Tris(hydroxymethyl)nitromethane

Crystals from ethyl acetate and benzene

White solid

Soluble in polar solvents such as methanol and isopropanol. Insoluble in non-polar solvents such as aliphatic and aromatic hydrocarbons.

Freely soluble in alcohols, sparingly soluble in benzene

Freely soluble in alcohols, sparingly soluble in benzene

In water, 2.20X10+6 mg/L at 20 °C

214 °C (pure)

MP: 180 °C (usual lab product); 175-176 °C (technical grade)

Liquid; Dry Powder

White solid; [Hawley] Light yellow crystals; [MSDSonline]

Warning

H302+H332 (58.6%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oral; acute toxicity, inhalation]

P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 162 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Chemical: 1,3-Propanediol, 2-(hydroxymethyl)-2-nitro-

1,3-Propanediol, 2-(hydroxymethyl)-2-nitro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Propanediol, 2-(hydroxymethyl)-2-nitro- 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)

1,3-Propanediol, 2-(hydroxymethyl)-2-nitro-: 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.

Two cases of allergic contact dermatitis in machinists were reported. Oral LD50 (rat) = 1900 mg/kg; No adverse effects were reported in a 90-day subchronic dermal toxicity study of rats; [HSDB] A skin and mucous membrane irritant; [Merck Index] Decomposes to formaldehyde in warm, alkaline conditions; [EPA REDs] A skin and eye irritant; [Hawley] An irritant; [MSDSonline] See Formaldehyde.

USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - Tris(hydroxymethyl)-nitromethane. EPA 738-F-93-016. The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of February 7, 2006: http://www.epa.gov/pesticides/reregistration/status.htm]

The U.S. high production volume (HPV) chemicals are those which are manufactured in or imported into the United States in amounts equal to or greater than one million pounds per year. Robust Summaries include health effects, ecotoxicity data, and environment fate information for selected chemicals. EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program's Robust Summaries and Test Plans. Available from: http://www.epa.gov/chemrtk/viewsrch.htm on 2-Hydroxymethyl-2-nitro-1,3-propanediol as of January 19, 2006.

Section 4(g)(2)(A) of FIFRA calls for the Agency to determine, after submission of relevant data concerning an active ingredient, whether products containing the active ingredients are eligible for reregistration. The Agency has previously identified and required the submission of the generic (i.e. active ingredient specific) data required to support reregistration of products containing 2-(hydroxymethyl)-2-nitro01,3-propanediol as the active ingredient. The Agency has completed its review of these generic data, and has determined that the data are sufficient to support reregistration of all products containing 2-(hydroxymethyl)-2-nitro-1,3-propanediol.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. 2-Hydroxymethyl-2-nitro-1,3-propanediol is found on List C. Case No: 3149; Pesticide type: antimicrobial; Case Status: RED Approved 09/93; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document .; Active ingredient (AI): 2-hydroxymethyl-2-nitro-1,3-propanediol; Data Call-in (DCI) Date(s): 09/29/92, 08/09/93, 01/31/94; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) for the case/AI.

The antimicrobial properties of 2-(hydroxymethyl)2-nitro-1,3-propanediol are due in large part to the slow release over time of formaldehyde (HCHO) from the active ingredient under alkaline conditions. The rate of release is highly dependent on the pH of the solution and on the temperature (the higher the pH of the solution and/or the higher the temperature, the faster the release). Since formaldehyde has significant toxic effect of its own, and has also been classified ... as a ... (probable human) carcinogen, the toxicity of formaldehyde is a primary consideration in evaluating the toxicity of 2-(hydroxymethyl)-2-nitro-1,3-propanediol ...

Safe Storage of Pesticides. Always store pesticides in their original containers, complete with labels that list ingredients, directions for use, and first aid steps in case of accidental poisoning. Never store pesticides in cabinets with or near food, animal feed, or medical supplies. Do not store pesticides in places where flooding is possible or in places where they might spill or leak into wells, drains, ground water, or surface water.

If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label.

After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide..To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash.

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.

Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal.

Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Do cut or puncture other empty pesticide containers made of metal or plastic to prevent someone from reusing them. Wrap the empty container and put it in the trash after you have rinsed it.

