Tosyl azide, CAS No. 941-55-9

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941-55-9

Catalog No. EBD33436

CAS 941-55-9

Name Tosyl azide

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Basic Information

Synonyms: p-Toluenesulfonylazide 4-Methylbenzenesulfonylazide 4-methyl-benzenesulfonylazid benzenesulfonylazide,4-methyl- p-toluenesulfonylazideor4-methylbenzenesulfonylazide 4-methylbenzenesulfonicacidazide p-methylbenzenesulfonicacidazide

Molecular Formula: C7H7N3O2S

Molecular Weight: 197.21

MDL Number: MFCD00180767

Categories: Synthetic Chemistry > Basic Synthetic Reagents > Other Basic Synthetic Reagents Synthetic Chemistry > Organic Building Blocks > Other Organic Building Blocks

Product Description:

P-Toluenesulfonyl azide is an organic azide compound characterized by the presence of a tosyl (p-toluenesulfonyl) group attached to an azide (-N₃) functionality. It is a pale yellow to colorless crystalline solid that is sensitive to light, heat, and shock, requiring careful handling due to its potential explosive nature. Its primary and most significant application is as a versatile reagent in organic synthesis, particularly for the generation of nitrenes. Upon thermal decomposition or photolysis, it serves as a convenient source of tosyl nitrene (TsN:), which can undergo various reactions such as C-H amination, aziridination of alkenes, and insertion into C-H bonds. It is also a key reagent in the classic Curtius rearrangement for the synthesis of isocyanates from carboxylic acids, via the intermediate formation of acyl azides. Beyond nitrene chemistry, p-toluenesulfonyl azide is used in the preparation of other azides and in cycloaddition reactions. Its utility as a specialized reagent for introducing nitrogen-containing functional groups makes it a valuable tool in medicinal chemistry and materials science research, despite its hazardous properties.

Physical Properties

Flash Point: 4 °C

Density: ~0.90 g/mL at 20 °C

Solubility: Dissolved in most organic solvents

Refractivity: n20/D 1.502

Storage: 2-8°C

Safety Information

Packing Level: II

Hazard Category: 3

Transport Codes: 1294

Analytical Data

Appearance: white crystal