96892-95-4

Usage

Uses

Used in Polymer Industry:
2,6-Naphthalenedithiol is used as a monomer in the preparation of polyaromatic ether. Its presence in the polymer structure contributes to enhanced thermal stability and mechanical properties, making it suitable for high-performance materials in demanding applications.
Used in Chemical Industry:
In the chemical industry, 2,6-Naphthalenedithiol is used to manufacture silicone rubber. Its incorporation into the silicone rubber formulation improves the material's flexibility, durability, and resistance to environmental factors, making it ideal for a wide range of applications, including automotive, aerospace, and electronics.
Used in Cosmetic Industry:
2,6-Naphthalenedithiol is used as an active ingredient in a cosmetic process for attenuating wrinkles. Its ability to interact with proteins and other biomolecules in the skin may contribute to improved skin elasticity and a reduction in the appearance of fine lines and wrinkles, offering potential benefits in anti-aging skincare products.

InChI:InChI=1/C10H8S2/c11-9-3-1-7-5-10(12)4-2-8(7)6-9/h1-6,11-12H

Synthetic route

2,6-naphthalenedisulfonyl dichloride (13827-62-8) → 2,6-naphthalene-dithiol (96892-95-4)

Conditions	Yield
With hydrogenchloride; tin(ll) chloride In acetic acid at 90℃; for 2h;	69%
With tin(ll) chloride In acetic acid at 90℃; for 2h;	39%
With hydrogenchloride; tin(II) chloride hydrate In water; acetic acid	23.3%
With hydrogenchloride; acetic acid; tin(ll) chloride

naphthalene-disulfonyl chloride-(2.6) → 2,6-naphthalene-dithiol (96892-95-4)

Conditions	Yield
With acetic acid; zinc

naphthalene-2,6-disulfonic acid (581-75-9) → 2,6-naphthalene-dithiol (96892-95-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 71 percent / PCl5 / 4 h / 130 °C 2: 69 percent / SnCl2, HCl(g) / acetic acid / 2 h / 90 °C View Scheme
Multi-step reaction with 2 steps 1: 3.2 g / PCl5 / 4 h / 130 °C 2: 39 percent / SnCl2 / acetic acid / 2 h / 90 °C View Scheme

disodium 2,6-naphthalenedisulfonate (1655-45-4) → 2,6-naphthalene-dithiol (96892-95-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: phosphorus pentachloride 2: hydrogenchloride; tin(II) chloride hydrate / water; acetic acid View Scheme

2,6-naphthalene-dithiol (96892-95-4) + acetyl chloride (75-36-5) → 2,6-di(acetylthio)naphthalene (1314140-60-7)

Conditions	Yield
With triethylamine In tetrahydrofuran	71%

2,6-naphthalene-dithiol (96892-95-4) + chloroacetic acid (79-11-8) → (2,6-naphthylenedithio)diacetic acid (96892-96-5)

Conditions	Yield
With sodium hydroxide at 70℃; for 2h;	67%
With alkali

2,6-naphthalene-dithiol (96892-95-4) + 6-deoxy-6-iodo-β-cyclodextrin (29390-66-7) → C94H144O68S2

Conditions	Yield
With ammonium bicarbonate In N,N-dimethyl-formamide at 85℃; for 22h;	3.5%

1-bromo-2,2-dimethoxyethane (7252-83-7) + 2,6-naphthalene-dithiol (96892-95-4) → 2,6-bis-(2,2-dimethoxy-ethylsulfanyl)-naphthalene

Conditions	Yield
With ethanol; sodium ethanolate; sodium iodide

2,6-naphthalene-dithiol (96892-95-4) + dimethyl sulfate (77-78-1) → 2,6-bis(methylthio)naphthalene (10075-77-1)

Conditions	Yield
With sodium hydroxide

2,6-naphthalene-dithiol (96892-95-4) + iodo-β-cyclodextrin → 2,6-bis(β-cyclodextrin-6-ylthio)naphthalene

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide Substitution;

2,6-naphthalene-dithiol (96892-95-4) → (2,6-naphthylenedisulfonyl)diacetic acid (96892-98-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 67 percent / 6percent aq. NaOH / 2 h / 70 °C 2: 84 percent / H2O2 / H2O / 3 h / 90 °C View Scheme

2,6-naphthalene-dithiol (96892-95-4) → (1,5-dinitro-2,6-naphthylenedithio)diacetic acid

Conditions	Yield
Multi-step reaction with 2 steps 1: 67 percent / 6percent aq. NaOH / 2 h / 70 °C 2: 0.2 g / 40percent aq. HNO3 / acetic acid / 2 h / 6 - 15 °C View Scheme

2,6-naphthalene-dithiol (96892-95-4) → naphtho[1,2-b:5,6-b′]dithiophene (217-13-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium ethylate; NaI; ethanol 2: phosphoric acid; phosphorus (V)-oxide / 150 °C View Scheme

Upstream product

• 581-75-9 naphthalene-2,6-disulfonic acid 
• 1655-45-4 disodium 2,6-naphthalenedisulfonate 
• 13827-62-8 2,6-naphthalenedisulfonyl dichloride 

Downstream Products

• 10075-77-1 2,6-bis(methylthio)naphthalene 

Relevant academic research and scientific papers

Dependence of single-molecule conductance on molecule junction symmetry

The symmetry of a molecule junction has been shown to play a significant role in determining the conductance of the molecule, but the details of how conductance changes with symmetry have heretofore been unknown. Herein, we investigate a naphthalenedithiol single-molecule system in which sulfur atoms from the molecule are anchored to two facing gold electrodes. In the studied system, the highest single-molecule conductance, for a molecule junction of 1,4-symmetry, is 110 times larger than the lowest single-molecule conductance, for a molecule junction of 2,7-symmetry. We demonstrate clearly that the measured dependence of molecule junction symmetry for single-molecule junctions agrees with theoretical predictions.

β-Cyclodextrin dimers as potential tumor pretargeting agents

A β-cyclodextrin dimer binds a di-tert-butylbenzyl-Cucyclen with high affinity, demonstrating potential as a receptor/ligand system for tumor pretargeting with monoclonal antibodies.

Process for preparation of aromatic thiols

Disclosed is a process for preparation of an aromatic thiol corresponding to the structure wherein A is a substituted or unsubstituted aromatic radical and n is 1, 2, 3, 4, 5 or 6 comprising contacting at a temperature of at least 80° C. an aromatic halide corresponding to the structure wherein A is the same as above, X is bromine or iodine and n is 1, 2, 3, 4, 5, or 6 with thiourea in the presence of nickel metal.

SYNTHESIS AND SOME TRANSFORMATIONS OF (2,7-NAPHTHYLENEDITHIO)- AND (2,6-NAPHTHYLENEDITHIO)DIACETIC ACID

(2,7-Naphthylenedithio)- and (2,6-naphthylenedithio)diacetic acids were obtained from 2,7- and 2,6-naphthalenedisulfonic acids respectively and were oxidized to (2,7-naphthylenedisulfonyl)diacetic acids with hydrogen peroxide in acetic acid.The nitration of (2,6-naphthylenedithio)diacetic acid leads to the formation of (1,5-dinitro-2,6-naphthylenedithio)diacetic acid.