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Methyl naphthalene-2-sulfonate typically appears as a crystalline solid or compact powder with low vapor pressure and minimal volatility.
Methyl naphthalene-2-sulfonate exhibits low water solubility due to the dominant hydrophobic aromatic framework but dissolves readily in many organic solvents such as aromatics, chlorinated hydrocarbons, ethers, and esters.
Methyl naphthalene-2-sulfonate demonstrates good thermal stability and maintains structural integrity under moderate processing temperatures.
CAS Number: 5138-53-4
Molecular Formula: C11H10O3S
Molecular Weight: 222.26
Synonyms: Methyl naphthalene-2-sulfonate, 2-Naphthalenesulfonic acid, methyl ester, Methyl 2-naphthalenesulfonate, Methyl naphthalene-2-sulphonate, Naphthalene-2-sulfonic acid methyl ester, 2-Naphthyl methanesulfonate (common variant usage), CAS-5138-53-4, DTXSID20509106, DTXCID00459913, RefChem:356778, InChIKey AFVPRVLDAPXRCX-UHFFFAOYSA-N, SCHEMBL3633735, SCHEMBL15352387, SCHEMBL29732529, 2-Naphthalenesulfonic acid, methyl ester
Methyl naphthalene-2-sulfonate is sulfonated using concentrated sulfuric acid under controlled conditions to yield a mixture of monosulfonated isomers, primarily naphthalene-1-sulfonic acid (α-isomer) and naphthalene-2-sulfonic acid (β-isomer).
The α-isomer dominates initially but is thermally isomerized to the β-isomer.
Methyl naphthalene-2-sulfonate is an aromatic sulfonate ester obtained by esterification of 2-naphthalenesulfonic acid with methanol, forming a stable organic ester containing a fused bicyclic naphthalene ring system.
The molecule combines a hydrophobic polycyclic aromatic structure with a polar sulfonyl ester group, giving moderate polarity, low water solubility, and good compatibility with many organic solvents.
Methyl naphthalene-2-sulfonate behaves as a neutral ester that is resistant to mild oxidation but can undergo hydrolysis under strong acidic or alkaline conditions.
From a molecular standpoint, the sulfonyl group (–SO₂–OCH₃) is strongly electron-withdrawing and influences the electronic distribution of the aromatic ring, enhancing thermal stability and reducing uncontrolled side reactions.
The rigid aromatic backbone contributes to high chemical durability and low volatility compared with aliphatic esters.
Methyl naphthalene-2-sulfonate does not ionize under neutral conditions and therefore remains electrically neutral in most formulation systems.
Methyl naphthalene-2-sulfonate typically appears as a crystalline or solid organic material with a faint aromatic odor and low vapor pressure.
Methyl naphthalene-2-sulfonate shows limited solubility in water but dissolves well in aromatic hydrocarbons, chlorinated solvents, ketones, and ester solvents.
The material should be stored in tightly sealed containers away from moisture, strong acids, and strong bases to prevent slow ester degradation.
Methyl naphthalene-2-sulfonate is a synthetic aromatic sulfonate ester formed by the condensation of methanol with 2-naphthalenesulfonic acid, producing a chemically stable ester linkage.
Methyl naphthalene-2-sulfonate contains a rigid polycyclic naphthalene ring system that provides strong π-electron conjugation, high thermal resistance, and hydrophobic character, while the sulfonate ester group introduces controlled polarity and electrophilic reactivity.
This structural balance allows the molecule to behave as a neutral organic ester with predictable solubility and chemical stability.
From a chemical reactivity perspective, the sulfonyl ester group is strongly electron-withdrawing, which stabilizes the aromatic ring and reduces susceptibility to uncontrolled oxidation or electrophilic attack.
Under neutral conditions, the compound remains chemically inert, but in the presence of strong acids, bases, or prolonged moisture exposure, slow hydrolysis may occur, regenerating the parent sulfonic acid and methanol.
The ester group can also function as a leaving group in nucleophilic substitution reactions during advanced organic synthesis.
