1516-70-7

Usage

Uses

Used in Organic Synthesis:
Methane sulfonyl azide is used as a high-energy azide compound for the preparation of sulfonylguanidines and sulfonylureas, which are important intermediates in the synthesis of various organic compounds.
Used in Pharmaceutical Production:
Methane sulfonyl azide is used as a reagent in the production of pharmaceuticals, where its unique properties contribute to the synthesis of specific drug molecules.
Used in Agrochemical Production:
Methane sulfonyl azide is also utilized in the production of agrochemicals, where it aids in the synthesis of compounds that are used in the development of pesticides and other agricultural products.
Safety Precautions:
Due to its high explosive nature, Methane sulfonyl azide is handled and stored with extreme care. It is tightly regulated to prevent accidents and misuse, ensuring that proper safety measures are in place during its transportation, storage, and use in various industries.

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 75-75-2 methanesulfonic acid 
• 10383-49-0 methyl α-disulfone 

Downstream Products

• 3144-09-0 methanesulfonamide 
• 37469-73-1 4-[diazo-(1-methyl-1-phenyl-ethoxycarbonyl)-acetyl]-thiomorpholine-3-carboxylic acid tert-butyl ester 
• 53422-98-3 4-[2-benzoylamino-N-methanesulfonyl-2-(5-morpholin-4-yl-2-phenyl-oxazol-4-yl)-acetimidoyl]-morpholine 
• 40468-71-1 N-(1,2,5-triphenyl-1H-1λ⁵-phosphol-1-ylidene)-methanesulfonamide 
• 3469-17-8 2-diazo-1,2-diphenylethan-1-one 
• 2085-31-6 2-diazo-1,3-diphenylpropane-1,3-dione 
• 210166-61-3 6-Azido-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene-6-carboxylic acid ethyl ester 
• 1085853-16-2 N'-(methanesulfonyl)-2-phenylacetamidine 
• 1119518-68-1 1-benzyl-5-methyl-1H-[1,2,3]triazole-4-carboxylic acid 5-(1-O-methyl-2,3-O-isopropylidene)-β-D-ribofuranose ester 

Relevant academic research and scientific papers

Taking diazo transfer to water: α-diazo carbonyl compounds from in situ generated mesyl azide

Mesyl azide generated in situ in aqueous medium converted a range of active methylene substrates into the corresponding diazo compounds in good yields and high purity with no need for chromatographic purification. The products thus obtained are suitable for the subsequent RhII-catalyzed O–H insertions with no need for chromatography in the interim.

Concise synthesis of dimethyl (2-oxopropyl)phosphonate and homologation of aldehydes to alkynes in a tandem process

The synthesis of dimethyl (diazomethyl)phosphonate, a useful reagent for the homologation of aldehydes to alkynes, is described as a one-pot process and comprises the generation of the azide transfer agent, diazotransfer to dimethyl (2-oxopropyl)phosphonate, and methanolysis, followed by a simple extraction protocol. Previously described syntheses for this bulk product are much more elaborate. The homologation of aldehydes to alkynes can also be extended to a single-step process by adding the aldehyde directly to the reaction mixture prior to isolation of the reagent. The homologation process using dimethyl (diazomethyl)phosphonate was shown to proceed also in nonprotic solvents with mild bases, emphasizing the importance of a facile access to the reagent. The oxidation of alcohols to the required aldehydes was performed by a TEMPO-mediated process using chloramine-T as electron acceptor. Copyright Taylor & Francis Group, LLC.

Mechanistic Study of In Situ Generation and Use of Methanesulfonyl Azide as a Diazo Transfer Reagent with Real-Time Monitoring by FlowNMR

The mechanistic pathway by which the hazardous diazo transfer reagent methanesulfonyl azide can be formed in situ, from methanesulfonyl chloride and aqueous sodium azide, has been investigated using real-time reaction monitoring by FlowNMR. In the presence of triethylamine, rapid generation of methanesufonyl azide is observed, via a mechanistic pathway consistent with involvement of a sulfene or methanesulfonyl triethylammonium intermediate. Accordingly, it is possible to generate and use methanesulfonyl azide in a single synthetic step for a diazo transfer process.

