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
Show more names
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
- Formal charge
- 0
- Complexity
- 231
Experimental & physicochemical properties
LogP
log Kow = 0.84 /Estimated/
0.84 (estimated)
Solubility
Insoluble in benzene, chloroform, and ether; decomposed by alcohol
Soluble in water.
Solubility in water, g/100ml at 25 °C: (good, trihydrate)
Physical Description
CBI
White or slightly yellow crystals or crystalline powder; [HSDB]
WHITE SOLID IN VARIOUS FORMS WITH CHARACTERISTIC ODOUR.
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 ℃]
- form
- Solid
- color
- White to off-white
- Water Solubility
- 150 g/L · 150g/L at 25℃
- Stability
- 130 C · Stable. Incompatible with strong oxidizing agents. May decompose violently if heated above 130 C. May decompose on exposure to air.
- Cosmetics Ingredients Functions
- ANTIMICROBIAL
- InChI
- InChI=1S/C7H7ClNO2S.Na/c1-6-2-4-7(5-3-6)12(10,11)9-8;/h2-5H,1H3;/q-1;+1
- InChIKey
- VDQQXEISLMTGAB-UHFFFAOYSA-N
- SMILES
- S(=O)(=O)(N(Cl)[Na])C1C=CC(C)=CC=1
- LogP
- -1.3 at · -1.3 at 20℃
- CAS DataBase Reference
- 127 · 127-65-1(CAS DataBase Reference)
- Indirect Additives used in Food Contact Substances
- SODIUM P-TOLUENESULFONCHLOROAMIDE
- FDA 21 CFR
- 178.101 · 178.1010
- EWG's Food Scores
- 1 · 1-6
- FDA UNII
- 328 AS34YM6 · 328AS34YM6
- ATC code
- 8 AX04 · D08AX04
- EPA Substance Registry System
- Chloramine T (127-65-1)
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319
- Precautionary statements
- 264 · P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
- Hazard Codes
- C,Xn
- Risk Statements
- 22 · 22-31-34-42
- Safety Statements
- 22 · 22-26-36/37/39-45-7-1/2
- RIDADR
- 3263 · UN 3263 8/PG 3
- WGK Germany
- 2 · 2
- TSCA
- TSCA listed
- HazardClass
- 8 · 8
- PackingGroup
- III
- HS Code
- 29242990 · 29242990
- Hazardous Substances Data
- 127 · 127-65-1(Hazardous Substances Data)
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
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
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
Hazards Summary
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
Hazard Classes and Categories
Acute Tox. 4 (100%)
Acute toxicity - category 4
Acute Tox. 4 *
Safety & protection
First Aid Measures
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 .
Spillage Disposal
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.
Toxicology
Ecotoxicity Excerpts
/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
Cough. Sore throat. Wheezing.
Redness. Pain.
Redness. Pain.
Nausea. Vomiting. Diarrhoea.
Human Toxicity Excerpts
/HUMAN EXPOSURE STUDIES/ The provocation of occupational asthma by aerogenic exposure to commercial chloramine-T solution was described. A 36 year old female cleaner who had never smoked regularly presented with sneezing, bronchial coughing and dyspnea shortly after starting the use of a new disinfectant at work. She cleaned showers and saunas at a municipal indoor swimming pool using chloramine-T (Alinex) in a 10% solution. The disinfectant was sprayed on walls and floors with pressurized water. The temperature at the job was 30 °C and the relative humidity was 50 to 80%. A provocative dose of chloramine-T was used in the testing at 2.0 micrograms. After 15 minutes the patient developed rhinorrhea, coughing, dyspnea and bronchial wheezes. Positive skin prick tests, RAST, bronchial provocation test results, adequate workplace exposure, and the onset of work related asthmatic symptoms confirmed the diagnosis.
/HUMAN EXPOSURE STUDIES/ As a dust in air it is irritating to eyes, causing conjunctivitis, but no serious injury.
