasser,Baghi Sefidan, Somayyeh. "Properties of a furan ring-opening reaction in aqueous micellar solutions for selective sensing of mesalazine". . . Retrieved 2021/05/04.