A new approach to macrocyclization via alkene formation in catalytic diazo decomposition. Synthesis of patulolides A and B.

[reaction: see text] Effective synthetic uses of bisdiazocarbonyl compounds for the selective construction of diverse macrocycles, including the synthesis of patulolides A and B, by catalytic "carbene dimer" formation are reported. Control of stereochemistry and efficient methods for product isomerization or kinetic isomer differentiation have been achieved.

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.

Development of prohibitin ligands against osteoporosis

Current therapeutic approaches to osteoporosis display some potential adverse effects and a limited efficacy on non-vertebral fracture reduction. Some sulfonylamidines targeting the scaffold proteins prohibitins-1 and 2 (PHB1/2) have been showed to inhibit the formation of osteoclasts in charge of bone resorption. Herein, we report the development of a second generation of anti-osteoclastic PHB ligands. The most potent compound, IN45, showed 88% inhibition at the low concentration of 5 μM, indicates that it might serve as a basis for the development of new antiosteoporotic drugs.

Formal Allylation and Enantioselective Cyclopropanation of Donor/Acceptor Rhodium(II) Azavinyl Carbenes

A highly efficient formal allylation of dihydronaphthotriazoles with alkenes under rhodium(II) catalysis is reported. Various allyl dihydronaphthalene derivatives were furnished via rhodium(II) azavinyl carbenes with moderate to good yields and excellent chemoselectivity. When monosubstituted alkenes are used, cyclopropanation occurs and good to excellent enantioselectivities have been achieved. Particularly noteworthy is the allylic C(sp2)-H activation instead of traditional C(sp3)-H activation in the formal allylation process.

A Base-Controlled Reaction of 2-Cyanoacetamidines (3,3-Diaminoacrylonitriles) with Sulfonyl Azides as a Route to Nonaromatic 4-Methylene-1,2,3-triazole-5-imines

Reactions of 2-cyanoacetamidines with sulfonyl azides were shown to take place via two different pathways to form a mixture of 1-substituted 5-amino-1,2,3-triazoles 3 and novel 4-methylene-1H-1,2,3-triazole-5(4H)-imine derivatives 4–14. In the absence of

One-Pot Copper-Catalyzed Three-Component Reaction of Sulfonyl Azides, Alkynes, and Allylamines to Access 2,3-Dihydro-1 H-imi-dazo[1,2-a]indoles

A copper-catalyzed multicomponent reaction of sulfonyl azides, alkynes, and allylamines affording 2,3-dihydro-1 H-imidazo-[1,2-a]indoles in moderate yields is reported. Four C-N bonds are constructed- by way of azide-alkyne cycloaddition (CuAAC) and double Ullmann-type coupling reactions in a one-pot process.

One-pot synthesis of sulfonyl-1H-1,2,3-triazolyl-thiomorpholine 1,1-dioxide derivatives and evaluation of their biological activity

A one-pot procedure for the synthesis of novel 1,2,3-triazole derivatives (5a–5l) in good yields (63 to 77%) using different sulfonic acids and 4-(prop-2-yn-1-yl)thiomorpholine 1,1-dioxide through the in situ generated sulfonyl azides was developed. The structures of the newly synthesized compounds were confirmed by 1H NMR, 13C NMR, mass spectrometry, and elemental analysis. The newly synthesized compounds were screened for in?vitro antibacterial activity and free radical scavenging activity in terms of hydrogen donating or radical scavenging ability by the DPPH method. Among all, the compound N-(4-((4-((1,1-dioxidothiomorpholino) methyl)-1H-1,2,3-triazol-1-yl)sulfonyl)phenyl) acetamide (5l) was found to exhibit potent activity as compared to the standard drugs.