2-Methylbenzenesulfonamide

log Kow = 0.84

0.84

0.84

Octahedral crystals from alcohol; prisms from water

Colorless crystals

In water, 1.62X10+3 mg/L at 25 °C

Slightly soluble in water

Soluble in alcohol; slightly soluble in ether

Slightly soluble in ether, DMSO; soluble in ethanol

Solubility in water, g/100ml at 25 °C: 0.162

214 °C at 10 mm Hg

>270 °C

156.3 °C

156 °C

0.00006 [mmHg]

Vapor pressure at 25 °C: negligible

This chemical does not meet GHS hazard criteria for 65.9% (112 of 170) of all reports.

Warning

H319 (28.2%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P203, P264+P265, P280, P305+P351+P338, P318, P337+P317, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 170 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Not Classified

Chemical: Benzenesulfonamide, 2-methyl-

Benzenesulfonamide, 2-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenesulfonamide, 2-methyl- 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: 15-06-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/10712

Benzenesulfonamide, 2(or 4)-methyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Toluene-2-sulfonamide: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

A mutagen, tumorigen, reproductive effector, and moderate eye irritant; [RTECS] Used therapeutically, sulfonamides can cause a range of hypersensitivity reactions including rashes and injury to the liver and kidneys; Methemoglobinemia has been reported after overdose; [HSDB] An eye irritant; [ICSC] An irritant; [MSDSonline] See p-Toluenesulfonamide and Toluenesulfonamide.

Eye Irrit. 2 (28.2%)

Not Classified

Not Classified

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

Rinse mouth.

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material; Contaminated packaging: Dispose of as unused product.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.

Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed. Normal measures for preventive fire protection.

Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.

Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.

The importance of the contaminant ortho-toluene sulfonamide (OTS) in the promoting activity of commercial saccharin on rat bladder neoplasia was investigated. OTS, OTS-free and OTS-contaminated saccharin were administered in the drinking water or diet for 2 years to groups of rats pretreated with an intravesical instillation of N-methyl-N-nitrosourea (MNU); OTS alone and OTS-free saccharin were also given to groups of rats not pretreated with MNU. Administration of OTS was not associated with changes in urinary pH, crystalluria or calculus formation, had no effect on the histology of normal rat bladder, and did not increase the incidence of bladder hyperplasia or neoplasia elicited by pretreatment with MNU. No differences could be found between the effect of OTS-free or OTS-contaminated saccharin on bladders of rats pretreated with MNU. These results indicate that OTS contamination played no part in the reported promoting activity of saccharin on the rat bladder. Administration of saccharin did not increase urinary pH, crystalluria or calculus formation, and failed to promote bladder neoplasia after a carcinogenic dose of MNU, though the numbers of proliferative lesions in the bladder were increased.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 36(SRC), determined from a log Kow of 0.84(2) and a regression-derived equation(3), indicates that o-toluenesulfonamide is expected to have very high mobility in soil(SRC). Volatilization of o-toluenesulfonamide from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.7X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(3). o-Toluenesulfonamide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.0X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(3). A 0% of theoretical BOD using activated sludge in the Japanese MITI test(4) suggests that biodegradation is not an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 36(SRC), determined from a log Kow of 0.84(2) and a regression-derived equation(3), indicates that o-toluenesulfonamide is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 4.7X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). According to a classification scheme(5), a BCF of range of 0.4-2.6(6), suggests bioconcentration in aquatic organisms is low(SRC). A 0% of theoretical BOD using activated sludge in the Japanese MITI test(6) suggests that biodegradation is not an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), o-toluenesulfonamide, which has an estimated vapor pressure of 6.0X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase o-toluenesulfonamide is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 13 days(SRC), calculated from its rate constant of 1.2X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Particulate-phase o-toluenesulfonamide may be removed from the air by wet and dry deposition(SRC). o-Toluenesulfonamide does not contain chromophores that absorb at wavelengths >290 nm(3) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

