N,N-Dimethylaniline

Hazardous Air Pollutants (HAPs)

Nitrogen Compounds -> Amines, Aromatic

Flammable agents - 2nd degree

Dye

log Kow = 2.31

2.31

2.3

2.29

0.9557 at 68 °F (NTP, 1992) - Less dense than water; will float

0.9537 g/cu cm at 20 °C

Relative density (water = 1): 0.96

0.96

0.9557 @ 20°C

0.96

Pale-yellow, oily liquid [Note: A solid below 36 degrees F]

Yellowish to brownish, oily liquid

less than 1 mg/mL at 70 °F (NTP, 1992)

In water, 1,454 mg/L at 25 °C

Freely soluble in alcohol, chloroform, ether

Soluble in acetone, benzene, organic solvents

Soluble in oxygenated and chlorinated solvents

Soluble in ethanol, ethyl ether, acetone, benzene; very soluble in chloroform

145 °F (NTP, 1992)

63 °C

145 °F (63 °C) (closed cup)

62 °C

142 °F

142 °F

381 °F at 760 mmHg (NTP, 1992)

193 °C

192-194 °C

378 °F

193.1 °C @760 [mm Hg]

378 °F

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P203, P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P318, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H301+H311+H331 (11.3%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

P203, P261, P262, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P318, P321, P330, P337+P317, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Chemical: Benzenamine, N,N-dimethyl-

Benzenamine, N,N-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenamine, N,N-dimethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.

Status: Active Update: 11-08-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/5396

Status: Active Update: 07-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/24634

Benzenamine, N,N-dimethyl-, oxidized, molybdatetungstatephosphates: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

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

· Combustible material: may burn but does not ignite readily.

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 62 °C explosive vapour/air mixtures may be formed.

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

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

N,N-Dimethylaniline is used as an intermediate in the manufacture of dyes and other substances. Acute (short-term) inhalation exposure to N,N-dimethylaniline has resulted in effects on the central nervous system (CNS) and circulatory system, with headache, cyanosis, and dizziness in humans. Effects on the blood have been reported in exposed workers. Chronic (long-term) inhalation exposure of animals resulted in effects on the CNS, blood, and liver. No information is available on the reproductive, developmental, or carcinogenic effects of N,N-dimethylaniline in humans. In a National Toxicology Program (NTP) study of rats and mice exposed via gavage, increased incidences of tumors of the spleen and forestomach were observed. EPA has not classified N,N-dimethylaniline for potential carcinogenicity.

N,N-diethylaniline and N,N-dimethylaniline are potent methemoglobin-inducers with toxicity similar to aniline. [ILO Encyclo, Aromatic Amino Compounds] Listed in a table of Industrial Chemicals for Which Methemoglobin Formation is the Principal Cause of Toxicity; [ACGIH] A skin and eye irritant that can induce methemoglobinemia; Inhalation of high concentrations can cause CNS depression; [ICSC]

2253 153

2253 153

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

Use water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. Combat fire from a sheltered position.

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give a slurry of activated charcoal in water to drink. Rest. Refer for medical attention .

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

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.

General First Aid:

(General first aid procedures)

· Wear positive pressure self-contained breathing apparatus (SCBA).

Biological Exposure Indices (BEI) [ACGIH] - Methemoglobin in blood = 1.5% of hemoglobin during or at end of shift. [ACGIH]

5.0 [ppm]

Special protective equipment for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.

To fight fire, use foam, carbon dioxide, dry chemical.

Use water spray to cool unopened containers.

Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations... Keep in suitable, closed containers for disposal.

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.

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

Dimethylaniline may be disposed of: 1) by absorbing it in vermiculite, dry sand, earth or a similar material ... 2) by atomizing in a suitable combustion chamber equipped with an appropriate effluent gas cleaning device.

The following wastewater treatment technologies have been investigated for N,N-dimethylaniline: Concentration process: Activated carbon.

