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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
NACRES:
NA.22

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

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

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H336,H351,H373

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

Certificates of Analysis (COA)

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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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