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N,N-Diphenylhydrazin
Ai3-23023 · Ccris 4562 · Brn 0957349 · hydrozobenzene · Einecs 208-483-1 · 1,1-diphenyl-hydrazin · 1,1-Diphenylhydrazine · hydrazine,1,1-diphenyl
Identifikatoren & physikalische Daten
| CAS No. | 530-50-7 |
|---|---|
| Summenformel | C12H12N2 |
| Durchschnittliche Molmasse | 184,24 g/mol |
| Monoisotopische Masse | 184,10004838 g/mol |
| SMILES | NN(c1ccccc1)c1ccccc1 |
| InChIKey | YHYKLKNNBYLTQY-UHFFFAOYSA-N |
| PubChem CID | 10739 |
| ChEMBL | CHEMBL3301770 |
| EC No. | 208-483-1 |
| DTXSID | DTXSID3043869 |
| Lokaler Name | N,N-Diphenylhydrazin |
Chemische & physikalische Eigenschaften
| XLogP | 2,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 29,3 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 14 |
| Formalladung | 0 |
| Komplexität | 140 |
| Stoffklassen | Nitrogen Compounds -> Hydrazines |
| SpringerMaterials Properties | 15N nuclear magnetic resonance spectrum |
| LogP (Verteilungskoeffizient) | log Kow = 2.80 |
| Dichte | 1.190 at 16 °C/4 °C1,12 g/cm3 |
| Color/Form | Yellow crystals |
| Löslichkeit | SOL IN CONCN SULFURIC ACIDSLIGHTLY SOL IN WATERVery soluble in benzene, ether, ethanol, and chloroform. |
| Siedepunkt | 220 °C at 40 mm Hg308.2°C (rough estimate) |
| Schmelzpunkt | 34.5 °Calso stated as 44 °C50.5°C |
| Dampfdruck | 0.00049 [mmHg]4.9X10-4 mm Hg at 25 °C |
| Heat of Vaporization | 15,940.4 gcal/gmole |
| Henry-Konstante | Henry's Law constant: 4.1X10-8 atm-cu m/mol at 25 °C /Estimated/2.4×102 mol/(m3Pa) at 25℃, HSDB (2015) |
| Physical Description | Yellow solid[Merck Index] Liquid[MSDSonline] |
| Brechungsindex | 1.6266 (estimate) |
| pKa (Säurekonstante) | 3.34±0.10(Predicted) |
| Aggregatzustand | powder to lump to clear liquid |
| Farbe | White or Colorles to Yellow to Orange |
| Merck | 14,3325 |
| InChI | 1S/C12H12N2/c13-14(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H,13H2 |
| InChIKey | YHYKLKNNBYLTQY-UHFFFAOYSA-N |
| SMILES | NN(c1ccccc1)c2ccccc2 |
| CAS Datenbank | 530-50-7(CAS DataBase Reference) |
| EPA chemische Informationen | 1,1-Diphenylhydrazine (530-50-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P321, P330, P332+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Gefahrenübersicht | Emergency treatment: HydrazinesHydrazines can cause severe eye damage. They can cause seizures, liver injury, hemolysis, and delayed pulmonary edema. [HSDB] May cause irritation[MSDSonline] See Hydrazine. See 1,1-Diphenylhydrazine hydrochloride. |
| TSCA-Anforderungen | Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Hydrazine, 1,1-diphenyl- is included on this list. |
| Clean Water Act Anforderungen | For the maximum protection of human health from the potential carcinogenic effects of exposure to diphenylhydrazine through ingestion of contaminated water and contaminated aquatic organisms ... the levels which may result in incremented increase of cancer risk over the lifetime are estimated at 1x10-5, 1x10-6, and 1x10-7 the corresponding criteria are: 422 ng/l, 42 ng/l, and 4.2 ng/l respectively. If these estimates are made for consumption of aquatic organisms only, excluding consumption of water, the levels are 5.6 ug/l, 0.56 ug/l, and 0.056 ug/l, respectively. /Diphenylhydrazine/Toxic pollutant designated pursuant to section 307(a)(1) of the Federal Water Pollution Control Act and is subject to effluent limitations. /Diphenylhydrazine/ |
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| Explosive Limits and Potential | Interaction, in presence of diluent below 0 °C, with 1,2-diphenylhydrazine caused separation of explosive solids. |
| Skin, Eye, and Respiratory Irritations | 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/ |
| Lagerbedingungen | 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/ |
| Entsorgungsverfahren | 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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations.The following wastewater treatment technology has been investigated for 1,1-diphenylhydrazine: Activated carbon. |
| Preventive Measures | 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. |
| Personal Protective Equipment (PPE) | ...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 leakssuch as full face shields, goggles, and full body protection clothing, including gloves and boots. /Hydrazine/ |
| Umweltverhalten | 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). |
| Lebensmitteluntersuchungswerte | 1,1-Diphenylhydrazine was identified as a volatile constituent, at unreported concentrations, in 1 of 3 apricot samples(1). |
| Unerwünschte Wirkungen | Neurotoxin - Other CNS neurotoxin |