Product: This combustible material may be burned in a chemical incinerator equipped with an afterburner and scrubber. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Contaminated packaging: Dispose of as unused product.

Personal protection: chemical protection suit. Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable metal or glass containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Hematologic

Blood, kidneys, liver, cardiovascular system

EC50; Species: Chlorella pyrenoidosa (Green Algae) 2x10+6 cells/mL; Conditions: freshwater, static, 22 °C, pH 7.4; Concentration: 22000 ug/L for 72 hr (95% confidence interval: 19000-27000 ug/L); Effect: decreased population growth rate /99% purity/

EC50; Species: Daphnia sp. (Water flea); Conditions: freshwater, static; Concentration: 16500 ug/L for 24 hr; Effect: intoxication, immobilization /99% purity/

EC50; Species: Daphnia magna (Water flea) age 24 hr; Conditions: freshwater, static, 18-20 °C, pH 8.0-8.3, dissolved oxygen 8.1-9.7 mg/L; Concentration: 29700 ug/L for 24 hr (95% confidence interval: 22000-48500 ug/L); Effect: intoxication, immobilization /99% purity/

EC50; Species: Daphnia magna (Water flea) age 24 hr; Conditions: freshwater, static, 18-20 °C, pH 8.0-8.3, dissolved oxygen 8.1-9.7 mg/L; Concentration: 13700 ug/L for 48 hr (95% confidence interval: 11200-16800 ug/L); Effect: intoxication, immobilization /99% purity/

For more Ecotoxicity Values (Complete) data for N,N-DIMETHYLANILINE (17 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 182(2), indicates that N,N-dimethylaniline is expected to have moderate mobility in soil(SRC). The pKa of N,N-dimethylaniline is 5.15(3), indicating that this compound will exist partially 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 N,N-dimethylaniline from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.7X10-5 atm-cu m/mole(SRC), based upon its vapor pressure, 0.76 mm Hg(5), and water solubility, 1,450 mg/L(6). N,N-Dimethylaniline is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(5). Utilizing the Japanese MITI test, 1.9% of the Theoretical BOD was reached in 2 weeks(7) indicating that biodegradation is not an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), a Koc value of 182(2), indicates that N,N-dimethylaniline is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 5.7X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 0.7 mm Hg(4), and water solubility, 1,450 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives of the neutral species for a model river and model lake are 20 hrs and 10 days, respectively(SRC). N,N-Dimethylaniline is degraded in aqueous environments by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in water is estimated to be 34 days(SRC), calculated from its rate constant of 1.4X10+10 cu cm/molecule-sec(6). According to a classification scheme(7), a measured BCF of 5.4(8) suggests the potential for bioconcentration in aquatic organisms is low(SRC). Utilizing the Japanese MITI test, 1.9% of the Theoretical BOD was reached in 2 weeks(8) indicating 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), N,N-dimethylaniline, which has a vapor pressure of 0.7 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase N,N-dimethylaniline 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 2 hrs(SRC), calculated from its rate constant of 1.48X10-10 cu cm/molecule-sec at 25 °C(3). Vapor-phase N,N-dimethylaniline is degraded in the atmosphere by reaction with photochemically-produced ozone radicals(SRC); the half-life for this reaction in air is estimated to be 29 hrs(SRC), calculated from the rate constant of 9.1X10-18 cu cm/molecule-sec at 25 °C(4). Night-time reaction with nitrate radicals may also contribute to the atmospheric transformation of N,N-dimethylaniline(4). A dilute aqueous solution of N,N-dimethylaniline exposed to fluorescent lamps having a continuous spectrum from 300-400 nm resulted in a 50% degradation in approximately 14 min(5); therefore, N,N-dimethylaniline may be susceptible to direct photolysis by sunlight(SRC).

