Chloramine-T

HCID 3641960CAS 127-65-1

Basic information

Standard SMILES
Cc1ccc(S(=O)(=O)[N-]Cl)cc1.[Na+]
InChIKey
VDQQXEISLMTGAB-UHFFFAOYSA-N
Molecular formula
C7H7ClNNaO2S
Average molar mass
227.64 g/mol
Monoisotopic mass
226.97837142

Overview

Chloramine T is an organic sodium salt derivative of toluene-4-sulfonamide with a chloro substituent in place of an amino hydrogen. It has a role as a disinfectant, an allergen and an antifouling biocide. It contains a chloro(p-tolylsulfonyl)azanide.

Names & identifiers

Preferred name
Chloramine-T
IUPAC
sodium chloro-(4-methylphenyl)sulfonylazanide
English name
Chloramine-T
Molecular formula
C7H7ClNNaO2S
Molecular weight
227.64

Names & synonyms

Chloramine-TCHLORAMINE T127-65-1ChlorazeneTosylchloramide sodiumChloraloneChlorasanChlorazoneTochlorineTolamineAktivinActi-chlore
Show more names
SodiuM chloro(tosyl)aMideSodium n-chloro-p-toluenesulfonamide trihydratehalamidtosylchloramideN-CHLORO-P-TOLUENESULFONAMIDE SODIUM SALTMI 9
ChlorozoneChlorseptolGyneclorinaMultichlorBerkendylChlorazanChlorosolHeliogen

Database identifiers

CAS
127-65-1
PubChem CID
3641960
DTXSID
DTXSID6040321
ChEMBL
CHEMBL1697734
ChEBI
CHEBI:53767
UNII
328AS34YM6
EC Number
204-854-7
Nikkaji
J3.263H

Properties

Computed structural properties

Topological polar surface area
43.5 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
1
Heavy atoms
13

Experimental & physicochemical properties

Chemical ClassesOther Uses -> Biocides/Disinfectants
CosmeticsAntimicrobial
LogP · 2 items

log Kow = 0.84 /Estimated/

0.84 (estimated)

OdorSlight odor of chlorine
DensityDensity (trihydrate): 1.4 g/cm³
Color/FormWhite or slightly yellow crystals or crystalline powder

Physicochemical properties

Melting point
167 · 167-170 °C(lit.)
Density
1.401 · 1.401[at 20℃]
vapor pressure
0 Pa · 0Pa at 25℃
storage temp.
2 · Sealed in dry,2-8°C
solubility
2 O: · H2O: >100 mg/mL
pka
0.39 · 0.39[at 20 ℃]

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P233, P260, P264, P270, P271, P280, P284, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P342+P316, P363, P403, P405, and P501 (click each P-code to see the statement)

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P233, P260, P261, P264, P264+P265, P270, P271, P272, P280, P284, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P333+P317, P342+P316, P362+P364, P363, P403, P405, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 5 items

Chemical: Benzenesulfonamide, N-chloro-4-methyl-, sodium salt

Hazard Traits - Respiratory Toxicity

Benzenesulfonamide, N-chloro-4-methyl-, sodium salt (1:1) is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenesulfonamide, N-chloro-4-methyl-, sodium salt (1:1) are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 31-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/25844

Chloramine-T: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Benzenesulfonamide, N-chloro-4-methyl-, sodium salt: Human health tier II assessment
Fire HazardsCombustible.
Hazards Summary · 1 item

Decomposes slowly in air, liberating chlorine. (Not to be confused with NH2Cl, which is also termed chloramine.) [Hawley] A severe skin, eye, and respiratory tract irritant; A skin sensitizer; May cause asthma; [ICSC] Causes immune contact urticaria; [Kanerva, p. 219] See Chloramine-B

EC ClassificationSymbol: C; R: 22-31-34-42; S: (1/2)-7-22-26-36/37/39-45
UN ClassificationUN Hazard Class: 8; UN Pack Group: III

Safety & protection

Fire FightingUse water spray, powder.
First Aid Measures · 4 items

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .

Safe StorageSeparated from acids and food and feedstuffs.
Storage ConditionsN-Chloramines should be stored cold and protected from light, water, amines and ammonium compounds, strong acids and bases, and easily oxidized organic materials. /N-Chloramines/
Spillage Disposal · 1 item

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Eye PreventionWear safety goggles or eye protection in combination with breathing protection if powder.

Toxicology

InteractionsIt has been suggested that chloramine T can react with some amino acids in gastrointestinal tract to form toxic cyanogen compounds.
Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
Exposure RoutesThe substance can be absorbed into the body by inhalation of its aerosol and by ingestion.
Ecotoxicity Excerpts · 1 item

/AQUATIC SPECIES/ Acute lethal effects of chloramine on eggs and larvae of spotted sea trout given. 48 hr medium tolerance limits for 2 hr old eggs, 10 hr eggs and 1 hr posthatch larvae respectively were 14.14 +/- 1.13, 0.57 +/- 0.28, & 5.75 +/- 3.01 ppm

Signs and Symptoms · 4 items

Cough. Sore throat. Wheezing.

Redness. Pain.

