908094-04-2

Basic information

• Product Name: phenyldiazomethane
• Synonyms: phenyldiazomethane
• CAS NO: 908094-04-2
• Molecular Weight: 118.138
• Mol File: 908094-04-2.mol

Chemical Properties

• CAS DataBase Reference: phenyldiazomethane(CAS DataBase Reference)
• NIST Chemistry Reference: phenyldiazomethane(908094-04-2)
• EPA Substance Registry System: phenyldiazomethane(908094-04-2)

Safety Data

• Hazardous Substances Data: 908094-04-2(Hazardous Substances Data)

Upstream product

• 5461-82-5 N-benzyl-N'-nitro-N-nitroso-guanidine 
• 10575-97-0 N-benzyl-N-nitrosoacetamide 
• 5281-18-5 benzaldehyde, hydrazone 
• 1666-17-7 benzaldehyde p-toluenesulfonylhydrazone 
• 3469-17-8 2-diazo-1,2-diphenylethan-1-one 
• 10575-94-7 N-benzyl-N-nitrosobenzamide 
• 75142-62-0 benzaldehyde 2,4,6-tri-isopropylbenzenesulphonyl hydrazone 
• 64-19-7 acetic acid 
• 100-46-9 benzylamine 
• 75-36-5 acetyl chloride 
• 775-11-1 N-nitroso-N-benzylurea 
• 18039-42-4 5-Phenyl-1H-tetrazole 
• 1199-02-6 5-phenyl-3H-[1,3,4]oxadiazol-2-one 
• 97025-65-5 N'-benzylidene-2-nitrobenzenesulfonohydrazide 

Downstream Products

• 1150-59-0 2-hydroxy-3-phenyl-1,4-naphthoquinone 
• 872274-10-7 4-(benzyloxy)-2-hydroxy-6-methoxybenzaldehyde 
• 767-90-8 (2-ethylphenyl)methanol 
• 879770-33-9 4-methyl-5-phenyl-1H-pyrazole-3-carboxylic acid 
• 19091-99-7 benzyl-nitro-amine 
• 873999-20-3 5-benzyloxy-6-methyl-pyridine-3,4-dicarboxylic acid diamide 
• 42976-06-7 N,N'-((Z,Z)-7,7-diphenyl-bicyclo[4.1.0]hept-3-ene-2,5-diylidene)-bis-benzenesulfonamide 
• 95845-61-7 5,6,7,8-tetrachloro-3-phenyl-1H-benzo[1,3,4]oxadiazine 
• 62173-99-3 benzyl 2-hydroxy-2-phenylacetate 
• 109865-49-8 benzenesulfonic acid-{benzyl-[1-(4-methoxy-phenyl)-ethylidene]-hydrazide} 
• 25939-13-3 N-(p-nitrophenyl)benzohydrazonoyl chloride 
• 14996-78-2 2-phenylcycloheptanone 
• 87874-45-1 2,2-diethoxy-1-phenylcyclopropane 
• 50561-87-0 4,5-diphenyl-1⁽²⁾H-pyrazole-3-carboxylic acid methyl ester 

Relevant articles and documents

Complexes of [(dadi)Ti(L/X)]m That Reveal Redox Non-Innocence and a Stepwise Carbene Insertion into a Carbon-Carbon Bond

The addition of donors to (dadi)Ti(THF) (1-THF, dadi = [{-CH=N(1,2-C6H4)N(2,6-iPr2-C6H3)}2]n) afforded the adducts [(dadi)Ti(L/X)]m (1-L, m = 0, N2CPh2; m = -1, X = Cl-, N3-, OiPr-, CH3-, neoPe-, CH=CH2-, CCPh-, CCTMS-, H(D)-). In all adducts, the chelate was in the (dadi)4- redox state. For certain anions, evidence for intimate binding of the Li+ counterion was explored spectroscopically. Treatment of 1-THF with PhHCN2, yielded {PhC3H3(-NC6H4-2-NAr)2}Ti(THF) (3, Ar = 2,6-iPr2-C6H3), which contains a cyclopropanated dadi ligand. The mechanism was explored by calculations, and the addition of Ph2CN2 to 3 produced a nacnac derivative, {PhC(CHNC6H4-2-NAr)2}Ti(??2-HNNCPh2) (4, Ar = 2,6-iPr2-C6H3), generated via hydrogen transfer from the cyclopropane.

Stereospecific synthesis of trans-2,3-diaryl substituted 1-aminocyclopropanecarboxylic acid derivatives

The stereospecific syntheses of trans-2,3-diaryl-l-aminocyclopropanecarboxylic acid derivatives are reported. They key step is a 1,3-dipolar cycloaddition of phenyldiazomethane to (Z)-2-phenyl-4-arylidene-5(4H)-oxazolones, followed by the extrusion of nitrogen in situ.

