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778583

Sigma-Aldrich

Azidobenzene solution

greener alternative

~0.5 M in 2-methyltetrahydrofuran, ≥95.0% (HPLC)

Synonym(s):

Phenyl azide solution

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About This Item

Empirical Formula (Hill Notation):
C6H5N3
CAS Number:
622-37-7
Molecular Weight:
119.12
Beilstein:
742248
MDL number:
MFCD00040895
UNSPSC Code:
12352200
PubChem Substance ID:
329767981
NACRES:
NA.22

Assay

≥95.0% (HPLC)

form

liquid

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

concentration

~0.5 M in 2-methyltetrahydrofuran

impurities

≤2.0% water

greener alternative category

Aligned,

storage temp.

−20°C

SMILES string

[N-]=[N+]=Nc1ccccc1

InChI

1S/C6H5N3/c7-9-8-6-4-2-1-3-5-6/h1-5H

InChI key

CTRLRINCMYICJO-UHFFFAOYSA-N

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General description

Azidobenzene is an aromatic azide generally used in copper(I)-catalyzed azide-alkyne cycloaddition reactions.
Azidobenzene solution can undergo click reaction with alkyne-functionalized oligomers to form O-ester-functionalized o-phenylenes, a group of aromatic foldamers with a good folding tendency in most solvents.

Application

Phenylazide in greener solvent, 2-methyltetrahydrofuran (2-MeTHF).

2-Methyltetrahydrofuran (2-MeTHF): A Biomass-Derived Solvent with Broad Application in Organic Chemistry

Signal Word

Danger

Hazard Statements

H225,H302,H315,H318,H373

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 2 - Skin Irrit. 2 - STOT RE 2

Supplementary Hazards

EUH019

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

10.4 °F

Flash Point(C)

-12 °C

Certificates of Analysis (COA)

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Solvent effects on the folding of o-phenylene oligomers
Vemuri GN, et al.
Organic & Biomolecular Chemistry, 15(4), 845-851 (2017)
A general approach to the covalent immobilization of single polymers.
Li Liu et al.
Angewandte Chemie (International ed. in English), 45(37), 6207-6210 (2006-08-15)
Azmi Naqvi et al.
Analytical biochemistry, 327(1), 68-73 (2004-03-23)
We report a rapid and versatile procedure for the preparation of photoreactive polymers and light-induced immobilization of proteins onto such polymers. Photoreactive controlled-pore glass, silica gel, glass slide, and polystyrene microtiter plate are prepared in 40-60s by microwave irradiation of
Jin Wang et al.
Organic letters, 9(20), 3973-3976 (2007-08-28)
Ultrafast photolysis (lambda(ex) = 308 nm) of phenyl azide in 100% formic acid produces a broadly absorbing transient within the instrument time resolution (300 fs), which is assigned to an excited state of the azide. The azide excited state fragments
P Nahar et al.
Analytical biochemistry, 294(2), 148-153 (2001-07-11)
A simple and mild procedure is developed for the preparation of an activated polymer surface, used for immobilization of a protein ligand through a covalent linkage. Activation of the polymer surface is carried out by attaching an active functional group
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