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HCID 7111Erstellt: 26. Oktober 2026

Benzidin

BENZIDINE-D8 · Benzidin · Benzidina · benzidine solution · BENZIDINE-RINGS-D8 · 4,4'-Diaminodiphenyl · biphenyl-4,4’-diamine · 4,4’-biphenylenediamine

https://huagongshe.com/de/chemical/7111

Molekülstruktur von Benzidin

Identifikatoren & physikalische Daten

CAS No.92-87-5
SummenformelC12H12N2
Durchschnittliche Molmasse184,24 g/mol
Monoisotopische Masse184,10004838 g/mol
SMILESNc1ccc(-c2ccc(N)cc2)cc1
InChIKeyHFACYLZERDEVSX-UHFFFAOYSA-N
PubChem CID7111
ChEMBLCHEMBL15901
ChEBICHEBI:80495
EC No.202-199-1
DTXSIDDTXSID2020137
Lokaler NameBenzidin

Chemische & physikalische Eigenschaften

XLogP1,3
Polarare Oberfläche (TPSA)52
H-Brücken-Donoren2
H-Brücken-Akzeptoren2
Frei drehbare Bindungen1
Schwere Atome14
Formalladung0
Komplexität145
StoffklassenHazardous Air Pollutants (HAPs)Nitrogen Compounds -> Benzidine and DerivativesCarcinogensSemi-Volatile Organic Compound (SVOC)
SpringerMaterials PropertiesChemical structure
PestizidePesticide -> EPA IRIS
LogP (Verteilungskoeffizient)log Kow= 1.341.53
Dichte2.15 at 68 °F (USCG, 1999) - Denser than waterwill sink1.250 @ 20 °C/4 °C1.3 g/cm³1.25 @ 20°C
Color/FormWhite or slightly-reddish, crystalline powderGrayish-yellow, reddish-gray, or white crystalline powder [Note: Darkens on exposure to air and light].
Löslichkeitless than 1 mg/mL at 72 °F (NTP, 1992)1 g dissolves in 2500 ml cold water1 g dissolves in 107 ml boiling water1 g dissolves in 5 ml boiling alcohol1 g dissolves in 50 ml etherIn water, 322 mg/l @ 25 °C0.322 mg/mL at 25 °CSolubility in water, g/100ml at 25 °C:(54 °F): 0.04%Soluble in ethanol (U.S. EPA, 1985) and ether (1 g/50 mL) (Windholz et al., 1983)Sparingly soluble. <0.1 g/100 mL at 22 ºC
Siedepunkt752 °F at 740 mmHg (NTP, 1992)401 °C401 °C @760 [mm Hg]402°C
DecompositionWhen heated to decomp it emits highly toxic fumes of /nitrogen oxides/.
Schmelzpunkt262 °F (NTP, 1992)120 °C127 °C239 °F127-128 °C
Dampfdichte6.36 (NTP, 1992) - Heavier than airwill sink (Relative to Air)6.36 (Air = 1)Relative vapor density (air = 1): 6.4
DampfdruckLow (NIOSH, 2024)0.0000009 [mmHg]Based on the specific vapor density value of 6.36 (Sims et al., 1988), the vapor pressure wascalculated to be 0.83 at 20 °C.
Brechungsindex1.6266 (estimate)
Flammpunkt11 °C
Lagerbedingungen2-8°C
pKa (Säurekonstante)4.66(at 30℃)
FarbeGrayish-yellow, crystalline powderwhite or sltlyreddish crystals, powder
Merck13,1077
BRN742770
Henry-Konstante(x 10-11 atmm3/mol): 3.88 at 25 °C (estimated, Howard, 1989)
StabilitätStable. Combustible. Incompatible with strong oxidizing agents.
InChIKeyHFACYLZERDEVSX-UHFFFAOYSA-N
CAS Datenbank92-87-5(CAS DataBase Reference)
NIST chemische InformationenBenzidine(92-87-5)
EPA chemische InformationenBenzidine (92-87-5)

