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Home > Encyclopedia > 2,5-Diaminotoluene sulfate

2,5-Diaminotoluene sulfate

2,5-Diaminotoluene sulfate structure

2,5-Diaminotoluene sulfate 

structure
  • CAS No:

    6369-59-1

  • Formula:

    C7H10N2.xH2O4S

  • Chemical Name:

    2,5-Diaminotoluene sulfate

  • Synonyms:

    1,4-Benzenediamine,2-methyl-,sulfate (1:?);Toluene-2,5-diamine,sulfate;1,4-Benzenediamine,2-methyl-,sulfate;C.I. 76043;C.I. Oxidation Base 4;Fouramine STD;p-Toluenediamine sulfate;2,5-Diaminotoluene sulfate;p-Toluylenediamine sulfate;81892-73-1

  • Categories:

    Organic Chemistry  >  Amides

Description

GREY-TO-WHITE POWDER.


2,5-toluenediamine sulfate is a light tan to light purple powder. (NTP, 1992)|GREY-TO-WHITE POWDER.


2,5-toluenediamine sulfate is a light tan to light purple powder. (NTP, 1992)|2,5-diaminotoluene sulfate is an organic sulfate salt obtained by combining 2,5-diaminotoluene with one molar equivalent of sulfuric acid; occurs as an intermediate during hair dye formulation. It has a role as an allergen. It is an organic sulfate salt and a diamine. It derives from a 2-methyl-1,4-phenylenediamine.

2,5-Diaminotoluene sulfate Basic Attributes

220.24600

220.05200

228-871-4

8PSD05SPE2

1544

1703

3143|2811

DTXSID9020405|DTXSID50872532

Grey to white powder|Off-white powder

Characteristics

135.02000

2.74980

2,5-toluenediamine sulfate is a light tan to light purple powder. (NTP, 1992)

1.366 g/mL at 20 deg C

40.6°C

Solubility in water: good

pH = 2.47, 20 °C; saturated aqueous solution

pKa1 = 6.39; pKa2 = 2.77 (calculated)

When heated to decompostion it emits toxic fumes of SOx and NOx

Insoluble in water.

Salts, Acidic

Acidic organic/inorganic salts, such as 2,5-TOLUENEDIAMINE SULFATE, are generally soluble in water. The resulting solutions contain moderate concentrations of hydrogen ions and have pH's of less than 7.0. They react as acids to neutralize bases. These neutralizations generate heat, but less or far less than is generated by neutralization of inorganic acids, inorganic oxoacids, and carboxylic acid. They usually do not react as either oxidizing agents or reducing agents but such behavior is not impossible. Many of these compounds catalyze organic reactions.

Safety Information

III

6.1(b)

UN 2811

20/21-25-43-51/53

(1/2)-24-37-45-61

XT0525000

T, N

P261, P264, P270, P271, P272, P273, P280, P301+P310, P302+P352, P304+P312, P304+P340, P312, P321, P322, P330, P333+P313, P363, P391, P405, P501

H301

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. 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 soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P271, P272, P273, P280, P301+P310, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P314, P321, P322, P330, P333+P313, P337+P313, P363, P391, P405, and P501|Aggregated GHS information provided by 189 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P261, P264, P270, P271, P272, P273, P280, P301+P310, P302+P352, P304+P312, P304+P340, P312, P321, P322, P330, P333+P313, P363, P391, P405, and P501|Aggregated GHS information provided by 26 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P271, P272, P273, P280, P301+P310, P302+P352, P304+P312, P304+P340, P312, P314, P321, P322, P330, P333+P313, P363, P391, P405, and P501|P264, P270, P301+P310, P305+P351+P338, P321, P330, P337+P313, P405, and P501

Fires involving this material should be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)|Use water spray, foam, dry powder, carbon dioxide.

Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then dampen the solid spill material with toluene, then transfer the dampened material to a suitable container. Use absorbent paper dampened with toluene to pick up any remaining material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent-wash all contaminated surfaces with toluene followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting.

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

The substance is mildly irritating to the eyes and skin.

Repeated or prolonged contact may cause skin sensitization.

NO open flames.

Use local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety goggles.

