Tosyl isocyanate
[CAS# 4083-64-1]

Identification

• Classification: Chemical reagent >> Organic reagent >> Cyanate ester / isocyanate
• Name: Tosyl isocyanate
• Synonyms: p-Toluenesulfonyl isocyanate; PTSI
• Molecular Formula: C₈H₇NO₃S
• Molecular Weight: 197.21
• CAS Registry Number: 4083-64-1
• EC Number: 223-810-8
• SMILES: CC1=CC=C(C=C1)S(=O)(=O)N=C=O

Properties

• Density: 1.295
• Boiling point: 144 ºC (10 mmHg)
• Refractive index: 1.533-1.535
• Flash point: 145 ºC
• Water solubility: reacts

Safety Data

• Hazard Symbols: GHS08;GHS07 Danger
• Hazard Statements: H315-H319-H334-H335
• Precautionary Statements: P233-P260-P261-P264-P264+P265-P271-P273-P280-P284-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P342+P316-P362+P364-P403-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Respiratory sensitization	Resp. Sens.	1	H334
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	3	H331

• Transport Information: UN 2206

Discovory and Applicatios

Tosyl isocyanate, also known as p-toluenesulfonyl isocyanate, is an important chemical compound characterized by its isocyanate functional group attached to a tosyl moiety. This compound has garnered attention in organic synthesis and pharmaceutical chemistry due to its versatile reactivity and ability to facilitate various chemical transformations.

The discovery of tosyl isocyanate can be traced back to the study of isocyanates, which have been widely researched since the late 19th century. Researchers sought to develop derivatives of isocyanates that could exhibit specific reactivity profiles for applications in synthetic chemistry. The introduction of the tosyl group was a strategic decision, as this functional group can enhance the electrophilicity of the isocyanate, making it a more reactive species. Tosyl isocyanate was subsequently synthesized and characterized, opening new avenues for its utilization in organic synthesis.

One of the primary applications of tosyl isocyanate is as a reagent in the synthesis of carbamates and ureas. The compound can react with alcohols and amines to produce carbamates, which are valuable intermediates in the preparation of pharmaceuticals and agrochemicals. This reaction occurs through a nucleophilic attack by the alcohol or amine on the isocyanate group, leading to the formation of a stable carbamate linkage. The ability of tosyl isocyanate to facilitate this transformation makes it a key tool for chemists looking to synthesize complex organic molecules.

Tosyl isocyanate is also utilized in the preparation of various heterocyclic compounds. Its reactivity allows it to participate in cyclization reactions, where it can form isocyanate-derived cyclic structures. These heterocycles are important in medicinal chemistry, as they often exhibit biological activity and can serve as scaffolds for drug discovery. The incorporation of the tosyl group can improve the solubility and stability of these compounds, further enhancing their potential therapeutic applications.

In addition to its role in synthetic organic chemistry, tosyl isocyanate is explored for its utility in materials science. It can be used in the development of polymers, particularly in the creation of polyurethane materials. By reacting with polyols, tosyl isocyanate can contribute to the formation of cross-linked networks, resulting in materials with desirable mechanical and thermal properties. This application is especially relevant in industries where durable and resilient materials are required, such as automotive and construction.

Despite its usefulness, handling tosyl isocyanate requires caution due to its potential hazards. Isocyanates are known to be respiratory sensitizers and can cause irritation upon contact with skin or mucous membranes. Consequently, appropriate safety measures, including the use of personal protective equipment and proper ventilation, are essential when working with this compound. Regulatory guidelines dictate that users should be trained in the safe handling of isocyanates to mitigate risks associated with exposure.

Ongoing research into tosyl isocyanate aims to further explore its applications and improve its reactivity profiles. Innovations in synthetic methods are focused on enhancing the efficiency of reactions involving tosyl isocyanate, potentially leading to the development of new materials and pharmaceuticals. As the demand for efficient and sustainable chemical processes increases, tosyl isocyanate remains a compound of interest for chemists seeking to optimize synthetic pathways.

In summary, the discovery and application of tosyl isocyanate underscore its significance in organic synthesis and materials science. Its ability to facilitate the formation of carbamates, ureas, and heterocycles makes it a valuable reagent for chemists, while its potential in polymer development further enhances its utility in various industries. Continued research into tosyl isocyanate promises to unlock new applications and refine existing methodologies in synthetic chemistry.