Dimethylhydantoin

128.12900

128.13

201-051-3

34032MQ9RO

8652

DTXSID5021754

White, crystalline solid|Prisms from dilute alcohol

2933990090

58.20000

-0.3

Liquid; OtherSolid

1.261 g/cm³

178 °C

Sublimes

193ºC

1.449

H2O: 0.1 g/mL hot, clear | soluble ;Very soluble in ethanol, ether, acetone, benzene, chloroform; soluble in DMSO

Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

2.8X10-6 mm Hg at 25 deg C (est)

LD50 oral in rabbit: 12660mg/kg

Henry's Law constant = 2.77X10-9 atm-cu m/mol at 25 °C (est)

pKa = 9.19

Hydroxyl radical reaction rate constant = 3.06X10-12 cu cm/molec-sec at 25 °C (est)

2

R36/37/38

S24/25

MU0977000

Xi

Stable under normal temperatures and pressures.

P264, P270, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P332+P313, P337+P313, P362, P501

H302

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.

|Warning|H302 (99.44%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P332+P313, P337+P313, P362, and P501|Aggregated GHS information provided by 479 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

5,5-Dimethylhydantoin was detected at a concentration of 456 mg/L in wastewater from a coal gasification plant in North Dakota, processing Indian Head lignite(1). Levels in four samples of coal-gasification condensate waters at this plant were 660, 150, 230, and 40 mg/L collected in June 1998, June 1981, September 1981, and April 1982, respectively, and immediately acidified to pH 2(2). The concentrations in samples where the pH was not adjusted and were allowed to stand for 30 days actually increased to 1,720, 300, 400, and 165 mg/L, respectively(2).

A case of allergic contact dermititis secondary to photographic print coating liquid is described ... . Patch test reactions to the mixture were positive, but negative to the individual components which included dimethylhydantoin formaldehyde resin, the logical allergen. ... In this patient, the combination of components was necessary to yield a sensitivity reaction. ... Dermatitis secondary to this product has not been previously reported.

LD50 Rabbit dermal (male & female) >3000 mg/kg|LC50 Rat inhalation, male & female, >14.68 mg/L/1 hr /Dantoin DMH, purity not stated/|LD50 Rat oral (male & female) >5000 mg/kg

/AQUATIC SPECIES/ In a chronic Flow through test of Pimephales promelas (fathead minnow) with nominal concentrations (ppm): 0, 7.5, 15, 30, 60 and 120 ppm and measured concentrations (ppm): 0, 6.8, 14, 29, 55 and 116 ppm. There were no treatment-related effects upon mean hatching success or on the survival of fathead minnow larvae during the 28-day post hatch exposure period at any concentration of 5,5-dimethylhydantoin (DMH) tested. Based upon the hatching success and survival data, the NOEC was 116 ppm and the LOEC was >116 ppm. The mean length of the fish in the 0, 6.8, 14, 29, 55 and 116 ppm groups at study termination were 18.3, 17.8, 18.7, 17.8, 17.6 and 17.9 cm, respectively. The mean wet weight of the fish in the 0, 6.8, 14, 29, 55 and 116 ppm groups at study termination were 66.5, 67.8, 72.4, 65.2, 62.0 and 65.5 mg, respectively, and the mean dry weight of the fish in the 0, 6.8, 14, 29, 55 and 116 ppm groups at study termination were 14.1, 14.2, 14.2, 12.5, 11.4 and 11.8 mg, respectively. There were no statistically significant differences in the mean total length or mean wet weight of fish exposed to any concentration of DMH. However, fish dry weights were significantly decreased in the 29, 55 and 116 ppm treatment groups when compared to the control group. This reduction appeared to be treatment related. Conclusions: Based on measurements of length, wet weight and dry weight of fathead minnows, the NOEC and LOEC of DMH were 14 and 29 ppm, respectively.|/AQUATIC SPECIES/ In a 21-day study of Daphnia magna using fresh water in a flow-through system, at nominal concentrations (ppm): 0, 15.6, 25.9, 43.2, 72.0 and 120 ppm and measured concentrations (ppm): 0, 15.7, 25.3, 42.2, 70.9 and 116 ppm, Mortality of the daphnids in the control group was 9% (2 of 22). Mortality of the daphnids in the 15.7, 25.3, 42.2 and 70.9 ppm groups ranged from 5 to 14% (1 to 3 of 22) and was considered similar to that of the control group. Mortality of the daphnids in the 116 ppm group was 55% (12 of 22) and was statistically different from the control group. Based on survival and clinical observations data, the NOEC for DMH was 70.9 ppm and the LOEC for DMH was 116 ppm. Mean neonatal production in the 0, 15.7, 25.3, 42.2, 70.9 and 116 ppm groups was 69, 104, 80, 85, 94 and 58 neonates per daphnid, respectively. Although the number of neonates per daphnid in the 116 ppm group was lower than any other treated group, it was not statistically different from the control group and therefore was not considered to be treatment-related. When compared to the control group, there were no significant decreases in the length or dry weight of daphnids at any of the concentrations of DMH tested. Conclusions: Based on neonate production and measurements of length and dry weight the NOEC for DMH was 116 ppm and the LOEC for DMH was >116 ppm.