Wear the items of protective clothing the label requires: for example, non-absorbent gloves (not leather or fabric), rubber footwear (not canvas or leather), a hat, goggles, or a dust-mist filter. If no specific clothing is listed, gloves, long-sleeved shirts and long pants, and closed shoes are recommended. You can buy protective clothing and equipment at hardware stores or building supply stores.

Indoor Applications. If the label directions permit, leave all windows open and fans operating after the application is completed. If the pesticide product is only effective in an unventilated (sealed) room or house, do not stay there. Put all pets outdoors, and take yourself any your family away from treated areas for at least the length of time prescribed on the label. Apply most surface sprays only to limited areas such as cracks; don't treat entire floors, walls, or ceilings. Don't let pesticides get on any surfaces that are used for food preparation. Wash any surfaces that may have pesticide residue before placing food on them.

Indoor Applications. When using total release foggers to control pests, use no more than the amount needed and to keep foggers away from ignition sources (ovens, stoves, air conditioners, space heaters, and water heaters, for example). Foggers should not be used in small, enclosed places such as closets and cabinets or under tables and counters.

Outdoor Applications. Never apply pesticides outdoors on a windy day (winds higher than 10 mph). Position yourself so that a light breeze does not blow pesticide spray or dust into your face.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit 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.

LC50 Colinus virginianus (Bobwhite quail, 10 days old) dietary >5000 ppm/8 days

LC50 Anas platyrhynchos (Mallard duck, 15 days old) dietary >40,000 ppm/8 days

LC50 Americamysis bahia (Opossum shrimp) >95.5 ppm/96 hr; flow through /Formulated product/

LC50 Crassostrea virginica (American or virginia oyster) 22.8 ppm/96 hr; flow through /Formulated product/

For more Ecotoxicity Values (Complete) data for 2-HYDROXYMETHYL-2-NITRO-1,3-PROPANEDIOL (9 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that 2-hydroxymethyl-2-nitro-1,3-propanediol is expected to have very high mobility in soil(SRC). Volatilization of 2-hydroxymethyl-2-nitro-1,3-propanediol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.8X10-12 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 2-Hydroxymethyl-2-nitro-1,3-propanediol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.2X10-7 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2006).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that 2-hydroxymethyl-2-nitro-1,3-propanediol is not 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 4.8X10-12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 1.3(SRC), from an estimated log Kow of -1.66(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 2-Hydroxymethyl-2-nitro-1,3-propanediol has reported hydrolysis half-lives of stable, 3.4 days and 2.4 days at pH values 5, 7 and 9, respectively(8). 2-Hydroxymethyl-2-nitro-1,3-propanediol decomposes to formaldehyde under alkaline conditions and at temperatures above 49 °C(9). Biodegradation data were not available(SRC, 2006).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-hydroxymethyl-2-nitro-1,3-propanediol, which has an estimated vapor pressure of 3.2X10-7 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-hydroxymethyl-2-nitro-1,3-propanediol 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 33 days(SRC), calculated from its rate constant of 1.9X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 2-hydroxymethyl-2-nitro-1,3-propanediol may be removed from the air by wet and dry deposition(SRC). 2-Hydroxymethyl-2-nitro-1,3-propanediol does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 2-hydroxymethyl-2-nitro-1,3-propanediol can be estimated to be 10(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-hydroxymethyl-2-nitro-1,3-propanediol is expected to have very high mobility in soil.

2-Hydroxymethyl-2-nitro-1,3-propanediol's production and use as bacteriacide, in cutting oils and non-protein glue sizings(1) may result in its release to the environment through various waste streams(SRC). 2-Hydroxymethyl-2-nitro-1,3-propanediol's use as an inhibitor of bacterial growth in circulating industrial water systems(1) will result in its direct release to the environment(SRC).

An estimated BCF of 1.3 was calculated for 2-hydroxymethyl-2-nitro-1,3-propanediol(SRC), using an estimated log Kow of -1.66(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The Henry's Law constant for 2-hydroxymethyl-2-nitro-1,3-propanediol is estimated as 4.8X10-12 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2-hydroxymethyl-2-nitro-1,3-propanediol is expected to be essentially nonvolatile from moist soil and water surfaces(2). 2-Hydroxymethyl-2-nitro-1,3-propanediol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.2X10-7 mm Hg(SRC), determined from a fragment constant method(3).

