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713589

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

Quality Level

100

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

Related Categories

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

EU REACH Annex XVII (Restriction List)

CAS No.

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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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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