PROCESS FOR THE CYCLOADDITION OF A HETERO(ARYL) 1,3-DIPOLE COMPOUND WITH A (HETERO)CYCLOALKYNE

A process is provided, comprising reacting a (hetero)aryl 1,3-dipole compound with a (hetero)cycloalkyne, wherein the (hetero)aryl 1,3-dipole compound comprises a 1,3-dipole functional group bonded to a (hetero)aryl group, and wherein the (hetero)aryl 1,3-dipole compound is a (hetero)aryl azide or a (hetero)aryl diazo compound; wherein: (i) the (hetero)aryl group of the (hetero)aryl 1,3-dipole compound comprises a substituent (ii) the (hetero)aryl group of the (hetero)aryl 1,3-dipole compound is an electron-poor (hetero)aryl group and wherein the (hetero)cycloalkyne is a (hetero)cyclooctyne or a (hetero)cyclononyne according to Formula (1). The invention also relates to the products obtainable by the process according to the invention.

Continuous Flow Synthesis and Purification of Aryldiazomethanes through Hydrazone Fragmentation

Electron-rich diazo compounds, such as aryldiazomethanes, are powerful reagents for the synthesis of complex structures, but the risks associated with their toxicity and instability often limit their use. Flow chemistry techniques make these issues avoidable, as the hazardous intermediate can be used as it is produced, avoiding accumulation and handling. Unfortunately, the produced stream is often contaminated with other reagents and by-products, making it incompatible with many applications, especially in catalysis. Herein is reported a metal-free continuous flow method for the production of aryldiazomethane solutions in a non-coordinating solvent from easily prepared, bench-stable sulfonylhydrazones. All by-products are removed by an in-line aqueous wash, leaving a clean, base-free diazo stream. Three successful sensitive metal-catalyzed transformations demonstrated the value of the method.

Cyclopropane compound as well as preparation method and application thereof

The invention discloses a cyclopropane compound as well as a preparation method and application thereof. The cyclopropane compound has a structure shown as formula I. The cyclopropane compound is prepared by taking a diazo compound and unsaturated ketone

Preparation method of mild diazomethane derivative

The invention discloses a preparation method of a mild diazomethane derivative. The preparation method comprises that EWG-substituted benzene sulfonyl chloride and hydrazine hydrate undergo a reaction to produce EWG-substituted benzene sulfonyl chloride, the EWG-substituted benzene sulfonyl chloride and aldehyde or ketone undergo a reaction to produce EWG-substituted benzenesulfonylhydrazone, and the EWG-substituted benzenesulfonylhydrazone, a base and an organic solvent are mixed and undergo a replacement reaction to produce a diazomethane derivative. The diazomethane derivative is not separated and purified and is further used for a tension small ring synthesis reaction and an insertion reaction. The benzene ring of benzenesulfonylhydrazone is introduced with an electron-withdrawing group EWG, and through electron effects and steric hindrance effects, the benzenesulfonyl group on the benzenesulfonylhydrazone is easily separated so that a diazomethane derivative is produced under very mild conditions and especially at the room temperature.

Benzylic Ammonium Ylide Mediated Epoxidations

A high yielding synthesis of stilbene oxides using ammonium ylides has been developed. It turned out that the amine leaving group plays a crucial role as trimethylamine gives higher yields than DABCO or quinuclidine. The amine group also influences the diastereoselectivity, and detailed DFT calculations to understand the key parameters of these reactions have been carried out.

The p: K a of Br?nsted acids controls their reactivity with diazo compounds

We study the O-alkylation of phosphate groups by alkyl diazo compounds in a range of small molecules and biopolymers. We show that the relatively high pKa of phosphate in comparison to the other naturally occurring Br?nsted acids can be exploited to control alkylation selectivity. We provide a simple protocol for chemical modification of some of the most important instances of phosphates in natural compounds including in small molecule metabolites, nucleic acids, and peptides.

SMALL MOLECULE LFA-1 INHIBITORS

The present invention relates to novel compounds which are capable of inhibiting the interaction of LFA-1 with its counter ligands.

Fluorogenic Strain-Promoted Alkyne-Diazo Cycloadditions

Fluorogenic reactions, in which non- or weakly fluorescent reagents produce highly fluorescent products, are attractive for detecting a broad range of compounds in the fields of bioconjugation and material sciences. Herein, we report that a dibenzocyclooctyne derivative modified with a cyclopropenone moiety (Fl-DIBO) can undergo fast strain-promoted cycloaddition reactions under catalyst-free conditions with azides, nitrones, nitrile oxides, as well as mono- and disubstituted diazo-derivatives. Although the reaction with nitrile oxides, nitrones, and disubstituted diazo compounds gave cycloadducts with low quantum yield, monosubstituted diazo reagents produced 1H-pyrazole derivatives that exhibited an approximately 160-fold fluorescence enhancement over Fl-DIBO combined with a greater than 10 000-fold increase in brightness. Concluding from quantum chemical calculations, fluorescence quenching of 3H-pyrazoles, which are formed by reaction with disubstituted diazo-derivatives, is likely due to the presence of energetically low-lying (n,π?) states. The fluorogenic probe Fl-DIBO was successfully employed for the labeling of diazo-tagged proteins without detectable background signal. Diazo-derivatives are emerging as attractive reporters for the labeling of biomolecules, and the studies presented herein demonstrate that Fl-DIBO can be employed for visualizing such biomolecules without the need for probe washout.