기본 정보
- 표준 SMILES
c1ccc(NNc2ccccc2)cc1- InChIKey
YBQZXXMEJHZYMB-UHFFFAOYSA-N- 분자식
- C12H12N2
- 평균 분자량
- 184.24 g/mol
- 단동위원소 질량
- 184.10004838
개요
1,2-Diphenylhydrazine is a white solid. There is no information on what it smells like or whether it will burn. It does not dissolve easily in water, but when placed in water, it rapidly breaks down into other chemicals. These include the toxic chemicals benzidine and azobenzene. It does not evaporate easily but may be released to air when attached to dust particles. 1,2-Diphenylhydrazine is a man-made chemical that was used in the past to make benzidine which was used to make various fabric dyes. Benzidine dyes are no longer used in the United States, but may still be used in other countries. The only current use of 1,2-diphenylhydrazine in the United States is in the production of medicines to treat inflammation and a type of arthritis.
이름 및 식별자
- 우선 이름
- Hydrazobenzene
- IUPAC
- 1,2-diphenylhydrazine
- 현지명
- 1,2-디페닐히드라진
- 영어명
- 1,2-Diphenylhydrazine
- 분자식
- C12H12N2
- 분자량
- 184.24
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
122-66-7、38622-18-3- PubChem CID
- 31222
- DTXSID
DTXSID7020710- ChEMBL
CHEMBL558459- UNII
- 1G3CS09TUK
- EC Number
- 204-563-5
- Nikkaji
- J5.359G
물성
구조 계산 물성
- XLogP
- 2.9
- 극성 표면적
- 24.1 Ų
- 수소 결합 공여자 수
- 2
- 수소 결합 수용자 수
- 2
- 회전 가능 결합 수
- 3
- 무거운 원자 수
- 14
- 형식 전하
- 0
- 복잡도
- 128
실험 및 물리화학적 성질
Chemical Classes
Hazardous Air Pollutants (HAPs)
Nitrogen Compounds -> Hydrazines
Carcinogens
Semi-Volatile Organic Compound (SVOC)
LogP
log Kow= 2.94
2.94
2.94
Density
1.158 at 61 °F (NTP, 1992) - Denser than water; will sink
1.158 at 16 °C/4 °C
1.16 g/cm³
1.158 @ 16°C
Color/Form
Tablets from alcohol and ether
Colorless crystals
Solubility
less than 0.1 mg/mL at 64 °F (NTP, 1992)
Slightly sol in benzene, deuterated dimethyl sulfoxide; insol in acetic acid; very soluble in ethanol
In water, 221 mg/L at 25 °C
Solubility in water, g/100ml at 20 °C:
Boiling Point
Decomposes (NTP, 1992)
293 °C at 760 mm Hg
293 °C @760 [mm Hg]
Decomposition
When heated to decomposition it emits toxic fumes of /nitrogen oxides/.
Decomposes, at its melting point, into azobenzene and aniline.
125-131 °C
Melting Point
268 °F (NTP, 1992)
131 °C, decomposes
Decomposes at its melting point, into azobenzene and aniline.
Heat of fusion at melting point= 1.7630X10+7 J/kmol
131 °C
Vapor Pressure
0.00044 [mmHg]
4.4X10-4 mm Hg at 25 °C
물리화학적 성질
- 녹는점
- 123 · 123-126 °C(lit.)
- 끓는 점
- 308.2 °C · 308.2°C (rough estimate)
- 밀도
- 1 · 1,158 g/cm3
- 증기압
- 2.6 x · 2.6 x 10-5 mmHg at 25 °C (Mabey et al., 1982)
- 굴절률
- 1.6266 · 1.6266 (estimate)
- 저장 조건
- Refrigerator
- 용해도
- 에탄올에 용해됨(Weast, 1986).
- 산도 계수 (pKa)
- 3.02 · 3.02±0.70(Predicted)
- 물리적 상태
- solid
- 색상
- 무색~담황색~주황색 결정
- 수용성
- 25 °C에서 · 25°C에서 221mg/L(미국 EPA, 1980a)
- BRN
- 639793 · 639793
- Henry's Law Constant
- 2.1 · 2.1×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- 안정성
- 안정적인. 강한 산화제, 강산과 호환되지 않습니다.
