1807-68-7

Basic information

• Product Name: DIAZODIMEDONE
• Synonyms: Diazodimedone >=98.0% (HPLC)
• CAS NO: 1807-68-7
• Molecular Formula: C₈H₁₀N₂O₂
• Molecular Weight: 166.18
• Product Categories: Azo/Diazo Compounds;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 1807-68-7.mol
• Article Data: 49

Chemical Properties

• Melting Point: 105-108 °C
• Appearance: /
• CAS DataBase Reference: DIAZODIMEDONE(CAS DataBase Reference)
• NIST Chemistry Reference: DIAZODIMEDONE(1807-68-7)
• EPA Substance Registry System: DIAZODIMEDONE(1807-68-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1807-68-7(Hazardous Substances Data)

Usage

General Description

Diazodimedone is a chemical compound with the molecular formula C7H6N2O2. It is a diazo compound, which means it contains a nitrogen-nitrogen double bond. Diazodimedone is a yellow, crystalline solid that is highly reactive and sensitive to light and heat. It is used in organic synthesis as a reagent for the preparation of diazo compounds, which are important intermediates in the synthesis of pharmaceuticals, dyes, and other organic molecules. Additionally, it has been studied for its potential application in photochemical reactions and as a photoinitiator for polymerization processes. Despite its utility in organic chemistry, diazodimedone should be handled with caution due to its potential for explosive decomposition when exposed to certain conditions.

InChI:InChI=1/C8H10N2O2/c1-8(2)3-5(11)7(10-9)6(12)4-8/h3-4H2,1-2H3

Upstream product

• 41893-63-4 2-amino-5,5-dimethylcyclohexane-1,3-dione 
• 32583-63-4 2-Amino-3-hydroxy-5,5-dimethyl-cyclohex-2-enone 
• 126-81-8 dimedone 
• 1516-60-5 4-nitrophenyl azide 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 83538-02-7 2-Hydroxydimedon 
• 61579-97-3 4,4-dimethyl-2-(2-morpholin-4-yl-cyclohex-1-enecarbonyl)-cyclopentanone 
• 7337-97-5 1.1.1'.1'-Tetramethyl-4.4'-azo-dicyclohexandion-(3.5) 
• 60532-82-3 6,6-dimethyl-2-p-tolyloxy-6,7-dihydro-5H-cyclopenta[e][1,3]oxazin-4-one 
• 67398-48-5 4,4-Dimethyl-2-oxocyclopentancarbonsaeure-p-bromanilid 
• 67398-49-6 4,4-Dimethyl-2-p-bromphenylaminocyclopent-1-en-carbonsaeure-p-bromanilid 
• 60532-83-4 2-(2,4-dimethyl-phenoxy)-6,6-dimethyl-6,7-dihydro-5H-cyclopenta[e][1,3]oxazin-4-one 
• 78102-67-7 2-Chlor-2-formyloxy-5,5-dimethyl-1,3-cyclohexandion 
• 94569-94-5 2-iodo-5,5-dimethyl-3-phenoxycyclohex-2-en-1-one 
• 35024-12-5 (4,4-dimethyl-2,6-dioxo-cyclohexyl)-phenyl-iodonium betaine 
• 59577-80-9 C₁₅H₁₇IO₂ 
• 94569-93-4 C₁₄H₁₄ClIO₂ 
• 116441-82-8 2-(4-methoxyphenyl)-4-oxo-6,6-dimethyl-4,5,6,7-tetrahydrobenzofuran 
• 120400-66-0 4,4-dimethyl-2-oxocyclopentane-1-carboxamide 

Relevant articles and documents

Mild Diazo Transfer Reaction Catalyzed by Modified Clays

A very mild method for the preparation of various 2-diazo-1,3-carbonyl compounds in the presence of environmentally attractive solid acids such as clays in a heterogeneous manner in moderate to good yield is reported.

