2,2-Dibromo-3-nitrilopropionamide

241.86900

241.87

233-539-7

7N51QGL6MJ

98283

2923

DTXSID5032361

White to "off white" crystalline solid

2926909090

66.88000

1.18168

Colorless to yellow liquid with a moldy pungent odor

2.451 g/cm3

123-126 °C

123-126 °C

87.8±27.3 °C

1.624

In acetone, 35 g/100 mL; in ethanol, 25 g/100mL

Keep in a cool, dry location in a tightly sealed container.

0.107mmHg at 25°C

Non-explosive, non-combustible.

Mild "medicinal antiseptic"

Henry's Law constant = 1.9X10-8 atm-cu m/mol at 25 °C (est)

2.375 at 21 °C

Hydroxyl radical reaction rate constant = 2.0X10-12 cu cm/molecule-sec at 25 °C (est)

Water soluble.

Amides and Imides

2,2-DIBROMO-3-NITRILOPROPIONAMIDE is incompatible with bases, metals, oxidizing agents, acids. Dangerous gases may accumulate as a result of ignition and fire.

Corrosive to mild steel, iron and aluminum

III

6.1(b)

UN 1759 8/PG 3

3

R20/21/22

S36/37

AB5956000

Xn

Stable, but may be moisture sensitive. Incompatible with strong oxidizing agents.

P273-P280-P305 + P351 + P338-P310

H314-H317-H400

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.

Incompatible with bases, reducing substances & nucleophiles.

2,2-Dibromo-3-nitrilopropionamide is an indirect food additive for use only as a component of adhesives. Limit: For use as a preservative only.

USEPA/Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision Document - 2,2-Dibromo-3-nitrilopropionamide (DBNPA) EPA 738-R-94-026 (September 1994). 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 November 4, 2014: http://www.epa.gov/pesticides/reregistration/status.htm]

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. For electric vehicles or equipment, ERG Guide 147 (lithium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. (ERG, 2016)

|Danger|H301 (83.06%): Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P262, P264, P270, P271, P272, P273, P280, P284, P301+P310, P301+P330+P331, P302+P350, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P320, P321, P322, P330, P332+P313, P333+P313, P361, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 548 companies from 29 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P310, P304+P340, P305+P351+P338, P310, P311, P321, P330, P403+P233, P405, and P501|P260, P264, P270, P271, P280, P284, P301+P310, P302+P352, P304+P340, P305+P351+P338, P310, P314, P320, P321, P330, P332+P313, P362, P403+P233, P405, and P501

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: SMALL FIRE: Dry chemical, CO2 or water spray. LARGE FIRE: Dry chemical, CO2, alcohol-resistant foam or water spray. Move containers from fire area if you can do it without risk. Dike fire-control water for later disposal; do not scatter the material. FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. (ERG, 2016)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-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 154 [Substances - Toxic and/or Corrosive (Non-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 154 [Substances - Toxic and/or Corrosive (Non-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)

Non-explosive, non-combustible.

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.

A severe skin & eye irritant.

IDENTIFICATION AND USE: 2,2-Dibromo-3-nitrilopropionamide (DBNPA) is white to "off white" crystalline solid. It is used as a pesticide(Trade Names: DBNPA, Slimicide 508, XD-7287L Antimicrobial, XD-1603.) Main uses include the following: algicide, bactericide and fungicide; preservative used mainly in pulp, paper and paperboard mill water systems and in industrial water cooling systems. It is also used as a preservative in animal glues, metalworking cutting fluids, oil recovery drilling muds, latex paints, resin/latex/polymer emulsions, latex/oil/varnish paints, and paper and paper products. HUMAN EXPOSURE AND TOXICITY: Several human incident reports concerning DBNPA are on file with the EPA. These include eye, throat, & respiratory irritation, runny nose, & headache. Generally the effects arose with spills or misuse. No treatment related effects on chromosome aberrations in proliferating cultured human lymphocyte were reported with or without metabolic activation. ANIMAL STUDIES: A primary eye irritation study in rabbits resulted in severe corneal damage. Dermal irritation was noted in rats of both sexes. Renal tubular alterations of the kidneys (minimal cytoplasmic swelling and vacuolization) were described in female rats. Developmental study in rabbits found retarded ossification of several fetal skeletal elements. The occurrence of structural alterations at a maternally non-toxic dose indicates that DBNPA is a developmental toxicant in rabbits. DBNPA did not induce micronuclei formation in mice. In Salmonella typhimurium TA98, TA100, TA1535, and TA1537 and Escherichia coli WP2uvrA the test material did not produce a positive increase in the number of revertants per plate of any of the test strains either in the presence or absence of microsomal activation. The positive controls were functional. Sister chromatid exchange (SCE) assay in Chinese hamster ovary cells after one hour exposures at DBNPA was negative.

