7H-Dibenzo[c,g]carbazole
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7H-Dibenzo[c,g]carbazole
structure -
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CAS No:
194-59-2
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Formula:
C20H13N
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Chemical Name:
7H-Dibenzo[c,g]carbazole
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Synonyms:
7H-Dibenzo[c,g]carbazole;7-Aza-7H-dibenzo[c,g]fluorene;3,4:5,6-Dibenzocarbazole;NSC 87519
- Categories:
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CAS No:
Description
Yellow Crystalline SolidCrystalline solid.
7h-dibenzo(c,g)carbazole is a crystalline solid.
7h-dibenzo(c,g)carbazole is a crystalline solid.|7H-Dibenzo[c,g]carbazole is a member of carbazoles.
7H-Dibenzo[c,g]carbazole Basic Attributes
267.32
267.32
205-895-3
SZF1OJI89D
87519
2811
DTXSID9059755
NEEDLES FROM ETHANOL
2933990090
Characteristics
15.8
6.18
7h-dibenzo(c,g)carbazole is a crystalline solid.
0.9889 (rough estimate)
158 °C
400.51°C (rough estimate)
246.5±14.1 °C
1.8610 (estimate)
63 ug/L
2-8°C
Vapor pressure: 3.4X10-9 mm Hg at 25 deg C(est)
Absorption coefficients at 313 and 366.0 nm are 4210 and 13,000 L/mol-cm, respectively. /5% acetonitrile, 95% water at pH 4.5/
No rapid reaction with air. No rapid reaction with water.
Amines, Phosphines, and Pyridines
7H-DIBENZO(C,G)CARBAZOLE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides.
Safety Information
III
6.1(b)
2811
HO5600000
P201, P202, P281, P308+P313, P405, P501
H351
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.|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/|PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /Chemical Carcinogens/|For more Disposal Methods (Complete) data for 7H-DIBENZO(C,G)CARBAZOLE (6 total), please visit the HSDB record page.
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. 7H-Dibenzo(c,g)carbazole (194-59-2) is listed as reasonably anticipated to be a human carcinogen. /Polycyclic Aromatic Hydrocarbons/[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s150pah.pdf]
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. For electric vehicles or equipment, ERG Guide 147 (lithium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. (ERG, 2016)
|Warning|H351: Suspected of causing cancer [Warning Carcinogenicity]|P201, P202, P281, P308+P313, P405, and P501
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: SMALL FIRE: Dry chemical, CO2 or water spray. LARGE FIRE: Dry chemical, CO2, alcohol-resistant foam or water spray. Move containers from fire area if you can do it without risk. Dike fire-control water for later disposal; do not scatter the material. FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. (ERG, 2016)
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. (ERG, 2016)|PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... 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. ... Gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the laboratory. /Chemical Carcinogens/
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/
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 7H-DIBENZO(C,G)CARBAZOLE (9 total), please visit the HSDB record page.
PRECAUTIONS FOR "CARCINOGENS": Procurement ... of unduly large amt ... should be avoided. To avoid spilling, carcinogens should be transported in securely sealed glass bottles or ampoules, which should themselves be placed inside strong screw-cap or snap-top container that will not open when dropped & will resist attack from the carcinogen. Both bottle & the outside container should be appropriately labelled. ... National post offices, railway companies, road haulage companies & airlines have regulations governing transport of hazardous materials. These authorities should be consulted before ... material is shipped. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": When no regulations exist, the following procedure must be adopted. The carcinogen should be enclosed in a securely sealed, watertight container (primary container), which should be enclosed in a second, unbreakable, leakproof container that will withstand chem attack from the carcinogen (secondary container). The space between primary & secondary container should be filled with absorbent material, which would withstand chem attack from the carcinogen & is sufficient to absorb the entire contents of the primary container in the event of breakage or leakage. Each secondary container should then be enclosed in a strong outer box. The space between the secondary container & the outer box should be filled with an appropriate quantity of shock-absorbent material. Sender should use fastest & most secure form of transport & notify recipient of its departure. If parcel is not received when expected, carrier should be informed so that immediate effort can be made to find it. Traffic schedules should be consulted to avoid ... arrival on weekend or holiday ... /Chemical Carcinogens/
Dibenzocarbazoles (isomers not specified) were found in sediment from the Black River, an industrial area in Ohio, at 1000 ng/g (dry weight)(1).
7H-Dibenzo(c,g)carbazole has been detected, but not quantified, in particulate matter in polluted atmsophere(1).
7H-Dibenzo(c,g)carbazole has been identified in cigarette smoke (0.07 ug/100 cigarettes)(1).