Sicherheit & Vorschriften

GHS-EinstufungDangerH302: 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)H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
Regulatorische InformationenChemical: [1,1'-Biphenyl]-4,4'-diamineS - indicates a substance that is identified in a final Significant New Use Rule.Restricted substance: Benzidine[1,1'-Biphenyl]-4,4'-diamine: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.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.)
Weitere SicherheitsinformationenIMAP assessments - [1,1'-Biphenyl]-4,4'-diamine: Environment tier I assessment
DOT-KennzeichnungPoison
BrandgefahrenSpecial Hazards of Combustion Products: Contain highly toxic NOx fumes.· Combustible material: may burn but does not ignite readily.Combustible. Gives off irritating or toxic fumes (or gases) in a fire.
BrandpotenzialBenzidine itself does not burn or burns with difficulty.
GesundheitsgefahrenPoisonous if inhaled, swallowed or absorbed through skin. May cause contact dermatitis, irritation or sensitization. Ingestion may cause nausea and vomiting. (USCG, 1999)· TOXIC and/or CORROSIVEinhalation, ingestion or skin contact with material may cause severe injury or death.
GefahrenübersichtBenzidine is a manufactured chemical that does not occur naturally. It is a crystalline solid that may be grayish-yellow, white, or reddish-gray. In the environment, benzidine is found in either its "free" state (as an organic base), or as a salt. Benzidine was used to produce dyes for cloth, paper, and leather. It is no longer produced or used commerically in the U.S.Benzidine is no longer produced in the United States, although benzidine-based dyes may be imported into this country. No information is available on the acute (short-term) effects of benzidine in humans by inhalation exposure but benzidine is considered to be very acutely toxic to humans by ingestion. Chronic (long-term) exposure to benzidine in humans may result in injury to the bladder. Epidemiological studies have shown occupational exposure to benzidine to result in an increased risk of bladder cancer. Animal studies have reported various tumor types at multiple sites from benzidine exposure via oral, inhalation, and injection exposure. EPA has classified benzidine as a Group A, known human carcinogen.Caused bladder cancer to workers in the pastboth the inhalation and skin routes are significant[ACGIH]A liver toxin and carcinogen in experimental animalshealth effects after acute exposure in the workplace have not been reported[NIOSH Guidelines for Chemical Hazards] May cause methemoglobinemia[HSDB] Known human carcinogen, including dyes metabolized to benzidine[IARC]
DOT-Nummer und Handbuch1885 153
Reaktive GruppeAmines, Aromatic
EG-EinstufungSymbol: T, NR: 45-22-50/53S: 53-45-60-61Note: E
UN-EinstufungUN Hazard Class: 6.1UN Pack Group: II
Special ReportsHEALTH HAZARD ALERT: BENZIDINE-, O-TOLIDINE-, & O-DIANISIDINE-BASED DYESDHHS (NIOSH) PUBL US (81-106) 39 PP (1980). A REVIEW WITH 42 REFERENCES ON THE HEALTH HAZARD OF BENZIDINE, O-TOLIDINE, & O-DIANISIDINE DYES & 118 DYES BASED ON THESE CMPD.SHRINER CR ET ALREVIEWS OF THE ENVIRONMENTAL EFFECTS OF POLLUTANTS: II. BENZIDINEREPORT ORNL/EIS-86, EPA-600/1-78-024 157 PP (1978). A REVIEW WITH 200 REFERENCES ON THE BIOLOGICAL AND ENVIRONMENTAL EFFECTS OF BENZIDINE.USEPAHealth Effects Review: Benzidine and Benzidine Based Dyes (1980) EPA 68-01-05861.U.S. Dept Health & Human Services/Agency for Toxic Substances Disease RegistryToxicological Profile for Benzidine (Update) (1995) NTIS # PB/95/264313For more Special Reports (Complete) data for BENZIDINE (6 total), please visit the HSDB record page.
BrandbekämpfungExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:Use water spray, foam, powder, carbon dioxide.
Erste-Hilfe-MaßnahmenFresh air, rest.Remove contaminated clothes. Rinse and then wash skin with water and soap. Wear protective gloves when administering first aid.Rinse with plenty of water (remove contact lenses if easily possible).Rinse mouth.
Freisetungsmaßnahmen· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.
Erste HilfeEYES: 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.General First Aid:(General first aid procedures)
Sichere LagerungProvision to contain effluent from fire extinguishing. Separated from strong oxidants and food and feedstuffs. Keep in the dark. Well closed. Store in an area without drain or sewer access.
Expositionsschutz und Persönliche Schutzausrüstung· Wear positive pressure self-contained breathing apparatus (SCBA).
BrandbekämpfungsverfahrenIf material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use foam, dry chemical, or carbon dioxide.
LagerbedingungenKEEP WELL CLOSED & PROTECTED FROM LIGHT.PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical 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/
ReinigungsverfahrenCover the spill with a 9:1 mixture of sand and soda ash.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/