LD50 Mouse iv 10 mg/kg|LD50 Mammal oral 118 mg/kg|LD50 Rat (male) oral 235 mg/kg /from table/|LD50 Rat (female) oral 178 mg/kg /from table/|For more Non-Human Toxicity Values (Complete) data for 2,2-DIBROMO-3-NITRILOPROPIONAMIDE (8 total), please visit the HSDB record page.

2,2-Dibromo-3-nitrilopropionamide's production and use as a bactericide and algicide in commercial water cooling and treatment systems and paper-pulp mill water systems(1) 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 58(SRC), determined from a log Kow of 0.80(2) and a regression-derived equation(3), indicates that 2,2-dibromo-3-nitrilopropionamide is expected to have high mobility in soil(SRC). Volatilization of 2,2-dibromo-3-nitrilopropionamide from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.9X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 9.0X10-4 mm Hg(2), and water solubility, 1.5X10+4 mg/L(2). 2,2-Dibromo-3-nitrilopropionamide is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). Biodegradation in soil may be an important environmental fate process; however, degradation in soil is expected to be due to both abiotic and biotic processes(2,4). 2,2-Dibromo-3-nitrilopropionamide is susceptible to aqueous hydrolysis in moist soils and susceptible to photodegradation when exposed to sunlight(2,4). Half-lives ranged from 4 to 25 hours in 7 different soils with pH values of 4.8 to 7.5(4).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 58(SRC), determined from a log Kow of 0.80(2) and a regression-derived equation(3), indicates that 2,2-dibromo-3-nitrilopropionamide is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 1.9X10-8 atm-cu m/mole(SRC), determined from its vapor pressure, 9.0X10-4 mm Hg(2) and water solubility, 1.5X10+4 mg/L(2). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Degradation in water is due to both abiotic and biotic processes(2,6). Hydrolysis half-lives of 67 days, 63 hours, and 73 minutes were measured for 2,2-dibromo-3-nitrilopropionamide at pH 5, 7, and 9, respectively(2). Dibromoacetic acid is the major degradate at pH 5 while dibromoacetonitrile is the major degradate at pH values of 7 and 9(2). The half-life of 2,2-dibromo-3-nitrilopropionamide is less than 4 hours in anaerobic and aerobic metabolism studies(2). Degradates include oxalic acid, 2-cyanoacetamide, bromoacetamide, dibromoacetic acid, bromoacetic acid, and dibromoacetonitrile; the concentration of each degradate over time varies with the oxygen condition(2). 2,2-Dibromo-3-nitrilopropionamide is susceptible to photodegradation in water(6); <1% of initial 2,2-dibromo-3-nitrilopropionamide remained after exposure to sunlight for 28 days(6). Sunlight degrades 2,2-dibromo-3-nitrilopropionamide in water at rates that become relatively fast compared to hydrolysis at pH less than 5(6).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,2-dibromo-3-nitrilopropionamide, which has a vapor pressure of 9X10-4 mm Hg at 25 °C(2), will exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,2-dibromo-3-nitrilopropionamide 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 8 days(SRC), calculated from its rate constant of 2.0X10-12 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). Based on photolysis studies showing degradation in aqueous solution exposed to sunlight (99% loss in 28 days)(4), 2,2-dibromo-3-nitrilopropionamide is expected to be susceptible to direct photolysis in the atmosphere(SRC).

The rate constant for the vapor-phase reaction of 2,2-dibromo-3-nitrilopropionamide with photochemically-produced hydroxyl radicals has been estimated as 2.0X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 8 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Less than 1% of a 4000 ppm aqueous solution of 2,2-dibromo-3-nitrilopropionamide remained after 28 days exposure to sunlight(2); 91% of the added 2,2-dibromo-3-nitrilopropionamide was still present in the dark control after the same period of time(2). Dibromoacetic acid (63.7%) is the major degradate at pH 5 (half-life of 14.8 hours; dark control forms dibromoacetic acid at 38.6%) and at pH 7 (half-life of 6.9 hours; dark control forms dibromoacetic acid at 74.9%) in aqueous photolysis studies(2). Hydrolysis half-lives of 155, 8.8, 5.8, 2.0, and 0.34 hours were measured at pH values of 6.0, 7.3, 7.7, 8.0, and 8.9, respectively(2). The half-life of 2,2-dibromo-3-nitrilopropionamide is 67 days at pH 5, 63 hours at pH 7, and 73 minutes at pH 9(3). Dibromoacetic acid (30.6% of applied), dibromoacetonitrile (54.5% of applied), and dibromoacetonitrile (38.6% of applied) are the major degradates at pH values of 5, 7, and 9, respectively(3).