Melting point: 56 °C
Boiling point: 379.3±11.0 °C(Predicted)
Density: 1.294±0.06 g/cm3(Predicted)
Methyl naphthalene-2-sulfonate is an aromatic sulfonate ester formed by esterification of 2-naphthalenesulfonic acid with methanol, giving a rigid polycyclic aromatic structure combined with a polar sulfonate ester functional group.
The molecule contains a fused naphthalene ring system that provides high thermal stability, hydrophobic character, and strong π-electron conjugation, while the sulfonate ester group contributes moderate polarity and chemical reactivity toward nucleophilic substitution and hydrolysis under harsh conditions.
Methyl naphthalene-2-sulfonate behaves as a neutral organic ester with low water solubility and good solubility in many organic solvents such as aromatic hydrocarbons, chlorinated solvents, and esters.
From a structural chemistry perspective, the sulfonyl group (–SO₂–O–CH₃) introduces strong electron-withdrawing character, which stabilizes the aromatic ring and influences electrophilic substitution patterns on the naphthalene backbone.
The ester linkage is relatively stable under neutral conditions but may hydrolyze in strong acidic or alkaline environments, regenerating the sulfonic acid and methanol.
The rigid aromatic framework provides high melting stability and resistance to oxidation compared with aliphatic esters.
Physically, methyl naphthalene-2-sulfonate typically appears as a crystalline solid or solid powder with low volatility and a faint aromatic odor.
It shows good thermal resistance, low vapor pressure, and limited miscibility with water due to the dominance of the hydrophobic naphthalene ring system.
The compound is chemically compatible with many organic reagents but should be protected from strong bases, strong acids, and prolonged moisture exposure.
In organic and industrial chemistry, methyl naphthalene-2-sulfonate functions as an intermediate for synthesis of surfactants, dyes, dispersants, pharmaceutical intermediates, and specialty aromatic derivatives.
The sulfonate ester group can act as a leaving group in substitution reactions, enabling functionalization of the naphthalene core for advanced chemical manufacturing.
Methyl naphthalene-2-sulfonates aromatic stability and controlled reactivity make it useful in fine chemical development, polymer additives research, and specialty formulation chemistry.
In formulation and materials chemistry, the molecule shows compatibility with a wide range of organic polymers, plasticizers, resins, and surfactant systems due to its aromatic stability and moderate polarity.
Methyl naphthalene-2-sulfonate can contribute to controlled viscosity behavior, dispersion stability, and interfacial activity in specialized formulations.
The aromatic sulfonate structure also makes it useful as a precursor for functional additives and surface-active derivatives.
From an analytical standpoint, methyl naphthalene-2-sulfonate can be characterized by infrared spectroscopy through strong sulfonyl stretching bands, by nuclear magnetic resonance for aromatic proton and ester confirmation, and by mass spectrometry for molecular identity verification.
Its purity and trace impurity levels are commonly monitored by chromatographic techniques.
These properties make it suitable as a reference compound and synthetic intermediate in fine chemical research and industrial development.
Methyl naphthalene-2-sulfonate can make the dye more brightly and colorful, increase color force, and uniformcoloring.
It can also be mixture formulation with all kinds of dispersants in order to adapt to the various customers requirements of disperse dyes and vat dyes.
Methyl naphthalene-2-sulfonate can be used as dispersing agent both in during grinding vat dyestuff and during dyeing with vat dye suspension, and stabilizer in rubber & latex industry, auxiliary tanning agent in leather industry.
Uses:
Methyl naphthalene-2-sulfonate is primarily used as an intermediate in organic synthesis for the preparation of sulfonated aromatic derivatives, specialty surfactants, and functional additives.
The sulfonate ester group can participate in substitution reactions, enabling controlled functionalization of the naphthalene ring for advanced chemical manufacturing.
Methyl naphthalene-2-sulfonate is widely applied in fine chemical laboratories for reaction development and structure–property studies.
In dye and pigment chemistry, the compound is used as a precursor for naphthalene-based colorants, optical brighteners, and dispersible aromatic intermediates.
The aromatic stability and sulfonyl functionality support controlled chromophore synthesis and improved solubility tuning in downstream products.
Methyl naphthalene-2-sulfonate contributes to consistent molecular architecture in high-performance coloring systems.
