2,4,6-Tris[(dimethylamino)methyl]phenol

265.39

265.39

202-013-9

2AGN35QF4W

3257

2735

DTXSID5026548

Clear, light yellow, viscous liquid

29222900

30

1.1

2,4,6-tridimethylaminomethyl phenol appears as an amber to red-brown liquid with an amine odor. Less dense than water. Vapors heavier than air. Corrosive to the eyes, skin, mouth, stomach and throat. Vapors may irritate the eyes and corrode the upper respiratory tract.

0.974 g/cm³ @ Temp: 15 °C

316℃

130-135 °C @ Press: 1 Torr

116.6±25.2 °C

1.548

In water, 1.64X10+5 mg/L at 25 deg C (est)

Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage.

<0.01 mm Hg ( 21 °C)

>1 (vs air)

LD50 oral in rat: 1200mg/kg

pKa1 = 8.41; pKa2 = 9.12; pKa3 = 9.75 (amines); pKa4 = 10.4 (hydroxyl) (est)

Hydroxyl radical reaction rate constant = 2.5X10-10 cu cm/molec-sec at 25 °C (est)

Moderately soluble in water.

Amines, Phosphines, and Pyridines

Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. TOXICITY - Variable. Some are very poisonous; others are only slightly toxic. Many amines are skin irritants, and some are sensitizers.

382 °C (720 °F)

Ⅱ

8

2735

1

8

S26-S28-S2

SN3500000

Xn:Harmful;

Stable under recommended storage conditions.

P273-P280-P305 + P351 + P338-P310

H314-H317-H412

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.|Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. Contaminated packaging: Dispose of as unused product.

Strong oxidizing agents, Strong acids

European Chemicals Agency (ECHA); REACH Registration for 2,4,6-tris(dimethylaminomethyl)phenol; This is unique source of information on the chemicals manufactured and imported in Europe. It covers their hazardous properties, classification and information on how to use them safely. It is generated by industry in line with their responsibilities under the EU chemicals legislation. This information is a valuable resource for advancing the safe use of chemicals and for the replacement of the most hazardous ones by safer alternatives.[European Chemicals Agency (ECHA); REACH Registration for 2,4,6-tris(dimethylaminomethyl)phenol; Available from, as of May 29, 2014: http://echa.europa.eu/]

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. (ERG, 2016)

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P332+P313, P337+P313, P362, and P501|Danger|H302 (92.26%): Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P272, P273, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P405, and P501|Aggregated GHS information provided by 1487 companies from 32 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H303: May be harmful if swallowed [Warning Acute toxicity, oral]|P264, P280, P302+P352, P305+P351+P338, P310, P312, P321, P332+P313, and P362|P260, P264, P270, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P363, P405, and P501

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (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)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: 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. (ERG, 2016)|Hand protection: Handle with gloves|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).|Eye protection: Tightly fitting safety goggles. Faceshield (8-inch minimum). Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin and body protection: Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.

Not flammable or combustible.

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Special protective equipment for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.

Accidental Release Measures. Personal precautions: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Environmental precautions: Do not let product enter drains. Methods and materials for containment and cleaning up: Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal.

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.|Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|Avoid contact with skin and eyes. Avoid inhalation of vapor or mist.

A severe skin and eye irritant.

| 3 - Materials that, under emergency conditions, can cause serious or permanent injury.| 0 - Materials that will not burn under typical fire conditions, including intrinsically noncombustible materials such as concrete, stone, and sand.| 0 - Materials that in themselves are normally stable, even under fire conditions.

