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Sigma-Aldrich

p-Toluenesulfonyl azide solution

11-15 % (w/w) in toluene, 97%

Synonym(s):

4-Methylbenzenesulfonyl azide solution, p-Toluenesulfonazide solution, Tosyl azide solution

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About This Item

Empirical Formula (Hill Notation):
C7H7N3O2S
CAS Number:
941-55-9
Molecular Weight:
197.21
MDL number:
MFCD00180767
UNSPSC Code:
12352125
PubChem Substance ID:
329763205
NACRES:
NA.22

Assay

≥96.5% (HPLC)
97%

form

liquid

concentration

11-15 % (w/w) in toluene

refractive index

n20/D 1.502

density

~0.90 g/mL at 20 °C

storage temp.

2-8°C

SMILES string

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

InChI

1S/C7H7N3O2S/c1-6-2-4-7(5-3-6)13(11,12)10-9-8/h2-5H,1H3

InChI key

NDLIRBZKZSDGSO-UHFFFAOYSA-N

General description

p-Toluenesulfonyl azide is used as a nitrene source and in the synthesis of N-sulfimines, N-tosylphosphinimines, and N-sulfoximines.

Application

p-Toluenesulfonyl azide solution can be employed as a reagent along with alkyne, and amine in the three-component coupling reaction for the synthesis of N-sulfonylamidines in presence of copper catalyst.
It can also be used in the synthesis of N-sulfonyl-1,2,3-triazoles by azide-alkyne cycloaddition reaction in the presence of copper catalyst.
Modifier of refractive index changes of transparent PMMA to generate permanent patterns in films

Signal Word

Danger

Hazard Classifications

Acute Tox. 2 Oral - Aquatic Chronic 3 - Asp. Tox. 1 - Flam. Liq. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 2 - STOT SE 3

Target Organs

Central nervous system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

39.2 °F - closed cup - Solvent

Flash Point(C)

4.0 °C - closed cup - Solvent

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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p-Toluenesulfonyl Azide
Heydt H, et al.
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
Highly efficient one-pot synthesis of N-sulfonylamidines by Cu-catalyzed three-component coupling of sulfonyl azide, alkyne, and amine
Bae I, et al.
Journal of the American Chemical Society, 127(7), 2038-2039 (2005)
Copper-Catalyzed Synthesis of N-Sulfonyl-1, 2, 3-triazoles: Controlling Selectivity.
Yoo EJ, et al.
Angewandte Chemie (International Edition in English), 46(10), 1730-1733 (2007)

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