BENZYL AZIDE Chemical Properties

Melting point:

157℃

Boiling point:

81-83°C 16mm

Density 

1.0655

refractive index 

1.5341

RTECS 

XS6650000

Flash point:

82-85°C/16mm

storage temp. 

2-8°C

form 

Liquid

Specific Gravity

1.0655

Water Solubility 

Insoluble in waterMiscible with ethanol and diethyl ether. Immiscible with water.

BRN 

636825

CAS DataBase Reference

622-79-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

2-11-48/20/21/22-40

Safety Statements 

15-17-33-36/37

RIDADR 

1993

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

3

PackingGroup 

III

HS Code 

29299090

MSDS

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BENZYL AZIDE Usage And Synthesis

Uses

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.

Uses

BENZYL AZIDE was used in the synthesis of stable 1,2,3-triazole derivatives.

Synthesis Reference(s)

Tetrahedron Letters, 16, p. 471, 1975 DOI: 10.1016/S0040-4039(00)71896-X
Journal 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.

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