186581-53-3

Basic information

• Product Name: diazomethane
• CAS NO: 186581-53-3
• Molecular Weight: 42.0403
• Mol File: 186581-53-3.mol

Chemical Properties

• CAS DataBase Reference: diazomethane(CAS DataBase Reference)
• NIST Chemistry Reference: diazomethane(186581-53-3)
• EPA Substance Registry System: diazomethane(186581-53-3)

Safety Data

• Hazardous Substances Data: 186581-53-3(Hazardous Substances Data)

Upstream product

• 67-66-3 chloroform 
• 684-93-5 1-methyl-1-nitrosourea 
• 615-53-2 ethyl N-methyl-N-nitrosocarbamate 
• 16339-21-2 N-nitroso-β-methylaminoisobutyl methyl ketone 
• 74-89-5 methylamine 
• 66395-18-4 streptozocin 
• 80-11-5 N-methyl-N-nitrosotoluene-p-sulfonamide 
• 16812-15-0 iodocarbenium iodide 
• 5694-02-0 2,3-epoxy-3-phenylpropanoic acid 
• 943-41-9 N-methyl-N-nitroso-4-nitroaniline 
• 288-94-8 2H-tetrazole 
• 60-29-7 diethyl ether 
• 7601-87-8 N,N'-dimethyl-N,N'-dinitroso-oxamide 
• 7664-41-7 ammonia 

Downstream Products

• 121971-87-7 3-α-L-arabinofuranosyloxy-2-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-chromen-4-one 
• 122147-54-0 (2R)-2r-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-3t-α-L-rhamnopyranosyloxy-chroman-4-one 
• 2317-95-5 tri-O-acetyl-2-[methyl-(toluene-4-sulfonyl)-amino]-2-deoxy-β-D-glucopyranosyl fluoride 
• 2317-94-4 tri-O-acetyl-2-[methyl-(toluene-4-sulfonyl)-amino]-2-deoxy-α-D-glucopyranosyl fluoride 
• 483-18-1 emetine 
• 51482-43-0 4-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)vanillin 
• 5522-73-6 rhodochlorin XV dimethyl ester 
• 480-43-3 5,7-dihydroxy-2-(4-methoxyphenyl)chroman-4-one 
• 466-95-5 8β-chloro-4,5α-epoxy-3-methoxy-17-methyl-morphin-6-ene 
• 13423-15-9 3-methyltetrahydrofuran 
• 96-47-9 2-methyltetrahydrofuran 
• 74-85-1 ethene 
• 10480-04-3 1,5-bis-(4-nitro-phenyl)-4,5-dihydro-1H-[1,2,3]triazole 
• 93900-31-3 bis-(2-chloroacetyl-phenyl)-disulfide 

Relevant articles and documents

Synthesis of cyclopropanated [2.2.1] heterobicycloalkenes: An improved procedure

A safer and improved method to our previous report on palladium-catalyzed cyclopropanation of heterobicyclic alkenes has been developed. By using tetrahydrofuran as the solvent and a more dilute aqueous NaOH solution for the generation of diazomethane fro

Scalable On-Demand Production of Purified Diazomethane Suitable for Sensitive Catalytic Reactions

We have developed a convenient development-scale reactor (0.44 mol/h) to prepare diazomethane from N-methyl-N-nitroso-p-toluenesulfonamide (MNTS) in ～80% yield. Diazomethane (CH2N2) made with this reactor is extracted into nitrogen gas from the liquid reaction mixture, effectively removing it from reagents and byproducts that may interfere in subsequent reactions. Vertically oriented tubular reactors were used to produce and consume diazomethane in situ. Key features of this reactor include high productivity and correspondingly low reactor volume (reactor volume/liquid flow rate = 6.5 min) and a commercially available gas/liquid separator equipped with a selectively permeating hydrophilic membrane. The design of the reactor keeps the inventory below 53 mg of CH2N2 during normal operation. The reactor was demonstrated by generating CH2N2 that was used in a connected continuous reactor. We evaluated esterification reactions and a continuous Pd-catalyzed cyclopropanation reaction with the reactor and achieved high conversion with 1.5 and 4.1 equiv of MNTS precursor, respectively.