- 주요 응용
- 청소용품화장품환경음식 및 음료개인 위생 관리
- InChI
- 1S/C12H12N2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10,13-14H
- InChIKey
- YBQZXXMEJHZYMB-UHFFFAOYSA-N
- SMILES
- N(Nc1ccccc1)c2ccccc2
- NIST
- 1 · Hydrazine, 1,2-diphenyl-(122-66-7)
- EPA
- 1 · 1,2-Diphenylhydrazine (122-66-7)
화학적 성질
yellow crystalline powder
안전 및 규제
GHS 분류
GHS Classification
Danger
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P203, P264, P270, P273, P280, P301+P317, P318, P330, P391, P405, and P501 (click each P-code to see the statement)
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P264, P270, P273, P280, P301+P317, P318, P330, P391, P405, and P501 (click each P-code to see the statement)
유해성 정보
Regulatory Information
Chemical: Hydrazine, 1,2-diphenyl-
Hazard Traits - Carcinogenicity
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Fire Hazards
Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Combustible. Gives off irritating or toxic fumes (or gases) in a fire.
Hazards Summary
1,2-Diphenylhydrazine is a white solid. There is no information on what it smells like or whether it will burn. It does not dissolve easily in water, but when placed in water, it rapidly breaks down into other chemicals. These include the toxic chemicals benzidine and azobenzene. It does not evaporate easily but may be released to air when attached to dust particles. 1,2-Diphenylhydrazine is a man-made chemical that was used in the past to make benzidine which was used to make various fabric dyes. Benzidine dyes are no longer used in the United States, but may still be used in other countries. The only current use of 1,2-diphenylhydrazine in the United States is in the production of medicines to treat inflammation and a type of arthritis.
1,2-Diphenylhydrazine was used in the past to produce benzidine-based dyes. Currently, the only use for it in the United States is in the production of anti-inflammatory drugs. Limited information is available on the health effects of 1,2-diphenylhydrazine. No information is available on the acute (short-term), chronic (long-term), reproductive, developmental, or carcinogenic effects of 1,2-diphenylhydrazine in humans. In a National Cancer Institute (NCI) study, liver tumors were observed in both sexes of rats and female mice exposed to 1,2-diphenylhydrazine in their diet. EPA has classified 1,2-diphenylhydrazine as a Group B2, probable human carcinogen.
1,2-Diphenylhydrazine oxidizes rapidly in the environment under aerobic conditions, with a half-life in water as short as 15 minutes. . . . it is possible that 1,2-diphenylhydrazine may cause methemoglobin in humans. However this would occur only if sufficient aniline were formed rapidly enough to exceed the capacity of methemoglobin reductase to reduce methemoglobin. Hepatic effects have been observed in high-dose animal experiments. [ATSDR ToxProfiles] See Phenylhydrazine.
Reactive Group
Amines, Phosphines, and Pyridines
Azo, Diazo, Azido, Hydrazine, and Azide Compounds
Special Reports
USEPA; Chemical Hazard Information Profile: Hydrazobenzene (Draft) (1981)
DHHS/ATSDR; Toxicological Profile for 1,2-Diphenylhydrazine (1990) ATSDR/TP-90/11
Bioassay of Hydrazobenzene for Possible Carcinogenicity (1978) Technical Rpt Series No. 92 DHEW Pub No. (NIH) 78-1342, U.S. Department of Health Education and Welfare, National Cancer Institute, Bethesda, MD 20014
National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. Hydrazobenzene (122-66-7) is listed as reasonably anticipated to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s097hydr.pdf]
RCRA Requirements
U109; As stipulated in 40 CFR 261.33, when hydrazine, 1,2-diphenyl-, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).
TSCA Requirements
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, 1,2-diphenyl- is included on this list.
Reactivity Profile
Toxic gases may be formed by mixing DIPHENYLHYDRAZINE with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. Flammable gases are formed by mixing materials in this group with alkali metals. Explosive combination can occur with strong oxidizing agents, metal salts, peroxides, and sulfides.
