624-90-8

Basic information

• Product Name: azidomethane
• Synonyms: azidomethane
• CAS NO: 624-90-8
• Molecular Formula: CH₃N₃O₂S
• Molecular Weight: 57.05
• Mol File: 624-90-8.mol
• Article Data: 58

Chemical Properties

• Boiling Point: 76.54°C (rough estimate)
• Appearance: /
• Density: 0.8690
• Refractive Index: 1.4200 (estimate)
• CAS DataBase Reference: azidomethane(CAS DataBase Reference)
• NIST Chemistry Reference: azidomethane(624-90-8)
• EPA Substance Registry System: azidomethane(624-90-8)

Safety Data

• Hazardous Substances Data: 624-90-8(Hazardous Substances Data)

Usage

General Description

Azidomethane is a chemical compound with the formula CH3N3, consisting of a methyl group attached to three nitrogen atoms. It is a highly reactive and potentially explosive substance that is primarily used as a reagent in organic synthesis and can be employed as a source of nucleophilic azide ions. Azidomethane is known for its toxic and hazardous properties, and great care must be taken when handling and storing it. Due to its instability and potential for explosive reactions, it is not commonly used in large-scale industrial processes but rather in small-scale laboratory applications. As a result of its reactivity and potential dangers, azidomethane is subject to strict regulations and safety precautions in its handling and use.

InChI:InChI=1/CH3N3/c1-3-4-2/h1H3

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 10383-49-0 methyl α-disulfone 
• 75-75-2 methanesulfonic acid 
• 51456-62-3 1-methyl-4,5-diphenyl-4,5-dihydro-1H-tetrazole 
• 41217-39-4 1,4-dimethyl-5-phenyl-4,5-dihydro-1H-tetrazole 
• 74-98-6 propane 
• 97325-81-0 1,5-Dimethyl-4,5-diphenyl-4,5-dihydro-1H-tetrazole 
• 97325-73-0 1-Benzyl-4-methyl-5-phenyl-4,5-dihydro-1H-tetrazole 
• 97325-80-9 1-Benzyl-4,5-dimethyl-5-phenyl-4,5-dihydro-1H-tetrazole 
• 97325-82-1 1-Methyl-4,5,5-triphenyl-4,5-dihydro-1H-tetrazole 
• 113893-43-9 1,4,5,5-Tetramethyl-4,5-dihydro-1H-tetrazole 
• 112359-25-8 5-(trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate 
• 4637-22-3 2-(Dimethylamino)-2-methoxyacetonitril 
• 4648-54-8 trimethylsilylazide 

Downstream Products

• 16681-69-9 1-methyl-1H-1,2,3-triazole-4-carbaldehyde 
• 3144-09-0 methanesulfonamide 
• 16681-71-3 1-methyl-1H-1,2,3-triazole-4-carboxylic acid 
• 55215-27-5 C₁₁H₂₀N₃P 
• 3893-35-4 1-diazo-1-phenyl-2-propanone 
• 105020-38-0 methyl 1-methyl-1H-1,2,3-triazole-5-carboxylate 
• 57362-82-0 1-Methyl-1,2,3-triazol-4-carbonsaeure-methylester 
• 15922-53-9 1,5-dimethyl-1H-[1,2,3]triazole 
• 60166-43-0 1,4-dimethyl-1H-[1,2,3]triazole 
• 15965-36-3 1-methyl-4-phenyl-1H-1,2,3-triazole 
• 175789-75-0 1-methyl-5-phenyl-1H-1,2,3-triazole-4-carbonitrile 
• 51787-69-0 1-methyl-4,5-diphenyl-1H-1,2,3-triazole 
• 51671-24-0 1,5-dimethyl-4-phenyl-1H-[1,2,3]triazole 
• 51671-28-4 1,4-dimethyl-5-phenyl-1H-[1,2,3]triazole 

Relevant articles and documents

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.

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.

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.