/HUMAN EXPOSURE STUDIES/ 7 brewery workers developed asthmatic symptoms after using Chloramine-T powder as sterilizing agent (0.25-2%). Positive wheal and flare reactions to skin-prick tests with solution of chloramine; no reaction in controls. Symptoms did not recur once men were removed from exposure.
/HUMAN EXPOSURE STUDIES/ In sera of exposed persons specific IgE antibodies demonstrated. These antibodies are directed against serum albumin treated with chloramine-t.
For more Human Toxicity Excerpts (Complete) data for CHLORAMINE T (10 total), please visit the HSDB record page.
Non-Human Toxicity Excerpts
/LABORATORY ANIMALS: Acute Exposure/ Rabbits under 3 wk of age were less tolerant to chloramine (CA) than adults. Lethal dose was 40-50 mg/kg. Symptoms were protracted collapse without manifestations of edema. Lethal dose adults: 60-70 mg/kg. Death occurred with acute edema of lungs.
/LABORATORY ANIMALS: Acute Exposure/ In adult rabbits edema occurred with death. In young rabbits typical edema of lungs occurred only with very high doses approx 200-250 mg/kg. Fluid is present in small amounts only; there is prevalence of hemorrhage possibly caused by effect of chloramine excreted through lung.
/LABORATORY ANIMALS: Acute Exposure/ 0.5 g of the test material, moistened, was applied on the intact skin of 6 New Zealand white rabbits. No skin irritation was observed in two animals. Slight irritation, which was reversible in 24 hours, was observed in another two animals. The remaining two animals showed eschar formation and slight edema and developed scar tissue on day 15 or 22.
/LABORATORY ANIMALS: Acute Exposure/ 0.1 ml of a 8% w/v solution of the test material in deionized water was instilled into the conjunctival sac of one eye of each of 6 rabbits. The 8% solution was found to be mildly irritating. ...In the Draize test; the 10% solution was found to be mildly irritating, whereas the 0.5% solution did not cause eye irritation.
For more Non-Human Toxicity Excerpts (Complete) data for CHLORAMINE T (12 total), please visit the HSDB record page.
Non-Human Toxicity Values
LD50 Rat oral 935 mg/kg bw
LD50 Mouse oral 1100 mg/kg bw
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
- Symbol(GHS)
- GHS07
- hazard_code
- C,Xn
- safety_code
- 22-26-36/37/39-45-7-1/2
- hazard_class
- 8
- packing_group
- III
- Hazard statements
- H315-H319
- REACH Registrations
- Active
- Precautionary statements
- P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
- Hazardous Substances Data
- 127-65-1(Hazardous Substances Data)
Chemistry & industry
Pharmacology
ATC Code
D08AX04
D - Dermatologicals
QD - Dermatologicals
Mechanism of Action
/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
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
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
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/
Methods of Manufacturing
... 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/
General Manufacturing Information
Agriculture, Forestry, Fishing and Hunting
Benzenesulfonamide, N-chloro-4-methyl-, sodium salt (1:1): ACTIVE
Tosylchloramide sodium is an organic chlorine compound with an available chlorine content of 28-30% and is intended for use in fish farming for prevention and control of bacterial gill disease. Recommended treatment schedules are as follows: 10 mg/L in water of flow-through basin for one hour for preventive purposes, which may be repeated every 15-30 days; 10 mg/L in water of flow-through basin for one hour for therapeutic purposes, which may be repeated up to 3 times within one week.
Tosylchloramide sodium is intended for teat and udder disinfection to prevent udder disease in lactating cows. To obtain effective concentrations at least 50 to 100 mg active chlorine/L solution are required. This is achieved if a 0.3% tosylchloramide solution is used. The teats of lactating cows are dipped in the solution after each milking throughout the lactation period and in nonlactating cows once daily. According to prescription 0.5 ml of the solution ready for application (3 mg/ml) should be used for each teat, i.e. 6 mg/animal.
Applications
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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
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
Linked notes
Loading…