Bis(p-(dimethylamino)phenyl)methane

Lustrous leaflets

Yellowish leaflets or glistening plates

Platelets or tablets from alcohol, ligand

less than 1 mg/mL at 72 °F (NTP, 1992)

Insoluble in water

Soluble in benzene, ether, carbon disulfide, acids; slightly soluble in cold alcohol, more soluble in hot alcohol

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

412 °F (NTP, 1992)

211 °C

734 °F at 760 mmHg (NTP, 1992)

390 °C decomposes

BP: 155-157 °C at 0.1 mm Hg

BP: 183 °C at 3 mm Hg

194 to 196 °F (NTP, 1992)

91.5 °C

less than 0.000075 mmHg at 68 °F (NTP, 1992)

0.0000175 [mmHg]

Yellowish glistening leaflets or plates or tan crystals. Weak odor. Sublimes without decomposition. (NTP, 1992)

Yellowish solid; [Hawley] Crystalline powder; [MSDSonline]

Danger

H350 (100%): May cause cancer [Danger Carcinogenicity]

P203, P273, P280, P318, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 46 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H350: May cause cancer [Danger Carcinogenicity]

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

Hazard Traits - Carcinogenicity

Substance: N,N,N',N'-tetramethyl-4,4'-methylenedianiline (Michler’s base)

4,4'-Methylenebis(N,N-dimethylbenzenamine): Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

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

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).

Carc. 1B (100%)

Acute toxicity (Oral) - Category 5

Carcinogenicity - Category 1B

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.

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.

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.

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 following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=101-61-1]

4,4'-Methylene bis(N,N'-dimethyl)aniline

Endocrine

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).

/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.

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).

Michler’s base [4,4´-methylenebis(N,N-dimethyl)­benzenamine]

Group 2B: Possibly carcinogenic to humans

Volume 27: (1982) Some Aromatic Amines, Anthraquinones and Nitroso Compounds, and Inorganic Fluorides Used in Drinking-water and Dental Preparations

2010

2008

4,4'-Methylenebis (n,n-dimethyl) benzenamine

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).

Used to manufacture dyes and as a reagent for lead; [Merck Index]

Has been used in manufacture of dyes. As reagent for lead.

... Used as an intermediate in the manufacture of at least six dyes and one pigment (including Methylene Red and C.I. Basic Yellow 2, Basic Orange 14, Solvent Orange 15, and Solvent Yellow 34). Its hydrochloride salt is used as an analytical reagent for the determination of lead.

Dye intermediate

(1973) 5.28X10+8 G

(1977) 4.53X10+8 G

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#4233]