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ In a 90-day subchronic dermal toxicity study, male and female Crl:CD BR rats were treated dermally for 6 hr per day, 5 days per week with a paste of 2-(hydroxymethyl)-2-nitro-1,3-propanediol in deionized water. Dosage levels were 0, 250, 500 and 1000 mg/kg/day. The test material was essentially non-irritating to the skin, although yellowish discoloration was noted at test sites. There were no treatment-related effects observed at any dosage level. The NOEL for systemic toxicity is >/+ 1000 mg/kg/day.

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ A developmental toxicity study was conducted with pregnant Sprague Dawley Crl:CD BR rats which were administered daily doses of 0, 50, 375 or 750 mg/kg/day of 2-(hydroxymethyl)-2-nitro-1,3-propanediol by gavage on days 6 through 15 of gestation. Treatment-related maternal effects were observed only in the high-dose group and included: increased mortality (7/25 or 28% of the group), decreased mean body weight gain, and clinical signs of toxicity (including head bobbing, tremors, and circling motions). A treatment-related developmental effect, observed at 375 mg/kg/day and 750 mg/kg/day, was increased mean number of resorptions per dam. At 750 mg/kg/day, fetal body weights were also reduced. Therefore, the NOEL and LOEL for maternal toxicity are 375 mg/kg/day and 750 mg/kg/day, respectively. The NOEL and LOEL for developmental toxicity are 50 mg/kg/day and 375 mg/kg/day, respectively. A slightly increased incidence of omphalocele in the 750 mg/kg/day fetuses in this study, when compared to historical control data, suggested the possibility of an additional developmental effect.

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ ... Pregnant New Zealand White rabbits were administered daily doses of 0, 10, 30 or 75 mg/kg/day of 2-(hydroxymethyl)-2-nitro-1,3-propanediol by gavage on days 7 through 19 of gestation. Treatment-related maternal effects were observed only in the high-dose group and included: decreased mean body weight gain, and decreased mean food consumption. No treatment-related developmental effects were observed ... Therefore, the NOEL and LOEL for maternal toxicity are 30 mg/kg/day and 75 mg/kg/day, respectively. The NOEL for developmental toxicity is >/+ 75 mg/kg/day.

/GENOTOXICITY/ A Salmonella typhimurium reverse mutation assay (Ames assay) was conducted using 2-(hydroxymethyl)-2-nitro-1,3-propanediol as the test material. Strains TA 98, TA 100, TA 1535, TA 1537 and TA 1538 were tested without and with S-9 metabolic activation. No increases in reverse mutations were observed at concentrations up to 1000 ug/plate.

For more Non-Human Toxicity Excerpts (Complete) data for 2-HYDROXYMETHYL-2-NITRO-1,3-PROPANEDIOL (6 total), please visit the HSDB record page.

The rate constant for the vapor-phase reaction of 2-hydroxymethyl-2-nitro-1,3-propanediol with photochemically-produced hydroxyl radicals has been estimated as 1.9X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 33 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2-Hydroxymethyl-2-nitro-1,3-propanediol has reported hydrolysis half-lives of stable days, 3.4 days and 2.4 days at pH values 5, 7 and 9, respectively(2). 2-Hydroxymethyl-2-nitro-1,3-propanediol decomposes to formaldehyde under alkaline conditions and at temperatures above 49 °C(3). 2-Hydroxymethyl-2-nitro-1,3-propanediol does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

