4-Azidotoluene solution

Name: 4-Azidotoluene solution
Brand: ALDRICH

~0.5 M in tert-butyl methyl ether, ≥95.0% (HPLC)

Synonym(s):

1-Azido-4-methylbenzene solution, 4-Methylphenyl azide solution, p-Tolyl azide solution

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About This Item

Empirical Formula (Hill Notation):

C₇H₇N₃

CAS Number:

2101-86-2

Molecular Weight:

133.15

UNSPSC Code:

12352200

NACRES:

NA.22

PubChem Substance ID:

329764321

MDL number:

MFCD09971470

Beilstein/REAXYS Number:

1841411

Key Documents

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Product Name

4-Azidotoluene solution, ~0.5 M in tert-butyl methyl ether, ≥95.0% (HPLC)

InChI

1S/C7H7N3/c1-6-2-4-7(5-3-6)9-10-8/h2-5H,1H3

SMILES string

Cc1ccc(cc1)N=[N+]=[N-]

InChI key

YVXDRCDGBCOJHX-UHFFFAOYSA-N

assay

≥95.0% (HPLC)

form

liquid

concentration

~0.5 M in tert-butyl methyl ether

impurities

≤2.0% water

storage temp.

−20°C

Quality Level

100

Related Categories

Azides

Chemical Building Blocks

Chemistry & Biochemicals

Organic Building Blocks

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Show Differences

1 of 4

This Item	778877	779164	778583
Sigma-Aldrich 727466 4-Azidotoluene solution	Sigma-Aldrich 778877 4-Azidobenzoic acid solution	Sigma-Aldrich 779164 2-Azidotoluene solution	Sigma-Aldrich 778583 Azidobenzene solution
assay ≥95.0% (HPLC)	assay ≥95.0% (HPLC)	assay ≥95.0% (HPLC)	assay ≥95.0% (HPLC)
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
form liquid	form liquid	form liquid	form liquid
storage temp. −20°C	storage temp. 2-8°C	storage temp. −20°C	storage temp. −20°C
concentration ~0.5 M in tert-butyl methyl ether	concentration ~0.2 M in tert-butyl methyl ether	concentration ~0.5 M in tert-butyl methyl ether	concentration ~0.5 M in 2-methyltetrahydrofuran
impurities ≤2.0% water	impurities ≤2.0% water	impurities ≤2.0% water	impurities ≤2.0% water

Application

4-Azidotoluene solution may be used for the functionalization at the axial position of boron subphthalocyanines with a terminal acetylene functionality via copper(I)-catalyzed azide-alkyne cycloaddition in the presence of Hunig′s base.[1]

General description

4-Azidotoluene is an aromatic azide generally used in copper(I)-catalyzed azide-alkyne cycloaddition reactions.[2]

pictograms

GHS02,GHS07

signalword

Danger

hcodes

H225,H315

pcodes

P210 - P233 - P240 - P241 - P242 - P303 + P361 + P353

Hazard Classifications

Flam. Liq. 2 - Skin Irrit. 2

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

-18.4 °F

flash_point_c

-28 °C

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Acetylenic Scaffolding with Subphthalocyanines.

Gotfredsen H, et al.

European Journal of Organic Chemistry, 2016(1), 17-21 (2016)

A Pathogen-Responsive Gene Cluster for Highly Modified Fatty Acids in Tomato.

Ju Eun Jeon et al.

Cell, 180(1), 176-187 (2020-01-11)

In response to biotic stress, plants produce suites of highly modified fatty acids that bear unusual chemical functionalities. Despite their chemical complexity and proposed roles in pathogen defense, little is known about the biosynthesis of decorated fatty acids in plants.

Cu-catalyzed azide? alkyne cycloaddition

Meldal M & Torn?e CW

Chemical Reviews, 108(8), 2952-3015 (2008)

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