5599-34-8

Basic information

• Product Name: TRIPHENYLSILYLAZIDE
• Synonyms: TRIPHENYLSILYLAZIDE;azidotriphenylsilane
• CAS NO: 5599-34-8
• Molecular Formula: C₁₈H₁₅N₃Si
• Molecular Weight: 301.42
• EINECS: 227-014-1
• Mol File: 5599-34-8.mol
• Article Data: 2

Chemical Properties

• Melting Point: 81 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: TRIPHENYLSILYLAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIPHENYLSILYLAZIDE(5599-34-8)
• EPA Substance Registry System: TRIPHENYLSILYLAZIDE(5599-34-8)

Safety Data

• Hazardous Substances Data: 5599-34-8(Hazardous Substances Data)

Usage

General Description

Triphenylsilylazide is a chemical compound with the formula (C6H5)3SiN3. It is a stable and highly reactive azide with a silyl group, commonly used in organic synthesis as a high-energy intermediate in the preparation of silyl-substituted molecules. It is known for its ability to undergo azide-alkyne cycloaddition reactions, providing a convenient method for the synthesis of triazoles. Triphenylsilylazide is also used as a reagent in the modification of surfaces and in the preparation of polymers. Additionally, it has been investigated for its potential use in explosives and propellants due to its high nitrogen content and energetic properties. However, its handling and storage require careful attention due to its explosive nature.

InChI:InChI=1/C18H16N3Si/c19-20-21-22(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15,19H/q+1

Upstream product

• 76-86-8 Triphenylsilyl chloride 

Downstream Products

• 59239-72-4 2,2,4,4,6,6-Hexamethyl-7,8,8-triphenyl-[1,3,5,7,2,4,6,8]trioxazatetrasilocane 
• 59239-74-6 1,2,2,3,4,4-Hexamethyl-5,6,6-triphenyl-[1,3,5,2,4,6]triazatrisilinane 
• 512-63-0 1,1,3,3,5,5-hexaphenylcyclotrisiloxane 
• 1124-52-3 N-(propan-2-ylidene)aniline 
• 108148-61-4 4,4-Dimethyl-3-(triphenylsilyl)-5,5-bis(trimethylsilyl)-1,2,3-triaza-4-sila-1-cyclopenten 
• 17599-59-6 diphenylmethyleneaminotrimethylsilane 
• 30006-66-7 bis(trimethylsilyl)diazomethane 
• 108148-62-5 silyl>(trimethylsilyl)diazomethan 
• 108148-40-9 5,5-Dimethyl-1,4-bis(triphenylsilyl)-1,2,3,4-tetraaza-5-sila-2-cyclopenten 
• 104837-17-4 1,3-Bis-triphenylsilyl-2,2,4,4-tetramethyl-cyclodisilazan 
• 108148-65-8 4,4-dimethyl-3-triphenylsilyl-5,5-bis(trimethylsilyl)-1,2,3-triaza-4-germa-1-cyclopentene 
• 108148-52-3 5,5-dimethyl-1,4-bis(triphenylsilyl)-1,2,3,4-tetraaza-5-germa-2-cyclopentene 
• 371161-64-7 HC(CCH₃NC₆H₃(C₃H₇)2)2AlNSi(C₆H₅)3 
• 1402222-83-6 C₄₅H₅₁Cl₂N₃Si₂ 

Relevant articles and documents

An ESR study on structures of a series of silylnitrenes

Structures of a series of silylnitrenes formed from silyl azides were investigated by means of ESR. γ-Irradiation and photo-illumination of all the silyl azides resulted in the formation of triplet states even for those having two or three Si-N3 groups in a molecule. ESR spectra of the silylnitrenes exhibited a part of the fine structure at around 820 mT. All the silyl azides studied gave nearly identical D-values (ca. 1.5cm-1) and much larger than those in phenylnitrenes. The results suggested that electron spins are localized in the nitrogen p-orbitals to a large extent and was interpreted in terms of a mono-silane linkage of nitrene, -Si-N:, i.e., interrupting spin delocalization.