For professionals in the chemical industry, a thorough understanding of a compound's synthesis, properties, and applications is crucial for effective utilization and procurement. 4-Methylbenzenesulfonhydrazide, identified by CAS number 1576-35-8, is a notable organic reagent widely employed across various sectors. This article provides an in-depth look at its synthesis and key characteristics.

Chemical Identity and Properties

Chemical Name: 4-Methylbenzenesulfonhydrazide

Synonyms: p-Toluenesulfonyl Hydrazide (TSH), p-Toluenesulfonhydrazide, Tosylhydrazide

CAS Number: 1576-35-8

Molecular Formula: C7H10N2O2S

Molecular Weight: 186.23 g/mol

Appearance: Typically appears as a white to off-white crystalline powder. This form is convenient for handling and weighing in laboratory and industrial settings.

Melting Point: Generally reported in the range of 103-108 °C, indicating its solid state under ambient conditions.

Solubility: While slightly soluble in water, it exhibits better solubility in polar organic solvents such as ethanol and methanol, which is typical for compounds with both polar and non-polar features.

Reactivity: Characterized by strong nucleophilic and reducing properties due to the hydrazide group (-NHNH2) and the electron-withdrawing sulfonyl group.

Synthesis of 4-Methylbenzenesulfonhydrazide

The synthesis of 4-Methylbenzenesulfonhydrazide typically involves a two-step process, starting from readily available materials:

  1. Preparation of p-Toluenesulfonyl Chloride (TsCl): The first step involves the chlorosulfonation of toluene. Toluene is reacted with chlorosulfonic acid (ClSO3H). This electrophilic aromatic substitution reaction introduces the chlorosulfonyl group onto the toluene ring, primarily at the para position due to the activating and ortho/para directing nature of the methyl group. The reaction requires careful control of temperature and reagent addition to maximize yield and minimize byproducts.
  2. Reaction with Hydrazine Hydrate: The obtained p-Toluenesulfonyl Chloride is then reacted with hydrazine hydrate (N2H4·H2O). Hydrazine, being a strong nucleophile, attacks the sulfur atom of the sulfonyl chloride, displacing the chloride ion. This nucleophilic substitution reaction forms the desired 4-Methylbenzenesulfonhydrazide. The reaction is typically carried out in a suitable solvent under controlled conditions to ensure high yield and purity.

Purification: The crude product is then purified, commonly through recrystallization from solvents like ethanol or methanol, to yield the pure crystalline powder. This purification step is critical for achieving the high purity required for its applications as a synthesis reagent.

Applications and Sourcing

The synthesis pathways highlight how this compound is manufactured, ensuring its availability for various applications including organic synthesis, as a blowing agent in polymers, and as an intermediate in pharmaceutical and agrochemical production. When you seek to buy 4-Methylbenzenesulfonhydrazide, understanding these synthetic routes can inform your choice of supplier. For consistent quality and competitive pricing, consider manufacturers with established expertise in sulfonation and hydrazide chemistry. As a trusted supplier, we provide high-purity 4-Methylbenzenesulfonhydrazide, manufactured under strict quality controls, ready for your diverse chemical needs.