N,N-Diphenylhydrazine

184.242

184.24

208-483-1

D133SQ5HMA

DTXSID3043869

Yellow crystals

2928000090

29.3

2.80

1.190 g/cm³ @ Temp: 16 °C

50.5 °C

220 °C @ Press: 40 Torr

180.5±7.2 °C

1.656

Very soluble in benzene, ether, ethanol, and chloroform.

All hydrazines should be stored at temperatures well below their boiling points. Hydrazines that are ignitable shall be stored in electrically grounded containers and isolated from ignition sources and oxidants. All containers of hydrazines shall be kept tightly closed when not in use and stored in a cool ventilated room or sheltered outside space. In the containers, a blanket of nitrogen or other inert gas should be placed over the hydrazines. /Hydrazines/

4.9X10-4 mm Hg at 25 deg C

Interaction, in presence of diluent below 0 deg C, with 1,2-diphenylhydrazine caused separation of explosive solids.

Henry's Law constant: 4.1X10-8 atm-cu m/mol at 25 °C /Estimated/

pKa = 3.7 /Estimated/

Heat of fusion: 22.89 cal/g|White to grayish white crystalline powder. Slightly soluble in water, freely soluble in alcohol. /1,1-Diphenylhydrazine hydrochloride/|Hydroxyl radical reaction rate constant: 2.5X10-11 cu cm/molec-sec at 25 °C /Estimated/

15,940.4 gcal/gmole

R36/37/38

S26-S36/37/39

MV3450000

Xn

P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, 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.|The following wastewater treatment technology has been investigated for 1,1-diphenylhydrazine: Activated carbon.

...Vinyl coated hand protection, natural or reclaimed rubber protection, rubber aprons, and plastic eye and face protection... used when working with small quantities. Where possibility of gross splashing exists, full protective clothing made of rubber, neoprene or vinyl-coated materials should be worn. For respiratory protection in situations where recommended tolerance limits... exceeded, respiratory protective equipment... must be used. /Hydrazine and derivatives/|All systems or equipment containing the hydrazines shall be designed to minimize the possibility of vapor or aerosol inhalation, skin or eye contact, and spill or leaks; such as full face shields, goggles, and full body protection clothing, including gloves and boots. /Hydrazine/

Interaction, in presence of diluent below 0 °C, with 1,2-diphenylhydrazine caused separation of explosive solids.

Inhalation of salt dusts should be avoided. /Hydrazine & derivatives/|Engineering controls, such as process enclosure or local exhaust ventilation, shall be used when needed to keep concentrations of airborne hydrazines within acceptable levels. Ventilation systems shall be designed to prevent accumulation or recirculation of airborne hydrazines in the workplace environment and to remove hydrazines from the breathing zone of workers. /Hydrazine/|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.

Moderate to high concentrations of hydrazine vapors are highly irritating to the eyes, nose and respiratory system. Skin irritation is pronounced with the propellant hydrazines ... /Hydrazine and derivatives/

Biological half-lives were significantly different among the three acetylation phenotypes (analysis of variance, P < 0.05): 3.94+/-1.70 hours for slow acetylators, 2.25+/-0.37 hours for intermediate acetylators, and 1.86+/-0.67 hours for rapid acetylators. /Hydrazine/

1,1-Dimethylhydrazine was identified in apricot volatiles(1).

