2-Brom-2-(brommethyl)pentandi-nitril

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

Use water spray, powder, foam, carbon dioxide.

Fresh air, rest.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

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

Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .

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.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

/The objective of this study was/ to determine whether there exists evidence for synergy between contact allergens during the induction phase of skin sensitization using the mouse local lymph node assay (LLNA) as a model system. Proliferative responses in draining lymph nodes were assessed with increasing concentrations of 1,4-phenylenediamine (PPD), methyldibromo glutaronitrile (MDBGN), and a combination of PPD and MDBGN. Data from each of two independent experiments show that lymph node cell proliferation associated with combined exposure to PPD and MDBGN was, in general, only modestly increased relative to that predicted from a simple summation of their individual responses. Although the increase in response is very modest, it does imply a relationship between this combination of sensitizers that may not be simply additive in terms of their ability to stimulate proliferative responses in draining lymph nodes...

The present study was undertaken to evaluate the combined effect of the preservative methyldibromo glutaronitrile (MDBGN) and sodium lauryl sulfate (SLS) on the elicitation response of allergic contact dermatitis. 20 volunteers with contact allergy to MDBGN were patch tested with 5 concentrations (10, 50, 100, 500 and 1000 p.p.m.) of MDBGN alone and in combination with 0.25% SLS on the upper arms for 24 hr. Skin reactions were evaluated by clinical scoring, and data were evaluated by logistic dose-response models. Additionally, evaluation of skin reactions was performed by measurement of transepidermal water loss (TEWL) and skin colour. Measurements were obtained at baseline and at D3 and D7. As evaluated by clinical assessment, allergic reactions to MDBGN were elicited at lower concentrations when applied in combination with SLS than when applied alone. The response was augmented by a factor of 6.4. An increased response to combined exposure to SLS and MDBGN as compared with MDBGN alone was confirmed by TEWL and colour measurements. Effects of exposure time and concentration of the detergent are discussed. In conclusion, an augmented response was found after concurrent application of MDBGN and SLS. The response was augmented by a factor of 6.4, with confidence limits of 2.8-14.6 (P < 0.0001). This result is important in relation to the determination of threshold values and the risk assessment of contact allergens in consumer and industrial products, where allergens are often present in combination with surfactants.

LD50; Species: Anas platyrhynchos (Mallard duck) 14 days old, oral 1038 mg/kg/14 days

LC50; Species: Anas platyrhynchos (Mallard duck) 14 days old, dietary >10000 ppm for 8 days

LC50; Species: Colinus virginianus (Northern bobwhite) 14 days old, dietary 4042 ppm for 8 days

LC50; Species: Americamysis bahia (Opossum shrimp); Conditions: flow through; Concentration: 2.7 ppm for 96 hr (95% confidence interval: 2.5-3.2 ppm) /formulated product/

For more Ecotoxicity Values (Complete) data for 1,2-DIBROMO-2,4-DICYANOBUTANE (14 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 528 to 33.4(2) indicate that 1,2-dibromo-2,4-dicyanobutane is expected to have moderate to very high mobility in soil(SRC). Volatilization of 1,2-dibromo-2,4-dicyanobutane from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.3X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 5.025X10-5 mm Hg(2), and water solubility, 2.12X10+3 mg/L(2). 1,2-Dibromo-2,4-dicyanobutane is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). Biodegradation data were not available(SRC, 2011).

AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 528 to 33.4(2) indicate that 1,2-dibromo-2,4-dicyanobutane 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 8.3X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 5.025X10-5 mm Hg(2), and water solubility, 2.12X10+3 mg/L(2). According to a classification scheme(4), an estimated BCF of five(SRC), from an estimated log Kow of 1.63(5) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2011).

AQUATIC FATE: Radio-labeled 1,2-dibromo-2,4-dicyanobutane at an initial concentration of 10 ug/g exhibited a half-life of 0.874 days in flooded sandy loam soil; degradates included 2-methyleneglutaronitrile and (E) and (Z) isomers of 1-bromo-2,4-dicyano-1-butene. Degradation appears to be controlled by alkaline hydrolysis and microbially-mediated processes(1).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,2-dibromo-2,4-dicyanobutane, which has a vapor pressure of 5.025X10-5 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,2-dibromo-2,4-dicyanobutane 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 18 days(SRC), calculated from its rate constant of 5.9X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 1,2-Dibromo-2,4-dicyanobutane does no contain chromophores that absorb at wavelengths >290 nm(4), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Based on the available data, the CIR Expert Panel concludes Methyldibromo Glutaronitrile to be safe as used in rinse off products, and safe up to 0.025% in leave on products.

Safe for use in cosmetics, with qualifications

Redness.

Redness. Pain.

Abdominal pain.

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: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=35691-65-7]

At concentrations of 0.1 to 1.0 ug/mL, 1,2-dibromo-2,4-dicyanobutane exhibited Koc values of 528 in sand, 87.8 in sandy loam soil, 72.9 in clay loam, and 33.4 in silt loam soil, corresponding to Freundlich coefficients of 0.264, 0.351, 0.474, and 0.701, respectively(1). According to a classification scheme(2), this Koc range suggests that 1,2-dibromo-2,4-dicyanobutane is expected to have moderate to very high mobility in soil.