Freisetung ohne BrandExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
EntsorgungsverfahrenGenerators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U021, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.The following wastewater treatment technologies have been investigated for benzidine: Concentration process: Biological treatment.This compound should be susceptible to removal from waste water by air stripping.For more Disposal Methods (Complete) data for BENZIDINE (12 total), please visit the HSDB record page.
Verschüttetes entsorgenPersonal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Sweep spilled substance into sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.
Toxikologische InformationenCDC-ATSDR Toxicological Profile
KörperbelastungBenzidine was detected in the urine of workers in India exposed to Direct Black 38 at concentrations of 2.4-362.5 ug/l(1,2).
Cancer SitesUrinary[liver, kidney & bladder cancer]
WechselwirkungenContinuous administration of neozone D to dogs and rats failed to reveal its carcinogenicity. Nor did the agent potentiate the carcinogenic effect of benzidine in rats. Conversely, neozone D was found to inhibit benzidine induced carcinogenesis in female rats.In an in vitro study designed to assess the percutaneous absorption and penetration of (14)C-benzidine in combination with various other chemical mixtures which might be found in occupational settings, isolated perfused porcine skin flaps were topically treated with benzidine + solvent (acetone or DMSO), benzidine + surfactant (sodium lauryl sulfate), benzidine + vasodilator (methyl nicotinate), benzidine + reducing agent (SnCl2), or various combinations of these mixtures ... . Flow-through diffusion call systems were also utilized. Absorption was defined as the total amt of radioactivity detected in the perfusate for the entire 8-hr perfusion period. Skin penetration was defined as the sum of total absorption and total radioactivity in the skin. Maximum absorption and maximum penetration over an 8-hr exposure period were approx 3 and 22%, respectively, for a mixture of benzidine + DMSO + surfactant + vasodilator. It was noted that DMSO enhanced absorption more than acetone, and that the reducing agent inhibited benzidine absorption. It was suggested that chemical-biological interactions between the surfactant and vasodilator might enhance benzidine absorption while chemical-chemical interactions between benzidine and SnCl2 might inhibit benzidine absorption.Though not universally found, synergistically elevated rates of bladder cancer in workers exposed to benzidine who also smoked were reported in several epidemiology studies ... . These findings suggest interactions between benzidine and the carcinogenic or enzyme-inducing cmpd found in cigarette smoke.It is also possible that alcohol might potentiate the toxicity of benzidine, probably by altering its metabolism. Exposing rats to 15% (v/v) ethanol in drinking water for 6 wk resulted in incr cytochrome P-450 content and enhanced N-acetylation capacity of isolated hepatocytes ... . Further, relative to the mutagenicity meditated by control hepatocytes, the in vitro mutagenicity of benzidine to bacteria was incr following metabolic activation by hepatocytes isolated from the ethanol-treated rats. Again, the relevance of these findings to humans is unclear, given that the bladder appears to be the principal human target organ, and that noncytochrome P-450 pathways may be significant in the human metabolism of benzidine.
ZielorganeCancer, Gastrointestinal (Stomach and Intestines, part of the digestive system), Hepatic (Liver), Renal (Urinary System or Kidneys)Bladder, skin, kidneys, liver, blood
Gesundheitliche AuswirkungenBenzidine is a known human carcinogen, most often associated with cancer of the urinary bladder. If benzidine comes in contact with skin it may cause a skin allergy. Liver, kidney, immune, and neurological effects have also been observed in animals exposed to benzidine. (L95)
ÖkotoxizitätswerteLC50 Gammarus pseudolimnaeus (scud) > 20,000 ug/l/96 hr /Conditions of bioassay not specified/Pimephales promelas (fathead minnow) > 20,000 ug/l/96 hr /Conditions of bioassay not specified/LC50 Salmo gairdneri (rainbow trout) 7400 ug/l/96 hr in a static unmeasured bioassayLC50 Salvelinus namaycush 4350 ug/l/96 hr in a static unmeasured bioassayFor more Ecotoxicity Values (Complete) data for BENZIDINE (6 total), please visit the HSDB record page.
