Tetramethyldiaminodiphenylmethane

254.37

254.37

479956

202-959-2

L6SPP9K4WQ

36782|9029|4892

3259

DTXSID5020869

C44402

Lustrous leaflets|Yellowish leaflets or glistening plates|Platelets or tablets from alcohol, ligand

29215990

6.5

4.37 (est)

Off-white or light gray or beige-brown Crystalline Powder, Crystals and/or Chunks

1.14 at 68° F (NTP, 1992)

90-91 °C

155-157 °C @ Press: 0.1 Torr

178 °C

1.5794 (estimate)

H2O: Insoluble ;Slightly soluble in ethanol; soluble in acid; very soluble in ether, benzene, carbon disulfide

2-8°C

3.32X10-6 mm Hg at 25 deg C (est)

Henry's Law constant = 1.21X10-7 atm-cu m/mol at 25 °C (est)

Sublimes with decomposition|Hydroxyl radical reaction rate constant = 2.06X10-10 cu cm/molecule-sec at 25 °C (est)

Insoluble in water.

Amines, Phosphines, and Pyridines

4,4'-METHYLENEBIS(N,N-DIMETHYL)BENZENAMINE is incompatible with acids, acid chlorides, acid anhydrides and oxidizing agents. It is also incompatible with active metals, potassium, oxides, chlorates, halogenated compounds, iron chloride, nitro compounds, peroxides, strong ammonia solutions, sulfides and vinyl polymers (NTP, 1992).

III

6.1(b)

UN 3077 9/PG 3

3

45-50/53

53-45-60-61

BY5250000

T,N,Xi

Harmful/Irritant

Stable. Combustible. Incompatible with strong oxidizing agents, acids, acid chlorides

P201-P273-P308 + P313-P501

H350-H410

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.

U.S. Department of Health & Human Services/National Toxicology Program; Twelfth Report on Carcinogens (2011). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. 4,4'-Methylenebis(N,N-dimethyl)-benzenamine (101-61-1) is listed as reasonably anticipated to be a human carcinogen. First listed in the Third Annual Report on Carcinogens (1983).[Available from, as of March 1, 2012: http://ntp.niehs.nih.gov/?objectid=03C9AF75-E1BF-FF40-DBA9EC0928DF8B15]|DHEW/NCI; Bioassay of 4,4'-Methylenebis-(N,N-dimethyl)benzenamine for Possible Carcinogenicity (1979) Technical Rpt Series No. 186 DHEW Pub No. (NIH) 79-1742

This chemical is combustible. (NTP, 1992)

|Danger|H350: May cause cancer [Danger Carcinogenicity]|P201, P202, P273, P281, P308+P313, P391, P405, and P501|H350 (100%): May cause cancer [Danger Carcinogenicity]|Aggregated GHS information provided by 44 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H303: May be harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P281, P308+P313, P312, P405, and P501|P201, P202, P260, P281, P308+P313, P314, P405, and P501

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (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 a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone 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 chemical under ambient temperatures, and keep it away from oxidizing materials and acids. (NTP, 1992)

MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)

Flammable liquid

Bis(p-(dimethylamino)phenyl)methane was detected in 2 of 3 sediment samples at concentrations of 0.004 and 0.01 ppm from the Buffalo River, Buffalo, NY, sampled in June 1979. Soil concentrations in 2 nearby river bank sampling sites were 200 and 400 ppm. The sampling area was the site of a former dump site of a dye manufacturing plant(1).

LD50 Mouse oral 3160 mg/kg

A bioassay for the possible carcinogenicity of 4,4'-methylenebis-(N,N-dimethyl)benzenamine was conducted using Fischer 344 rats and B6C3F1 mice. /The cmpd/ was administered in the feed, ... /to/ 50 male and 50 female animals of each species. Twenty animals of each sex and species were placed on test as controls. The high and low dietary concentrations /of the cmpd/ were, respectively, 750 and 375 ppm for rats and 2,500 and 1250 ppm for mice. The cmpd was administered for 59 wk to rats and for 78 wk to mice. The period of cmpd administration was followed by an observation period of 45 wk for rats and 13 wk for mice. ... For both male and female rats, there was a significant positive association between concentrations of /the cmpd/ administered and the incidences of follicular cell carcinomas of the thyroid (ie, 1/18, 4/50, and 21/46 in the control, low dose, and high dose males, respectively; and 0/20, 3/46, and 23/45 in the control, low dose, and high dose females, respectively). ... Liver neoplasms were observed among male and female mice. There were elevated incidences of hepatocellular adenomas in dosed mice when compared to controls (ie, 2/20, 3/50, and 16/48 in control, low dose, and high dose males, respectively; and 1/19, 18/49, and 22/48 in control, low dose, and high dose females). The incidences of hepatocellular carcinomas in dosed mice did not differ greatly from those in controls (ie, 3/20, 9/50, and 6/48 in control, low dose, and high dose males, respectively; and 0/19, 1/49, and 1/48 in control, low dose, and high dose females). Among both sexes of mice, there was a significant positive association between the concentrations of the cmpd administered and the incidences of a combination of hepatocellular adenomas and hepatocellular carcinomas. ... Under the conditions of this bioassay, 4,4'-methylenebis(N,N-dimethyl)benzamine was carcinogenic in Fischer 344 rats, inducing thyroid follicular cell carcinomas in both males and females. Administration of this cmpd was carcinogenic in female B6C3F1 mice, inducing liver neoplasms. There was no conclusive evidence that /this cmpd/ was carcinogenic in male B6C3F1 mice.