| Medical Surveillance | Placement medical examinations shall include at least: comprehensive medical and work historiescomprehensive physical examinationspecific clinical tests including complete and differential blood countliver function tests including serum glutamic pyruvic transaminase (SGPT), urinalysis including specific gravity, glucose, protein, and microscopic examination, and a 14 x 17 inch posteroanterior chest roentenograma judgement of the worker's ability to use positive pressure respiratorsand urobilinogen and serum bilirubin tests shall be considered by the responsible physician. Periodic examinations shall be made available at least annually to those working with hydrazines. /Hydrazines/ |
| Soil Adsorption/Mobility | 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). |
| Natural Pollution Sources | 1,1-Dimethylhydrazine was identified in apricot volatiles(1). |
| Human Toxicity Excerpts | /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. |
| Artificial Pollution Sources | 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). |
| Environmental Biodegradation | In a static biodegradation screening test using an activated sludge inoculum, 1,1,-diphenylhydrazine (at an initial concentration of 2 ppm) underwent 46-100% loss during a 7 day test period(1). |
| Environmental Bioconcentration | 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). |
| Volatilization from Water/Soil | 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). |
| Non-Human Toxicity Excerpts | /LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ ...Daily doses of 0.5 mg unsymmetrical 1,1-diphenylhydrazine in water 5 days/wk for 40 weeks /given by gavage/ to a group of 25 female Swiss mice. Lung tumors were found in 1/8 mice (0.25 tumors/mouse) dying between 40 and 45 weeks and in 4/9 mice (2.6 tumors/mouse) dying between 50 and 60 weeks. In 85 controls, 2/37 mice (0.05 tumors/mouse) and 6/42 mice (0.2 tumors/mouse) developed lung tumors within the same periods./LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ ...A series of 55 compounds /including 1,1-diphenylhydrazine,/ was administered to timed-pregnant ICR/SIM mice during organogenesis. ...A single dose level, at or near the level producing overt maternal toxicity in preliminary range-finding studies, was administered by gavage on gestation days 8-12. Females were allowed to deliverlitter size and weight on the day of birth and 2 days postpartum were recorded, and stillborns were examined. Dams that had not given birth by gestation days 21 or 22 were killed and their uteri were examined. /No significant (P<0.05) change in maternal body weight between control and treated mice was found. At the treatment concentration (525 mg/kg bw/day), 2 mice died. There were no significant (P<0.05) effects on progeny counts or number of resorptions reported.//GENOTOXICITY/ After ozonization, 1,1-diphenylhydrazine was weakly mutagenic in Salmonella TA1535 and TA100./GENOTOXICITY/ The Friedman-Staub assay was used to study the inhibition of testicular DNA synthesis by 100 compounds. Male mice were administered compound ip or orally. Of the 100 tested substances approximately 86% of the known carcinogens and/or mutagens show up positively in this test, whereas only 10% of noncarcinogenic and nonmutagenic compounds depress DNA synthetic activity significantly. Hydrazine and most of its derivatives inhibited DNA synthesis. 28% inhibition of thymidine incorportion into testicular DNA occurred with n,n-diphenylhydrazine (100 mg/kg, ip). |
| Wassergefährdungsklasse (WGK) | WGK 3 |
| Zollcode | 2928009090 |
| RTECS-Nr. | MV3450000 |
| R-Sätze (R) | 36/37/38-22 |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 26-36/37/39 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 530-50-7(Hazardous Substances Data) |
| Gefahrenklasse | Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1 |
Anwendungen & Verwendung
Beschreibung
Diphenylhydrazine is a man-made chemical that occurs in two isomeric forms: 1,1-diphenylhydrazine and 1,2-diphenylhdrazine. Diphenylhydrazine is produced by the reduction of nitrobenzene. Little or no information is available for 1,1-diphenylhydrazine. Most toxicological and use data pertain to 1,2-diphenylhydrazine.
Verwenden
Previously, 1,2-diphenylhydrazine was used for producing benzidine that was used in the synthesis of benzidine-based dyes. However, these dyes are no longer produced in the United States. The primary use of 1,2-diphenylhydrazine is in the production of the anti-inflammatory agent phenylbutazone and sulfinpyrazone, a uricosuric agent.