UmweltverhaltenTERRESTRIAL FATE: Based on a classification scheme(1), Koc values in the range of 227,000 to 882,000, measured in 4 soils(2), indicate that benzidine is expected to be essentiallyo immobile in soil(SRC). Benzidine is a weak base with 2 amine functional groups having pKa values of 4.3 and 3.3(3). These values indicate that benzidine can partially exist in the protonated form under acidic conditions(SRC). Volatilization of the neutral species of benzidine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.2X10-11 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). The conjugate acid will not volatilize since cations are non-volatile(SRC). Benzidine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7X10-7 mm Hg(SRC), determined from a fragment constant method(5). Benzidine is generally resistant to biodegradation in soil at high concentrations, but may biodegrade at lower concentrations(SRC). Aqueous solutions of benzidine (0.01%) were reported to be stable for 9 weeks to degradation by soil/river water inoculum(6). In Drummer silty clay loam, benzidine applied at a concn of 10 ppb was degraded 79% after 4 weeks(7). Benzidine is rapidly oxidized by Fe(III) and other cations which are frequently found in soils and clay(8).AQUATIC FATE: Based on a classification scheme(1), Koc values of benzidine adsorbed to 3 estuarine sediments in the range of 462-4,899(2), indicate that benzidine is expected to adsorb to suspended solids and sediment(SRC). Benzidine is a weak base with 2 amine functional groups with pKa values of 4.3 and 3.3(3). These values indicate that benzidine can partially exist in the protonated form under acidic conditions(SRC). Volatilization of the free base from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 5.2X10-11 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). The conjugate acid will not volatilize since cations are non-volatile(SRC). According to a classification scheme(6), BCF values of 40 and 55 measured in fish(7,8), suggest bioconcentration in aquatic organisms is moderate(SRC). When aerated solutions of benzidine (100 ppb) were exposed to light from a xenon lamp (300-400 nm), complete degradation was observed in 12 hrs(9). Benzidine is rapidly oxidized by Fe(III) and other cations which are frequently found in environmental waters(10). Aqueous solutions of benzidine (0.01%) were reported to be stable for 9 weeks to degradation by soil/river water inoculum(11).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), benzidine, which has an estimated vapor pressure of 7X10-7 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase benzidine 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 2 hours(SRC), calculated from its rate constant of 1.5X10-10 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). Benzidine also absorbs light greater than 290 nm and may undergo direct photolysis(4). Over 40% photodegradation was observed when benzidine adsorbed to silica gel plates was irradiated with UV light > 290 nm for 17 hours(5). Particulate- phase benzidine may be removed from the air by wet and dry deposition(SRC).
Unerwünschte WirkungenOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
ExpositionspfadeThe substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.inhalation, skin absorption, ingestion, skin and/or eye contactOral (L95)inhalation (L95)dermal (L95)
ToxizitätsübersichtN-acetylated benzidine metabolites are believed to form adducts with nucleic acids. Carcinogenesis is initiated when they are activated by peroxidation by prostaglandin H synthetase, oxidation by cytochrome P-450, or O-esterification by O-acetyltransferase or N,O-acetyltransferase. Benzidine has also been shown to bind to RNA and hemoglobin. (L95, A55)
Signs and SymptomsMAY BE ABSORBED!hematuria (blood in the urine)secondary anemia from hemolysisacute cystitisacute liver disordersdermatitispainful, irreg urination[potential occupational carcinogen]
RCRA-AnforderungenU021As stipulated in 40 CFR 261.33, when benzidine, 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-AnforderungenPursuant 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. 1,1'-Biphenyl-4,4'-diamine is included on this list.
LuftstandardsListed 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. Benzidine is included on this list.
CERCLA-MeldepflichtmengenPersons 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 1 lb or 0.454 kg. The toll free number of the NRC is (800) 424-8802In 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 AnforderungenToxic pollutant designated pursuant to section 307(a)(1) of the Federal Water Pollution Control Act and is subject to effluent limitations.The levels which may result in incremental increase of cancer risk over the lifetime are estimated at 1X10-5, 1X10-6, and 1X10-7. The corresponding recommended criteria are 1.2 ng/l, 0.12 ng/l, and 0.01 ng/l, respectively.
Landesrichtlinien für Trinkwasser(AZ) ARIZONA 0.0001 ug/l(FL) FLORIDA 250 ug/l(NH) NEW HAMPSHIRE 0.0002 ug/l
F8
Wassergefährdungsklasse (WGK)3
TSCA-Inventar-StatusTSCA listed
UN-TransportnummerUN 1885
Zollcode29215900
RTECS-Nr.DC9625000
R-Sätze (R)45-22-50/53-52/53-39/23/24/25-23/24/25-11-36/37/38-20/21/22-51/53-67
ToxizitätAcute oral LD50 for mice 214 mg/kg, rats 309 mg/kg (quoted, RTECS, 1985).
GefahrensymboleT,N,F,Xn
Sicherheitshinweise (S)53-45-60-61-36/37-16-7-36-26
Gefahrenklasse6.1
VerpackungsgruppeII
Gefahrstoffdaten92-87-5(Hazardous Substances Data)