1,2-DIPHENYLHYDRAZINE is a mild reducing agent. Incompatible with strong oxidizing agents, strong acids, acid chlorides and acid anhydrides. Interaction with perchloryl fluoride in the presence of a dilutent below 32 °F has caused separation of explosive solids. Is readily oxidized by nitric acid, silver nitrate or permanganate. Is reduced under alkaline conditions (NTP, 1992).
안전 및 보호
Fire Fighting
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)
Use water spray, powder, foam, carbon dioxide.
First Aid Measures
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. Refer for medical attention .
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
Storage Conditions
PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practicable to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/
Cleanup Methods
PRECAUTIONS FOR "CARCINOGENS": A high efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes, or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/
Cleavage of hydrazine as a method of preventing environmental contamination was investigated. 1,1-Diethylhydrazine, ...Hydrazine compounds were dissolved in a solution of potassium-hydroxide or of methanol and potassium-hydroxide, followed by addition of an aluminum/nickel alloy. The reaction mixture was injected into a gas chromatography equipped with a flame ionization detector. The quantity of amine present was determined. ...Residual hydrazine could not be detected in any of the reactions after 24 hr of exposure to the reductant. Amines corresponding to the reduced hydrazine were the only products detected by gas chromatography. Yields ranged from 73 to 104%, with a detection limit of 1% of the theoretical yield. No benzidine was found from reduction of 1,2-diphenylhydrazine. /It was/ concluded that the procedures provide a reliable, efficient, one step approach to conversion of potentially carcinogenic hydrazines to innocuous products in laboratory wastes or in the environment.
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
Disposal Methods
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U109, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
1,2-Diphenylhydrazine is a potential candidate for rotary kiln incineration with a temperature range of 820 to 1600 °C and residence times of seconds for liquids and gases; hours for solids. Also a potential candidate for fluidized bed incineration with a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases; longer for solids.
Physical chemical treatment (coagulation/flocculation followed by sedimentation), with hauling of the sludge. ... /Another method is/ wet air oxidation, using a starting concentration of 5 g/l hydrazobenzene, 99.98% of the 1,2-diphenylhydrazine was destroyed in 1 hr at 275 °C and at 320 °C.
PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/
For more Disposal Methods (Complete) data for 1,2-DIPHENYLHYDRAZINE (10 total), please visit the HSDB record page.
Spillage Disposal
Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.
Preventive Measures
PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one piece & close fitting at ankles & wrists), gloves, hair covering, & overshoes. ... clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Vertical laminar flow biological safety cabinets may be used for containment of in vitro procedures ... provided that the exhaust air flow is sufficient to provide an inward air flow at the face opening of the cabinet, & contaminated air plenums that are under positive pressure are leak tight. Horizontal laminar flow hoods or safety cabinets, where filtered air is blown across the working area towards the operator, should never be used ... Each cabinet or fume cupboard to be used ... should be tested before work is begun (eg, with fume bomb) & label fixed to it, giving date of test & avg air flow measured. This test should be repeated periodically & after any structural changes. /Chemical Carcinogens/
For more Preventive Measures (Complete) data for 1,2-DIPHENYLHYDRAZINE (10 total), please visit the HSDB record page.
독성 정보
Treatment
Consider gastric lavage after ingestion of a potentially life-threatening amount of poison if it can be performed soon after ingestion. Following inhalation, move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. Irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. If the exposure occurs through dermal contact remove contaminated clothing and wash exposed area thoroughly with soap and water. A physician may need to examine the area if irritation or pain persists. (T36)
Ecotoxicity Values
LC50 Daphnia magna (water flea) 8.1 mg/L/24 hr /Conditions of bioassay not specified/
LC50 Daphnia magna (water flea) 4.1 mg/L/48 hr /Conditions of bioassay not specified/
LC50 Lepomis macrochirus (bluegill) 1.2 mg/L/24 hr (static bioassay, total water hardness 28-44 mg/L calcium carbonate, pH 6.7-7.4, oxygen concn 5.3-7.0 mg/L)
LC50 Lepomis macrochirus (bluegill) 0.27 mg/L/96 hr (static bioassay, total water hardness 28-44 mg/L calcium carbonate, pH 6.7-7.4, oxygen concn 5.3-7.0 mg/L)
LC50 Daphnia magna (cladoceran) static method 4,100 ug/L/96 hr
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 950(SRC), determined from a log Kow of 2.94(2)and a regression-derived equation(3), indicates that 1,2-diphenylhydrazine is expected to have low mobility in soil(SRC). Volatilization of 1,2-diphenylhydrazine from moist soil surfaces is not expected based upon an estimated Henry's Law constant of 4.8X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 4.4X10-4 mm Hg(4), and water solubility, 221 mg/L(5). Based on limited aqueous screening study data, 1,2-diphenylhydrazine is expected to biodegrade in soil under aerobic conditions (80% degradation in 7 days)(6). 1,2-Diphenylhydrazine, may also oxidize to azobenzene by air or cations in the soil(7).
