2,3-Diaminotoluene
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2,3-Diaminotoluene
structure -
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CAS No:
2687-25-4
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Formula:
C7H10N2
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Chemical Name:
2,3-Diaminotoluene
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Synonyms:
1,2-Benzenediamine,3-methyl-;Toluene-2,3-diamine;3-Methyl-1,2-benzenediamine;2,3-Diaminotoluene;2,3-Tolylenediamine;3-Methyl-o-phenylenediamine;3-Methyl-1,2-phenylenediamine;1,2-Diamino-3-methylbenzene;2,3-Toluylenediamine;1-Methyl-2,3-phenylenediamine;2-Amino-3-methylaniline;3-Methyl-1,2-diaminobenzene;2-Methyl-1,6-benzenediamine
- Categories:
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CAS No:
2,3-Diaminotoluene Basic Attributes
122.171
122.17
220-248-5
SR8WC7LLQ2
DTXSID4027494
Crystals
2921590090
Characteristics
52
0.9
OtherSolid
1.1±0.1 g/cm3
63-64 °C
255 °C
131.1±21.3 °C
1.636
Very soluble in acetone, benzene, ethanol
1.20 kPa at 150 deg C /0.000553 mm Hg at 25 deg C/ (extrapolated)
Henry's Law constant = 9.52X10-10 atm-cu m/mol at 25 °C (est)
pKa = 4.91 (est)
Hydroxyl radical reaction rate constant = 2.0X10-10 cu cm/molec-sec at 25 °C (est)
Safety Information
III
6.1(b)
2811
3
R20/21/22;R36/37/38
S26-S36-S36/37/39
XS9550000
Xi:Irritant
P261-P280-P305 + P351 + P338
H302 + H312 + H332-H315-H319-H335
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.|SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.
Anon; Diaminotoluenes, World Health Organization, 1211 Gen'eve 27, p. 1-67 (1987)
|Danger|H301 (83.88%): Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P272, P273, P280, P281, P301+P310, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P312, P314, P321, P322, P330, P332+P313, P333+P313, P337+P313, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 242 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P272, P280, P281, P301+P312, P302+P352, P308+P313, P321, P330, P333+P313, P363, P405, and P501
Wear appropriate personal protective clothing to prevent skin contact. /Toluenediamine/|Wear appropriate eye protection to prevent eye contact. /Toluenediamine/|Eyewash fountains should be provided in areas where there is any possbility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection. /Toluenediamine/|Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.] /Toluenediamine/|For more Personal Protective Equipment (PPE) (Complete) data for 2,3-DIAMINOTOLUENE (6 total), please visit the HSDB record page.
The worker should immediately wash the skin when it becomes contaminated. /Toluenediamine/|The worker should wash daily at the end of each work shift, and prior to eating, drinking, smoking, etc. /Toluenediamine/|Work clothing that becomes wet or significantly contaminated should be removed or replaced. /Toluenediamine/|Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises. /Toluenediamine/|SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.
/GUIDE 151: SUBSTANCES - TOXIC (NON-COMBUSTIBLE)/ Health: Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. /2,4-Toluenediamine; 2,4-Toluylenediamine; 2,4-Toluylenediamine, solid; 2,4-Toluylenediamine, solution/|/GUIDE 151: SUBSTANCES - TOXIC (NON-COMBUSTIBLE)/ Fire or Explosion: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Containers may explode when heated. Runoff may pollute waterways. /2,4-Toluenediamine; 2,4-Toluylenediamine; 2,4-Toluylenediamine, solid; 2,4-Toluylenediamine, solution/|/GUIDE 151: SUBSTANCES - TOXIC (NON-COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at lease 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. /2,4-Toluenediamine; 2,4-Toluylenediamine; 2,4-Toluylenediamine, solid; 2,4-Toluylenediamine, solution/|/GUIDE 151: SUBSTANCES - TOXIC (NON-COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /2,4-Toluenediamine; 2,4-Toluylenediamine; 2,4-Toluylenediamine, solid; 2,4-Toluylenediamine, solution/|For more DOT Emergency Guidelines (Complete) data for 2,3-DIAMINOTOLUENE (8 total), please visit the HSDB record page.
