Sodium 1-naphthalenesulfonate
[CAS# 130-14-3]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Cyanopyridine
• Name: Sodium 1-naphthalenesulfonate
• Synonyms: Sodium naphthalene-1-sulphonate; 1-Naphthalenesulfonic acid sodium salt
• Molecular Formula: C₁₀H₇NaO₃S
• Molecular Weight: 230.21
• CAS Registry Number: 130-14-3
• EC Number: 204-976-0
• SMILES: C1=CC=C2C(=C1)C=CC=C2S(=O)(=O)[O-].[Na+]

Properties

• Melting point: 299-301 ºC (Expl.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

Sodium 1-naphthalenesulfonate is the sodium salt of 1-naphthalenesulfonic acid, a sulfonated aromatic compound derived from naphthalene. It is an organic sodium salt with the molecular formula C₁₀H₇SO₃Na and a molecular weight of approximately 216.21 g/mol. The compound appears as a white to off-white crystalline solid and is known for its high solubility in water, a property attributed to the presence of the sulfonate group.

The discovery of sodium 1-naphthalenesulfonate is linked to early developments in sulfonation reactions of aromatic hydrocarbons during the 19th century. The sulfonation of naphthalene using concentrated sulfuric acid results in the formation of naphthalenesulfonic acid isomers, predominantly the 1- and 2-substituted derivatives, depending on reaction conditions such as temperature and acid concentration. The sodium salt form is prepared by neutralization of the corresponding acid with sodium hydroxide or other suitable sodium bases.

Sodium 1-naphthalenesulfonate is widely used in the chemical industry as a dispersant, intermediate, and additive due to its surface-active properties. Its application as a dispersing agent is particularly important in the dye and pigment industry, where it helps stabilize suspensions of insoluble materials in aqueous media. This function supports the production and formulation of dyes for textiles and coatings, enhancing color uniformity and preventing particle aggregation during processing and application.

In synthetic organic chemistry, sodium 1-naphthalenesulfonate serves as an intermediate in the production of various naphthalene derivatives, especially azo dyes. Azo coupling reactions between diazonium salts and 1-naphthalenesulfonic acid derivatives yield a broad range of vividly colored compounds that are extensively used in commercial dyeing operations. The compound’s sulfonate group not only improves solubility but also facilitates the formation of strong ionic interactions with substrates such as cellulose and protein fibers.

Sodium 1-naphthalenesulfonate has also found utility in polymer chemistry and the preparation of surfactant formulations. It can be incorporated into polymer systems to modify surface characteristics or used as an additive in detergent formulations to enhance emulsification and solubilization of hydrophobic substances. Additionally, it may be employed in the formulation of dispersing agents in agricultural and construction products.

Its sulfonate group enables sodium 1-naphthalenesulfonate to participate in coordination with metal ions and interact with charged surfaces. This property has been used in the formulation of specialty chemicals, including corrosion inhibitors and scale control agents. Its interactions with metal ions can influence solubility and reactivity in aqueous environments, making it useful in industrial water treatment applications.

Analytically, sodium 1-naphthalenesulfonate is characterized using techniques such as nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy, mass spectrometry (MS), and ultraviolet-visible (UV-Vis) spectroscopy. These methods confirm the aromatic structure and the presence of the sulfonate functionality. The compound exhibits typical aromatic absorption bands in IR spectra and strong UV absorption due to the conjugated naphthalene ring.

In toxicological terms, sodium 1-naphthalenesulfonate is generally considered to have low acute toxicity when handled appropriately, but it may cause irritation upon contact with the eyes or skin. Standard precautions, including the use of personal protective equipment and proper ventilation, are recommended when handling the substance in laboratory or industrial settings.

The compound is commercially available and manufactured in bulk quantities to meet the demands of industries such as dye manufacturing, water treatment, textiles, and specialty chemicals. Its stability in aqueous solution and compatibility with a variety of formulation ingredients contribute to its widespread use.

Sodium 1-naphthalenesulfonate continues to be a functional component in a range of chemical processes and products, valued for its solubility, chemical reactivity, and ability to act as a dispersant and surfactant in multiple industrial applications.

References

2023. Simple solid-phase colorimetry for trace Cr(VI) by combination of complexation with diphenylcarbazide and ion-pair solid-phase extraction with sedimentable dispersed particulates. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry, 39(5).
DOI: 10.1007/s44211-023-00286-9

2022. Highly stable gold nanoparticles in an aqueous solution without any stabilizer prepared by a solution plasma process evaluated through capillary zone electrophoresis. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry, 38(9).
DOI: 10.1007/s44211-022-00149-9

2021. Electrochemical and thermomechanical behavior of nickel-graphene oxide (2-4L GO) nanocomposite coatings. Applied Physics A, 127(3).
DOI: 10.1007/s00339-021-04307-0