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

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

Uses

Used in Organic Synthesis:
Diazodimedone is used as a reagent in organic synthesis for the preparation of diazo compounds, which are important intermediates in the synthesis of various organic molecules, including pharmaceuticals and dyes.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, diazodimedone is utilized as a precursor for the synthesis of diazo compounds that are key components in the development of new drugs.
Used in Dye Industry:
Diazodimedone is employed as a starting material for the production of dyes, where its reactivity and ability to form diazo compounds contribute to the creation of a wide range of colorants.
Used in Photochemical Reactions:
Diazodimedone has been studied for its potential application in photochemical reactions, where its light sensitivity can be harnessed to initiate or catalyze certain chemical processes.
Used in Polymerization Processes:
As a photoinitiator, diazodimedone is used in the polymerization of monomers to form polymers, particularly in processes that require light activation for the initiation of polymerization.

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 
• 67398-46-3 4,4-dimethyl-2-oxo-N-phenylcyclopentane-1-carboxamide 
• 60585-44-6 methyl 4,4-dimethyl-2-oxocyclopentanecarboxylate 
• 61579-97-3 4,4-dimethyl-2-(2-morpholin-4-yl-cyclohex-1-enecarbonyl)-cyclopentanone 
• 60532-70-9 3-(4-chloro-phenyl)-6,6-dimethyl-6,7-dihydro-5H-cyclopenta[e][1,3]oxazine-2,4-dione 
• 7337-97-5 1.1.1'.1'-Tetramethyl-4.4'-azo-dicyclohexandion-(3.5) 
• 31164-41-7 2-(dimethyl(oxo)-λ⁶-sulfaneylidene)-5,5-dimethylcyclohexane-1,3-dione 
• 60532-84-5 2-dimethylamino-6,6-dimethyl-6,7-dihydro-5H-cyclopenta[e][1,3]oxazin-4-one 
• 60532-82-3 6,6-dimethyl-2-p-tolyloxy-6,7-dihydro-5H-cyclopenta[e][1,3]oxazin-4-one 
• 22704-18-3 4,4-Dimethyl-2-phenylaminocyclopent-1-en-carbonsaeureanilid 
• 60532-77-6 6,6-dimethyl-3-phenyl-2-phenylimino-2,3,6,7-tetrahydro-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 

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.

Enantioselective Total Synthesis of Chondrosterins I and J by Catalytic Asymmetric Intramolecular Aldol Reaction Using Chiral Diamine Catalyst

The first enantioselective total synthesis of chondrosterins I and J was accomplished. The synthetic method focuses on an intramolecular aldol reaction through catalytic asymmetric desymmetrization using chiral diamine catalyst. An intensive investigation of this reaction improved the enantiomeric excess up to 92 percent ee. In addition, stereoselective reduction of the ketone moiety efficiently converted chondrosterin I to chondrosterin J.

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.

Catalyst-Free Electrophilic Ring Expansion of N-Unprotected Aziridines with α-Oxoketenes to Efficient Access 2-Alkylidene-1,3-Oxazolidines

2-(2-Oxoalkylidene)-1,3-oxazolidine derivatives were synthesized in good to excellent yields regiospecifically through the catalyst-free electrophilic ring expansion of N-unprotected aziridines and the ketene C=O double bond of α-oxoketenes, in situ generated from the microwave-assisted Wolff rearrangement of 2-diazo-1,3-diketones. The ring expansion predominantly underwent an SN1 process and the hydrogen bond decides the (E)-configuration of products. (Figure presented.).

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.

Construction of isoxazolone-fused phenanthridinesviaRh-catalyzed cascade C-H activation/cyclization of 3-arylisoxazolones with cyclic 2-diazo-1,3-diketones

A Rh(iii)-catalyzed cascade C-H activation/intramolecular cyclization of 3-aryl-5-isoxazolones with cyclic 2-diazo-1,3-diketones was described, leading to the formation of isoxazolo[2,3-f]phenanthridine skeletons. The protocol features the simultaneous one-pot formation of two new C-C/C-N bonds and one heterocycle in moderate-to-good yields with good functional group compatibility. It is amenable to large-scale synthesis and further transformation.

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.

Rh(II)-mediated one-pot synthesis of dihydrobenzofuran and spiro[2.5]oct-1-ene: Experimental and DFT studies

This study represents an experimental and computational approach to investigate the rhodium-catalyzed one-pot synthesis of dihydrobenzofuran-4-one (DBF) and spiro[2.5]oct-1-ene (SOE) derivatives. Density functional theory (DFT) calculations were performed at B3LYP and M06-2X level theory. For mechanistic studies, the calculation employing B3LYP/GenECP/LanL2DZ/6-311++G(d,p) level of theory demonstrated that a [3 + 2] cycloaddition reaction between diazo compound and phenylacetylene (PhA) proceeds through a two-step mechanism via a barrierless and highly exergonic process with relative free energy 73.61 kcal/mol to yield the kinetically favored DBF derivatives (50%–62.5%). In contrast, the assemble of SOE derivatives follows [2 + 1] cycloaddition between in situ generated cyclohexane-1,3-dione carbene-2 and PhA, with the potential energy barrier 4.41 kJ/mol. Thermochemistry calculation disclosed that the cycloaddition reactions are spontaneous, and DBF (6a) is thermodynamically more stable than its constitutional isomer SOE (7a) by 42.59 kcal/mol. However, natural bond orbital (NBO), HOMO–LUMO energy gaps (4.62–4.89 eV), dipole moments, polarizability, first-order hyperpolarizability, and global reactivity descriptors were calculated to understand products' structural features. Additionally, Merck Molecular Force Field (MMFF94), followed by the B3LYP level of theory, was applied to predict the relative stability for the various conformations of 6b and 7b. The Boltzmann weighted average 1H chemical shift computed by GIAO-B3LYP/6-311+(2d,p) method and UV-Vis absorption calculated using time-dependent density functional theory (TD-DFT) agree with experimental results. Finally, the synthesis of DBF and SOE derivatives is herein illustrated.