An estimated BCF of 3 was calculated in fish for 2,2-dibromo-3-nitrilopropionamide(SRC), using a log Kow of 0.80(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 carp (Cyprinus carpio) which were exposed over an 8-week period, 2,2-dibromo-3-nitrilopropionamide was reported to have low bioconcentration (BCF value not available)(4).

The Koc of 2,2-dibromo-3-nitrilopropionamide is estimated as 58(SRC), using a log Kow of 0.80(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2,2-dibromo-3-nitrilopropionamide is expected to have high mobility in soil.

The Henry's Law constant for 2,2-dibromo-3-nitrilopropionamide is estimated as 1.9X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 9.0X10-4 mm Hg(1), and water solubility, 1.5X10+4 mg/L(1). This Henry's Law constant indicates that 2,2-dibromo-3-nitrilopropionamide is expected to be essentially nonvolatile from water surfaces(2). 2,2-Dibromo-3-nitrilopropionamide's estimated Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). 2,2-Dibromo-3-nitrilopropionamide is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

According to the 2012 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of 2,2-dibromo-3-nitrilopropionamide is 25-49 (one of the two companies listed claimed Confidential Business Information for the number of persons exposed); the data may be greatly underestimated(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 9,829 workers (108 of these were female) were potentially exposed to 2,2-dibromo-3-nitrilopropionamide in the US(1). Occupational exposure to 2,2-dibromo-3-nitrilopropionamide may occur through inhalation and dermal contact with this compound at workplaces where 2,2-dibromo-3-nitrilopropionamide is produced or used(SRC). The general population may be exposed to 2,2-dibromo-3-nitrilopropionamide via dermal contact with consumer products such as latex paint containing 2,2-dibromo-3-nitrilopropionamide(SRC).

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-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 154 [Substances - Toxic and/or Corrosive (Non-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 if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the 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. /Poisons A and B/|/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 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 0.9% saline (NS) 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 ... . /Poisons A and B/|/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 ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /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. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/SIGNS AND SYMPTOMS/ Several human incident reports concerning DBNPA are on file with the /EPA/. These include eye, throat, & respiratory irritation, runny nose, & headache. Generally the effects arose with spills or misuse.|/GENOTOXICITY/ Samples of proliferating cultured human lymphocytes were exposed to C-103 (2,2-Dibromo-3- Nitrilopropionamide, DBNPG, lot 23/1817, 98% stated purity) with and without metabolic activation (S-9 fraction of Aroclor-1254 induced rat liver homogenates) for 2 hours, incubated for 22 or 46 hours, arrested in metaphase with colchicine, fixed, stained and microscopically examined for chromosome aberrations. 100 cells were evaluated per sample with two samples per treatment. Treatment levels without S-9 were 0, 25, 37.5 and 50 ug/mL (22 hour incubation) and 0 and 37.5 ug/mL (46 hour incubation) and with S-9 were 0, 5, 25, and 50 ug/mL (22 hour incubation) and 0 and 37.5 ug/mL (46 hour incubation). Positive controls were adequate. No treatment related effects on chromosome aberrations were reported.

2,2-dibromo-3-nitrilopropionamide

The National Pesticide Information Retrieval System (NPIRS) identifies 16 companies with active labels for products containing the chemical 2,2-dibromo-3-nitrilopropionamide. To view the complete list of companies, product names and percent 2,2-dibromo-3-nitrilopropionamide in formulated products click the following url and enter the CAS Registry number in the Active Ingredient field.|DBNPA 100 Powder (Dow Chemical Company, The): Active ingredient: 2,2-dibromo-3-nitrilopropionamide 97.6%.|Antimicrobial 7287 (Dow Chemical Company, The): Active ingredient: 2,2-dibromo-3-nitrilopropionamide 20.0%.|Dow Antimicrobial 8536 (Dow Chemical Company, The): Active ingredient: 2,2-dibromo-3-nitrilopropionamide 5.0%.|For more Formulations/Preparations (Complete) data for 2,2-DIBROMO-3-NITRILOPROPIONAMIDE (29 total), please visit the HSDB record page.

Acetamide, 2,2-dibromo-2-cyano-: ACTIVE