/HUMAN EXPOSURE STUDIES/ A 2% dilution of the commercial solution containing 20% Methyldibromo Glutaronitrile in phenoxyethanol was applied in a single 24 hr occlusive patch to the inner forearm of 30 panelists. Observations made at the time of patch removal and at 48 hr and 72 hr after initial exposure revealed no reactions.

/HUMAN EXPOSURE STUDIES/ ... From January 1993 until July 1994, all consecutive patients attending for routine patch testing were also tested with 1,2-dibromo-2,4-dicyanobutane (0.1% petrolatum): one of 281 (0.3%), nine of 281 (3.2%) and six of 247 (2.4%) were found to be positive in the first and second halves of 1993 and the first half of 1994, respectively. In at least 12 of 16 patients this allergy was responsible for their presenting complaint (perianal and facial dermatitis).

/HUMAN EXPOSURE STUDIES/ ... Seven presensitized individuals (37%) developed allergic contact dermatitis from the soap containing MDBGN. The mean dose of MDBGN per application was 2.2 ug/ sq cm and the reactions appeared between days 6 and 34. ... The difference in reactivity between test subjects and controls was significant (one-sided Fisher's exact test, P = 0.04). Patch test threshold values ranged from < 0.001% to 0.2% MDBGN in ethanol/water.

/HUMAN EXPOSURE STUDIES/ ... A study group of 1,307 patients (Group 1) suspected of having allergic contact dermatitis was given patch tests using a standard series. Patch tests with Euxyl-K-400, its components methyldibromoglutaronitrile and phenoxyethanol (122996), and imidazolidinyl were performed on 1,109 patients (Group 2). Allergic reactions to Euxyl-K-400 were seen in 24 subjects (2.4%), all of whom also exhibited positive reactions to methyldibromoglutaronitrile. ... Of the chemicals in the supplementary series, allergic reactions were produced in 2.4% of the subjects by Euxyl-K-400 and methyldibromoglutaronitrile.

For more Human Toxicity Excerpts (Complete) data for 1,2-DIBROMO-2,4-DICYANOBUTANE (31 total), please visit the HSDB record page.

1,2-Dibromo-2,4-dicyanobutane's production may result in its release to the environment through various waste streams; its use as a microbiocide/microbiostat against slime-forming bacteria and fungi(1) for latex paints, adhesives, latex emulsions, dispersed pigments, joint cements, and metal working fluids(2) will result in its direct release to the environment(SRC).

1,2-Dibromo-2,4-dicyanobutane is an indirect food additive for use only as a component of adhesives. Limit: for use as a preservative only.

(a) Slimicides may be safely used in the manufacture of paper and paperboard that contact food, in accordance with the following prescribed conditions: (1) Slimicides are used as antimicrobial agents to control slime in the manufacture of paper and paperboard. (2) Subject to any prescribed limitations, slimicides are prepared from one or more of the slime-control substances named in paragraph (c) of this section to which may be added optional adjuvant substances as provided for under paragraph (d) of this section. (3) Slimicides are added to the process water used in the production of paper or paperboard, and the quantity added shall not exceed the amount necessary to accomplish the intended technical effect. (b) To insure safe usage, the label or labeling of slimicides shall bear adequate directions for use. c) Slime-control substances permitted for use in the preparation of slimicides include substances subject to prior sanction or approval for such use and the following: 1,2-Dibromo-2,4-dicyanobutane; Limitation: At a maximum level of 0.005% of dry weight fiber.

Based on the reviews of the generic data for the active ingredient dibromodicyanobutane, the Agency has sufficient information on the health effects of dibromodicyanobutane and on its potential for causing adverse effects in fish, wildlife and the environment. The Agency has determined that dibromodicyanobutane products, labeled and used as specified in this Reregistration Eligibility Decision, will not pose unreasonable risks or adverse effects to humans or the environment. Therefore, the Agency concludes that products containing dibromodicyanobutane for all uses are eligible for reregistration.

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. 1-Bromo-1-(bromomethyl)-1,3-propanedicarbonitrile is found on List B. Case No: 2780; Pesticide type: fungicide, herbicide, antimicrobial; Case Status: RED Approved 6/96; 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): 1-Bromo-1-(bromomethyl)-1,3-propanedicarbonitrile; Data Call-in (DCI) Date(s): 6/14/91; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) for the case/AI.

CIR ingredient: Methyldibromo Glutaronitrile

Euxyl K-400 is a biocide used in cosmetics, cleaning solutions, glues, paints, and metalworking fluids. Sensitization reported in masseurs, a beautician, an offset printer, machinists, and a hospital cleaner; [Kanerva, p. 1795]

Metal Machining [Category: Heat or Machine]

For 1-bromo-1-(bromomethyl)-1,3-propanedicarbonitrile (USEPA/OPP Pesticide Code: 111001) 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./

Preservative for latex paints, adhesives, latex emulsions, dispersed pigments, joint cements, metal working fluids.

Methyldibromo Glutaronitrile is used in cosmetic formulations as a preservative.

Data in industry submissions indicate that Methyldibromo Glutaronitrile is used in cosmetic products as a 98.5% pure substance. Impurities found are as follows: water 1.5% (maximum); bromide 0.1% (maximum); total organic impurities 100 ppm (maximum); and iron 5 ppm (maximum).

Methyldibromoglutaronitrile is prepared by reacting bromine with 2-methyleneglutaronitrile at temperatures below 30 °C.

Preparation: S.J. Lederer, DE 2164723 corresponding to US 3833731 (1972, 1974 to Merck & Co.)