2-Hydroxymethyl-2-nitro-1,3-propanediol's production and use as bacteriacide, in cutting oils and non-protein glue sizings may result in its release to the environment through various waste streams. 2-Hydroxymethyl-2-nitro-1,3-propanediol's use as an inhibitor of bacterial growth in circulating industrial water systems will result in its direct release to the environment. If released to air, an estimated vapor pressure of 3.2X10-7 mm Hg at 25 °C indicates 2-hydroxymethyl-2-nitro-1,3-propanediol will exist in both the vapor and particulate phases in the atmosphere. Vapor-phase 2-hydroxymethyl-2-nitro-1,3-propanediol will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 33 days. Particulate-phase 2-hydroxymethyl-2-nitro-1,3-propanediol will be removed from the atmosphere by wet and dry deposition. 2-Hydroxymethyl-2-nitro-1,3-propanediol does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight. If released to soil, 2-hydroxymethyl-2-nitro-1,3-propanediol is expected to have very high mobility based upon an estimated Koc of 10. Volatilization from moist soil and water surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 4.8X10-12 atm-cu m/mole. 2-Hydroxymethyl-2-nitro-1,3-propanediol is not expected to volatilize from dry soil surfaces based upon its vapor pressure. Biodegradation data were not available. If released into water, 2-hydroxymethyl-2-nitro-1,3-propanediol is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. An estimated BCF of 1.3 suggests the potential for bioconcentration in aquatic organisms is low. 2-Hydroxymethyl-2-nitro-1,3-propanediol has reported hydrolysis half-lives of stable, 3.4 days and 2.4 days at pH values 5, 7 and 9, respectively. 2-Hydroxymethyl-2-nitro-1,3-propanediol decomposes to formaldehyde under alkaline conditions and at temperatures above 49 °C. Occupational exposure to 2-hydroxymethyl-2-nitro-1,3-propanediol may occur through dermal contact with this compound at workplaces where 2-hydroxymethyl-2-nitro-1,3-propanediol is produced or used. (SRC)

Section 4(g)(2)(A) of FIFRA calls for the Agency to determine, after submission of relevant data concerning an active ingredient, whether products containing the active ingredients are eligible for reregistration. The Agency has previously identified and required the submission of the generic (i.e. active ingredient specific) data required to support reregistration of products containing 2-(hydroxymethyl)-2-nitro01,3-propanediol as the active ingredient. The Agency has completed its review of these generic data, and has determined that the data are sufficient to support reregistration of all products containing 2-(hydroxymethyl)-2-nitro-1,3-propanediol.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. 2-Hydroxymethyl-2-nitro-1,3-propanediol is found on List C. Case No: 3149; Pesticide type: antimicrobial; Case Status: RED Approved 09/93; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document .; Active ingredient (AI): 2-hydroxymethyl-2-nitro-1,3-propanediol; Data Call-in (DCI) Date(s): 09/29/92, 08/09/93, 01/31/94; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) for the case/AI.

Used as a general disinfectant, bactericide (circulating industrial water systems, cutting oils, secondary oil field recovery waters, and paper mills), and preservative (latex paints, polishes, non-protein glues, sizings, and detergents); Also used as a disinfectant in livestock and poultry farms; [HSDB]

Metal Machining [Category: Heat or Machine]

For 2-hydroxymethyl-2-nitro-1,3-propanediol (USEPA/OPP Pesticide Code: 083902) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Bactericide for inanimate objects. To inhibit bacterial growth in circulating industrial water systems, cutting oils, non-protein glues and sizings.

Disinfectant (general); microbicide/microbiostat (slime-forming bacteria and fungi) ... industrial preservative/preservative (bacteriostat)

Microbiocide and bacteriostat in disinfectants and industrial preservatives. Specifically ... used as an industrial preservative in metalworking fluids, secondary oil field recovery waters, paper mills, and commercial/industrial water cooling systems; as an in-can preservative in latex paints, polishes, and detergents; and as a disinfectant to control disease organisms in livestock and poultry areas on farms and equipment.

2023: 11,139,774 lb

This chemical is listed as a High Production Volume (HPV) (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).

(1986) >1 million-10 million pounds

(1990) >1 million-10 million pounds

(1994) >1 million-10 million pounds

For more U.S. Production (Complete) data for 2-HYDROXYMETHYL-2-NITRO-1,3-PROPANEDIOL (6 total), please visit the HSDB record page.

...three moles of formaldehyde react with nitromethane via the Henry reaction.

Prepn from trioxymethylene and nitromethane

Trade name: Cimcool wafers

Technical grade active ingredient, manufacturing use, end use; soluble concentrate/liquid, soluble concentrate/solid, pelleted/tableted, crystalline (19.2-100% active ingredient)

Miscellaneous Manufacturing

1,3-Propanediol, 2-(hydroxymethyl)-2-nitro-: ACTIVE