AQUATIC FATE: 1,2-Diphenylhydrazine rearranges intramolecularly to benzidine in aq acid. Although the concn of aq acid that is necessary for this reaction is unlikely to be found in ambient surface waters, this rearrangement can proceed easily in presence of anionic micelles such as would be formed from commercial laundry detergents.
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 950(SRC), determined from a log Kow of 2.94(2) and a regression-derived equation(3), indicates that 1,2-diphenylhydrazine is 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 4.8X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 4.4X10-4 mm Hg(4), and water solubility, 221 mg/L(5). According to a classification scheme(6), an average BCF of 29 measured in fish and shellfish(7), suggests that bioconcentration in aquatic organisms is low(SRC). 1,2-Diphenylhydrazine undergoes rapid reversible oxidation in solution in the presence of dissolved oxygen and environmentally common cations (e.g. copper(II) and Fe(III)) to azobenzene(8); thus conversion to azobenzene in well-aerated waters should be a major fate process for this compound(SRC). If the conditions of the water body become reducing, the azobenzene will revert to 1,2-diphenylhydrazine(8). Based on limited aqueous screening study data, 1,2-diphenylhydrazine is expected to biodegrade in water under aerobic conditions (80% degradation in 7 days)(9). 1,2-Diphenylhydrazine absorbs light >290 nm(10) and may be subject to direct photolysis in sunlit surface waters, but the rate of this potential reaction is not known.
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,2-diphenylhydrazine, which has a vapor pressure of 4.4X10-4 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 1,2-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 5 hours(SRC), from its rate constant of 8.5X10-11 cu cm/molecule-sec at 25 °C(SRC) derived using a structure estimation method(3). Particulate-phase 1,2-diphenylhydrazine may be physically removed from the air by wet and dry deposition(SRC). 1,2-Diphenylhydrazine absorbs light greater than 290 nm(4), and may be susceptible to direct photolysis; however, the rate of this potential reaction is not known(SRC).
Toxicity Summary
Two of the known metabolites, aniline and benzidine, may contribute to the toxicity and/or carcinogenicity of 1,2-diphenylhydrazine. Nonneoplastic liver lesions, hepatocellular carcinomas and/or neoplastic liver nodules indicate that the liver is a target of 1,2-diphenylhydrazine toxicity. As aniline and other aromatic amino metabolites of 1,2-diphenylhydrazine (e.g., aminophenols) are methemoglobinforming compounds by either oral or inhalation routes of exposure, it is possible that 1,2-diphenylhydrazine may cause methemoglobinemia in humans. (L463)
Signs and Symptoms
Cough.
Redness.
Irritatinon to the eyes, nose and respiratory system, depending on the route of exposure. Cough, redness of the exposed surface. (L463)
Ongoing Test Status
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. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=122-66-7]
규제 정보
RCRA Requirements
U109; As stipulated in 40 CFR 261.33, when hydrazine, 1,2-diphenyl-, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).
TSCA Requirements
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, 1,2-diphenyl- is included on this list.
Atmospheric Standards
Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. 1,2-Diphenylhydrazine is included on this list.
CERCLA Reportable Quantities
Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 10 lb or 4.54 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).
Clean Water Act Requirements
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/
State Drinking Water Guidelines
(AZ) ARIZONA 0.05 ug/l
(FL) FLORIDA 10 ug/l
(NH) NEW HAMPSHIRE 0.05 ug/l
안전 데이터
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- MW2625000
- ridadr
- UN 3077 9/PG 3
- 독성
- Acute oral LD50 for rats 301 mg/kg (quoted, RTECS, 1985).