In polymer and materials science, methyl naphthalene-2-sulfonate is explored as a modifier, compatibility agent, or functional intermediate for resin systems, plastic additives, and surface-active materials.
Its aromatic backbone enhances thermal stability and rigidity in derivative polymers and coatings.
The sulfonate functionality enables chemical anchoring and polarity adjustment in advanced material formulations.
In pharmaceutical and agrochemical research, the compound serves as a building block for synthesis of biologically active aromatic intermediates and screening compounds.
Methyl naphthalene-2-sulfonate supports medicinal chemistry programs requiring rigid aromatic scaffolds with tunable polarity.
The ester group allows further derivatization for structure–activity relationship studies.
In analytical and academic research laboratories, methyl naphthalene-2-sulfonate is used as a reference compound for chromatographic method development, reaction mechanism studies, and spectral interpretation training.
It assists in validation of sulfonate ester behavior under different chemical environments.
These applications make it valuable in research-driven chemical development rather than direct consumer use.
Methyl naphthalene-2-sulfonate is widely used as a synthetic intermediate in the manufacture of surfactants, wetting agents, dispersants, and specialty sulfonated aromatic compounds.
The activated sulfonate ester group enables nucleophilic substitution and functional group transformation, allowing production of tailored amphiphilic molecules for industrial formulations.
Methyl naphthalene-2-sulfonate supports scalable synthesis routes in fine chemical and specialty chemical production.
In dye, pigment, and optical material industries, the compound is applied as a precursor for naphthalene-derived colorants, fluorescent intermediates, and UV-active aromatic compounds.
The rigid aromatic skeleton provides color stability, photochemical durability, and controlled electronic properties in advanced chromophore systems.
Methyl naphthalene-2-sulfonate assists in synthesis of high-purity intermediates used in textile, plastic, and ink applications.
In polymer chemistry and materials engineering, methyl naphthalene-2-sulfonate is utilized to introduce aromatic sulfonate functionality into polymer backbones, coatings, and composite materials.
It enables modification of surface energy, adhesion behavior, and dispersion stability in engineered materials.
The compound also supports development of ion-conducting polymers, specialty resins, and functional coatings.
In pharmaceutical and agrochemical research, the compound serves as a scaffold for preparation of aromatic intermediates and lead structures used in screening libraries and medicinal chemistry programs.
It allows fine-tuning of molecular polarity, lipophilicity, and reactivity for structure–activity relationship optimization.
The ester group facilitates selective derivatization during multistep synthesis routes.
In analytical chemistry, methyl naphthalene-2-sulfonate is used as a reference standard for sulfonate ester characterization, chromatographic calibration, and degradation pathway studies.
It assists in validating reaction kinetics, hydrolysis behavior, and impurity profiling in quality control environments.
These applications make it valuable for both industrial R&D and academic chemical research programs.
Safety Profile:
Methyl naphthalene-2-sulfonate may cause irritation to the eyes, skin, and respiratory tract if dust or vapors are inhaled or if direct contact occurs.
Fine particles can produce mechanical irritation, redness, tearing, or mild burning sensations, especially in sensitive individuals.
Prolonged or repeated exposure without protective equipment may increase discomfort or dryness of exposed tissues.
Inhalation of dust or decomposition fumes may lead to coughing, throat irritation, headache, or short-term respiratory discomfort.
Heating the material to high temperatures or burning it can generate irritating and potentially toxic fumes such as sulfur oxides, carbon monoxide, and aromatic vapors.
Adequate ventilation and temperature control are essential during thermal processing or reaction handling.
Skin contact with the solid or concentrated solutions may cause mild irritation, particularly after prolonged exposure or in the presence of moisture or solvents that enhance skin penetration.
Eye contact can result in temporary inflammation and blurred vision until rinsed thoroughly with water.
Accidental ingestion may cause gastrointestinal irritation, nausea, or discomfort.
The compound is combustible and may contribute to fire spread under intense heat or ignition conditions.
During combustion, dense smoke and sulfur-containing gases may be released, which require respiratory protection for emergency responders.
Suitable extinguishing media include dry chemical, foam, carbon dioxide, or water spray depending on surrounding materials.
