4,4′-Methylenebis[N-methylbenzenamine]

226.32 g/mol

226.32

217-309-3

7AUF08SV1M

DTXSID7061986

24.1 Ų

log Kow = 3.28 (est)

55-56 °C

250-260 °C @ Press: 4 Torr

Soluble in carbon tetrachloride, carbon disulfide.|In water, 50.7 mg/L at 25 °C (est)

1.76X10-5 mm Hg at 25 °C (et)

Henry's Law constant = 2.9X10-10 atm-cu m/mol at 25 °C (est)

Hydroxyl radical reaction rate constant = 1.1X10-10 cu cm/molec-sec at 25 °C (est)

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.

4,4'-Methylenebis(N-methylaniline)'s former production and use as a chemical intermediate may have resulted in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.0X10+4(SRC), determined from a structure estimation method(2), indicates that 4,4'-methylenebis(N-methylaniline) is expected to be immobile in soil(SRC). Volatilization of 4,4'-methylenebis(N-methylaniline) from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.9X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 4,4'-Methylenebis(N-methylaniline) is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.8X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2009).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.0X10+4(SRC), determined from a structure estimation method(2), indicates that 4,4'-methylenebis(N-methylaniline) is 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 2.9X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 66(SRC), from an estimated log Kow of 3.28(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Biodegradation data were not available(SRC, 2009).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4,4'-methylenebis(N-methylaniline), which has an estimated vapor pressure of 1.8X10-5 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 4,4'-methylenebis(N-methylaniline) 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 3.6 hours(SRC), calculated from its rate constant of 1.1X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 4,4'-methylenebis(N-methylaniline) may be removed from the air by wet or dry deposition(SRC). 4,4'-Methylenebis(N-methylaniline) contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of 4,4'-methylenebis(N-methylaniline) with photochemically-produced hydroxyl radicals has been estimated as 1.1X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3.6 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 4,4'-Methylenebis(N-methylaniline) is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). 4,4'-Methylenebis(N-methylaniline) contains chromophores that absorb at wavelengths >290 nm(2) and therefore may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 66 was calculated for 4,4'-methylenebis(N-methylaniline)(SRC), using an estimated log Kow of 3.28(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 4,4'-methylenebis(N-methylaniline) can be estimated to be 1.0X10+4(SRC). According to a classification scheme(2), this estimated Koc value suggests that 4,4'-methylenebis(N-methylaniline) is expected to be immobile in soil.

The Henry's Law constant for 4,4'-methylenebis(N-methylaniline) is estimated as 2.9X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 4,4'-methylenebis(N-methylaniline) is expected to be essentially nonvolatile from water surfaces(2). 4,4'-Methylenebis(N-methylaniline) is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.8E-5 mm Hg(SRC), determined from a fragment constant method(3).

Occupational exposure to 4,4'-methylenebis(N-methylaniline) may occur through dermal contact with this compound at workplaces where 4,4'-methylenebis(N-methylaniline) is produced or used. (SRC)

Studies on the in vivo and in vitro disposition of 4,4'-[14C]-methylenebis(N,N-dimethyl)benzamine (reduced Michler's ketone, RMK) were performed. Osborne-Mendel rats retained, after 24 hr, 78% of a /oral/ dose of [14C]RMK. At 24 hr after an i.p. dose, fat, liver, and intestine represented major sites for deposition of radioactivity. ...

... The major urinary metabolite of 4,4'-[14C]-methylenebis(N,N-dimethyl)benzamine (RMK), representing 36% of the total radioactivity recovered in the urine /of rats/, was N,N'-diacetyl-4,4'-(hydroxymethylene)dianiline. In vitro microsomal metabolism of RMK involved demethylation. Products included N,N-dimethyl-4,4'-methylenedianiline, N,N'-dimethyl-4,4'-methylenedianiline, N-methyl-4,4'-methylenedianiline, and 4,4'-methylenedianiline, representing 44.7, 5.3, 11.8, and 6.9%, respectively, of the total radioactivity recovered from the reaction mixture. ...

/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 as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on 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. /Aniline 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 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 ... . /Aniline 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. 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. Consider vasopressors if hypotensive with a normal fluid volume. 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. DIRECT PHYSICIAN ORDER ONLY ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aniline and related compounds/

4,4'-Methylenebis(N-methylaniline)

Benzenamine, 4,4'-methylenebis[N-methyl-: ACTIVE