- HS 번호
- 29280000
- risk_code
- 45-22-50/53
- hazard_code
- T,N
- safety_code
- 53-45-60-61
- 포장분류
- III
- 위험 등급
- 6.1
- F 고인화성물질
- 10-23
- Hazard Classifications
- Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Carc. 1B
- 스토리지 클래스
- 6.1D - Non-combustible acute toxic Cat.3toxic hazardous materials or hazardous materials causing chronic effects
- 유해 물질 데이터
- 122-66-7(Hazardous Substances Data)
화학 및 산업
약리 정보
Metabolism/Metabolites
Thin layer chromatographic analysis of the urine of rats given an oral dose of 200 or 400 mg/kg revealed the presence of hydrazobenzene, benzidine, and two other unidentified metabolites. At an ip dose of 100 or 200 mg/kg, hydrazobenzene, aniline, benzidine, p-aminophenol, and o-aminophenol were identified in the urine. After iv or intratracheal administration of hydrazobenzene, only one urinary metabolite, which appeared to be phenolic, was found.
In the stomach, 1,2-diphenylhydrazine can be converted into benzidine, a known human carcinogen.
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 intemediates in the case of 1,2-disubstituted hydrazines and to unstable monoazo (diazene) metabolites in the case of monosubstituted hydrazines and hydrazides. /Substituted hydrazines/
Unchanged 1,2-diphenylhydrazine was detected following treatment by all routes, and aniline and benzidine were identified following oral and intraperitoneal treatments. Other metabolites included two unspecified hydroxy derivatives of benzidine (oral route), 2- and 4- aminophenol (intraperitoneal route), and unidentified compounds (oral, intravenous, and intratracheal routes). Aniline is oxidized by hydroxylation of a ring carbon to form 2-or 4-aminophenol or of the nitrogen to form phenylhydroxylamine, and then is conjugated to glucuronic or sulfuric acid. Benzidine is formed readily from 1,2-diphenylhydrazine by acid rearrangement. It has been suggested that benzidine may be produced from 1,2-diphenylhydrazine by acidity in the stomach. (L463)
용도 및 제조
Uses
1,2-Diphenylhydrazine is no longer produced in the United States. 1,2-Diphenylhydrazine is used in the production of anti-inflammatory drugs.
Used in the past in the United States to produce benzidine; the last manufacturer of benzidine-based dyes in the U.S. ceased production in 1988; Used as an intermediate in the pharmaceutical industry to produce phenylbutazone and sulfinpyrazone; [ATSDR ToxProfiles]
Chemical intermediate for benzidine, an intermediate for dyes, in synthesis of phenylbutazone (antiarthritic drug)
Antisludging additive to motor oil, /evaluated as/ agent for insecticidal and insecticidal synergistic activity, desuckering agent for tobacco plants, reductant in reclamation of rubber, component of experimental organometallic polymers, use in photochromic resin compositions, in polymerization reactions.
Used as a chemical intermediate for the synthesis of phenylbutazone; sulfinpyrazone
1,2-Diphenylhydrazine is used to make fabric dyes in other countries, and to make certain medicines. Exposure may result from breathing in dust coated with 1,2-diphenylhydrazine and eating dirt or smearing contaminated dirt on the skin. (L463)
U.S. Imports
(1978) 7.21X10+7 G (PRINCPL CUSTMS DISTS)
(1982) 2.32X10+7 G (PRINCPL CUSTMS DISTS)
Methods of Manufacturing
Hydrazobenzene is formed when nitrobenzene reacts with zinc dust in an alkaline solution.
Nitrobenzene (reductive coupling)
General Manufacturing Information
Hydrazine, 1,2-diphenyl-: ACTIVE
Can be used in mfr of hydrogen peroxide
Rearranges to benzidine in strong mineral acid.
Hydrazobenzene can be protonated, and this is an essential step in the conversion of hydrazobenzene to benzidine.
The technical grade substances used show considerable impurities and may contain benzidine as a contaminant. In 1 of 16 samples from a manufacturer's continuous production, 25 ug benzidine/g hydrazobenzene were found... .
응용 분야
개요Diphenylhydrazine 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.
용도Previously, 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.
일반 설명Orange powder or a bright orange crystalline solid.
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