5,5-Dimethylhydantoin's production and use as a chemical intermediate(1) may result in its release to the environment through various waste streams(SRC). Its use as an inert ingredient in some pesticide formulations(2) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 13(SRC), determined from a log Kow of -0.48(2) and a regression-derived equation(3), indicates that 5,5-dimethylhydantoin is expected to have very high mobility in soil(SRC). Volatilization of 5,5-dimethylhydantoin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.8X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(4). 5,5-Dimethylhydantoin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.8X10-6 mm Hg(SRC), determined from a fragment constant method(5). Biodegradation half-lives range from 194 days using static tests and sewage inoculum to 5 days using a SCAS test and activated sludge(6); these diverse test conditions and results indicate that biodegradation may be a slow environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 13(SRC), determined from a log Kow of -0.48(2) and a regression-derived equation(3), indicates that 5,5-dimethylhydantoin 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 2.8X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation half-lives range from 194 days using static tests and sewage inoculum to 5 days using a SCAS test and activated sludge(7); these diverse test conditions and results indicate that biodegradation may be a slow environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 5,5-dimethylhydantoin, which has an estimated vapor pressure of 2.8X10-6 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 5,5-dimethylhydantoin 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 5 days(SRC), calculated from its rate constant of 3.1X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 5,5-dimethylhydantoin may be removed from the air by wet or dry deposition(SRC). 5,5-Dimethylhydantoin does not absorb light at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of 5,5-dimethylhydantoin with photochemically-produced hydroxyl radicals has been estimated as 3.1X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 5,5-Dimethylhydantoin is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2); a hydrolysis half-life of 1,000 days at pH 7 has been reported(3). 5,5-Dimethylhydantoin does not absorb light at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 3 was calculated in fish for 5,5-dimethylhydantoin(SRC), using a log Kow of -0.48(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 Koc of 5,5-dimethylhydantoin is estimated as 13(SRC), using a log Kow of -0.48(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 5,5-dimethylhydantoin is expected to have very high mobility in soil.

The Henry's Law constant for 5,5-dimethylhydantoin is estimated as 2.8X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 5,5-dimethylhydantoin is expected to be essentially nonvolatile from water surfaces(2). 5,5-Dimethylhydantoin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.8X10-6 mm Hg(SRC), determined from a fragment constant method(3).

Occupational exposure to 5,5-dimethylhydantoin may occur through inhalation and dermal contact with this compound at workplaces where 5,5-dimethylhydantoin is produced or used. (SRC)

CD Rats, /male and female,/ were administered single oral doses of dimethylhydantoin-14C (DMH-14C) at either 100 (high dose) or 20 mg/kg (low dose). The disposition of the 14C was followed for a seven-day period. ... Urine and feces were collected and measured for the amount of 14C at the following periods: 0 - 8 hours, 8 - 16 hours, 15 - 24 hours, 24 - 32 hours, 32 - 48 hours, then 24 hour collections on Study Days 2 through 5. All animals were killed on Study Day 6. The following tissues were removed and immediately frozen: heart, liver, kidneys, spleen, abdominal fat, right leg muscle, leg bone, gonads and brain tissue. These tissues were measured for amount of 14C. The interior of the cage was washed with methanol and 14C was measured in the wash liquid. ... The average recovery of 14C from the rats was 95%. The compound was absorbed rapidly and was eliminated primarily in the urine with only minor metabolic conversion. ... The average amount eliminated in the urine was 91% of the dose. The elimination also was rapid, as 88% was eliminated in the first 24 hours after dosing. ... In the case of rats receiving the high dose, low levels of 14C were detected in kidney and bone tissues; however all measurements were not significant. ...

CD Rats, /male and female,/ were administered single oral doses of dimethylhydantoin-14C (DMH-14C) at either 100 (high dose) or 20 mg/kg (low dose). ... The parent DMH-14C was the only major radioactive component found in urine by thin layer chromatographic analysis. One minor metabolite was detected, which amounted to 2.5% of the urinary 14C. ...

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/|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/|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 /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's 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/ Central nervous system depressant

5,5-dimethylhydantoin

Reagent grade: 97%

All other basic organic chemical manufacturing|2,4-Imidazolidinedione, 5,5-dimethyl-: ACTIVE|...derivatives have been patented as color photographic couplers ... /Some/ 5,5-disubstituted hydantoins ... are used in medicine /5,5-Domethylhydantoins/|Several hydantoin derivatives are found in various consumer items; hair sprays, cosmetics, acne medications, and photographic film. Several amino acids are produced commercially from hydantoins. /Hydantoins/|Hydantoin epoxy-resins are used in ... industry when weather resistance, high temperature resistance, good color, or high filler loading is required. /Hydantoins/

QUANTITATIVE ASSESSMENT BY GAS-LIQUID OR THIN-LAYER CHROMATOGRAPHY ON CROPS & SOIL.|MICROCHEMICAL (DILLE-KOPPANYL & ZWIKKER) TESTS FOR HYDANTOINS & BARBITURATE-HYDANTOIN MIXTURES.|A ... combination of analytical techniques was employed to identify polar organic cmpd, including the first report of hydantoins, in condensate waters from a slagging fixed-bed coal-gasification process. The analytical technique consists of high-performance liquid chromatography (HPLC) separation and gas chromatography-mass spectrometry (GC-MS) analysis of HPLC fractions. Entrainer distillation was used to concentrate the HPLC fractions and remove water before GC-MS analysis. Analyses of four samples accounted for 69-84% of the measured chemical oxygen demand (COD), including 1-6% of the COD as dimethylhydantoin. This cmpd is highly polar and difficult to remove by solvent extraction.

Cosmetics -> Hair conditioning; Viscosity controlling