NIOSH considers toluenediamine be a potential occupational carcinogen. NIOSH usually recommends that occupational exposures to carcinogens be limited to the lowest feasible concentration. /Toluenediamine/
The major hazards encountered in the use and handling of 2,3-diaminotoluene stem from its toxicologic properties. Toxic by inhalation and ingestion, exposure to this crystalline substance may occur from its use as a chemical intermediate for corrosion inhibitors, and antioxidants (eg, benzimidazolethiol derivatives). In activities and situations where over-exposure may occur, wear protective clothing and a self-contained breathing apparatus. If contact should occur, irrigate exposed eyes with copious amounts of tepid water for at least 15 minutes, and wash expsosed skin thoroughly with soap and water. Remove contaminated clothing and shoes at the site. While 2,3-diaminotoluene does not ignite easily, it may burn with the production of irritating or poisonous gases. Runoff from fire control water may cause pollution. For fires involving this substance, extinguish with dry chemical, CO2, Halon, water spray, fog, or standard foam. Small spills of 2,3-diaminotoluene should be placed in a clean, dry, covered container (if in solution, take up with sand or other noncombustible absorbent) for later disposal. For large spills of 2,3-diaminotoluene solution, dike far ahead of the spill for later disposal.
U221; A toxic waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or manufacturing chemical intermediate.
U221; As stipulated in 40 CFR 261.33, when 2,3-Diaminotoluene as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).
Toxicity
LD50 Mouse intraperitoneal 286 mg/kg
2,3-Diaminotoluene's formation as a minor by-product during the industrial manufacture of other diaminotoluene isomers(1) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 56(SRC), determined from a structure estimation method(2), indicates that 2,3-diaminotoluene is expected to have high mobility in soil(SRC). However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(3,4), suggesting that mobility may be much lower in some soils. Volatilization of 2,3-diaminotoluene from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 9.5X10-010 atm-cu m/mole(SRC), using a fragment constant estimation method(5). 2,3-Diaminotoluene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 5.53X10-4 mm Hg at 25 °C(6). Biodegradation data in soil were not available(SRC, 2012).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 56(SRC), determined from a structure estimation method(2), indicates that 2,3-diaminotoluene is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 9.5X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of 0.71(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC, 2012).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,3-diaminotoluene, which has a vapor pressure of 5.53X10-4 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 2,3-diaminotoluene 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 1.2 hours(SRC), calculated from its rate constant of 2.0X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 2,3-diaminotoluene will be removed from the atmosphere by wet and dry deposition. By analogy to toluene-2,4-diamine which absorbs light at wavelengths >294 nm(4), 2,3-diaminotoluene may be susceptible to direct photolysis by sunlight(SRC).
The rate constant for the vapor-phase reaction of 2,3-diaminotoluene with photochemically-produced hydroxyl radicals has been estimated as 2.0X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1.2 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2,3-Diaminotoluene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). By analogy to toluene-2,4-diamine which absorbs light at wavelengths >294 nm(3), 2,3-diaminotoluene may be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 3 was calculated in fish for 2,3-diaminotoluene(SRC), using an estimated log Kow of 0.71(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
Using a structure estimation method based on molecular connectivity indices(1), the Koc of 2,3-diaminotoluene can be estimated to be 56(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2,3-diaminotoluene is expected to have high mobility in soil. However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(3,4), suggesting that mobility may be much lower in some soils(SRC). Aromatic amines (such as the toluidine isomers) have been observed to undergo rapid and reversible covalent bonding with humic materials in aqueous solution; the initial bonding reaction is followed by a slower and much less reversible reaction believed to represent the addition of the amine to quinoidal structures followed by oxidation of the product to give an amino-substituted quinone; these processes represent pathways by which aromatic amines may be converted to latent forms in the biosphere(5). The estimated pKa of 2,3-diaminotoluene is 4.91(6), indicating that this compound will exist partially in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(7).
The Henry's Law constant for 2,3-diaminotoluene is estimated as 9.5X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2,3-diaminotoluene is expected to be essentially nonvolatile from water and moist soil surfaces(2). 2,3-Diaminotoluene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 5.53X10-4 mm Hg(3).