IDENTIFICATION AND USE: 2,4,6-tris(dimethylaminomethyl)phenol (tris-DMP) is a clear, light yellow, viscous liquid. It is used as a catalyst and co-curing agent for room temperature cure of epoxides and as a paint hardener. HUMAN EXPOSURE AND TOXICITY: A group of industrial painters was followed to assess the incidence of allergic contact dermatitis (ACD) caused by exposure to epoxy resin systems. The study lasted for 4 years and included 2236 workers, contributing 5113 person years. Of 57 patch-tested workers, 23 with ACD caused by epoxy resin systems were found, indicating an incidence rate of 4.5/1000 person years. 4 workers (17%) were identified solely by patch tests to tris-DMP, m-xylene-alpha, alpha-diamine (XAD), and/or 2,2,4 trimethylhexamethylenediamine. Positive patch tests to tris-DMP were seen in 7 workers indicating that this chemical is an important sensitizer in industrial painters. Tris-DMP was non-clastogenic to human lymphocytes in vitro. ANIMAL STUDIES: Rats were exposed dermally to tris-DMP at dose levels of 0, 5, 25, and 125 mg/kg/day, 5 days/week for 4 weeks. Treatment-related signs and symptoms included slight to moderate excitability and/or hypertonicity in the 25- and 125-mg/kg dose groups. Slight to moderate erythema, occasionally accompanied by edema and necrosis, was observed in the 125- mg/kg dose group. Histopathology revealed moderate to marked hydropic change and slight parakeratosis in the epidermis in the 125-mg/kg dose group. Slight hydropic change without parakeratosis was noted in the 25-mg/kg dose group. In developmental study, rats were exposed via oral gavage to tris-DMP at dose levels of 0, 15, 50, and 150 mg/kg/day for two weeks prior to mating, during gestation and for 4 days postpartum. There were no unscheduled deaths during the study and no clinical signs of toxicity were observed. No adverse effect on mating performance, fertility, or gestation length was detected. Litter data at 15 mg/kg/day were unaffected by treatment. There were no adverse effects of maternal treatment on offspring growth or development including pinna unfolding and surface righting reflex. No treatment-related macroscopic abnormalities were detected in the offspring of all treatment groups.There were no treatment-related changes observed in the reproductive or accessory reproductive organs for parental rats of either sex. At 50 and 150 mg/kg/day treatment appeared to be associated with a higher level of preimplantation loss although there was no subsequent effect on post-natal survival, growth or development. Tris-DMP diluted in sterile water was not mutagenic in a Salmonella typhimurium-Escherichia coli direct plate incorporation assay performed using S. typhimurium strains TA1535, TA1537, TA98, and TA100 and E. coli strain WP2uvrA- over a dose range of 50 to 5,000 ug/plate in both the presence and absence of a metabolic activation system. Tris-DMP was considered to be non-mutagenic to L5178Y cells under the conditions of the test with and without activation. ECOTOXICITY STUDIES: Tris-DMP is practically nontoxic to fish and aquatic invertebrates.

LD50 Rat skin 1280 mg/kg|LD50 Rat oral 1200 mg/kg|LD50 Rats oral 2169 mg/kg bw[US EPA; High Production Volume (HPV) Challenge Program Data Analysis and Test Plan For Phenol, 2,4,6-tris

2,4,6-Tris(dimethylaminomethyl)phenol's production and use as a catalyst and hardener in epoxy resins(1) and a paint hardener(2) 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 1480(SRC), determined from a structure estimation method(2), indicates that 2,4,6-tris(dimethylaminomethyl)phenol is expected to have low mobility in soil(SRC). Estimated pKa values of 8.41, 9.12 and 9.75 for the three amine groups(3), indicate that this compound will exist almost entirely in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of 2,4,6-tris(dimethylaminomethyl)phenol from moist soil surfaces is not expected to be an important fate process(SRC) based on the estimated pKa values(3). 2,4,6-Tris(dimethylaminomethyl)phenol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.6X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Biodegradation data in soil were not available(SRC, 2014).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1480(SRC), determined from a structure estimation method(2), indicates that 2,4,6-tris(dimethylaminomethyl)phenol is expected to adsorb to suspended solids and sediment(SRC). Estimated pKa values of 8.41, 9.12 and 9.75 for the three amine groups(3), indicate 2,4,6-tris(dimethylaminomethyl)phenol will exist almost entirely in the cation form at pH values of 5 to 9 and, therefore, volatilization from water surfaces is not expected to be an important fate process(SRC). Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions (pH 5 to 9)(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of 0.77(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC, 2014).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,4,6-tris(dimethylaminomethyl)phenol, which has an estimated vapor pressure of 1.6X10-6 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 2,4,6-tris(dimethylaminomethyl)phenol 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 1.4 hours(SRC), calculated from its rate constant of 2.5X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Particulate-phase 2,4,6-tris(dimethylaminomethyl)phenol may be removed from the air by wet and dry deposition(SRC). 2,4,6-Tris(dimethylaminomethyl)phenol does not contain chromophores that absorb at wavelengths >290 nm(3) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of 2,4,6-tris(dimethylaminomethyl)phenol with photochemically-produced hydroxyl radicals has been estimated as 2.5X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1.4 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions (pH 5 to 9)(2). 2,4,6-Tris(dimethylaminomethyl)phenol 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).

An estimated BCF of 3 was calculated in fish for 2,4,6-tris(dimethylaminomethyl)phenol(SRC), using an estimated log Kow of 0.77(1) and a regression-derived equation(1). According to a classification scheme(2), 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 2,4,6-tris(dimethylaminomethyl)phenol can be estimated to be 1480(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2,4,6-tris(dimethylaminomethyl)phenol is expected to have low mobility in soil. The estimated pKa's of 2,4,6-tris(dimethylaminomethyl)phenol are estimated as 8.41, 9.12 and 9.75 for the three amine groups and 10.4 for the hydroxyl group(3), indicating that this compound will exist almost entirely in cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).