BACKBONE REARRANGEMENTS OF METHYL (-)-KAUR-9(11)-EN-19-OATE AND ITS EPOXIDE: STRUCTURES OF TWO DITERPENES OF A NEW SKELETAL TYPE

Cleavage of the epoxide (2) of methyl (-)-kaur-9(11)-en-19-oate (1b) with boron trifluoride-ether in benzene and in acetic anhydride yielded (3a) and (3b), respectively.On epoxidation with m-chloroperbenzoic acid in the presence of N-nitrosomethyl urea, (1b) suffered a backbone rearrangement to form (6).

How nucleophilic are diazo compounds?

The kinetics of the reactions of benzhydryl cations with eight diazo compounds 1a-g were investigated photometrically in dichloromethane. The nucleophilicity parameters N and slope parameters s of these diazo compounds were derived from the equation log k

A carbonyl ylide cycloaddition approach to platensimycin

(Chemical Presented) Short and to the point: A formal synthesis of platensimycin has been accomplished by employing a carbonyl ylide [3+2] cycloaddition reaction (see scheme). This short and facile enantioselective synthesis of the pivotal tetracyclic precursor requires 11 steps and proceeds in 20% overall yield from isopropyl cyanoacetate.

The synthesis of O-substituted 3-oximes of 6α -methyl-16α, 17α-cyclohexanopregn-4-ene-3,20-diones tritium-labeled in the 1,2-position

1,2-Tritium-labeled 3-(O-carboxypropyl)- and 3-(O-carbomethoxypropyl)- oximes of 6α-methyl-16α,17α-cyclohexanopregn-4-ene-3,20-diones were obtained by the homogeneous catalytic hydrogenation of 1,2-dehydroprecursors with gaseous tritium and the subsequent separation of the resulting mixtures by HPLC. The specific radioactivities of 50-55 Ci/mmol were prepared using tris-(triphenylphosphine)-rhodium chloride.

Concise synthesis of alkaloid (-)-205B

Described herein is a short total synthesis of alkaloid (-)-205B (1) by means of an anti-selective SN2 alkylation of an attractively functionalized cyclopropanol and diastereoselective cyclization of the resulting aminoallene adduct for bicyclic ring formation. The synthesis features a general route to cis- or trans-2,6-disubstituted piperidines by lithium aluminum hydride reduction of the imine intermediate by an appropriate choice of solvent and cis- or trans-2,5-disubstituted pyrrolidines by an exceptional level of chirality transfer from a pendant allene. Particularly noteworthy are the brevity and convergence made possible by a segment-coupling strategy.

Preparation of a bicyclic analogue of qinghao (artemisinic) acid via a Lewis acid catalyzed ion Diels-Alder reaction involving a hydroxy diene and cyclic enone and facile conversion into (±)-6,9-desdimethylqinghaosu

Treatment of 6-methylcyclohex-2-enone (8) and hexa-3,5-dien-1-ol (14) either in dichloromethane at -20 to 0°C with aluminum chloride (1 equiv) or in acetonitrile at -20°C with Cu(II) trifluoromethanesulfonate (1 equiv) rapidly provides in a highly stereoselective reaction the hemiacetal Diels-Alder adduct 15, which with a trans ring junction and anti methyl group is considered to arise via an ionic Gassman-type Diels-Alder reaction involving prior formation of a hemiacetal between the alcohol and enone followed by generation of an allylic cation from the hemiacetal mediated by the Lewis acid. The adduct 15 is then converted in straightforward fashion into the methyl ester of the desdimethyl analogue of qinghao (artemisinic) acid, which upon sequential photosensitized oxygenation and then Fe(phen)3(PF6)3/copper(II) triflate catalyzed cleavage-oxygenation provides (±)-6,9-desdimethylqinghaosu.

An enantiospecific synthesis of a komarovispirane

The enantiospecific total synthesis of a komarovispirane, containing the complete carbon framework, trans-bicyclo[4.3.0]nonanespiro[8.1′]cyclohexane, of the spiroditerpene komarovispirone, starting from the readily available campholenaldehyde is described

Design and Discovery of Functionally Selective Serotonin 2C (5-HT2C) Receptor Agonists

On the basis of the structural similarity of our previous 5-HT2C agonists with the melatonin receptor agonist tasimelteon and the putative biological cross-talk between serotonergic and melatonergic systems, a series of new (2,3-dihydro)benzofu