5-Methyl-1,3-benzenediamine

122.1677

122.17

203-609-1

7J9L7YYO3E

DTXSID2051558

2921519090

52.04000

0.15

1.0343 (rough estimate)

<0 °C

283-285 °C

152.9±21.3 °C

1.6100 (estimate)

VERY SOL IN WATER; SOL IN ALC, ETHER

0.00159 mm Hg at 25 deg C(est).

/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 3,5-DIAMINOTOLUENE (8 total), please visit the HSDB record page.

Toluene-3,5-diamine is formed as a minor by-product during the industrial manufacture of other toluenediamine isomers, such as the 2,4- and 2,6-isomers(1); wastewater streams generated at sites of 2,4- and 2,6-toluenediamine manufacture contain toluenediamine isomers(2).

TERRESTRIAL FATE: By analogy to similar aromatic amines, when toluene-3,5-diamine is released to soil it may undergo a covalent chemical bonding with humic materials which can result in its chemical alteration to a latent form and tight adsorption(1); when covalently bound in this latent form, leaching in soil systems is not generally expected to occur(1). This covalent bonding proceeds in two steps(1); a rapid and reversible bonding followed by a slower and much less reversible reaction(1). Leaching in soil may be possible prior to the occurrence of the slower bonding reaction. In the absence of covalent bonding, leaching may be possible based upon an estimated Koc of 1.34(2,SRC). A single biological screening study has indicated that toluene-3,5-diamine is resistant to biodegradation(3); however, insufficient data are available to assess the relative importance of biodegradation in soil(SRC).|AQUATIC FATE: By analogy to similar aromatic amines(1), toluene-3,5-diamine may undergo covalent bonding with humic materials in the water column and in sediment(1); partitioning from the water column to sediment and suspended material may therefore be an important transport mechanism. By analogy to the aromatic amine chemical class(2), toluene-3,5-diamine in the water column may be susceptible to photooxidation via hydroxyl and peroxy radicals. A single biological screening study has indicated that toluene-3,5-diamine is resistant to biodegradation(3); however, insufficient data are available to assess the relative importance of biodegradation in water. Aquatic hydrolysis, volatilization, and bioconcentration do not appear to be environmentally important(SRC).|ATMOSPHERIC FATE: Based upon an estimated vapor pressure of 0.00159 mm Hg at 25 °C(1), toluene-3,5-diamine is expected to exist primarily in the vapor-phase in the ambient atmosphere(2,SRC). It is degraded relatively rapidly in an average ambient atmosphere by reaction with photochemically produced hydroxyl radicals at an estimated half-life rate of about 1.6 hr(3,SRC).

The rate constant for the vapor-phase reaction of toluene-3,5-diamine with photochemically produced hydroxyl radicals has been estimated to be 2.4X10-10 cu cm/molecule-sec at 25 °C which corresponds to an atmospheric half-life of about 1.6 hr at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Aromatic amines are generally resistant to aqueous environmental hydrolysis(2); therefore, toluene-3,5-diamine is not expected to hydrolyze in water(SRC). As a class, aromatic amines react relatively rapidly in sunlit natural water via reaction with photochemically produced hydroxyl radicals and peroxy radicals(3); typical half-lives for hydroxyl radical and peroxy radical reaction are on the order of 19-30 sunlight hours(3); however, rate data specific to toluene-3,5-diamine were not located(SRC).

Based on an estimated log Kow of 0.337(1), the bioconcentration factor (BCF) for toluene-3,5-diamine can be estimated to be 1.06 from a recommended regression-derived equation(2,SRC). This BCF value is not indicative of significant bioconcentration in aquatic organisms(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(1). In the absence of covalent bonding, a Koc value of approximately 1.34 can be estimated from toluene-3,5-diamine estimated log Kow of 0.337(2) using an appropriate regression-derived equation(3,SRC); this Koc values indicates very high soil mobility(4).

The Henry's Law constant for toluene-3,5-diamine can be estimated to be 7.43X10-10 atm-cu m/mole using a structure estimation method(1,SRC); this value of Henry's Law constant indicates that a compound is essentially non-volatile from environmental waters(2).

Toluene-3,5-diamine is formed as a minor by-product during the industrial manufacture of other toluenediamine isomers(1); occupational exposure to toluenediamines occurs through dermal contact and inhalation, with skin contact being the most likely route of exposure(2).

Environmental and medical surveys were conducted ... to evaluate dinitrotoluene and toluenediamine exposures /of/ workers. ... Dinitrotoluene and toluenediamine concentrations ranged from 0.013-0.42 mg/cu m during the initial survey and from undetectable to 0.10 mg/cu m during the follow-up survey. ... Medical findings included a significant reduction in sperm count among exposed workers. A slight excess of miscarriages among the wives of exposed workers was found, but could not be conclusively related to the exposures. ...|... Toluenediamine used as a dye on the eyelashes is reported in one instance to have caused keratoconjunctivitis and blepharitis with opacities of the cornea which gradually cleared in the course of several weeks. /Toluenediamine/

The commercial synthetic mixture contains all six toluene diamine isomers.

1,3-Benzenediamine, 5-methyl-: ACTIVE

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.