Benzothiazol-2-ylhydrazine
[CAS# 615-21-4]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Lactone and oxygen-containing heterocyclic compound >> Thiazole, thiophene and pyridine
• Name: Benzothiazol-2-ylhydrazine
• Synonyms: 1,3-benzothiazol-2-ylhydrazine
• Molecular Formula: C₇H₇N₃S
• Molecular Weight: 165.22
• CAS Registry Number: 615-21-4
• EC Number: 210-416-6
• SMILES: C1=CC=C2C(=C1)N=C(S2)NN

Properties

• Melting point: 202 °C

Safety Data

• Hazard Symbols: GHS06;GHS07 Danger
• Risk Statements: H301-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P316-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

Benzothiazol-2-ylhydrazine, a compound featuring a benzothiazole ring fused with a hydrazine group, is notable in organic chemistry for its versatile applications and synthetic utility. This chemical substance combines the heterocyclic structure of benzothiazole with hydrazine, creating a molecule with diverse reactivity and application potential.

The discovery of benzothiazol-2-ylhydrazine can be traced back to the early 20th century when researchers were investigating the properties and applications of benzothiazole derivatives. Benzothiazole itself is a well-known heterocycle used in various chemical and pharmaceutical applications. By introducing a hydrazine group at the 2-position of the benzothiazole ring, scientists created benzothiazol-2-ylhydrazine, a compound with enhanced reactivity and new functional possibilities.

Benzothiazol-2-ylhydrazine is particularly valued in organic synthesis as a versatile reagent for the formation of a range of chemical compounds. Its hydrazine group is highly reactive and can participate in condensation reactions, making it useful for synthesizing various hydrazone and azo derivatives. These reactions often involve the formation of Schiff bases and other condensation products, which are valuable intermediates in organic synthesis.

In the pharmaceutical industry, benzothiazol-2-ylhydrazine has been studied for its potential biological activities. The compound and its derivatives have shown promise as intermediates in the synthesis of bioactive molecules. For example, benzothiazol-2-ylhydrazine has been explored as a starting material for developing compounds with potential antimicrobial, anti-inflammatory, and antitumor properties. Its ability to form various derivatives with diverse biological activities makes it a valuable compound in drug discovery and development.

In addition to its pharmaceutical applications, benzothiazol-2-ylhydrazine is employed in the synthesis of dyes and pigments. The presence of both the benzothiazole ring and hydrazine functionality allows for the creation of vibrant, color-stable dyes. These dyes are used in textiles, inks, and other colorant applications where stability and color quality are essential.

Benzothiazol-2-ylhydrazine also finds applications in materials science. Its reactivity can be harnessed to modify polymer structures or to create new materials with specific properties. By incorporating benzothiazol-2-ylhydrazine into polymer matrices, researchers can develop materials with unique optical, electronic, or mechanical properties, expanding the range of applications in which these materials can be used.

Overall, benzothiazol-2-ylhydrazine is a valuable compound in both organic synthesis and applied chemistry. Its ability to participate in a range of chemical reactions and its utility in developing pharmaceuticals, dyes, and advanced materials highlight its significance in various scientific and industrial fields.

References

2023. A new pre-concentration procedure based on poly(styrene-co-maleamide and imide) copolymers modified with 2-hydrazinobenzothiazole prior to spectrophotometric monitoring of inorganic as (as As(III)) in edible vegetable oils. Food Chemistry, 403.
DOI: 10.1016/j.foodchem.2022.135335

2023. Structural investigations, DFT, anti-oxidant and α-amylase inhibitory activity of metal complexes of benzothiazole based hydrazone. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 103(5-6).
DOI: 10.1007/s10847-023-01196-z

2023. Pyrazoline-Based Fluorescent Probe: Synthesis, Characterization, Theoretical Simulation, and Detection of Picric Acid. Journal of Fluorescence, 33(3).
DOI: 10.1007/s10895-023-03414-w