Toxicity
There is no commercial production of 7H-dibenzo(c,g)carbazole(1). Polynuclear nitrogen compounds are released in various combustion processes. 7H-Dibenzo(c,g)carbazole is found in coal tar and coal distillates as well as cigarette smoke(1,2) and may be released to the environment as emissions and residues from these combustion sources(SRC).
TERRESTRIAL FATE: 7H-Dibenzo(c,g)carbazole adsorbs very strongly to soil and if released on soil will remain in the surface layer of soil. It undergoes direct photolysis in water and would be expected to photolyze on the soil surface. It is resistant to biodegradation and would be expected to be persistent in the soil(SRC).|AQUATIC FATE: The results of laboratory investigations suggest that 99% of 7H-dibenzo(c,g)carbazole entering natural waters will be adsorbed onto sediment and that the remaining 1% will be photochemically transformed to yield two products, one of which is phenolic(1). Photolysis is expected to be the dominant process in clear waters and adsorption will be most important in turbid waters(1). Based on experimental photolysis rates at midday, the photolysis half-life of 7H-dibenzo(c,g)carbazole in winter is expected to be 1.0 hr in a model river, 0.5 hr in an oligotrophic lake, and 1.5 hr in a eutrophic lake or pond(1). While the photolysis rate will vary with the time of day, photolysis will be an important process with a half-life of less than a day(1). Since biodegradation appears to be unlikely, desorption from sediment may maintain a low concn of 7H-dibenzo(c,g)carbazole in a water body almost indefinitely(1). Between 50 and 82% of 7H-dibenzo(c,g)carbazole present in most natural waters would be adsorbed to suspended sediment(1). 7H-Dibenzo(c,g)carbazole would be expected to bioconcentrate in aquatic organisms(SRC).|ATMOSPHERIC FATE: Based on its estimated vapor pressure, 3.4X10-9 mm Hg at 25 °C(2), 7H-dibenzo(c,g)carbazole should exist in the atmosphere as an aerosol(4,SRC) and be removed by gravitational settling(SRC). Vapor-phase 7H-dibenzo(c,g)carbazole would react with photochemically-produced hydroxyl radicals resulting in an estimated half-life of 13.8 hr(3,SRC). However, it is not clear what would happen with the adsorbed chemical. 7H-Dibenzo(c,g)carbazole is readily photolyzed in water and may photolyze in atmospheric droplets and while adsorbed to particulate matter(SRC).
The pKa of 7H-dibenzo(c,g)carbazole is not known, but by analogy with carbazole is expected to be less than zero(1). Therefore 7H- dibenzo(c,g)carbazole will be present as the free base in the environment. It absorbs UV radiation to 390 nm, having a long wavelength molar extinction coefficient of 10 L/mol-cm at 390 nm and a peak extinction coefficient of 13,000 L/mol-sec at 366 nm(1,2). It therefore may undergo direct photolysis. Its rate constant when illuminated at 366 nm in pure water was 1.52X10-3/sec(1). Its rate constant in pure water at noon in mid January was measured to be 5.18X10-4/sec (half-life 0.37 hr)(1,2). Its calculated photolysis half-life in pure water at noon for midwinter and mid-summer are approximately 0.85 and 0.35 hr, respectively(1). The presence of humic material or other substances in the water can attenuate the light or sensitize the phototransformation(3). When illuminated at 366 nm, its rate constants in Lake Tahoe water, Coyote Creek water, and Searville Pond water are 1.42X10-3/sec, 1.17X10-3/sec, and 1.80X10-3/sec, respectively, which are not very different from that in pure water(1). The presence of oxygen does not affect the photolysis rate(2). A free radical oxidation rate by alkoxy radicals (half-life 10 days) is clearly not competitive with photolysis(1).|7H-Dibenzo(c,g)carbazole is estimated to have a vapor pressure of 3.4X10-9 mm Hg at 25 °C(3) and therefore in the atmosphere, it will exist primarily as an aerosol(2) and be removed by gravitational settling(SRC). Vapor-phase 7H-dibenzo(c,g)carbazole would react with photochemically-produced hydroxyl radicals with an estimated rate constant of 28.0X10-12 cu cm/molecule-s(1). Assuming a hydroxyl radical concn of 5X10+5 radicals/cu cm, the half-life of 7H-dibenzo(c,g)carbazole in the atmosphere would be 13.8 hr(SRC).
The estimated log Kow for 7H-dibenzo(c,g)carbazole is 5.58(1). Using this log Kow, one can estimate a BCF of 10,000 for 7H-dibenzo(c,g)carbazole using a recommended regression equation(2). This BCF indicates that 7H-dibenzo(c,g)carbazole has a very high potential for bioconcentration in fish and aquatic organisms(SRC).
