N-CHLORO-P-TOLUENESULFONAMIDE

N-chloro-p-toluenesulfonamide is a white to yellow crystalline powder with characteristic odor. 
N-chloro-p-toluenesulfonamide is an air sensitive and corrosive, cause eye and skin burns and chemical dangers: Chloramine T is known to explode on heating above 130°C (anhydrous). 
N-chloro-p-toluenesulfonamide decomposes slowly under the influence of air producing chlorine (trihydrate). 

CAS Number: 7080-50-4
Molecular Formula: C7H11ClNNaO3S
Molecular Weight: 247.67
EINECS Number: 615-172-8

Synonyms: N-Chloro-p-toluenesulfonamide, tosylchloramide, Tosylchloramide, Chloramine-T, p-Toluenesulfonamide, N-chloro-, Benzenesulfonamide, N-chloro-4-methyl-, N-chloro-4-, ethylbenzenesulfonamide, n-chloro-4-methyl-benzenesulfonamide, N-chlorotoluene-p-sulfonamide, N-chloro-4-methylbenzene-1-sulfonamide, CAS 144-86-5, UNII-UF17KA8AC5, CHEBI:53782, CHEMBL1625750, UF17KA8AC5, DTXSID9047627, RefChem:898633, DB14708, SCHEMBL43534, AKOS004909750, EBC-49029, NS00005965, EN300-215534, SR-01000944411, SR-01000944411-1, BRD-K93546328-236-02-8, Q27124208CHLORAMINE T 3-HYDRATE;Chloramine-T trihydrate, ACS, 98.0-103.0%;Chloroamine t trihydrate;Benzenesulfonamide, N-chloro-4-methyl-, sodium salt, trihydrate;chloramine-t trihydrate, acs;CHLORAMINE T REAGENT (ACS);N-Chloro-p-toluenesulfonamide sodium salt, Chloraminum;Chloramine-T trihydrate,97+%

N-chloro-p-toluenesulfonamide is commercially available in the form of a trihydrate and is a stable white to pale yellow solid. 
N-chloro-p-toluenesulfonamide is a reagent for selective oxidation of methionine. 
On heating or on contact with acids it decomposes and produce toxic gases.

N-chloro-p-toluenesulfonamide is used as an antibacterial agent; a topical antiseptic. 
Capable of oxidative cyclization to produce various heterocycles. 
Nitrene source for aziridinations and aminohydroxylations. 

Reactant for Preparation of factor Xa inhibitors as novel anticoagulants.
N-chloro-p-toluenesulfonamide is the organic compound with the formula CH3C6H4SO2NClNa. 
Both the anhydrous salt and its trihydrate are known. 

N-chloro-p-toluenesulfonamide is used as a reagent in organic synthesis.
It is commonly used as cyclizing agent in the synthesis of aziridine, oxadiazole, isoxazole and pyrazoles.
It's inexpensive, has low toxicity and acts as a oxidizing agent. 

In addition, it also acts as a source of nitrogen anions and electrophilic cations. 
N-chloro-p-toluenesulfonamide may undergo degradation on long term exposure to atmosphere such that care must be taken during its storage.
N-chloro-p-toluenesulfonamide contains active (electrophilic) chlorine. 

Its reactivity is similar to that of sodium hypochlorite. 
Aqueous solutions of chloramine-T are slightly basic (pH typically 8.5). 
The pKa of the closely related N-chloro-p-toluenesulfonamide C6H5SO2NClH is 9.5.

N-chloro-p-toluenesulfonamide contains an N–Cl bond that is relatively stable yet highly reactive under suitable conditions.
This bond allows the compound to act as a mild, selective oxidant compared with elemental chlorine or hypochlorite.
Its reactivity can be tuned by pH, solvent, and temperature, which makes it useful in controlled chemical processes.

In aqueous solution, N-chloro-p-toluenesulfonamide can slowly release active chlorine species.
This controlled release provides disinfecting and antimicrobial action without the rapid decomposition seen in free chlorine systems.
As a result, it has been used in applications requiring sustained oxidative activity.