1,1-Diphenylhydrazine's production and use in the manufacture of 1,1-diphenylhydrazine hydrochloride, a reagent for arabinose and lactose(1), may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 790(SRC), determined from a measured log Kow of 2.8(2) and a regression-derived equation(3), indicates that 1,1-diphenylhydrazine will have low mobility in soil(SRC). Volatilization of 1,1-diphenylhydrazine from moist soil surfaces is not expected to be an important environmental fate process given an estimated Henry's Law constant of 4.1X10-8 atm-cu m/mole(SRC), calculated using a fragment constant estimation method(4). Based on limited aqueous screening study data, 1,1-diphenylhydrazine is expected to biodegrade in aerobic soils(SRC). Over a 7 day period, 46-100% biodegradation was reported for 1,1-diphenylhydrazine following inoculation with activated sludge(5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 790(SRC), determined from a measured log Kow of 2.8(2) and a regression-derived equation(3), indicates that 1,1-diphenylhydrazine is expected to adsorb to suspended solids and sediment in water(SRC). 1,1-Diphenylhydrazine is not expected to volatilize from water surfaces(SRC) based on an estimated Henry's Law constant of 4.1X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF value of 28(SRC), from a measured log Kow(2), and a regression derived equation (6) suggests that bioconcentration in aquatic organisms is low (SRC). Photolysis in sunlit surface waters may be significant since this compound absorbs light above 290 nm(7), but the rate of this reaction is not known(SRC). Based on limited aqueous screening study data, 1,1-diphenylhydrazine is expected to biodegrade in aerobic water(SRC). Over a 7 day period, 46-100% biodegradation was reported for 1,1-diphenylhydrazine following inoculation with activated sludge(8). Although no data are available for 1,1-diphenylhydrazine, hydrazines are degraded rapidly in water containing trace metals such as copper(II) or iron(III)(9).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,1-diphenylhydrazine, which has a vapor pressure of 4.9X10-4 mm Hg at 25 deg(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 1,1-diphenylhydrazine 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 about 16 hours(SRC), calculated from its rate constant of 2.5X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 1,1-diphenylhydrazine may be physically removed from the air by wet and dry deposition(SRC). 1,1-Diphenylhydrazine may undergo direct photolysis(SRC) as it absorbs UV light >290 nm(4), but the rate of this potential reaction is not known(SRC).

1,1-Diphenylhydrazine in methanol solution has been found to strongly absorb UV light in the environmentally significant range (wavelengths >290 nm)(1), suggesting that 1,1-diphenylhydrazine may be susceptible to photolysis upon exposure to sunlight(SRC). The rate constant for the vapor-phase reaction of 1,1-diphenylhydrazine with photochemically-produced hydroxyl radicals has been estimated as 2.5X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(2). This corresponds to an atmospheric half-life of about 16 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(SRC). Although no data are available for 1,1-diphenylhydrazine, hydrazines are degraded rapidly in water containing trace metals such as copper(II) or iron(III)(3).

An estimated BCF value of 28 was calculated for 1,1-diphenylhydrazine(SRC), using a measured log Kow of 2.80(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is low(SRC).

The Koc of 1,1-diphenylhydrazine is estimated as 790(SRC), using a measured log Kow of 2.80(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 1,1-diphenylhydrazine has low mobility in soil(SRC).

The Henry's Law constant for 1,1-diphenylhydrazine is estimated as 4.1X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that 1,1-diphenylhydrazine will be essentially nonvolatile from water and moist soil surfaces(2). 1,1-Diphenylhydrazine is not expected to volatilize from dry soil surfaces(SRC) based on a vapor pressure of 4.9X10-4 mm Hg at 25 °C(3).

1,1-Diphenylhydrazine was identified as a volatile constituent, at unreported concentrations, in 1 of 3 apricot samples(1).

Occupational exposure may be through inhalation and dermal contact with this compound at workplaces where 1,1-diphenylhydrazine is produced or used. (SRC)

