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Tosyl isocyanate
1. Basic Information
Name: Tosyl isocyanate
Alias: p-Toluenesulfonyl isocyanate, TSI
CAS No.: 4083-64-1
Molecular Formula: C8H7NO3S
Molecular Weight: 197.21
Category: Highly active acylating synthetic reagent, pharmaceutical intermediate, analytical derivatization reagent, cross-coupling substrate
2. Physical and Chemical Properties
Physical Properties
- Appearance: Colorless to light yellow transparent oily liquid
- Odor: Sharp pungent irritating acid gas odor
- Solubility: Miscible with DCM, chloroform, THF, toluene, DMF; reacts violently with water, methanol, ethanol and other protic solvents
- Boiling Point: 94–96 ℃ (0.4 mmHg vacuum)
- Density (20℃): 1.265–1.275 g/cm3
- Refractive Index nD20: 1.542–1.546
- Hygroscopy: Extremely hygroscopic, immediately reacts with water vapor in air
- Aqueous property: Violent exothermic hydrolysis in water, generates p-toluenesulfonamide and carbon dioxide
Chemical Properties
- Molecular structure: Toluene para-substituted sulfonyl isocyanate, -SO2-NCO dual high-activity functional group
- Nucleophilic addition activity: Rapidly reacts with alcohols, amines, carboxylic acids, phenols to form sulfonyl urea, carbamate derivatives
- Water sensitivity: Trace water triggers hydrolysis, releases CO2 gas, product deactivates quickly when exposed to air
- Thermal stability: Stable under anhydrous low temperature; heating above 120 ℃ decomposes and releases toxic sulfur dioxide fumes
- Photostability: Light-sensitive; long-term light exposure turns dark yellow and produces polymer impurities
- Compatibility: Only compatible with anhydrous aprotic solvents; strictly incompatible with water, alcohols, amines, strong bases
3. Main Application Fields
1. Fine Pharmaceutical Synthetic Reagent (Core Application)
Selective derivatization reagent for constructing urea, carbamate fragments in small-molecule drug intermediates; used for modifying amino/hydroxyl groups
2. Analytical Chemistry Derivatization Agent
Derivatization reagent for HPLC/GC detection of alcohols, amines, trace carboxylic acid substances to improve chromatographic peak separation
3. Organic Synthesis Research Tool
Standard reagent for synthesizing sulfonyl urea herbicide intermediates, heterocyclic nitrogen compounds
4. Polymer Modification Additive
Low-volume additive for introducing crosslinkable isocyanate groups into polymer chains under anhydrous conditions
4. Quality Specification Table
| Test Item | Standard Specification |
| CAS Number | 4083-64-1 |
| Molecular Formula | C8H7NO3S |
| Appearance | Colorless clear liquid without turbidity |
| GC Purity | Synthetic Grade ≥98.5% |
| Water Content (KF) | ≤0.05% |
| Chroma (APHA) | ≤100 |
| Hydrolysis Impurity (p-Toluenesulfonamide) | ≤0.30% |
| Heavy Metals (Pb) | ≤10 ppm |
| Packaging | Nitrogen-filled anhydrous amber glass bottle; bulk 200L nitrogen-sealed lined iron drum |
| Storage Condition | Hermetically sealed anhydrous cool warehouse 2–20 ℃, full light shielding, isolated from humid air, alcohol and amine raw materials |
| Transportation Requirement | Water-reactive toxic corrosive liquid, fully sealed anhydrous packaging, separated from water-based, alcohol, alkaline dangerous goods |
| Shelf Life | 18 months under nitrogen vacuum anhydrous sealed storage |
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