Melting point : 167–170 °C
Density : 1.43
Bulk density : 540–680 kg/m³
Flash point : 92 °C
Storage temperature : Store at +2 °C to +8 °C
Solubility : H₂O, passes test
Form : Crystalline powder
pKa : pK₁ = 4.54 (25 °C)
Color : White to off-white
pH : 8–10 (50 g/L, H₂O, 20 °C)
Odor : Chlorine-like
pH range : 8–10
Water solubility : Soluble in water and ethyl alcohol; insoluble in benzene and ethers
Sensitivity : Moisture sensitive
Merck Index : 14,2075
BRN : 3924168
LogP : 2.111 (estimated)
InChI : 1S/C7H7ClNO2S.Na.3H2O/c1-6-2-4-7(5-3-6)12(10,11)9-8;;;;/h2-5H,1H3;;3*1H2/q-1;+1;;;
InChIKey : NZYOAGBNMCVQIV-UHFFFAOYSA-N
SMILES : O.O.O.Cc1ccc(cc1)S(=O)(=O)N([Na])Cl

N-chloro-p-toluenesulfonamide shows strong activity against bacteria, fungi, and some viruses.
This antimicrobial behavior arises from oxidation of cellular proteins and enzymes essential for microbial survival.
Because of this mechanism, it has historically been applied in sanitation and disinfection contexts.

From a structural perspective, the p-tolyl group increases stability and reduces volatility.
This makes the compound easier to store, transport, and handle than many other chlorinating agents.
Its solid form also allows accurate dosing in laboratory and industrial use.

N-chloro-p-toluenesulfonamide has been extensively studied in kinetic and mechanistic chemistry.
It is often used as a model compound to understand N-halogen chemistry and oxidation pathways.
These studies contribute to broader knowledge of chloramine behavior in both synthetic and environmental systems.

N-chloro-p-toluenesulfonamide is an organic chloramine compound belonging to the sulfonamide family and is commonly known as chloramine-T.
Its chemical structure consists of a p-toluenesulfonamide group in which the nitrogen atom is substituted with a chlorine atom.
This N–Cl bond gives the compound strong oxidizing and chlorinating properties.

N-chloro-p-toluenesulfonamide is typically a white to pale crystalline solid that is stable under normal storage conditions.
It is soluble in water and polar solvents, forming solutions that release active chlorine species.
Because of this behavior, it acts as a controlled source of chlorine rather than free chlorine gas.

Chemically, it functions as an electrophilic chlorinating and oxidizing agent.
In aqueous media, it can generate hypochlorous acid–like activity while remaining more stable and easier to handle.
This controlled reactivity makes it useful in applications where gradual or selective oxidation is required.

N-chloro-p-toluenesulfonamide has been widely studied in organic synthesis and analytical chemistry.
It is used to introduce chlorine into organic molecules and to oxidize sulfur-, nitrogen-, and carbon-containing functional groups.
Its predictable reactivity and solid-state stability distinguish it from many other chlorine-based reagents.

Uses: 
N-chloro-p-toluenesulfonamide is used as an intermediate in the manufacture of chemical substances such as pharmaceuticals. 
N-chloro-p-toluenesulfonamide combines with iodogen or lactoperoxidase and is commonly used for labeling peptides and proteins with radioiodine isotopes. 
Hypochlorite released from N-chloro-p-toluenesulfonamide acts as an effective oxidizing agent for iodide to form iodine monochloride (ICl).

N-chloro-p-toluenesulfonamide is a strong oxidant. 
It oxidizes hydrogen sulfide to sulfur, and mustard gas (bis(2-chloroethyl) sulfide) to yield a harmless crystalline sulfimide.
It converts iodide to iodine monochloride (ICl). 

