Tris(hydroxymethyl)nitromethane
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Tris(hydroxymethyl)nitromethane
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CAS No:
126-11-4
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Formula:
C4H9NO5
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Chemical Name:
Tris(hydroxymethyl)nitromethane
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Synonyms:
1,3-Propanediol,2-(hydroxymethyl)-2-nitro-;2-(Hydroxymethyl)-2-nitro-1,3-propanediol;Isobutylglycerol,nitro-;2-Nitro-2-(hydroxymethyl)-1,3-propanediol;Trihydroxymethylnitromethane;Trimethylolnitromethane;Tris(hydroxymethyl)nitromethane;Nitroisobutylglycerol;2-(Hydroxymethyl)-2-nitropropanediol;Nitrotris(hydroxymethyl)methane;1,3-Dihydroxy-2-(hydroxymethyl)-2-nitropropane;Tris Nitro;Nitrotrimethylolmethane;NSC 17675;NSC 2344;1-Nitro-1,1,1-tris(hydroxymethyl)methane
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CAS No:
Tris(hydroxymethyl)nitromethane Basic Attributes
151.118
151.12
204-769-5
3E794G4ZRB
17675|2344
DTXSID8027034
Crystals from ethyl acetate and benzene|White solid
29221990
Characteristics
107
-1.66 at 25 deg C
Liquid
1.458 g/cm3
165 °C
273.1°C (rough estimate)
209.3±17.2 °C
1.4183 (estimate)
H2O: soluble 220g/100ml at 20°C
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.
3.2X10-7 mm Hg at 25 deg C (est)
Odorless
Henry's Law constant = 4.8X10-12 atm-cu m/mole at 25 °C (est)
Hydroxy radical reaction rate constant = 1.9X10-12 cu cm/ molec-sec at 25 °C (est)
Safety Information
NONH for all modes of transport
3
R22;R36/37/38
26-36
TY7350000
Xn
/2-(hydroxymethyl)-2-nitro-1,3-propanediol/ is stable only under acidic conditions of pH 5.0 and below, and is unstable and decomposes to formaldehyde under alkaline conditions and at temperatures above 49 deg C.
P261-P305 + P351 + P338
H302-H315-H319-H335
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.
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 ...
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.
|Warning|H302+H332 (12.41%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oral; acute toxicity, inhalation]|P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 137 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
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.
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.
Irritating to skin, mucous membranes.
Toxicity
LD50 Rat oral 1900 mg/kg|LD50 Mouse ip 4000 mg/kg|LD50 Mouse oral 1900 mg/kg
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).
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).
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).
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).
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.
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).
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)
Drug Information
Basic treatment: Establish a patent airway. 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 normal saline 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 ... . /Poison 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 respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/
/CASE REPORTS/ Two machinists were seen whose chronic hand dermatitis was explained by allergic sensitivity to a biocide, Tris Nitro (2-[hydroxymethyl]-2-nitro-1,3-propanediol).
2-(hydroxymethyl)-2-nitro-1,3-propanediol
Tris(hydroxymethyl)nitromethane Use and Manufacturing
...three moles of formaldehyde react with nitromethane via the Henry reaction.|Prepn from trioxymethylene and nitromethane
Bactericide for inanimate objects. To inhibit bacterial growth in circulating industrial water systems, cutting oils, nonprotein glues and sizings.
Intermediates
Water treatment products
1,000,000 - 10,000,000 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.
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)
All other basic organic chemical manufacturing|1,3-Propanediol, 2-(hydroxymethyl)-2-nitro-: ACTIVE
Cosmetics -> Viscosity controlling
Computed Properties
Molecular Weight:151.12
XLogP3:-2.2
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:3
Exact Mass:151.04807239
Monoisotopic Mass:151.04807239
Topological Polar Surface Area:107
Heavy Atom Count:10
Complexity:107
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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