Anwendungen & Verwendung

Beschreibung

Die Benzidinbase bildet ein graubraunes, wasserunlösliches Pulver. Die Verbindung wird zur Herstellung einer sehr großen Zahl von Azofarbstoffen verwendet. Der erste, direkt auf Baumwolle ziehende Azofarbstoff, das Kongorot, ist z.B. ein Benzidinfarbstoff.

Beschreibung

Benzidine is a white, greyish-yellow, or slightly reddish crystalline solid or powder. The major use for benzidine is in the production of dyes, especially azo dyes in the leather, textile, and paper industries and as a synthetic precursor in the preparation and manufacture of dyestuffs. It is also used in the manufacture of rubber, as a reagent, and as a stain in microscopy. It is slightly soluble and slowly changes from a solid to a gas.

Verwenden

Benzidine was used extensively in the manu facture of dyes. Because of its cancer-causingeffects in humans, its application in dyes hasbeen curtailed. Other uses of this compoundare in chemical analysis: as a reagent for thedetermination of hydrogen peroxide in milkand in the analysis of nicotine. Its hydrochlo ride is used as a reagent to analyze metalsand sulfate.

Herstellung & Synthese

synthetische

1-Nitrobenzene restore 1,2-Diphenylhydrazineturn with acid rearrangement.