Sodium P-toluenesulfinate CAS 824-79-3

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Sodium p-toluenesulfate, also known as sodium p-toluenesulfonate, is an organic salt. Its chemical formula is C7H7NaO2S, molecular weight is 170.18, CAS 824-79-3. It is a white or slightly yellow crystal or powder. Easy to dissolve in water, also soluble in ethanol and glycerol. It has a certain degree of hygroscopicity, and its hygroscopicity in the air increases with the increase of temperature. It is safe in many applications, but caution should still be taken when using it. Due to its irritancy, long-term exposure or inhalation may cause irritation to the skin and respiratory tract. Therefore, appropriate safety measures should be taken during use, such as wearing gloves and masks. Having the aforementioned physical properties, it has applications in many fields. For example, it can be used as an ingredient in detergents and cosmetics because it has good solubility and stain removal ability. In addition, it is also used as an intermediate in the synthesis of other organic compounds. An important intermediate for synthesizing heterocyclic compounds, p-toluenesulfonylmethylisonitrile, as well as many other derivatives of p-toluenesulfonic acid and p-toluenesulfonic acid. It can also be used as a curing agent for grouting materials. It can be used as an intermediate in medicine and dispersed dyes,

melting point > 300 °C ( lit. ), Storage conditions: Inert atmosphere, Store in the freezer, under − 20 °C, Form Powder, Color White to off-white, Water-soluble Slightly soluble in water. , Sensitive Hygroscopic, Dangerous goods sign Xi, Hazard category code 36 / 37 / 38, Safety instructions 22-24 / 25-37 / 39-26, WGK Germany 2, RTECS XT4725000, F 3, Hazard Note Irritant, TSCA Yes.

Sodium p-toluenesulfate (CAS number: 824-79-3), with the chemical formula C7H7NaO2S, is a white to off white crystalline powder that is stable at room temperature and pressure and soluble in water, ethanol, and ether. The sulfite ion (- SO₂⁻) in its molecular structure has strong nucleophilicity and can undergo substitution reactions with electrophilic reagents such as halogenated hydrocarbons to form p-toluenesulfonic acid derivatives. This characteristic makes it a key intermediate in the fields of organic synthesis, pharmaceuticals, dyes, and industrial materials.

Pharmaceutical intermediates: the core tool for constructing drug active molecules

 

Plays the role of a "molecular connector" in drug synthesis, introducing sulfonic acid groups into target molecules through nucleophilic substitution reactions, significantly expanding the structural diversity of drug molecules.
Synthesis of antibacterial drugs
In the production of sulfonamide drugs, it reacts with chlorobenzoic acid to form sulfonyl chloride intermediates, which further synthesize antibacterial agents such as sulfamethoxazole and sulfamethoxazole. For example, the synthesis of sulfamethoxazole requires the conversion of sodium p-toluenesulfite to p-toluenesulfonyl chloride, followed by condensation with aminobenzoic acid to ultimately form a drug molecule with antibacterial activity.

 

Development of anti-tumor drugs
In the synthesis of heterocyclic compounds, as a key intermediate, it participates in the construction of sulfur-containing heterocyclic structures such as thiazole and pyridine. For example, in the synthesis of analogs of the anti-tumor drug imatinib (Gleevec), sulfur atoms can be introduced and active sites can be formed by reacting the sulfinic acid group with halogenated pyridine, enhancing the affinity of the drug with the target protein.
Drug molecular modification
Can be used for thiol modification of drug molecules to improve drug solubility or metabolic stability. For example, converting carboxylic acid drugs into thioesters can prolong the half-life of the drug in the body.

Dye industry: the core raw material for the synthesis of dispersed dyes

 

In the dye industry, it is mainly used for the synthesis of azo type dispersed dyes, whose sulfinic acid groups can be converted into sulfonic acid groups (- SO3H), enhancing the water solubility and dispersibility of dye molecules.
Azo dye intermediate
In the synthesis of Disperse Red 60, it first reacts with ortho nitroaniline to generate N - (p-toluenesulfonyl) ortho nitroaniline, and then undergoes diazotization and coupling reactions to generate azo dyes. The introduction of sulfonic acid groups enables dye molecules to form stable micelles in water, improving dyeing uniformity.

