Sign In

19.29 : Amines to Sulfonamides: The Hinsberg Test

The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with benzenesulfonyl chloride, also known as the Hinsberg reagent, in the presence of an excess of aqueous base, followed by acidification. Based on the nature of the amines, differentchanges are observed.

Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing sulfonyl group makes the N–H proton acidic, enablingready deprotonation in a base to form awater-soluble salt. Further acidification of the clear solution results in the precipitation of anN-substituted benzenesulfonamide.

Secondary amines generate an insolubleN,N-disubstituted sulfonamideupon reaction with benzenesulfonyl chloride. Due to the lack of an N–H proton, the compound does not reactwith the base. Tertiary amines do not react with the Hinsberg reagent. However, upon acidification, tertiary amines are protonated and become water-soluble.

Figure1

Tags
Hinsberg TestAminesSulfonamidesPrimary AmineSecondary AmineTertiary AmineBenzenesulfonyl ChlorideHinsberg ReagentN substituted BenzenesulfonamideNN disubstituted SulfonamideProtonation

From Chapter 19:

article

Now Playing

19.29 : Amines to Sulfonamides: The Hinsberg Test

Amines

2.7K Views

article

19.1 : Amines: Introduction

Amines

3.8K Views

article

19.2 : Nomenclature of Primary Amines

Amines

3.0K Views

article

19.3 : Nomenclature of Secondary and Tertiary Amines

Amines

3.2K Views

article

19.4 : Nomenclature of Aryl and Heterocyclic Amines

Amines

2.0K Views

article

19.5 : Structure of Amines

Amines

2.2K Views

article

19.6 : Physical Properties of Amines

Amines

2.6K Views

article

19.7 : Basicity of Aliphatic Amines

Amines

5.3K Views

article

19.8 : Basicity of Aromatic Amines

Amines

6.6K Views

article

19.9 : Basicity of Heterocyclic Aromatic Amines

Amines

4.9K Views

article

19.10 : NMR Spectroscopy Of Amines

Amines

7.4K Views

article

19.11 : Mass Spectrometry of Amines

Amines

3.8K Views

article

19.12 : Preparation of Amines: Alkylation of Ammonia and Amines

Amines

2.9K Views

article

19.13 : Preparation of 1° Amines: Azide Synthesis

Amines

3.6K Views

article

19.14 : Preparation of 1° Amines: Gabriel Synthesis

Amines

3.2K Views

See More

JoVE Logo

Privacy

Terms of Use

Policies

Research

Education

ABOUT JoVE

Copyright © 2025 MyJoVE Corporation. All rights reserved