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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)
David Evrard et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 14(30), 9286-9291 (2008-09-10)
The electrochemical reduction of phenylazide or phenylacetylene diazonium salts leads to the grafting of azido or ethynyl groups onto the surface of carbon electrodes. In the presence of copper(I) catalyst, these azide- or alkyne-modified surfaces react efficiently and rapidly with
Manabu Mizutani et al.
Biomacromolecules, 3(4), 668-675 (2002-07-09)
Photoreactive phenylazide-end-capped liquid copolymers were prepared by ring-opening copolymerization of epsilon-caprolactone (CL) and trimethylene carbonate (TMC) at an equimolar monomer feed ratio in the presence of a polyol, namely, a low-molecular-weight alcohol (di-, tri-, and tetraol) or poly(ethylene glycol) (PEG)
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)
Andrew L Hook et al.
Biomacromolecules, 10(3), 573-579 (2009-01-23)
The fabrication and characterization of chemical patterns using a technique that can be readily integrated with methods currently used for the formation of microarrays is presented. A high density poly(ethylene glycol) coating was deposited on glass slides as a background
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