2-Naphthalen-2-ylsulfanylethanol is a β-hydroxy sulfide in which a 2-naphthylthio group is linked to the 2-position of ethanol. The compound exhibits good thermal stability and is freely soluble in dichloromethane, chloroform, ethyl acetate and hot ethanol, sparingly soluble in water (≈ 0.4 g L⁻¹ at 25 °C). The terminal hydroxyl function is readily esterified or etherified, while the electron-rich naphthylthio moiety makes the molecule a useful nucleophilic building block. Commercial lots are released at ≥98 % purity.
Key Physicochemical Data:
Melting point: 64–66 °C (lit.)
Predicted boiling point: 379 °C / 760 mmHg
Density: 1.21 g cm⁻³ (25 °C, solid)
Flash point: 184 °C (closed cup)
Log P (octanol/water): 3.2 (predicted)
Typical Uses:
Precursor to naphthylthioethyl esters and phospholipids used in fluorescence probes and drug-delivery vectors.
Chain-transfer agent in controlled/living radical polymerisations (RAFT, NMP) yielding poly(naphthylthioethyl methacrylate) scintillating resins.
Intermediate for the synthesis of β-naphthylthioethyl-substituted heterocycles with potential anti-inflammatory or anti-oxidant activity.
Quality Specification (Commercial Grade):
Purity (GC): ≥98 %
Water content (KF): ≤0.3 %
Free acid (as acetic acid): ≤0.2 %
Residue on ignition: ≤0.1 %
Heavy metals: ≤20 ppm
Hazard Statement:
Causes skin and eye irritation (H315 + H319). Avoid inhalation of dust; use gloves, goggles and adequate ventilation. Store in a cool, dry place away from oxidants and strong bases. SDS available on request.