1.07e+06 L/kg|The soil/water distribution constant of 7H-dibenzo(c,g)carbazole to Des Moines River sediment (0.08% OC), Coyote Creek sediment (1.9% OC), and Searsville Lake sediment (5% OC) was 32,600, 18,500, and 27,600, respectively(1). The respective Koc values are 40,800,000, 970,000 and 550,000(SRC). The Koc for 7H-dibenzo(c,g)carbazole estimated from molecular structure is 1.5X10+6(2). According to a suggested classification scheme(3), these experimental and estimated Kocs suggest that 7H-dibenzo(c,g)carbazole would be immobile in soil(SRC).
Volatilization of 7H-dibenzo(c,g)carbazol from water in laboratory experiments was undetectable(1). The Henry's Law constant for 7H-dibenzo(c,g)carbazole estimated from molecular structure is 2.45X10-9 atm-cu m/mol(2). Chemicals with such low Henry's Law constants are nonvolatile from water(3).
THE CONCN OF 7H-DIBENZO[C,G]CARBAZOLE FROM AN ASPHALT HOT MIXT WAS BELOW HAZARDOUS LEVELS.|The primary routes of potential human exposure to PAHs are inhalation of polluted air, wood smoke, and tobacco smoke, as well as ingestion of contaminated water, foodstuffs, and foods normally containing ug quantities of PAHs ... . Potential human exposure to PAHs may also occur by dermal contact with PAH-containing products such as creosote-treated wood products, asphalt roads, or coal tar. Consumers may be exposed to PAHs that are present in dermatological preparations containing coal tar ... . /Polycyclic aromatic hydrocarbons/|There is potential occupational exposure to PAHs for workers at coal tar production plants, coking plants, coal gasification sites, smoke houses, foundries, aluminum production plants, bitumen and asphalt production plants, road and roof tarring operations, municipal incineration sites, other facilities that burn carbonaceous materials, and in kitchens where high-temperature fryers and broilers are used ... . /Polycyclic aromatic hydrocarbons/|The general population would be exposed to 7H-dibenzo(c,g)carbazole via inhalation of cigarette smoke and polluted air. Exposure would occur via dermal contact with dirt or objects where combustion emissions containing 7H-dibenzo(c,g)carbazole products settled. (SRC)
Drug Information
Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included. (See all compounds classified as Carcinogens.)
3H-/labeled/ 7H-Dibenzo[c,g]carbazole (3 mg), administered intratracheally in saline or water to hamsters, was cleared from the respiratory tract with a half-life of 1-3 hr, which was several times faster than the rate observed for benzo[a]pyrene ... 7H-Dibenzo[c,g]carbazole was distributed to the liver, kidney, brain and fat, with highest concn observed in the intestine; 6 hr after administration, five times as much radioactivity was observed in the feces (16%) as in the urine (3%).
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. (ERG, 2016)|Carcinogens
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim calm and warm. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. (ERG, 2016)
Mortality studies have demonstrated that exposure to coke oven emissions, which contain a variety of PAHs, caused increased incidences of lung and genitourinary cancer mortality in coke oven workers ... . /Polycyclic aromatic hydrocarbons/|Workers exposed to creosote containing numerous PAHs developed skin tumors ... . /Polycyclic aromatic hydrocarbons/|Exposures to other chemical mixtures that contain PAHs, such as cigarette smoke, coal tar, coal tar pitch, and bitumens, have been associated with increased incidences of lung cancer in humans. /Polycyclic aromatic hydrocarbons/|Dermal exposure to coal tar and shale oils containing PAHs have been associated with increased incidences of skin tumors in humans ... . /Polycyclic aromatic hydrocarbons/
7H-dibenzo(c,g)carbazole
7H-Dibenzo[c,g]carbazole Use and Manufacturing
A heterocyclic aromatic compound with potent mutagenic and carcinogenic properties
(1977) NOT PRODUCED COMMERCIALLY IN US|(1979) NOT PRODUCED COMMERCIALLY IN US
GAS CHROMATOGRAPHY-MASS SPECTROMETRY WITH COMPUTER DATA SYSTEM WAS USED TO ANALYZE POLYCYCLIC MATERIALS IN ASPHALT HOT MIX PLANTS.|USEPA Method 8100. Polynuclear Aromatic Hydrocarbons. Capillary column gas chromatography with FID detection. Detection limit not reported.
Health Hazards -> Carcinogens
Computed Properties
Molecular Weight:267.3
XLogP3:5.9
Hydrogen Bond Donor Count:1
Exact Mass:267.104799419
Monoisotopic Mass:267.104799419
Topological Polar Surface Area:15.8
Heavy Atom Count:21
Complexity:355
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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