Vibrational normal modes of diazo-dimedone: A comparative study by Fourier infrared/Raman spectroscopies and conformational analysis by MM/QM

The 2-diazo-5,5-dimethyl-cyclohexane-1,3-dione (3) was synthesized and the FT-IR/Raman spectra were measured with the purpose of obtain a full assignment of the vibrational modes. Singular aspects concerning the -C{double bond, long}N{double bond, long}N oscillator are discussed in view of two strong bands observed in the region of 2300-2100 cm-1 in both, Infrared and Raman spectra. The density functional theory (DFT) was used to obtain the geometrical structure and for assisting in the vibrational assignment joint to the traditional normal coordinate analysis (NCA). The observed wavenumbers at 2145 (IR), 2144(R) are assigned as the coupled ν(N{double bond, long}N) + ν(C{double bond, long}N) vibrational mode with higher participation of the N{double bond, long}N stretching. A 2188 cm-1 (IR) and at 2186 cm-1 (R) can be assigned as a overtone of one of ν(CC) normal mode or to a combination band of the fundamentals δ(CCH) found at 1169 cm-1 and the δ (CC{double bond, long}N) found at 1017 cm-1 enhanced by Fermi resonance.

2-azido-1,3-dimethylimidazolinium chloride: An efficient diazo transfer reagent for 1,3-dicarbonyl compounds

Diazo transfer from 2-azido-1,3-dimethylimidazolinium chloride to 1,3-dicarbonyl compounds has been developed. The -reaction proceeds under mild conditions to give 2-diazo-1,3-dicarbonyl compounds in high yields, which are easily isolated because the by-products are highly soluble in water. Georg Thieme Verlag Stuttgart.

Amino-modified Merrifield resins as recyclable catalysts for the safe and sustainable preparation of functionalized α-diazo carbonyl compounds

Amino-functionalized polystyrene polymers derived from Merrifield resins were prepared and characterized. These basic materials were successfully employed as heterogeneous catalysts in the diazo transfer reaction to 1,3-dicarbonyl compounds, furnishing the corresponding diazo compounds in good to excellent yields and in relatively short reaction times. In addition, the work-up and purification protocols are simple and do not generate large amounts of waste, which are important features in sustainable catalysis and environmentally benign processes. The feasibility of the recovery and reuse of the amino-modified catalysts was also verified, since they can be employed up to five times without appreciable loss of catalytic activity. This straightforward procedure can be readily scaled up to gram scale, enabling the wide application of this method. The synthetic potential was demonstrated through the two-step preparation of 2-amino-N-dodecylacetamide (ANDA), a small molecule of commercial relevance.

Iridium(III)-Catalyzed C(3)-H Alkylation of Isoquinolines via Metal Carbene Migratory Insertion

An Ir(III)-catalyzed C(3)-H alkylation of N-acetyl-1,2-dihydroisoquinolines with diverse acceptor-acceptor diazo compounds has been achieved under a single catalytic system via metal carbene migratory insertion. Moreover, further synthetic transformations of the alkylated products such as aromatization, selective decarboxylation, and decarbonylation lead to the formation of several synthetically viable isoquinoline derivatives having immense potentials.

Rhodium-Catalyzed [4+2] Annulation of N-Aryl Pyrazolones with Diazo Compounds To Access Pyrazolone-Fused Cinnolines

An efficient synthesis of novel dinitrogen-fused heterocycles such as pyrazolo[1,2-a]cinnoline derivatives have been accomplished by the rhodium(III)-catalyzed reaction of N-arylpyrazol-5-ones with α-diazo compounds. This reaction proceeds through a cascade C?H activation/intramolecular cyclization with a broad substrate scope. Furthermore, this protocol is successfully extended to the unusual phosphorus-containing α-diazo compounds and cyclic diazo compounds as the cross-coupling partners to deliver the two new kinds of pyrazolo[1,2-a]cinnolinones. The control experiments were performed to reveal insight into the mechanism of this reaction, involving reversible C?H activation, migratory insertion of the diazo compound, and cascade cyclization as the key steps of the transformation. Moreover, gram-scale synthesis and further transformation of the target product demonstrate the synthetic utility of the present protocol.