IDENTIFICATION AND USE: o-Toluenesulfonamide is a solid. It is used in the manufacture of saccharin. It is also used as a carrier in fluorescent pigments. The ortho- and para-toluenesulfonamide mixture is used as a reactive plasticizer in hot-melt adhesives to improve the flow properties of thermosetting resins and to impart flexibility to coatings based on resins made from casein, shellac, zein and soya protein. HUMAN STUDIES: There are no data available. ANIMAL STUDIES: Rats (5 animals/sex/group) were administered by gavage with o-toluenesulfonamide at single doses of 0, 700, 1,000, 1,400 and 2,000 mg/kg bw. Three females given 1,400 mg/kg bw and two females given 2,000 mg/kg bw were found dead, but there were no death in males at any dose. Sedation, passivity, catalepsy and prostration appeared even at the lowest dose of 700 mg/kg bw. Lateral position, abnormal breathing and hypothermia were also found in both sexes of the higher dosing groups. Three groups of female rats were given pure ortho-toluenesulfonamide at a concentration of 0 or 0.1% in the drinking-water or 79 mg/kg bw in the diet for two years. The survival rates were similar in all groups at 84 weeks. No difference in overall tumor incidence was observed between control and test groups. No bladder tumors were observed in any group. o-Toluenesulfonamide was administered to rats by gavage at doses of 0, 20, 100 and 500 mg/kg b.w. from 14 days before mating to 14 days after mating in males and from 14 days before mating to day 3 of lactation in females. There were signs of maternal toxicity. In the 500 mg/kg bw group, the delivery index, number of pups alive on day 0 of lactation, and birth index were slightly decreased but not statistically significant. There was no effect of the test compound on the ovulation, copulation, fertility, delivery and lactation at dose levels up to 100 mg/kg bw. Significant reduction in body weights of pups was observed on days 0 and 4 in both sexes at 500 mg/kg bw. o-Toluenesulfonamide exhibited weak mutagenic effects in a modified Salmonella/microsome test and in Drosophila.

EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPA; ICSS Dashboard Application; Available from, as of November 16, 2017: http://actor.epa.gov/dashboard/]

o-Toluenesulfonamide was identified at a concentration of 1.88 ug/L in wastewater collected from an industrial landfill leachate during December 1996; it was not detected from the same location during sampling March 1997. o-Toluenesulfonamide was not detected in wastewater from a petrochemical plant collected in July 1996, January 1997,and March 1997(1).

... The presence of benzosulfonamides (BeSAs) has been evaluated during seven consecutive days in influent and effluent samples from the wastewater treatment plant of Athens, Greece. o-TSA and p-TSA were detected in 100% of the samples, while BSA was detected in all the influents and in 43% of the effluents. All three compounds were determined in relevant concentrations (up to 1.4 ug/L in the case of p-TSA), constituting the first evidence of the presence of these compounds in Greece, and contributing to the scarce occurrence data. Removal efficiencies of BeSAs during wastewater treatment was also assessed and discussed. In this regard, different behaviors were observed: while BSA and p-TSA were removed in different rates, o-TSA was formed during wastewater treatment. A daily load of 0.48 kg of o-TSA and 0.47 kg of p-TSA was discarded in the receiving Saronikos Gulf.

The Koc of o-toluenesulfonamide is estimated as 36(SRC), using a log Kow of 0.84(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that o-toluenesulfonamide is expected to have very high mobility in soil.

AEROBIC: o-Toluenesulfonamide, present at 100 mg/L, reached 0% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(1). Three sulfonamides -para-toluenesulfonamide (p-TSA), ortho-toluenesulfonamide (o-TSA) and benzenesulfonamide (BSA) - have recently been detected in groundwater within a catchment area (Lake Muegglesee, Berlin, Germany) of the Frierichshagen drinking water treatment plant (DWTP), which is located downstream of a former sewage farm. The degradation pathways of p-TSA, o-TSA and BSA were investigated during drinking water treatment with incubation experiments and an experimental filter. Incubation experiments showed that p-TSA is removed during the treatment by microbiological processes. o-Toluenesulfonamide, present at 10 ug/L, was not degraded using 250 mL of polluted groundwater with adapted microorganisms in incubation experiments examining polluted drinking water treatments under conditions encountered. p-TSA, o-TSA and BSA were only measured in the low ug/L concentrations range in the purified water(2).

An experimental BCF range of 0.4-2.6 was calculated in fish for o-toluenesulfonamide using carp (Cyprinus carpio) which were exposed over a 6-week period to concentrations of 0.3 and 3 mg/L(1). According to a classification scheme(2), this BCF range suggests bioconcentration in aquatic organisms is low(SRC).

