Hydrazobenzol

Hydrazobenzene

HCID 31222CAS 122-66-7

Grundinformationen

Standard-SMILES
c1ccc(NNc2ccccc2)cc1
InChIKey
YBQZXXMEJHZYMB-UHFFFAOYSA-N
Summenformel
C12H12N2
Durchschnittliche Molmasse
184,24 g/mol
Monoisotopische Masse
184,10004838

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
Hydrazobenzene
IUPAC
1,2-diphenylhydrazine
Lokaler Name
Hydrazobenzol
Englischer Name
1,2-Diphenylhydrazine
Summenformel
C12H12N2
Molmasse
184.24

Namen und Synonyme

1,2-DIPHENYLHYDRAZINEHydrazobenzene122-66-7Hydrazine, 1,2-diphenyl-N,N'-BianilineN,N'-DiphenylhydrazineHydrazobenzenBenzene, hydrazodi-(sym)-DiphenylhydrazineNCI-C01854Benzene, 1,1'-hydrazobis-1,1'-Hydrazodibenzene
Weitere Namen anzeigen
NSC 3510RCRA U-109NCI-C-018451,2-Diphenyln,n’-bianilineHydroazobenzene
Symmetrical diphenyl hydrazineDTXSID70207101G3CS09TUKNSC-3510DTXCID90710NSC3510hydrazodibenzenen,n-Bianiline

Datenbank-Bezeichner

CAS
122-66-7、38622-18-3
PubChem CID
31222
DTXSID
DTXSID7020710
ChEMBL
CHEMBL558459
UNII
1G3CS09TUK
EC Number
204-563-5
Nikkaji
J5.359G

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2,9
Polarare Oberfläche (TPSA)
24,1 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
3
Schwere Atome
14

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 4 Einträge

Hazardous Air Pollutants (HAPs)

Nitrogen Compounds -> Hydrazines

Carcinogens

Semi-Volatile Organic Compound (SVOC)

SpringerMaterials Properties15N nuclear magnetic resonance spectrum
PesticidesPesticide -> EPA IRIS
LogP · 3 Einträge

log Kow= 2.94

2.94

2.94

Density · 4 Einträge

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 · 2 Einträge

Tablets from alcohol and ether

Colorless crystals

Physikochemische Eigenschaften

Schmelzpunkt
123 · 123-126 °C(lit.)
Siedepunkt
308.2 °C · 308.2°C (rough estimate)
Dichte
1 · 1,158 g/cm3
Dampfdruck
2.6 x · 2.6 x 10-5 mmHg at 25 °C (Mabey et al., 1982)
Brechungsindex
1.6266 · 1.6266 (estimate)
storage temp.
Refrigerator

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

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)

Gefahrenhinweise

Regulatory Information · 3 Einträge

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.)

Other Safety InformationIMAP assessments - Hydrazine, 1,2-diphenyl-: Human health tier II assessment
DOT LabelPoison
Fire Hazards · 2 Einträge

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.

Health HazardsSYMPTOMS: Symptoms of exposure to this compound may include irritation.
Hazards Summary · 3 Einträge

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.

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

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 · 4 Einträge

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 · 1 Eintrag

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.

Safe StorageSeparated from food and feedstuffs. Store in an area without drain or sewer access.
Storage Conditions · 1 Eintrag

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 · 2 Einträge

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.

Toxikologische Informationen

Toxicological InformationCDC-ATSDR Toxicological Profile
Treatment · 1 Eintrag

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)

Cancer SitesHepatic
Target OrgansCancer, Hepatic (Liver)
Health EffectsNonneoplastic liver lesions, hepatocellular carcinomas and/or neoplastic liver nodules; seizures and coma. (L463)
Ecotoxicity Values · 5 Einträge

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

Regulatorische Informationen

RCRA Requirements · 1 Eintrag

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 · 1 Eintrag

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 · 1 Eintrag

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 · 1 Eintrag

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 · 2 Einträge

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 · 3 Einträge

(AZ) ARIZONA 0.05 ug/l

(FL) FLORIDA 10 ug/l

(NH) NEW HAMPSHIRE 0.05 ug/l

Sicherheitsdaten

F
10-23
wgk
3
tsca
TSCA listed
ridadr
UN 3077 9/PG 3
hs_code
29280000
RTECS-Nr.
MW2625000

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 4 Einträge

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)

Verwendung und Herstellung

Uses · 6 Einträge

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 · 2 Einträge

(1978) 7.21X10+7 G (PRINCPL CUSTMS DISTS)

(1982) 2.32X10+7 G (PRINCPL CUSTMS DISTS)

U.S. Production(1977) AT LEAST 4.5X10+8 G
Methods of Manufacturing · 2 Einträge

Hydrazobenzene is formed when nitrobenzene reacts with zinc dust in an alkaline solution.

Nitrobenzene (reductive coupling)

Use ClassificationChemical Classes -> Benzidines/Aromatic amines
General Manufacturing Information · 5 Einträge

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... .

Anwendungen · 2 Einträge

BeschreibungDiphenylhydrazine 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.

VerwendenPreviously, 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.

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