622-79-7

Basic information

• Product Name: BENZYL AZIDE
• Synonyms: triazotoluene;(Azidomethyl)benzene, Pract.;Benzylazide 98%;Phenylmethyl Azide;benzyl(diazonio)azanide;diazonio(phenylmethyl)azanide;NSC 26304;α-Azidotoluene
• CAS NO: 622-79-7
• Molecular Formula: C₇H₇N₃
• Molecular Weight: 133.15
• Mol File: 622-79-7.mol
• Article Data: 287

Chemical Properties

• Melting Point: 157℃
• Boiling Point: 81-83°C 16mm
• Flash Point: 82-85°C/16mm
• Appearance: /
• Density: 1.0655
• Refractive Index: 1.5341
• Storage Temp.: 2-8°C
• Water Solubility: Insoluble in waterMiscible with ethanol and diethyl ether. Immiscible with water.
• BRN: 636825
• CAS DataBase Reference: BENZYL AZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL AZIDE(622-79-7)
• EPA Substance Registry System: BENZYL AZIDE(622-79-7)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 2-11-48/20/21/22-40
• Safety Statements: 15-17-33-36/37
• RIDADR: 1993
• WGK Germany: 3
• RTECS: XS6650000
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 622-79-7(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 622-79-7 differently. You can refer to the following data:
1. BENZYL AZIDE was used in the synthesis of stable 1,2,3-triazole derivatives.
2. Benzyl azide is used in the synthesis of 1,2,3-triazole derivatives. It serves as a reagent used to introduce a PhCH2N group into a molecule.

Synthesis Reference(s)

Tetrahedron Letters, 16, p. 471, 1975 DOI: 10.1016/S0040-4039(00)71896-XJournal of the American Chemical Society, 91, p. 4323, 1969 DOI: 10.1021/ja01043a071

General Description

Benzyl azide is an aromatic azide generally used in copper(I)-catalyzed azide-alkyne cycloaddition reactions.

Safety Profile

A heat-sensitive explosive.Explosive reaction with bis(trifluoromethyl)nitroxide.Upon decomposition it emits toxic fumes of NOx. Seealso AZIDES.

Synthesis

Sodium azide (3.58 g, 55.0 mmol) was added to DMSO (120 mL) and stirred vigorously until fully dissolved. Benzyl bromide 168 (6.54 mL, 55 mmol) was added. The reaction mixture was stirred at RT overnight. The colourless liquid was worked up with water (100 mL), and extracted with diethyl ether (3 x 100 mL). The extractions were washed with water (2 x 80 mL) and brine (80 mL). The ether layer was dried over MgSO4 and after filtration, it was evaporated to dryness, giving benzyl azide 73 as a colourless oil (6.9 g, 51.8 mmol, 94%): IR (neat) νm a x / cm– 1 3455, 3028, 2970, 2946, 2093, 1605, 1586, 1496, 1454, 1349, 1252; 1H NMR (400 MHz, CDCl 3 ) δ 7.44 – 7.28 (m, 5H), 4.33 (s, 2H); 1 3C NMR (100 MHz, CDCl 3 ) δ 135.55, 129.05, 128.52, 128.44, 55.00.

InChI:InChI=1/C7H8N3/c8-10-9-6-7-4-2-1-3-5-7/h1-5,8H,6H2/q+1

Upstream product

• 100-44-7 benzyl chloride 
• 620-05-3 iodomethylbenzene 
• 100-46-9 benzylamine 
• 351-70-2 benzyl trifluoroacetate 
• 4648-54-8 trimethylsilylazide 
• 100-39-0 benzyl bromide 
• 100-53-8 phenylmethanethiol 
• 108-88-3 toluene 
• 160732-56-9 1-azido-1λ³-benzo[d][1,2]iodaoxol-3(1H)-one 
• 71-43-2 benzene 
• 2037-26-5 ⁽²⁾H₈-toluene 
• 629-05-0 n-octyne 
• 768-60-5 4-methoxyphenylacetylen 
• 772-38-3 4-tert-Butylphenylacetylene 

Downstream Products

• 493-77-6 2,4,6-triphenyl-1,3,5-triazine 
• 780-25-6 N-benzylidene benzylamine 
• 642-04-6 2,3,5,6-tetraphenylpyrazine 
• 108842-69-9 1-benzyl-5-phenyl-1H-1,2,3-triazole-4-carboxylic acid 
• 25784-56-9 4-amino-3-benzyl-1,2,3-triazole-5-carboxylic acid 
• 108717-96-0 1-benzyl-4-phenyl-1H-[1,2,3]triazole 
• 51118-27-5 1-benzyl-5-phenyl-1H-1,2,3-triazole 
• 20271-33-4 1-benzyl-5-amino-1,2,3-triazole-4-carboxylic acid ethyl ester 
• 52826-45-6 (benzylimino)triphenylphosphorane 
• 726-25-0 1-benzyl-3-phenylthiourea 
• 56599-00-9 diethyl N-benzyl-2-aminomalonate 
• 100-46-9 benzylamine 
• 4368-68-7 1-benzyl-1H-[1,2,3]triazole 
• 47038-16-4 1-benzyl-4,5-bis-(α-hydroxy-isopropyl)-1H-[1,2,3]triazole 

Relevant articles and documents

Mutagenicity of alkyl azides

Alkyl azides showed mutagenicity for S. typhimurium TA100 strain with S9 mix. However, no significant activity was observed for TA98 either with or without S9 mix or for TA100 without S9 mix. On the other hand, 3-azido-1,2- propanediol showed the enantios

Combinatorial synthesis of new fluorescent scaffolds using click chemistry

Azides and acetylenes are bio-orthogonal functional groups that can be readily coupled using copper(I)- or ruthenium(II)- catalyzed 1,3-dipolar cycloaddition reactions. Using non-fluorescent aromatic azides and aromatic acetylenes, covering a range of electron rich and poor building blocks, the Huisgen cycloaddition afford 1,4-disubstituted or 1,5-disubstituted 1,2,3-triazoles. Using a combinatorial approach by running reaction in parallel in polypropylene 96-well plates we discovered several new fluorescent 1,2,3-triazoles scaffolds. These compounds show diverse interactions with biomolecules that could find applications in biology in, for example, fluorescence microscopy or biomolecule quantification.

Alkylphosphinites as Synthons for Stabilized Carbocations

We present a new acid-free method for the generation of carbocations based on a redox condensation reaction that enables SN1 reactions with a variety of nucleophiles. We utilize readily synthesized phosphinites that are activated by diisopropyl azodicarboxylate to form betaine structures that collapse upon adding a pronucleophile, thereby yielding reactive carbocation intermediates. We also employ this approach for the alkylation of some bioactive molecules.

NOVEL DIBENZOOXAPHOSPHININE OXIDE DERIVATIVE COMPOUNDS AND PHARMACEUTICAL COMPOSITION FOR PREVENTING OR TREATING DEGENERATIVE DISEASE COMPRISING THE SAME AS AN ACTIVE INGREDIENT

The present invention relates to a novel dibenzooxininin oxide derivative compound having various nitrogen-containing substituents introduced at 6-position of a dibenzooxaphosphorin oxide mononuclear, and to the use thereof. The present invention relates to a pharmaceutical composition for preventing or treating degenerative diseases and a health supplement food composition for preventing or treating degenerative diseases, comprising the dibenzooxaphosphorin oxide derivative compound of the present invention.