...50% of administration ortho- and para-toluenesulfonamides excreted in urine had been metabolized to ortho- and para-sulfamoylbenzoic acids, respectively.

In female Wistar rats given single oral doses of 20, 125 or 200 mg/kg bw (14)C-orthotoluenesulfonamide, 79, 58 and 36% of the activity was recovered in 24 hr urine samples ... . The main metabolites in the urine were 2-sulfamoylbenzyl alcohol and its sulfate or glucuronic acid conjugates (80%), N-acetyltoluene-2-sulfonamide (6%), saccharin (3%) and 2-sulfamoylbenzoic acid (2%).

... After a single dose of 300 mg/kg bw of (35)S o-toluenesulfonamide to male Wistar rats ... . Approximately 50% of metabolites excreted in urine were o-sulfamoylbenzoic acid, while the compound excreted in feces was unchanged.

Low oral doses of 0.2-0.4 mg/kg bw (14)C-ortho-toluenesulfonamide were excreted more slowly in humans than in rats ... . The main urinary metabolites were 2-sulfamoylbenzoyl alcohol (unconjugated, 7%; conjugated with glucuronic acid, 11%; conjugated with sulfate, 20%), saccharin (35%) 2-sulfanoylbenzoic acid (4%) and N-acetyltoluene-2-sulfonamide (2%).

... After a single dose of 300 mg/kg bw of (35)S o-toluenesulfonamide to male Wistar rats, the radioactivity was recovered about 85% in urine and about 10% in feces mostly within 48 hr.

In female Wistar rats given single oral doses of 20, 125 or 200 mg/kg bw (14)C-orthotoluenesulfonamide, 79, 58 and 36% of the activity was recovered in 24 hr urine samples; elimination at 24-48 hr was 7, 14 and 33% of the dose, respectively. Within seven days, 4.5, 5.9 and 7% of the activity was recovered from the feces. ...

Low oral doses of 0.2-0.4 mg/kg bw (14)C-ortho-toluenesulfonamide were excreted more slowly in humans than in rats, an average of 56% of the activity being excreted in the urine within 24 hr and almost 90% within 48 hr. Less than 1% of the activity was found in feces.

Used in mixtures with p-toluenesulfonamide as reactive plasticizer; Also used as a plasticizer for hot-melt adhesives and a chemical intermediate for fluorescent pigments and plasticizer resins; [HSDB] Used to make saccharin; [eChemPortal: SIDSUNEP] A contaminant of saccharin; [IARC]

Plasticizer

Used in manufacture of saccharin.

The ortho- and para-toluenesulfonamide mixture is used as a reactive plasticizer in hot-melt adhesives to improve the flow properties of thermosetting resins (e.g., melamine, urea and phenolic resins) and to impart flexibility to coatings based on resins made from casein, shellac, zein and soya protein. /Ortho- and para-toluenesulfonamide mixture/

... carrier in fluorescent pigments. /Ortho- and para-toluenesulfonamide mixture/

(1981) 1.31X10+7 GRAMS (PRINCPL CUSTMS DISTS)

(1982) 1.24X10+7 GRAMS (PRINCPL CUSTMS DISTS)

2023: <75,000 lb

(1979) MORE THAN 2.27X10+6 G (O-, P- MIXTURE)

(1981) MORE THAN 2.27X10+6 G (O-, P- MIXTURE)

Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Benzenesulfonamide, 2-methyl:

... obtained by treating 2-methylbenzenesulfonyl chloride with aqueous ammonia (d 0.910). Purified by fractional precipitation: hydrochloric acid is added to a solution which has been rendered alkaline with sodium hydroxide; the impurities are precipitated first.

REACTION OF O-TOLUENESULFONYL CHLORIDE WITH AMMONIA

Plastics Material and Resin Manufacturing

Benzenesulfonamide, 2-methyl-: ACTIVE

ortho-Toluenesulfonamide is not produced commercially as a separate chemical in USA, however, a product consisting of a mixture of unknown proportions of the ortho- and para-isomers of toluenesulfonamide is produced in the USA.

Until 1972, ortho-toluenesulfonamide was used in the USA as a chemical intermediate for the commercial production of saccharin.