The pKa's of 2,4,6-tris(dimethylaminomethyl)phenol are estimated as 8.41, 9.12 and 9.75 for the three amine groups and 10.4 for the hydroxyl group(1), indicating that this compound will exist almost entirely in cation form in the environment. Volatilization from moist soil and water surfaces is not expected because cations do not volatilize. 2,4,6-Tris(dimethylaminomethyl)phenol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.6X10-6 mm Hg(SRC), determined from a fragment constant method(2).

Occupational exposure to 2,4,6-tris(dimethylaminomethyl)phenol may occur through dermal contact with this compound at workplaces where 2,4,6-tris(dimethylaminomethyl)phenol is produced or used. (SRC)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. 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. (ERG, 2016)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim calm and warm. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. (ERG, 2016)

/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. /Phenols 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 ... . Administer activated charcoal ... . Dilution may be contraindicated because if may increase absorption. Do not use emetics. Cover skin burns with dry, sterile dressings after decontamination ... . Maintain body temperature. /Phenols 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 if 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 patient is 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. ... Treat seizures with diazepam or lorazepam. ... Use proparacaine hydrochloride to assist eye irrigation ... . /Phenols and related compounds/

/CASE REPORTS/ Epoxy resin compounds (ERC) include a large number of sensitizing chemicals such as epoxy resins (ER), hardeners (curing agents), and reactive diluents. Allergic contact dermatitis (ACD) caused by ERCS is often occupational. The study reports a patient, sensitized to a hardener of a two-component epoxy paint. Three conventional patch test sessions were performed to diagnose the causative chemical. Lliterature on sensitizing epoxy-resin hardeners is also reviewed. A 47-year-old nonatopic woman developed dermatitis from a two-component epoxy paint. Patch testing with epoxy resin was negative, but 2,4,6-tris(dimethylaminomethyl)phenol (tris-DMP), used in the paint hardener, induced an allergic patch test reaction. ... No one chemical can be used to screen for sensitization to the many different epoxy hardeners. Extensive patch testing may be required to reveal the hardener that has caused the allergy. The hardener, 2,4,6-tris-(dimethylaminomethyl)phenol (tris-DMP), is a new sensitizer. To verify ACD caused by tris-DMP, patch-testing at 1% in petrolatum is suggested.|/SURVEILLANCE/ A group of industrial painters employed in 6 companies of the Norwegian oil industry was followed to assess the incidence of allergic contact dermatitis (ACD) caused by exposure to epoxy resin systems. The study lasted from 1 September 1997 to 31 August 2001 and included 2236 workers, contributing 5113 person years. Commercially available patch test series were supplemented with a special study series based on known or suspected sensitizers present at the workplaces. Of 57 patch-tested workers, 23 with ACD caused by epoxy resin systems were found, indicating an incidence rate of 4.5/1000 person years. In /this/ study patch test series, 4 workers (17%) were identified solely by patch tests to 2,4,6-tris-(dimethylaminomethyl)phenol (tris-DMP), m-xylene-alpha,alpha-diamine (XAD), and/or 2,2,4 trimethylhexamethylenediamine. Positive patch tests to tris-DMP and XAD were seen in 7 and 8 workers, respectively, indicating that the 2 chemicals are important sensitizers in industrial painters. They are, however, not classified as skin sensitizers according to the European regulations on the classification and labelling of dangerous chemicals. The results show the usefulness of including patch tests based on an investigation of known and suspected skin sensitizers present at the workplaces.|/GENOTOXICITY/ Duplicate cultures of human lymphocytes, treated with the test material, were evaluated for chromosome aberrations at up to four dose levels, together with vehicle and positive controls. In Experiment 1, cells were treated for 4 hours in the presence of an induced rat liver homogenate metabolizing system (S9) at a 2% final concentration with cell harvest after a 20-hour expression period and a second group of cells were treated for 4 hours in the absence of metabolic activation (S9) with a 20-hour expression period. In Experiment 2, the 4-hour exposure with addition of S9 was repeated (using a 1% final S9 concentration), whilst in the absence of metabolic activation the exposure time was increased to 24 hours. The test material did not induce a statistically significant increase in the numbers of polyploid cells or a statistically significant increase in the frequency of cells with chromosome aberrations in either the absence or presence of a liver enzyme metabolising system at any dose level in either of two separate experiments. Using a dose range that included a dose level that induced mitotic inhibition, 2,4,6-tris[(dimethylamino)methyl]phenol was non-clastogenic to human lymphocytes in vitro.

2,4,6-tris(dimethylaminomethyl)phenol

Adhesive manufacturing|Phenol, 2,4,6-tris[(dimethylamino)methyl]-: ACTIVE