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

inhalation, skin absorption, ingestion, skin and/or eye contact

IDENTIFICATION AND USE: N,N-Dimethylaniline is a pale-yellow, oily liquid with amine-like odor that solidifies below 36 degrees F. It is used as a solvent; an intermediate in the manufacture of vanilin, methyl violet, other dyes, and Michler's ketone; as a reagent; as a catalytic hardener in certain fiberglass resins; and as an acid scavenger or acceptor in the manufacture of semisynthetic penicillins and cephalosporins. HUMAN EXPOSURE AND TOXICITY: N,N-Dimethylaniline has been reported to be quantitatively less toxic than aniline but produces a very similar effect notably, methemoglobinemia. The human lethal oral dose is 50 mg/kg. Short-term exposure: contact may irritate or burn the eyes, and may irritate the nose and throat. It can be absorbed through the skin, thereby increasing exposure. Swallowing the liquid may cause aspiration into the lungs with the risk of chemical pneumonia. The chemical may affect the blood, resulting in formation of methemoglobin. Symptoms of anoxia, cyanosis, weakness, dizziness, ataxia. Symptoms may be delayed. Long term exposure: repeated or prolonged contact with skin may cause dermatitis. While this chemical has not been identified as a reproductive hazard, there are some evidence that women working with aniline, a related compound, have a higher incidence of reproductive cycle disorders and abortions. There are case reports of two workers who showed symptoms very similar to aniline poisoning. One of the workers, who was exposed for only a few minutes to hot vapors from a vat containing dimethylaniline and phenol, collapsed immediately, was unconscious for 8 hours, and complained of visual disturbances, noise in the ears, and intense abdominal pain. The other worker was less severely poisoned after 7 hours of baling dimethylaniline from one container to another. The compound was not irritating when approximately 0.1 g of petrolatum containing 0.6% N,N-Dimethylaniline was applied to the backs of human subjects for 24 hours. There is inadequate evidence in humans for the carcinogenicity of N,N-dimethylaniline. ANIMAL STUDIES: When mice were injected with 65 mg/kg N,N-Dimethylaniline for 3 days, 1.8 % metHb and 2.0 % sulfhemoblobin were found in the blood 48 hours after the last dose. Rats inhaling dimethylaniline at 0.3 mg/cu m for 24 hours/day for 100 days showed significant changes in the central nervous system, blood, and liver, including changes in the correlation of muscle antagonist chronaxy, a reduced number of erythrocytes and hemoglobin, increased methemoglobin level, reticulocytosis, leukopenia, hypoproteinemia, a reduced sulfhydryl group content in the serum, and accumulation of pyruvic acid in the liver and serum. Dimethylaniline increased the coproporphyrin urinary excretion and reduced the adrenal ascorbic acid level. Dimethylaniline at 0.005 mg/cu m did not change the above parameters. In other experiments, splenomegaly was observed in rats and mice given a daily dose of up to 500 mg of N,N-dimethylaniline/kg body weight 5 days/wk for 13 wk. Microscopic examination revealed the presence of hemosiderosis and hematopoiesis in the spleens, livers, and kidneys of treated rats and mice. Bone marrow hyperplasia was noted in treated rats but not mice. N,N-Dimethylaniline was evaluated for developmental toxicity (litter size as well as the birth weight, neonatal growth, and survival of pups) in a short-term in vivo animal bioassay. Fifty pregnant mice were given 365 mg/kg/day N,N-dimethylaniline in corn oil by gavage on days 6-13 of gestation. N,N-Dimethylaniline had no toxic effect in the dams or in their offspring for the parameters assayed. N,N-dimethylaniline was found to be negative when tested for mutagenicity in the Salmonella/microsome preincubation assay in 5 Salmonella typhimurium strains (TA1535, TA1537, TA97, TA98, and TA100). The highest ineffective dose tested in any Salmonella typhimurium strain was 333.000 ug/plate. There is limited evidence in experimental animals for the carcinogenicity of N,N-dimethylaniline. Urinary metabolites of N,N-dimethylaniline produced in dogs were 4-aminophenol, 4-(methylamino)phenol, 4-(dimethylamino)phenol, 2-aminophenol, and N-methylaniline.