Toxicity

LD50 Rat oral 98 mg/kg /oil-in-water emulsion/|LD50 Rat ip 49 mg/kg /in dimethylsulfoxide/

/OTHER TERRESTRIAL SPECIES/ ...The toxicity of 10 benzamines was tested by the well diffusion assay technique against 18 common bacterial species including the nitrogen-fixing bacterium Azotobacter vinelandii. ... 2,5-Diaminotoluene was inhibitory to the growth of P. fluorescens and Streptococcus mitis. The growth of A. vinelandii was inhibited by p-phenylenediamine and 2,5-diaminotoluene in the well diffusion assay. ... The nitrogenase activity of A. vinelandii was inhibited by p-phenylenediamine, 2,5-diaminotoluene, p-nitroaniline, 2-nitro-p-phenylenediamine, 3-nitro-o-phenylenediamine, and 4-nitro-o-phenylenediamine. Because many of these organisms are common soil and aquatic bacteria, the accumulation of these benzamine compounds in the environment may have an adverse impact on soil biochemical activities. /2,5-diaminotoluene/

A bioassay for possible carcinogenicity of 2,5-toluenediamine sulfate was conducted using Fischer 344 rats and B6C3F1 mice. 2,5-Toluenediamine sulfate was administered in the feed, at either of two concentrations, to groups of 50 males and 50 females of each species. The high and low time-weighted average concentrations of the compound were, respectively, 0.2 and 0.06% for rats and 0.1 and 0.6% for mice. Because compound administration to the high and low dose groups of each species was not begun simultaneously, each dosed group was assigned a control group. All control groups consisted of 50 animals, except for the high dose male and female rat control groups which were composed of 25 animals. The dosing period was for 78 weeks, followed by an additional 28 to 31 weeks of observation in rats and an additional 16 to 19 weeks in mice. Under the conditions of this bioassay, sufficient evidence was not obtained to demonstrate the carcinogenicity of 2,5-toluenediamine sulfate in either Fischer 344 rats or B6C3F1 mice. Levels of Evidence of Carcinogenicity: Male Rats: Negative; Female Rats: Negative; Male Mice: Negative; Female Mice: Negative.

NIOSH (NOES Survey 1981-1983) has statistically estimated that 39,400 workers (32,217 of these were female) were potentially exposed to 2,5-diaminotoluene sulfate in the US(1). Occupational exposure to 2,5-diaminotoluene sulfate may occur through inhalation and dermal contact with this compound at workplaces where 2,5-diaminotoluene sulfate is produced or used. Use data indicate that the general population may be exposed to 2,5-diaminotoluene sulfate via dermal contact with consumer products containing 2,5-diaminotoluene sulfate(SRC).

