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
• Article Data: 3

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

General Description

5-Diazomeldrum's acid is a diazo compound with the chemical formula C8H12N2O2. This chemical is highly sensitive and explosive in nature, making it a potentially hazardous substance. It is primarily used as a reagent in organic chemistry for various reactions, such as the synthesis of other compounds and the preparation of diazo compounds. Due to its unstable nature, special precautions must be taken when handling and storing 5-diazomeldrum's acid to minimize the risk of accidents and exposure. Additionally, it is important to follow strict safety protocols and use appropriate protective equipment when working with this chemical.

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

Upstream product

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

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 
• 3709-18-0 2,2,5-trimethyl-1,3-dioxane-4,6-dione 
• 1436430-75-9 ethyl 2-(3-methyl-2-(pyrimidin-2-yl)phenyl)acetate 
• 1436430-76-0 ethyl 2-(2-(pyridin-2-yl)phenyl)acetate 

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.

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.