Abdominal pain. Blue lips, fingernails and skin. Confusion. Convulsions. Dizziness. Headache. Laboured breathing. Nausea. Unconsciousness. Vomiting. Ringing in the ears. Visual disturbances.

MAY BE ABSORBED! Redness.

Redness. Pain.

See Inhalation.

Anoxia symptoms: cyanosis, lassitude (weakness, exhaustion), dizziness, ataxia; methemoglobinemia

EPA has released the first beta version (version 0.5) of the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The beta version of the iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays; See the data in Chemical Explorer/[USEPA; ICSS Dashboard Application; Available from, as of June 27, 2014: http://actor.epa.gov/dashboard/]

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, as of June 30, 2014: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=121-69-7]

N-N-Dimethylaniline

Hematologic

2 x 10 ^-3 mg/kg-day

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date: 8/4/95; Reporting date: 10/3/95.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Dimethylaniline is included on this list. Effective date: 8/4/95; Sunset date: 6/30/98.

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. N,N-Dimethylaniline is produced, as an intermediate or a final product, by process units covered under this subpart.

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. N,N-Dimethylaniline is included on this list.

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV.D.3.b).

... N,n-dimethylaniline ... has been shown to be demethylated by rat liver preparation.

N,N-dimethylaniline in rat and pig yields N,N-dimethylaniline-N-oxide. /From table/

Urinary metabolites of N,N-dimethylaniline produced in dogs were 4-aminophenol, 4-(methylamino)phenol, 4-(dimethylamino)phenol, 2-aminophenol, & N-methylaniline.

Carbon monoxide diminished max velocity of N-oxide formation from N,N-dimethylaniline in rabbit liver microsomes.

For more Metabolism/Metabolites (Complete) data for N,N-DIMETHYLANILINE (10 total), please visit the HSDB record page.

N,N-Dimethylaniline has known human metabolites that include N-Methylaniline.

Dimethylaniline can be absorbed throurgh the skin, thereby increasing exposure.

... Readily absorbed ... by inhalation of vapors.

N,N-Dimethylaniline is used as an intermediate in the manufacture of vanillin, Michler's ketone, methyl violet, and other dyes and also as a solvent, an alkylating agent, and a stabilizer.

Used in the synthesis of vanillin, methyl violet, and Michler's ketone; also used as a hardener for plastic resins and a acid scavenger in the manufacture of semisynthetic penicillins and cephalosporins; [ACGIH]

Plastic Composites Manufacturing [Category: Industry]

Sculpturing plastics [Category: Hobbies]

Unsaturated polyester resin curing accelerator; extraction solvent (sulphur dioxide refining); acylation reagent

Dimethylaniline is used as a solvent; an intermediate in the manufacture of vanillin, methyl violet, other dyes, and Michler's ketone; as a reagent for methanol, methyl furfural, hydrogen peroxide, nitrate, alcohol, and formaldehyde; as a catalytic hardener in certain fiberglass resins; and as an acid scavenger or acceptor in the manufacture of semisynthetic penicillins and cephalosporins.

2023: 317,462 lb

(1972) 3.67X10+9 GRAMS (SALES)

(1975) 4.6X10+9 GRAMS

Benzenamine, N,N-dimethyl- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#2961]

For more U.S. Production (Complete) data for N,N-DIMETHYLANILINE (6 total), please visit the HSDB record page.

Dimethylaniline is produced from aniline and methanol under pressure in the presence of acidic catalysts or by passing dimethyl ether and aniline vapor over highly activated aluminum oxide at 230-295 °C.

Made by heating aniline, methyl alcohol, and H2SO4 under pressure, the sulfate formed being converted by NaOH to the free base.

By heating a mixture of aniline, aniline hydrochloride, and methyl alcohol (free from acetone) in an autoclave and distilling.

All Other Chemical Product and Preparation Manufacturing

Benzenamine, N,N-dimethyl-: ACTIVE