Drug Information

2,5-Diaminotoluene sulfate is absorbed through the skin of dogs and excreted in the urine. About 40 mg of the compound were absorbed from 50 mL of a lauryl sulfate-based gel containing 1.4 g 2,5-diaminotoluene within 3 hr. When 6% hydrogen peroxide was added to the gel immediately before use, the amount of 2,5-diaminotoluene sulfate absorbed was less than 3 mg|Ten milligrams of 2,5-diaminotoluene sulfate (equivalent to 5.54 mg 2,5- diamino-toluene) injected subcutaneously into six adult volunteers were excreted in the urine as the N,N'-diacetyl derivative, which accounted for approximately half of the injected dose, over 48 hr. During the process of hair dyeing with a dye formulation in which a total of 2.5 g 2,5-diaminotoluene sulfate were applied in conjunction with 6% hydrogen peroxide added just before application, it was estimated that 4.6 mg 2,5-diaminotoluene sulfate had been absorbed through the skin of five volunteers.|The absorption and elimination of toluene-2,5-diamine were studied in 5 male human subjects. A test formulation was prepared with [Me-(14)C]-toluene-2,5-diamine plus unlabeled toluene-2,5-diamine sulfate in a hair dye cream formulation containing 0.825% resorcinol. The final concentration of toluene-2,5-diamine sulfate was 1.65%. This formulation was then mixed with either 100 g of water (1:1) or 100 g of 6% hydrogen peroxide to produce formulation 1 and formulation 2, respectively. The subjects received 1 of the 2 formulations (45 g, containing a total of 371 mg of toluene-2,5-diamine) on a 250-sq cm area of the scalp. The formulation was thoroughly rinsed off after 30 minutes and the hair was shampooed. The mean total elimination rate of radioactivity of the applied dose in the urine and the feces was 4.81% +/-0.62% for formulation 1 and 1.31% +/- 0.14% in formulation 2. The amounts of toluene-2,5-diamine sulfate were 71 +/- 9.26 mgeq/ sq cm for formulation 1 and 20 +/- 2.02 mgeq/sq cm for formulation 2. The area under the curve (AUC) for whole blood recovery was 41.6 +/- 1.7 ngeq.hr/L and 9.2 +/- 3.1 ngeq.hr/L for formulations 1 and 2, respectively. The total recovery for formulation 1 was 91.2% +/- 1.73%, whereas the total recovery for formulation 2 was 47.64% +/- 3.43%. The authors concluded that the lower recovery for formulation 2 was due to higher retention of radiolabel in the hair as a result of the oxidative hair coloring process.|Percutaneous absorption of toluene-2,5-diamine sulfate in human skin samples was studied... Radiolabeled (97.2% pure) and non-radiolabeled (99.7% pure) toluene-2,5-diamine sulfate was added to a final concentration of 9% to 2 hair dye bases, one of which contained an equimolar amount of m-aminophenol as a coupler. The formulation containing the coupler was mixed with hydrogen peroxide (50:50) to yield a test substance with a final toluene-2,5-diamine sulfate concentration of 4.5%. The formulation base without the coupler was mixed with water or hydrogen peroxide, in both cases 50:50, to yield 2 other test substances with final concentrations of toluene-2,5-diamine sulfate of 4.5%. The formulations were then applied over an area of 2-sq cm to 350-mm-thick human skin (20 mg/sq cm) or samples of isolated epidermis mounted in perfusion cells. After an application period of 30 minutes, the test substance was rinsed off with water and a solution of sodium lauryl sulfate. Most of the test substance (93.5% of the applied dose) was recovered during rinsing at 30 minutes post application. Cumulative penetration (based on radioactivity in the receptor fluid) neared a plateau at approximately 5 hours. The total absorption in the formulation without coupler mixed with water was 4.17% +/- 2.54% (40.31 +/- 23.77 mgeq/sq cm). In the formulations mixed with peroxide, the total absorption was 3.41% +/- 1.32% (31.26 +/- 11.64 mgeq/sq cm) with the coupler and 3.44% +/- 2.84% (32.03 +/- 26.58 mgeq/sq cm) without the coupler.|The absorption, distribution, metabolism, and excretion of (14)C-toluene-2,5-diamine sulfate were investigated in rats in a series of studies... Groups of female Wistar Kyoto rats (4 per group in the mass balance portion of the study and 6 per group in the toxicokinetics portion of the study) received the test substance at either 2.5 or 25.0 mg/kg of body weight in a single oral gavage dose or at 33.3 mg/kg of body weight as a dermal application. Vehicle for the oral groups was water, whereas in the dermal group it was water/acetone (1:1). In the urine of the oral dose groups after 96 hours, the mean cumulative recovery of the applied dose was 62.2% in the 2.5-mg/kg dose group and 72.9% in the 25-mg/kg dose group, whereas in the feces, the recovery was 31.4% and 22.0%, respectively. The mean mass balance for both oral doses was about 98%. In the dermal application groups, 10.9% and 2.7% of the applied dose were recovered in the urine and feces, respectively. The mean mass balance for the dermal dose was nearly 100%. ...In plasma kinetics results, the time to peak concentration (Tmax) was 0.5 hours and 0.25 hours for the low- and high-dose oral groups, respectively, indicating rapid absorption. The AUC values for the 2 oral dose groups were 17.59 and 174 mgeq.hr/L, respectively, and for the dermal dose group 4.39 mgeq.hr/L.

Incubation of the (14)C-toluene-2,5-diamine sulfate with the human hepatocytes yielded an acetylated metabolite but no sulfated, glucuronidated, or monohydroxylated metabolites.|Three major metabolites were observed in the urine /of female Wistar Kyoto rats/ after oral dosing /of (14)C-toluene-2,5-diamine sulfate/, with the main metabolite identified as N,N-diacetyl-toluene-2,5-diamine. No parent compound was identified in the urine. Radioactivity in the urine of the dermal dose group was too low for separation and detection of metabolites.

The Scientific Committee on Consumer Products also reported that toluene-2,5-diamine sulfate (concentration of solution not provided) had greater than 98% wt/wt HPLC quantitative purity, greater than 99% HPLC qualitative (254 nm) purity, a solvent content less than 1%, and the potential impurity o-toluidine less than 50 ppm.

SYMPTOMS: Symptoms of exposure to this compound may include skin irritation. ACUTE/CHRONIC HAZARDS: This compound may cause irritation on contact. When heated to decomposition it emits very toxic fumes. It is an experimental carcinogen. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)


Fresh air, rest.


Remove contaminated clothes. Rinse and then wash skin with water and soap.