Redness. Pain.

Nausea. Vomiting. Diarrhoea.

ICSC Environmental DataThe substance is toxic to aquatic organisms. The substance may cause long-term effects in the aquatic environment.

Safety data

wgk
2
tsca
TSCA listed
ridadr
UN 3263 8/PG 3
hs_code
29242990
risk_code
22-31-34-42
Signal word
Warning

Chemistry & industry

Pharmacology

ATC Code · 3 items

D08AX04

D - Dermatologicals

QD - Dermatologicals

Mechanism of Action · 5 items

/Immunoglobulin E/ mediation is a possible mechanism of action for induction of environmental or occupational asthma by Chloramine T. /from table/

The major elastase inhibitor of human serum, alpha-1 proteinase inhibitor (A1PI), is susceptible to oxidative inactivation by a variety of agents, including chloramine T. We have examined the effects of chloramine T on the catalytic activity of porcine pancreatic (PPE) and human leukocyte elastase (HLE) and on the elastase inhibitory capacity of hamster, rat, and human serum as well as pure human A1PI. Both PPE and HLE, but not trypsin, were inhibited in a concentration-dependent manner by concentrations of chloramine T >0.1 mM. The abilities of rat and human serum and pure human A1PI to inhibit both PPE and HLE were inhibited in a concentration-dependent manner by chloramine T. In contrast only the ability of hamster serum to inhibit HLE was altered by exposure to chloramine T: inhibition of PPE was not effected. Gel exclusion chromatography disclosed the existence of two major peaks of elastase inhibitory activity in hamster plasma: one, with an approximate molecular weight of 55 K, eluting in the region of A1PI that was sensitive to chloramine T inactivation and one with a molecular weight of approximately 180 K which was chloramine T insensitive. The parenteral administration of chloramine T to hamsters resulted in a modest and transient diminution of the serum HLE inhibitory activity and an equally modest and transient elevation of PPE inhibitory activity.

Treatment of human erythrocyte membranes with active forms of chlorine (... chloramine T) resulted in a concentration-dependent inhibition of the membrane Na(+), K(+)- and Mg(2+)-ATPases. Membrane protein thiol group oxidation was consistent with inactivation of enzymes and preceded oxidation of tryptophan residues and chloramine formation.

The hypothesis that chloramine-T stimulates the basal Na+ efflux in barnacle fibers as the result of the entry of trigger Ca2+ into the myoplasm from the bathing medium was examined in this study. Two reasons for doing so can be given. One is that the oxidant is known to abolish inactivation in sodium and potassium channels. The other is that L-type Ca2+ channels are present in barnacle fibers, and an increase in internal free Ca2+ in these fibers is known to ... (i) Chloramine-T exerts a biphasic effect on the Na+ efflux: inhibition is followed by stimulation, the threshold concentration being 10-5 M. This is also found to be the threshold concentration for shortening of these fibers. ... (vii) The dose-response curve for chloramine-T shows a shift to the left in poisoned fibers. (viii) The magnitude of the rise in light emission depends on the external Ca2+ concentration. A rise fails to take place in the nominal absence of external Ca2+. Taken together, these results support the above hypothesis that chloramine-T causes the entry of trigger Ca2+ into the myoplasm from the outside and provide evidence that stimulation of the Na+ efflux is associated not only with this event but also with a reduced Na+ gradient resulting from inhibition of the membrane Na+/K(+)-ATPase system by the oxidant.

... The effect of chloramine-T on the inactivation of IK1 was examined in guinea-pig ventricular myocytes using the patch-clamp technique. Chloramine-T (2 mM) irreversibly inhibited the time-dependent decay of whole-cell IK1 inactivation. As a result, the negative slope region of the current-voltage (I-V) relationship was abolished. In cell-attached single channel recordings, the number of active channels in the patch decreased with time during the voltage-clamp step to the K+ equilibrium potential (EK) of -100 mV. Chloramine-T prevented this time-dependent decrease in channel number, and ensemble averaged currents exhibited abolishment of time-dependent decay of channel activity at EK -100 mV.

MeSH Pharmacological Classification · 4 items

Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects.

Substances used on inanimate objects that destroy harmful microorganisms or inhibit their activity. Disinfectants are classed as complete, destroying SPORES as well as vegetative forms of microorganisms, or incomplete, destroying only vegetative forms of the organisms. They are distinguished from ANTISEPTICS, which are local anti-infective agents used on humans and other animals. (From Hawley's Condensed Chemical Dictionary, 11th ed)

Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499)

Electron-accepting molecules in chemical reactions in which electrons are transferred from one molecule to another (OXIDATION-REDUCTION).

