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742430

Sigma-Aldrich

Benzyl azide solution

~0.5 M in dichloromethane, ≥95.0% (HPLC)

Synonym(s):

α-Azidotoluene solution, (Azidomethyl)benzene solution

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About This Item

Empirical Formula (Hill Notation):
C7H7N3
CAS Number:
622-79-7
Molecular Weight:
133.15
Beilstein:
636825
MDL number:
MFCD00013836
UNSPSC Code:
12352125
PubChem Substance ID:
329765573

Quality Level

100

Assay

≥95.0% (HPLC)

form

solution

concentration

~0.5 M in dichloromethane

impurities

≤2.0% water

storage temp.

2-8°C

SMILES string

[N-]=[N+]=NCc1ccccc1

InChI

1S/C7H7N3/c8-10-9-6-7-4-2-1-3-5-7/h1-5H,6H2

InChI key

UDLLFLQFQMACJB-UHFFFAOYSA-N

Related Categories

General description

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

Application

  • Synthesis of Estrone Heterodimers and Evaluation of Their In Vitro Antiproliferative Activity.: This research investigates the synthesis of estrone heterodimers using benzyl azide as a key reagent, demonstrating significant antiproliferative activity, thus highlighting its potential in pharmaceutical intermediate synthesis (Bózsity N et al., 2024).
  • Fluoride Abstraction Induced by Tris(pentafluoroethyl)difluorophosphorane: A Convenient Way to Synthesize Cationic N-Heterocyclic Carbene- and Cyclic (Alkyl)(amino)carbene-Ligated Copper Alkyne and Arene Complexes.: This paper describes a method for synthesizing copper alkyne and arene complexes using benzyl azide, emphasizing its role in innovative click chemistry applications (Riethmann M et al., 2024).

Pictograms

Exclamation markHealth hazard
GHS07,GHS08

Signal Word

Warning

Hazard Classifications

Carc. 2 - Eye Irrit. 2 - Skin Irrit. 2 - STOT RE 2 - STOT SE 3

Target Organs

Central nervous system

Storage Class Code

6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

EU REACH Annex XVII (Restriction List)

CAS No.

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Lachlan S Campbell-Verduyn et al.
Chemical communications (Cambridge, England), 16(16), 2139-2141 (2009-04-11)
Monodentate phosphoramidite ligands are used to accelerate the copper(i)-catalyzed 1,3-dipolar cycloaddition of azides and alkynes (CuAAC) rapidly yielding a wide variety of functionalized 1,4-disubstituted-1,2,3-triazoles; Cu(i) and Cu(ii) salts both function as the copper source in aqueous solution to provide excellent
Cu-catalyzed azide? alkyne cycloaddition
Meldal M & Torn?e CW
Chemical Reviews, 108(8), 2952-3015 (2008)
Tommy Siu-Ming Tang et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 21(30), 10729-10740 (2015-06-23)
The synthesis, characterization, photophysics, lipophilicity, and cellular properties of new phosphorescent ruthenium(II) polypyridine complexes functionalized with a dibenzocyclooctyne (DIBO) or amine moiety [Ru(N^N)2 (L)](PF6 )2 are reported (L=4-(13-N-(3,4:7,8-dibenzocyclooctyne-5-oxycarbonyl) amino-4,7,10-trioxa-tridecanyl-aminocarbonyl-oxy-methyl)-4'-methyl-2,2'-bipyridine bpy-DIBO, N^N=2,2'-bipyridine bpy (1 a), 1,10-phenanthroline phen (2 a); L=4-(13-amino-4,7,10-trioxa-tridecanylaminocarbonyl-oxy-methyl)-4'-methyl-2,2'-bipyridine bpy-NH2 , N^N=bpy
Daniel Zewge et al.
Bioconjugate chemistry, 25(12), 2222-2232 (2014-11-15)
Chemical modification of siRNA is achieved in a high-throughput manner (96-well plate format) by copper catalyzed azide-alkyne cycloadditions. This transformation can be performed in one synthetic operation at up to four positions with complete specificity, good yield, and acceptable purity.

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