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Merck
CN

778583

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
UNSPSC Code:
12352200
NACRES:
NA.22
PubChem Substance ID:
329767981
MDL number:
MFCD00040895
Beilstein/REAXYS Number:
742248
Assay:
≥95.0% (HPLC)
Form:
liquid

Key Documents

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InChI

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

SMILES string

[N-]=[N+]=Nc1ccccc1

InChI key

CTRLRINCMYICJO-UHFFFAOYSA-N

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

Quality Level

100

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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

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Danger

Hazard Classifications

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

supp_hazards

EUH019

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

10.4 °F

flash_point_c

-12 °C

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
BCCF8444
BCBW7438
BCBP7894V
BCBN9946V
BCBL7898V

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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)
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)
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
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
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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