GROUNDWATER: 2,3-Diaminotoluene was detected in 1 of 3 groundwater samples collected from beneath a former munitions plant Elsnig, Saxony, Germany at a concentration of 1.4 ug/L. It was not detected at 5-7 meters nor 16-18 m depth but was detected at 25-27 meters(1).
According to the 2006 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of 2,3-diaminotoluene is 1 to 99; the data may be greatly underestimated(1).|Occupational exposure to 2,3-diaminotoluene may occur through inhalation and dermal contact with this compound at workplaces where 2,3-diaminotoluene is produced or used. 2,3-Diaminotoluene is formed as a minor by-product during the industrial manufacture of other diaminotoluene isomers(1). The greatest potential for dermal and inhalation exposure to 2,3-diaminotoluene is expected at the manufacturing site and to a lesser extent during activities at the consumer site(SRC).
Drug Information
The acetylation of amino groups, oxidation of methyl groups, and ring hydroxylation appear to be the major metabolic steps. Phenolic metabolites and trace amounts of unchanged diaminotoluenes are excreted in the urine of experimental animals.
/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/
2,3-diaminotoluene
2,3-Diaminotoluene Use and Manufacturing
4.0 g of 10 percent palladium-carbon catalyst (water content, 51.5 percent) was added to ethanol (200 ml) solution of 8.50 g (55.9 mmol) of 2-methyl-6-nitroaniline, and the resulting mixture was stirred under atmospheric pressure hydrogen at room temperature for 4 hours. The catalyst was removed through filtration, and the solvent was evaporated from the filtrate to obtain 6.64 g (97 percent) of a crude product of the entitled compound as a black crystal. This compound was directly used in the next reaction.1H-NMR(CDCl3)δ: 2.22(3H, s), 3.35-3.40(4H, m), 6.62-6.68(3H, m).o-Diamines 5a and 5b were obtained following a standard reduction procedure [28]. Twenty-seven milliliters of concentrated HCl were added gradually, through a condenser, to a mixture of 10g (0.066mol) of 4-methyl-2-nitroaniline (4a) or 2-methyl-6-nitroaniline (4b) and 12g (0.1mol) of granulated Sn. During the addition of the acid the reaction mixture was vigorously stirred. After that, the reaction mixture was refluxed for 1h, cooled to room temperature and made alkaline with a solution of 20g of NaOH in 33mL of water. (0008) The reduction product of compound 4b, 3-methylbenzene-1, 2-diamine (5b), was isolated from the reaction mixture by steam distillation. Compound 5b was “salted out” by saturating the distillate with NaCl and extracted with EtTo a stirred solution of 2-methyl-6-nitroaniline (0.3 g, 1.97 mmol) in ethyl acetate (10 mL), 1.7 g (11.84 mmol) of stannous chloride was added and the mixture was refluxed for 6 h. The reaction was cooled and added into ice water. The ethyl acetate layer was collected and repeatedly washed with sodium bicarbonate solution. The organic layer was concentrated under vacuum and the product was obtained as orange solid (0.17 g, 70percent). m.p. 52-55° C.
Inducer of CYP1A activity, and possible mutagenic carcinogen.
Corrosion inhibitors and anti-scaling agents
(1977) AT LEAST 1.45X10+9 GRAMS|(1982) MORE THAN 2.27X10+6 G-AS ISOMERIC MIXT|1,2-Benzenediamine, 3-methyl- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).|Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#5694]|Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 1,2-Benzenediamine, 3-methyl-. Aggregated National Production Volume: 1 to < 10 million pounds.
All other basic organic chemical manufacturing|1,2-Benzenediamine, 3-methyl-: ACTIVE|Formed as a minor by-product during the industrial manufacture of other diaminotoluene isomers
Several qualitative and quantitative procedures for the determination of diaminotoluenes have been developed using thin- layer, high-performance-liquid, or gas chromatography, methods. Detection limits in air samples range from 0.1 to 10 ug/cu m. The isomeric ratios in technical grade mixtures have been determined by nuclear magnetic resonance and infra-red spectrometry.|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.
Computed Properties
Molecular Weight:122.17
XLogP3:0.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:122.084398327
Monoisotopic Mass:122.084398327
Topological Polar Surface Area:52
Heavy Atom Count:9
Complexity:92.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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