The present study provides the first evidence for in vitro metabolic conversion of a 1,1-disubstituted hydrazine to the corresponding nitrosamine. The study shows that superoxide radical which is generated by NADPH-cytochrome reductase is involved in the oxidation of 1,1-diphenylhydrazine to N-nitrosodiphenylamine catalyzed by rat liver microsomes.|The enzyme systems in rat liver and lung responsible for the oxidative metabolism of hydrazine derivatives were studied to determine whether these enzymes, cytochrome P450 and monoamine oxidase, were responsible for metabolically activating hydrazines to carcinogenic/toxic metabolites. Cytochrome P450 preferentially oxidized the nitrogen to nitrogen bond of 1,2-disubstituted hydrazines and hydrazides, while monoamine oxidase oxidized the nitrogen to nitrogen bond of all the classes of hydrazine derivatives that were tested. Oxidation of the nitrogen to nitrogen bond led to the formation of stable azo intermediates in the case of 1,2-disubstituted hydrazines and to unstable monoazo (diazene) metabolites in the case of monosubstituted hydrazines and hydrazides. /Substituted hydrazines/|By microsomes obtained from bovine ciliary body, 1,1-diphenylhydrazine was oxidized to N-nitrosodiphenylamine in the presence of NADPH. This reaction was stimulated by riboflavin which was recognized to be an electron carrier. The oxidizing activity by microsomes was markedly inhibited by superoxide dismutase, but not by SKF 525-A or carbon monoxide. Similarly, the oxidation of 1,1-diphenylhydrazine to its corresponding nitrosamine occurred in varying degrees when the hydrazine derivative was exposed to visible light in the presence of photosensitizers such as riboflavin, flavin adenine dinucleotide, flavin mononucleotide, lumiflavin, lumichrome, NAD+, NADH, NADP+, or NADPH. The photochemical oxidation was inhibited by active oxygen-scavengers such as superoxide dismutase, L-ascorbic acid or alpha-tocopherol. The superoxide radical involved in the photochemical reaction was determined by measuring the oxidation of epinephrine to adrenochrome. The oxidation of epinephrine was well correlated to that of 1,1-diphenylhydrazine. Thus, the present study provided evidence that the superoxide radical is responsible for the oxidation of a hydrazine derivative to a corresponding nitrosamine by ocular tissue microsomes and by photosensitizers.|The first evidence for the reductive metabolism of a noncyclic nitrosamine to the corresponding hydrazine derivative in vivo and in vitro is provided. Under anaerobic conditions, N-nitrosodiphenylamine was reduced by guinea pig liver 9000 g supernatant to 1,1-diphenylhydrazine in the presence of 2-hydroxypyrimidine or to acetaldehyde diphenylhydrazone in the presence of acetaldehyde. These metabolites were identified unequivocally by comparative study with authentic samples. In addition, the study shows that such reductive reactions of the nitrosamine can be catalyzed by guinea pig and rabbit liver aldehyde oxidase in the presence of its electron donors. When the nitrosamine was given orally to acetaldehyde-treated guinea pigs, a metabolite was detected from plasma and identified as acetaldehyde diphenylhydrazone by comparison with the authentic sample.

Specific treatment for exposure consists of thorough washing of all exposed skin areas with soap and water, copious irrigation of the eyes, and prompt removal of the patient from the source of exposure. /Hydrazines/|After inhalation, observation for progressive respiratory distress is necessary. Chest X-ray and arterial blood gases should be monitored. Administration of oxygen, intubation, and assisted ventilation may become necessary. Pneumonia and bronchitis need to be excluded. /Hydrazines/|Pyridoxine may be antidotal. ...Seizures should be controlled with diazepam, phenytoin, or phenobarbital. Blood sugar levels should be monitored for severe hypoglycemia, which may appear with or without preceding significant hyperglycemia. The patient should be observed for evidence of intravascular hemolysis, methemoglobinemia, and consequent deterioration of renal function. Patients who are symptomatic or who demonstrate a methemoglobin level greater than 30 per cent should be treated with methylene blue 1 to 2 mg per kg slowly IV every 4 hours as needed. Improvement is dramatic if diagnosis is correct. Liver function should be monitored because hydrazines are known hepatotoxins. /Hydrazines/|Elimination is enhanced by forced diuresis and acidification of the urine. Hemodialysis and peritoneal dialysis should be effective, but insufficient human data exist on the use of these modalities. Treatment is otherwise symptomatic and supportive. /Hydrazines/|For more Antidote and Emergency Treatment (Complete) data for 1,1-DIPHENYLHYDRAZINE (6 total), please visit the HSDB record page.

/SIGNS AND SYMPTOMS/ Diphenylhydrazine and diisopropylhydrazine are active hemolysins. /Diphenylhydrazine/|/SIGNS AND SYMPTOMS/ ...Workers experienced respiratory distress and later, nausea and vomiting after accidental exposure to .../1,1-diphenylhydrazine/ vapor. Others have observed that acute accidental exposures will produce nose and throat irritation, mild conjunctivitis, and nausea.

1,1-diphenylhydrazine

Hydrazine, 1,1-diphenyl-, hydrochloride (1:1): ACTIVE