Absorption, Distribution and Excretion · 2 items

Fingerlings and juvenile trout were exposed to 20 mg/L (twice the therapeutic concentration) of ring UL-14C-tosylchloramide sodium (purity 93.7%, specific activity 1.2 uCi/uM) for up to 1 hr and then transferred to fresh water for recovery to assess tissue accumulation and distribution of resulting residues. The temperature of the well water was 11.6 to 12.2 °C. The estimated half-life of para-toluenesulfonamide equivalents in fingerlings was 27.3 hours whereas determined by HPLC the half-life of para-toluenesulfonamide residues in whole-body homogenates was 36.3 hours. The estimated half-life of residues in juvenile fish was 32.6 hours, based on radiometric data, while determined by HPLC the half-life for para-toluenesulfonamide residues in whole body samples was 40.3 hours. Elimination of total tosylchloramide sodium residues from fingerlings and juvenile whole-body homogenates, based on radiometric counts, was rapid but significantly faster from fingerlings (t1/2 of 27.3 hours) than from juveniles (t1/2 of 32.5 hours). ...Tosylchloramide sodium was poorly absorbed form the bath by both fingerling and juvenile trout. No residues of tosylchloramide sodium, only of the primary metabolite para-toluenesulfonamide, were found in any of the fish tissues in this study therefore, all tissue residues determined either by radiometric or by HPLC methods were reported on the basis of equivalent concentrations of para-toluenesulfonamide. The para-toluenesulfonamide equivalents concentration in whole body homogenates after 1 hr, based on radiometric analysis, was 980 ug/kg, a value about 5% of that in the exposure water, in fingerlings. In juveniles, this value was 570 ug/kg or about 3% of the concentration ing the exposure bath. The exposure of para-toluenesulfonamide in whole body homogenates, after 1 hr, based on HPLC analyses was 360 ug/kg in fingerlings and 170 ug/kg in juveniles.

The percutaneous absorption of tosylchloramide sodium was investigated. Five lactating cows were treated twice daily during milking for 8 days. The teats were cleaned before milking with udder tissues dipped in a solution containing 0.5% tosylchloramide and thereafter dipped after milking into the same solution. The solutions containing 0.5% tosylchloramide were freshly prepared every day. Blood samples were taken from the Vena jugularis during the treatment, immediately before the last treatment and 30 minutes, 1, 2, 4, 8, 16, and 24 hours after the last treatment. The samples were tested with a HPLC method where tosylchloramide is hydrolysed into para-toluenesulfonamide before analyzing of the samples. The detection limit of the method was 5 ug/kg of para-toluenesulfonamide and 8 ug/kg for tosylchloramide. No residues of para-toluenesulfonamide could be detected in any blood samples. It is concluded that the absorption of tosylchloramide in blood in negligible after percutaneous application to the teat.

Uses & manufacturing

Uses · 6 items

Occupational asthma reported in janitors, brewery workers, and chemical workers; [Malo] Allergic contact dermatitis in housekeeping workers; [Marks]

Using Disinfectants or Biocides [Category: Clean]

For chloramine t (USEPA/OPP Pesticide Code: 076502) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Detection of bromate and halogens; antibacterial; VET: antiseptic (topical).

Antiseptic /Trihydrate/

Chloramines are no longer employed for irrigation of wounds... but are used in the emergency sterilization of drinking water and for sanitization. /Chloramines/

U.S. Production2023: <50,000 lb
Consumer UsesOther
Industry UsesPreservative
Methods of Manufacturing · 2 items

... Prepared in 75-95% yield by passing chlorine into a sodium hydroxide solution of p-toluenesulfonamide.

Reaction of ammonia and paratoluene-sulfochloride under pressure. The latter is reacted with sodium hypochlorite in presence of an alkali and the chloramine produced by crystallization. /Trihydrate/

Use ClassificationCosmetics -> Antimicrobial
Applications · 4 items

DescriptionThe sodium salt of p-toluenesulfochloramide, commonly known as chloramine-T, exerts strong oxidizing action in both acidic and alkaline media and thus has been widely used for the oxidimetric determination of a large number of inorganic and organic substances. Oxidation of some aldehydes by chloramine-T has been reported to occur quantitatively in an alkaline solution, giving the corresponding acid as the end product. Both direct and indirect methods have been carried out to estimate aldehydes by chloramine-T. Chloramine-T (CAT) is also commonly used in radiolabeling bioactive molecules by halogenation. CAT is used to release radioactive elemental iodine by oxidation of its salts. Unfortunately, CAT is a strong oxidizing agent and can cause significant damage to peptides and proteins. This may lower the yield of the iodination reaction and may produce undesirable side products[1-2].

Usesantiseptic, disinfestant, antiproliferative

UsesThis disinfectant is for external use only, it can exterminate bacteria, viruses, fungi, spore. The action principle is that chlorine can sterilize slowly and lastingly, and also can dissolve necrotic tissue, chlorine come from hypochlorous acid which is produced by Chloramine-T solution. Apply to disinfect drinking water container,food,all kind of tableware, fruits and vegetables,and cleaning wound, mucous membrane.

Usessterilizer, antiseptic, disinfectant, and chemical reagent in the medical and pharmaceutical fields.

Suppliers50 total

衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
南京兰亚化工贸易有限公司+86-25-8331-5620 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Chloramine T is an organic sodium salt derivative of toluene-4-sulfonamide with a chloro substituent in place of an amino hydrogen. It has a role as a disinfectant, an allergen and an antifouling biocide. It contains a chloro(p-tolylsulfonyl)azanide.

Related reactions

1 records

Linked notes

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