N-chloro-p-toluenesulfonamide rapidly undergoes electrophilic substitution predominantly with activated aromatic rings, such as those of the amino acid tyrosine. 
This makes it a useful reagent in combination with an iodide ion source for iodination of peptides and proteins. 
N-chloro-p-toluenesulfonamide together with iodogen (1,3,4,6-Tetrachloro-3a,6a-diphenyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione) or lactoperoxidase is commonly used for labeling peptides and proteins with radioiodine isotopes.

N-chloro-p-toluenesulfonamide is widely used as a disinfectant and antimicrobial agent.
It is effective against bacteria, fungi, and some viruses due to its controlled release of active chlorine.
This makes it suitable for sanitation in medical, veterinary, and laboratory environments.

In organic synthesis, it is used as a chlorinating and mild oxidizing reagent.
N-chloro-p-toluenesulfonamide enables selective chlorination of organic compounds and oxidation of functional groups without the harshness of elemental chlorine.
This controlled reactivity is valuable in fine chemical and pharmaceutical synthesis.

N-chloro-p-toluenesulfonamide is applied in analytical chemistry as an oxidizing agent.
N-chloro-p-toluenesulfonamide is used in redox titrations and kinetic studies because of its predictable reaction behavior.
This allows accurate and reproducible analytical measurements.

In water treatment and hygiene applications, it has been used as a source of stable chlorine.
Compared to hypochlorite, it offers improved storage stability and easier handling.
This makes it useful in controlled disinfection systems.

N-chloro-p-toluenesulfonamide is also used in biochemical and microbiological research.
The compound helps study oxidative stress and protein oxidation mechanisms.
These applications support research in enzymology and microbial physiology.

N-chloro-p-toluenesulfonamide is used in veterinary medicine as a topical antiseptic and wound-cleansing agent.
It helps control bacterial and fungal infections in animals by providing sustained antimicrobial activity.
Its stability allows safe preparation of aqueous solutions for routine hygienic use.

In pharmaceutical manufacturing, it is employed for controlled oxidation steps during intermediate synthesis.
N-chloro-p-toluenesulfonamides selectivity reduces unwanted side reactions compared with stronger chlorinating agents.
This improves yield and purity in multistep synthetic routes.

The compound is used in food and dairy sanitation for equipment and surface disinfection.
It provides effective microbial control without producing strong odors or excessive corrosive effects.
This makes it suitable for cleaning pipelines, containers, and processing tools.

In environmental and water microbiology studies, it is used to model chloramine behavior.
Researchers use it to study chlorine demand, oxidative degradation, and disinfection by-product formation.
These studies help optimize safer water disinfection strategies.

N-chloro-p-toluenesulfonamide is also applied in textile and paper industries as a bleaching and sanitizing aid.
N-chloro-p-toluenesulfonamide assists in removing microbial contamination during processing stages.
Its controlled oxidizing strength minimizes damage to fibers compared to harsher chlorine sources.

Safety Profile:
N-chloro-p-toluenesulfonamide is a strong oxidizing and chlorinating agent and can be hazardous upon direct contact.
N-chloro-p-toluenesulfonamide may cause irritation or burns to the skin, eyes, and mucous membranes due to the release of active chlorine.
Eye exposure can result in severe irritation and potential damage if not promptly treated.

Inhalation of dust or vapors can irritate the respiratory tract.
Exposure may lead to coughing, throat irritation, or breathing discomfort, especially in poorly ventilated areas.
Prolonged or repeated inhalation should be avoided through proper ventilation and respiratory protection.

Ingestion of N-chloro-p-toluenesulfonamide is harmful and may cause gastrointestinal irritation or systemic effects.
The compound can react with biological tissues through oxidative mechanisms.
Accidental ingestion requires immediate medical attention.

The substance can react vigorously with reducing agents, acids, or organic materials.
Improper storage or mixing may lead to decomposition with the release of chlorine-containing gases.
N-chloro-p-toluenesulfonamide should be stored away from incompatible materials in tightly sealed containers.