Bis(p-(dimethylamino)phenyl)methane's production and use as a reagent(1) and dye intermediate(2) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), a log Koc of 3.26(2) (Koc of 9,100(SRC)), determined from a structure estimation method(2), indicates that bis(p-(dimethylamino)phenyl)methane is expected to be immobile in soil(SRC). Volatilization of bis(p-(dimethylamino)phenyl)methane from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.2X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Bis(p-(dimethylamino)phenyl)methane is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.3X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). A 0% of theoretical BOD using activated sludge in the Japanese MITI test(5) suggests that biodegradation is not an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), a log Koc of 3.26(2) (Koc of 9,100(SRC)), determined from a structure estimation method(2), indicates that bis(p-(dimethylamino)phenyl)methane 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 1.2X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), BCF values of 423 and 629(8), suggest that bioconcentration in aquatic organisms is high(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), bis(p-(dimethylamino)phenyl)methane, which has an estimated vapor pressure of 3.3X10-6 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 bis(p-(dimethylamino)phenyl)methane 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 hour(SRC), calculated from its rate constant of 2.1X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase bis(p-dimethylamino)phenyl)methane may be removed from the air by wet or dry deposition(SRC). Bis(p-dimethylamino)phenyl)methane does not contain chromophores that absorb at wavelengths >290 nm(4), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of bis(p-(dimethylamino)phenyl)methane with photochemically-produced hydroxyl radicals has been estimated as 2.1X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about one hour at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Bis(p-(dimethylamino)phenyl)methane is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Bis(p-(dimethylamino)phenyl)methane does not contain chromophores that absorb at wavelengths >290 nm(2), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Bis(p-(dimethylamino)phenyl)methane, present at 0.50 and 0.050 mg/L resulted in BCF of 629 and 423, respectively, in fish using carp (Cyprinus carpio) which were exposed over an 4-week period(1). According to a classification scheme(2), these BCF values suggest that bioconcentration in aquatic organisms is high(SRC).

9.12e+03 L/kg|The measured log Koc for bis(p-(dimethylamino)phenyl)methane is reported to be 3.96(1), corresponding to a Koc of 9,100(SRC). According to a classification scheme(2), this estimated Koc value suggests that bis(p-(dimethylamino)phenyl)methane is expected to be immobile in soil(SRC).

The Henry's Law constant for bis(p-dimethylamino)phenyl)methane is estimated as 1.2X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that bis(p-dimethylamino)phenyl)methane is expected to be essentially nonvolatile from water and moist soil surfaces(2). Bis(p-dimethylamino)phenyl)methane is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.3X10-6 mm Hg(SRC), determined from a fragment constant method(3).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 4,140 workers (none of these were female) were potentially exposed to bis(p-dimethylamino)phenyl)methane in the US(1). Occupational exposure to bis(p-dimethylamino)phenyl)methane may occur through inhalation and dermal contact with this compound at workplaces where bis(p-dimethylamino)phenyl)methane is produced or used. Limited monitoring data indicate that the general population may be exposed to bis(p-dimethylamino)phenyl)methane via dermal contact with contaminated soil at disposal sites from dye manufacturing(SRC).

Following injection of randomly labelled (3)H-4,4'-methylenebis(N,N-dimethyl)- benzenamine to rats, radioactivity was found bound to liver nucleic acids.

0.91 Days

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes and respiratory tract; respiratory distress, kidney damage and liver damage, reproductive effects and birth defects. ACUTE/CHRONIC HAZARDS: This compound is harmful if swallowed, inhaled or absorbed through the skin. It is an irritant of the skin, eyes and respiratory tract. When heated to decomposition it emits toxic fumes of carbon monoxide, carbon dioxide and nitrogen oxides. (NTP, 1992)|Carcinogens

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. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. 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. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)

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. /Poisons A and B/|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 needed. 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 patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|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 ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . 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 if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/GENOTOXICITY/ : Chronic Exposure or Carcinogenicity/ Four chemicals that are known to induce in rats thyroid follicular-cell adenomas and carcinomas were assayed for their ability to induce DNA damage and DNA repair synthesis in primary cultures of human thyroid cells. Significant dose-dependent increases in the frequency of DNA single-strand breaks and alkali-labile sites, as measures by the Comet assay, were obtained after a 20-h exposure to the following subtoxic concentrations of the four test compounds: 2,4-diaminoanisole (DAA) from 0.10 to 1.0 mM, 4,4'-methylene-bis(N,N-dimethyl)benzenamine (MDB) from 0.32 to 1.8 mM, propylthiouracil (PTU) from 1.8 to 5.6 mM, and 4,4'-thiodianiline (THA) from 0.032 to 0.18 mM. Under the same experimental conditions, DNA repair synthesis, as evaluated by quantitative autoradiography, was present in thyreocytes exposed to DAA but absent after treatment with MDB, PTU, and THA.

4,4'-methylenebis(N,N-dimethylbenzenamine)

ESSENTIALLY 100% AS CHEM INT

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

Method: EPA-RCA 8270D; Procedure: gas chromatography/mass spectrometry; Analyte: 4,4'-methylenebis(N,N-dimethyl) benzenamine; Matrix: solid waste matrices, soils, air sampling media and water; Detection Limit: not provided.

Health Hazards -> Carcinogens