35374-43-7

Usage

Structure

A naphthalene ring with a thioether functional group (-S-) and a chloroethyl substituent (-CH2CH2Cl) attached to it.

Uses

Primarily used as an intermediate in the synthesis of other organic compounds, such as pharmaceuticals, agrochemicals, and dyes.

Hazards

Known to have cytotoxic and mutagenic properties, which can be harmful to human health and the environment.

Handling and disposal

Proper handling and disposal procedures should be followed to minimize the risks associated with the chemical.

Upstream product

• 17225-95-5 2-(2-naphthylthio)ethanol 
• 107-06-2 1,2-dichloro-ethane 
• 91-60-1 2-Naphthalenethiol 

Downstream Products

• 90395-98-5 β-naphthyl 2-chloroethyl sulfone 
• 1207324-81-9 2-(2-chloroethylsulfinyl)naphthalene 

Relevant academic research and scientific papers

Divergent electrolysis for the controllable coupling of thiols with 1,2-dichloroethane: A mild approach to sulfide and sulfoxide

Organosulfurs are important commodity chemicals and indispensable synthetic intermediates in modern chemistry that were traditionally synthesized using metal catalysts, oxidants or strong bases, which caused numerous environmental pollution issues. The divergent synthesis of these scaffolds via a single catalysis under catalyst and oxidant free conditions is a fantastic idea to overcome these drawbacks. Here, we report a safe, practical and eco-friendly electrochemical methodology for the controllable dechloro-coupling of 1,2-dichloroethane (DCE) with thiols, providing value-added β-chloroethylsulfurs, which serve as versatile building blocks in the efficient late-stage conversion to bioactive molecules. The mildness and practicality of this protocol was further demonstrated by the total synthesis of anti-gout drug sulfinpyrazone in a 32% total yield over three steps.

Locus-specific microemulsion catalysts for sulfur mustard (HD) chemical warfare agent decontamination

The rates of catalytic oxidative decontamination of the chemical warfare agent (CWA) sulfur mustard (HD, bis(2-chlororethyl) sulfide) and a range (chloroethyl) sulfide simulants of variable lipophilicity have been examined using a hydrogen peroxide-based microemulsion system. SANS (small-angle neutron scattering), SAXS (small-angle X-ray scattering), PGSE-NMR (pulsed-gradient spin-echo NMR), fluorescence quenching, and electrospray mass spectroscopy (ESI-MS) were implemented to examine the distribution of HD, its simulants, and their oxidation/hydrolysis products in a model oil-in-water microemulsion. These measurements not only present a means of interpreting decontamination rates but also a rationale for the design of oxidation catalysts for these toxic materials. Here we show that by localizing manganese-Schiff base catalysts at the oil droplet-water interface or within the droplet core, a range of (chloroethyl) sulfides, including HD, spanning some 7 orders of octanol-water partition coefficient (Kow), may be oxidized with equal efficacy using dilute (5 wt. % of aqueous phase) hydrogen peroxide as a noncorrosive, environmentally benign oxidant (e.g., t1/2 (HD) ～ 18 s, (2-chloroethyl phenyl sulfide, C6H5SCH2CH 2Cl) ～ 15 s, (thiodiglycol, S(CH2CH 2OH)2) ～ 19 s {20°C}). Our observations demonstrate that by programming catalyst lipophilicity to colocalize catalyst and substrate, the inherent compartmentalization of the microemulsion can be exploited to achieve enhanced rates of reaction or to exert control over product selectivity. A combination of SANS, ESI-MS and fluorescence quenching measurements indicate that the enhanced catalytic activity is due to the locus of the catalyst and not a result of partial hydrolysis of the substrate.