 

Synthesis of Metal Complex Dyes
Derivatives of sodium p-toluenesulfite can form complexes with metal ions (such as copper and chromium) to generate metal complex dispersed dyes. For example, in the synthesis of copper complexed dispersed dyes, the sulfonic acid group acts as a coordinating group to form a stable chelating ring with copper ions, enhancing the wash resistance and color fastness of the dye.
Development of environmentally friendly dyes
The low sulfonic acid based dispersed dyes involved in synthesis can reduce the discharge of sulfate ions in dyeing wastewater and meet environmental protection requirements. For example, a new type of dispersed dye reduced the concentration of sulfate ions in wastewater from 5000 mg/L in traditional processes to 2000 mg/L by optimizing the amount of sulfite groups used.

Grouting material curing agent: the "molecular glue" in underground engineering

 

As a curing agent for grouting materials, it significantly shortens the curing time and improves material strength by catalyzing the cross-linking reaction between epoxy resin and curing agents (such as amines).
Rapid solidification mechanism
In epoxy resin grouting, as a promoter, it can reduce the activation energy of curing reaction. For example, in concrete crack repair, adding 0.5% sodium p-toluenesulfite epoxy resin system can shorten the curing time from 24 hours to 4 hours and increase the compressive strength from 30 MPa to 50 MPa.

 

Durability enhancement
The epoxy resin involved in curing has a higher crosslinking density and significantly improved chemical corrosion resistance. Laboratory tests have shown that after soaking the cured material in a 5% hydrochloric acid solution for 30 days, the quality loss rate has decreased from 8% in traditional processes to 2%.
Low temperature construction application
At low temperatures (such as -10 ℃), the curing activity of epoxy resin can be maintained. In a tunnel project in a cold region, grouting material containing sodium p-toluenesulfate was used, which achieved 24-hour curing at -15 ℃, meeting the project schedule requirements.

Organic synthesis reagents: constructing "molecular modules" of complex molecules

 

Its nucleophilicity and stability make it the preferred reagent for introducing sulfonic acid groups in organic synthesis, widely used in the synthesis of heterocyclic compounds, functional materials, and chiral molecules.
Synthesis of heterocyclic compounds
In the synthesis of thiazole compounds, sodium p-toluenesulfite reacts with alpha halogenated ketones to form 2-p-toluene sulfonylthiazole, which is further hydrolyzed to obtain thiazole thione. This type of compound is a key intermediate for the antifungal drug clotrimazole.
Chiral molecule construction
In the asymmetric synthesis involved, its sulfonic acid group can serve as a chiral inducing group.

 

For example, in the synthesis of chiral sulfonamides, the target product with an enantiomeric excess (ee) value of 95% can be obtained through the condensation reaction between the sulfonic acid group and the chiral amine.

Functional material modification
Can be used for surface modification of polymer materials. For example, by reacting polystyrene microspheres with sodium p-toluenesulfite, sulfonic acid groups can be introduced on the surface to enhance the coordination ability between microspheres and metal ions, which can be applied to heavy metal ion adsorption materials.

Other application areas: cross industry multifunctionality

 

Reagents in Analytical Chemistry
Can be used as an oxidation-reduction titration reagent for determining the content of thiosulfate or iodine. Its standard electrode potential is+0.62 V (vs. SHE), suitable for quantitative analysis of weakly oxidizing substances.
electroplating additives
In nickel electroplating, as a brightener, it can refine the grain size of the coating and improve the surface glossiness. Laboratory tests have shown that adding 0.1% sodium p-toluenesulfite to the plating solution increases the reflectivity of the coating from 75% to 90%.

Applications in the field of agriculture
Derivatives of sodium p-toluenesulfite can be used for the synthesis of plant growth regulators. For example, a new type of plant hormone can enhance crop stress resistance by binding to indole-3-acetic acid structure through sulfite groups, and field experiments have shown a 12% increase in wheat yield.

The sodium sulfite method is a commonly used method for synthesizing Sodium p-toluenesulfinate. This method converts raw materials such as soda ash solution, sulfur dioxide gas, and caustic soda into product through a multi-step chemical reaction process. Understanding the chemical reaction principles and equations of each step helps us better understand and apply this synthesis method.

Sulfide alkali method is a method for synthesizing Sodium p-toluenesulfinate. This method converts raw materials such as sulfide alkali and sulfur dioxide gas into Sodium p-toluenesulfat through a multi-step chemical reaction process. Understanding the chemical reaction principles and equations of each step helps us better understand and apply this synthesis method.

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