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

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Organic bases/Amines and related compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . Cover skin burns with dry sterile dressings after decontamination ... . /Organic bases/Amines and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. If patient is unresponsive to these measures, vasopressors may be helpful. Watch for signs of fluid overload ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic bases/Amines and related compounds/

/HUMAN EXPOSURE STUDIES/ The degree and pattern of hand eczema in hairdresser trainees and hairdressers was compared in Norway. 75 hairdressers affected by hand eczema and 74 hairdresser trainees with or without hand eczema were examined and patch tested with a hairdressers' series and some additional substances from the standard series. 2.7% of the hairdressers affected by hand eczema were test positive to toluene-2,5-diamine sulfate, compared to 0% of the hairdresser trainees.|/HUMAN EXPOSURE STUDIES/ 103 hairdressers (not dermatitis patients) in the Netherlands (96 females and 8 males) were patch tested with a special series including standard allergens and hairdressers' allergens. 2% were positive to toluene-2,5-diamine sulfate, 6% to p-phenylenediamine and 4% to 2-nitro-4-phenylenediamine.|/HUMAN EXPOSURE STUDIES/ In a multi-center study by the German Contact Dermatitis Group (DKG), 178 dermatitis patients (hairdressers) were patch tested with hairdressers' allergens in 11 centers. 18.0% were test positive to toluene-2,5-diamine, 8.4% to toluene-2,5-diamine sulfate, 18.0% to p-phenylenediamine base, 0.6% to resorcinol, 1.1% to 3-aminophenol, 2.2% to p-aminodiphenylamin hydrochloride, 3.4% to 4-aminophenol and 6.2% to o-nitro-p-phenylendiamine.|/HUMAN EXPOSURE STUDIES/ In a multi-center study by the Italian Contact Dermatitis Research Group (GIRDCA), a total of 302 dermatitis patients (hairdressers) (259 females and 43 males) were patch tested with hairdressers' allergens in 9 Italian centers. 13.2% were positive to toluene-2,5-diamine sulfate, 16.6% to p-phenylenediamine base (in 1989-1990), 7.6% to p-phenylenediamine dihydrochloride (in 1985-1988), 7.9% to o-nitro-p-phenylenediamine, 1.3% to resorcinol and 10.6% to p-aminodiphenylamine.|For more Human Toxicity Excerpts (Complete) data for 2,5-DIAMINOTOLUENE SULFATE (10 total), please visit the HSDB record page.

2,5-diaminotoluene

The substance can be absorbed into the body through the skin and by ingestion.

Redness.


Redness.

2,5-Diaminotoluene sulfate Use and Manufacturing

Methods of Manufacturing

REDUCTION OF AMINO-AZOTOLUENE WITH ZINC DUST AND HYDROCHLORIC ACID AND CONVERSION TO THE SALT BY ACID TREATMENT.

2,5-Diaminotoluene sulfate is available in the USA as a commercial grade with the following typical specifications: purity, 95% minimum.; residue on ignition, 0.2% maximum.; loss on drying, 0.5% maximum.; and iron content, 25 mg/kg maximum.

1,4-Benzenediamine, 2-methyl-, sulfate (1:?): ACTIVE|According to a survey of current use concentrations conducted by the Cosmetic, Toiletry, and Fragrance Association (CTFA), ... toluene-2,5-diamine sulfate is used at concentrations of 0.1% to 4.0%in hair dyes and colors and at 3% in hair bleaches.|2,5-Diaminotoluene sulfate was first produced commercially in the USA in 1927.

Hair dyes have been analyzed for aromatic amines, including 2,5-diaminotoluene, by extraction with methanol, separation by thin layer chromatography and visualization with para-dimethylaminobenzaldehyde. Gas chromatography has been used to determine isomeric diaminotoluenes ...|EPA Method 8250. Packed column gas chromatography/mass spectrometry technique for the determination of semivolatile organics in extracts prepared from all types of solid waste matrices, soils, and groundwater. This method is applicable to quantify most neutral, acidic, and basic organic compounds that are soluble in methylene chloride and capable of being eluted without derivatization as sharp peaks from a gas chromatographic packed column such compounds include ... anilines ... . The detection limit was not given for this compound.

Cosmetics -> Hair dyeing

Computed Properties

Molecular Weight:220.25
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:6
Exact Mass:220.05177804
Monoisotopic Mass:220.05177804
Topological Polar Surface Area:135
Heavy Atom Count:14
Complexity:174
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

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