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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

Quality Level

100

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)
Yutaka Sadakane et al.
Analytical sciences : the international journal of the Japan Society for Analytical Chemistry, 22(2), 209-218 (2006-03-04)
Photoaffinity labeling enables the direct probing of a target protein through a covalent bond between a ligand and its binding protein, and even a complex formed by weak interactions can be isolated by the method. The photochemical fishing approach accelerates
Emily J Borda et al.
Nucleic acids research, 33(3), 1058-1068 (2005-02-22)
We have used photo-crosslinking to investigate the structure and dynamics of four-way junction hairpin ribozyme constructs. Four phenylazide photo-crosslinkers were coupled to 2'-NH2-modified U+2 in the substrate and irradiated at different Mg2+ concentrations and temperatures. Consistent with the role of
Luís M T Frija et al.
The journal of physical chemistry. A, 111(15), 2879-2888 (2007-03-29)
A combined matrix isolation FT-IR and theoretical DFT(B3LYP)/6-311++G(d,p) study of the molecular structure and photochemistry of 5-ethoxy-1-phenyl-1H-tetrazole (5EPT) was performed. A new method of synthesis of the compound is described. Calculations show three minima, very close in energy and separated
C Malaveille et al.
Cancer research, 42(4), 1446-1453 (1982-04-01)
3-Methyl-1-phenyltriazene and a series of ring-substituted derivatives (4-methylphenyl, 4-chlorophenyl, and 2,4,6-trichlorophenyl), structurally related benzenediazonium fluoborates and phenyl azides, as well as the recently isolated [1-methyl-3-(2,4,6-trichlorophenyl)-2-triazeno]methyl-beta-D-glucopyranoside uronic acid, were studied for their mutagenic activity in Salmonella typhimurium strains. Of these compounds
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