7270-63-5

Basic information

• Product Name: 5-DIAZOMELDRUM'S ACID
• Synonyms: AURORA KA-3831;DIAZOMALONIC ACID CYCLIC ISOPROPYLIDENE ESTER;DIAZOMALONIC ACID CYCLIC ISOPROPYLIDINE ESTER;CYCLO-ISOPROPYLIDENE DIAZOMALONATE;CYCLIC-ISOPROPYLIDENE DIAZOMALONATE;CYCL-ISOPROPYLIDENE DIAZOMALONATE;5-DIAZO-2,2-DIMETHYL-1,3-DIOXANE-4,6-DIONE;5-DIAZO-2,2-DIMETHYL-1,3-DIOXOLANE-4,6-DIONE
• CAS NO: 7270-63-5
• Molecular Formula: C₆H₆N₂O₄
• Molecular Weight: 172.14
• Product Categories: Dioxanes;Dioxanes & Dioxolanes
• Mol File: 7270-63-5.mol

Chemical Properties

• Melting Point: 95 °C
• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: soluble in Methanol
• CAS DataBase Reference: 5-DIAZOMELDRUM'S ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-DIAZOMELDRUM'S ACID(7270-63-5)
• EPA Substance Registry System: 5-DIAZOMELDRUM'S ACID(7270-63-5)

Safety Data

• RIDADR: 1325
• HazardClass: 4.1
• PackingGroup: III
• Hazardous Substances Data: 7270-63-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
5-Diazomeldrum's acid is used as a reagent for facilitating a range of chemical reactions. Its application is crucial in the synthesis of other compounds and the preparation of diazo compounds, which are essential in various chemical processes.
Used in Research and Development:
In the field of research and development, 5-Diazomeldrum's acid is utilized for exploring new chemical reactions and syntheses. Its unique properties allow scientists to investigate novel pathways and mechanisms in organic chemistry.
Used in Pharmaceutical Industry:
5-Diazomeldrum's acid is employed in the pharmaceutical industry as a key intermediate in the synthesis of certain pharmaceutical compounds. Its reactivity and ability to participate in various chemical reactions make it a valuable tool in drug development.
Used in Chemical Synthesis:
In chemical synthesis, 5-Diazomeldrum's acid is used as a versatile building block for creating complex organic molecules. Its reactivity and compatibility with a wide range of other chemicals make it an essential component in the synthesis of various organic compounds.
Safety Precautions:
Due to the unstable and explosive nature of 5-Diazomeldrum's acid, it is crucial to follow strict safety protocols when handling and storing this chemical. Appropriate protective equipment, such as gloves, goggles, and lab coats, should be worn at all times. Additionally, it is essential to work in a well-ventilated area and avoid any sources of ignition or heat to minimize the risk of accidents and exposure.

InChI:InChI=1/C6H6N2O4/c1-6(2)11-4(9)3(8-7)5(10)12-6/h1-2H3

Upstream product

• 81539-54-0 isonitroso Meldrum’s acid 
• 538-75-0 dicyclohexyl-carbodiimide 
• 67-56-1 methanol 
• 68695-08-9 6,6-dimethyl-4,8-dioxo-5,7-dioxa-1,2-diazaspiro<2.5>oct-1-ene 

Downstream Products

• 68695-08-9 6,6-dimethyl-4,8-dioxo-5,7-dioxa-1,2-diazaspiro<2.5>oct-1-ene 
• 2033-24-1 cycl-isopropylidene malonate 
• 62609-79-4 methyl 2,2-dimethyl-5-oxo-1,3-dioxolane-4-carboxylate 
• 97801-91-7 2,2-dimethyl-4,6-dioxo-5-methoxy-1,3-dioxane 
• 73466-63-4 C₁₅H₂₂O₄ 
• 73466-66-7 2-(2,2-dimethyl-1,3-dioxolan-4-on-5-yl)-2,6,6-trimethylcyclohexanecarboxylic acid 
• 80-69-3 tartronic acid 
• 141-82-2 malonic acid 
• 62609-78-3 2,2-dimethyl-5-oxo-1,3-dioxolane-4-carboxylic acid 
• 70912-53-7 2,2-dimethyl-5-(piperidin-2-ylidene)-1,3-dioxane-4,6-dione 
• 1436430-74-8 ethyl 2-(2-(1H-pyrazol-1-yl)phenyl)acetate 
• 1436430-75-9 ethyl 2-(3-methyl-2-(pyrimidin-2-yl)phenyl)acetate 
• 1436430-76-0 ethyl 2-(2-(pyridin-2-yl)phenyl)acetate 
• 1458694-71-7 2,4-di-p-tolyl-6H-furo[2,3-b]pyran-6-one 

Relevant articles and documents

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

The photochemical or thermal decomposition of diazo Meldrum's acid (1) in methanolic solutions yields ketoester 3a, the product of the Wolff rearrangement, while products produced from the singlet carbene were not detected. This observation, combined with the analysis of activation parameters for the thermal decomposition of 1, as well as with the results of DFT B3PW91/6-311+G(3df,2p) and MP2/aug-cc-pVTZ//B3PW91/6-311+G(3df,2p) calculations, allows us to conclude that the Wolff rearrangement of 1 is a concerted process. The outcome of the photolysis of diazo Meldrum's acid depends on the wavelength of irradiation. Irradiation with 254 nm light results in an efficient (Φ254 = 0.34) photo-Wolff reaction, while at 355 nm, the formation of diazirine 2 becomes the predominant process (Φ 350 = 0.024). This unusual wavelength selectivity indicates that Wolff rearrangement and isomerization originate from different electronically excited states of 1. The UV irradiation of diazirine 2 leads to the loss of nitrogen and the Wolff rearrangement, apparently via a carbene intermediate. This process is accompanied by a reverse isomerization to diazo Meldrum's acid. Triplet-sensitized photolysis of both isomers results in the formation of Meldrum's acid, the product of a formal reduction of 1 and 2. Mild heating of diazirine 2 produces quantitative yields of diazo Meldrum's acid. The activation parameters for thermal reactions of diazo 1 and diazirino 2 isomers were determined in aqueous and dioxane solutions.

Wavelength-dependent photochemistry of diazo Meldrum's acid and its spirocyclic isomer, diazirino Meldrum's acid: Wolff rearrangement versus isomerization

Photoreaction of diazo Meldrum's acid (1) shows a unique wavelength selectivity. At 254 nm it results in efficient (φ254 = 0.34) Wolff rearrangement, while irradiation with 355 nm light leads to a completely different process, isomerization into corresponding cyclic α,α″-dicarbonyl diazirine 2 (φ350 = 0.024). UV photolysis of diazirine 2 is accompanied by two competing processes: loss of nitrogen followed by the Wolff rearrangement and isomerization into diazo compound 1. Thermal decomposition of 1 leads to clean Wolff rearrangement, while heating of 2 causes quantitative conversion into diazo isomer 1. Copyright

Reaction of 5-hydroxyimino-1,3-dioxine-4,6-dione (isonitroso meldrum's acid) with carbodiimides to give parabanic acids

Reaction of 5-hydroxyimino-1,3-dioxine-4,6-dione (isonitroso Meldrum's Acid) with carbodiimides gave cyanoformamide derivatives in quantitative yields, which cyclized to iminoparabanic acids and parabanic acids under basic and acidic conditions, respectively.