| Identification | More | [Name]
Chrysene | [CAS]
218-01-9 | [Synonyms]
Crysene
CHRYSEN
CHRYSENE
Chrycene
NSC 6175
Chrysene,90%
Chrysene,98%
[4]Phenacene
CHRYSENE PURUM
Chrysene (purity)
Chrysene Standard
chrysene solution
Benz(a)phenanthrene
rcrawastenumberu050
1,2-Benzphenanthrene
BENZO[A]PHENANTHRENE
Chrysene in Methanol
1,2-Benzophenanthrene
Benzo[a]Phenanthrenee
CHRYSENE 100MG NEAT
Rcra waste number U050
1,2-benzophenanthracene
BENZO[ALPHA]PHENANTHRENE
CHRYSENE OEKANAL, 100 MG
45248, Chrysene (purity)
1,2,5,6-dibenzonaphthalene
CHRYSENE FOR SYNTHESIS 1 G
ChryseneSolution,50mg/L,1mL
ChryseneSolution,10mg/L,1ml
Chrysene @100 μg/mL in MeOH
CHRYSENE ZONE-REFINED 98%
2,2-DIMETHYLPHENYLPROPANONE
ChryseneSolution,200mg/L,1ml
Chrysene@50 μg/mL in Toluene
ChryseneSolution,100mg/L,1ml
Chrysenesolution,500mg/L,1mL
ChryseneSolution,100mg/L,5ml
ChryseneSolution,2000mg/L,1ml
Chrysene @0.2 mg/mL in CH2Cl2
ChryseneSolution,1000mg/L,1mL
Chrysene 200 μg/mL In Toluene
ChryseneSolution,100mg/L,2x5ml
coaltarpitchvolatiles:chrysene
benzo(a)phenanthrene(chrysene)
CHRYSENE, 1X1ML, ACET, 1000UG/ML
CHRYSENE, 1X1ML, CH2CL2, 200UG/ML
Chrysene@0.5 mg/mL in Acetonitrile
DI-POT.HYDROGEN PHOSPHATE 3-HYDRATE
Chrysene @2.0 mg/mL in Dichloromethane
Benzo[a]phenanthrene (purified by sublimation)
Benzo[a]phenanthrene (purified by sublimation) >
1,2-benzophenanthrene1.1.1-trichloro-2-methyl-2-propanolbenzo(a)phenanthrene | [EINECS(EC#)]
205-923-4 | [Molecular Formula]
C18H12 | [MDL Number]
MFCD07698607 | [Molecular Weight]
228.29 | [MOL File]
218-01-9.mol |
| Chemical Properties | Back Directory | [Appearance]
Chrysene is a combustible, white (when pure), red, or blue, fluorescent crystalline solid. Odorless. Chrysene 859 Polycyclic aromatic hydrocarbons (PAHs) are compounds containing multiple benzene rings and are also called polynuclear aromatic hydrocarbons | [Melting point ]
252-254 °C (lit.) | [Boiling point ]
448 °C (lit.) | [density ]
1.274 | [vapor pressure ]
4.3 at 25 °C (de Kruif, 1980) | [refractive index ]
1.7480 (estimate) | [Fp ]
-17℃ | [storage temp. ]
2-8°C | [solubility ]
<0.0001g/l | [form ]
neat | [color ]
White to Light yellow to Light orange | [Stability:]
Stable. Combustible. Incompatible with strong oxidizing agents. | [Water Solubility ]
insoluble | [Merck ]
2255 | [BRN ]
1909297 | [Henry's Law Constant]
1.97, 6.91, 18.8, 52.3, and 118 at 4.1, 11.0, 18.0, 25.0, and 31.0 °C, respectively (Bamford et al.,
1998) | [InChIKey]
WDECIBYCCFPHNR-UHFFFAOYSA-N | [Uses]
Organic synthesis. | [CAS DataBase Reference]
218-01-9(CAS DataBase Reference) | [IARC]
2B (Vol. 92) 2010 | [NIST Chemistry Reference]
Chrysene(218-01-9) | [EPA Substance Registry System]
218-01-9(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T,N,Xn,F | [Risk Statements ]
R45:May cause cancer.
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R68:Possible risk of irreversible effects.
R40:Limited evidence of a carcinogenic effect.
R67:Vapors may cause drowsiness and dizziness.
R66:Repeated exposure may cause skin dryness or cracking.
R36:Irritating to the eyes.
R11:Highly Flammable. | [Safety Statements ]
S53:Avoid exposure-obtain special instruction before use .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S36/37:Wear suitable protective clothing and gloves .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
UN 3077 9/PG 3
| [WGK Germany ]
3
| [RTECS ]
GC0700000
| [HazardClass ]
9 | [PackingGroup ]
III | [HS Code ]
29029090 | [Safety Profile]
Confirmed carcinogen
with experimental carcinogenic,
neoplastigenic, and tumorigenic data by skin
contact. Human mutation data reported.
When heated to decomposition it emits
acrid smoke and fumes. | [Hazardous Substances Data]
218-01-9(Hazardous Substances Data) | [Toxicity]
Acute LC50 for Neanthes arenaceodentata >50 μg/L (Rossi and Neff, 1978). |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Maleic anhydride-->ASPHALTUM-->Polishing oil-->1,2,4-Trimethylbenzene-->1-Naphthalenecarboxaldehyde, 2-(2-formylphenyl)--->2-BROMOCHRYSENE-->Benzene, 1,1'-(1E)-1,2-ethenediylbis[2-ethynyl--->1,2,3,4-TETRAHYDROCHRYSENE-->1-(2-((4-Methoxyphenyl)ethynyl)phenyl)ethanone-->2-ETHYNYLBENZALDEHYDE-->2,5-Norbornadiene-->2-Bromobenzoyl chloride-->1-Iodonaphthalene-->2-(TRIMETHYLSILYL)PHENYL TRIFLUOROMETHANESULFONATE | [Preparation Products]
DIBENZO(A,E)PYRENE-->6,12-Dibromochrysene-->Crisnatol |
| Hazard Information | Back Directory | [General Description]
A crystalline solid. Denser than water and insoluble in water. The primary hazard is the threat to the environment. Immediate steps should be taken to limit spread to the environment. Toxic by ingestion. Used to make other chemicals. | [Reactivity Profile]
Vigorous reactions, sometimes amounting to explosions, can result from the contact between aromatic hydrocarbons, such as CHRYSENE(218-01-9), and strong oxidizing agents. They can react exothermically with bases and with diazo compounds. Substitution at the benzene nucleus occurs by halogenation (acid catalyst), nitration, sulfonation, and the Friedel-Crafts reaction. | [Air & Water Reactions]
Insoluble in water. | [Hazard]
Possible carcinogen. | [Health Hazard]
ACUTE/CHRONIC HAZARDS: Toxic. | [Potential Exposure]
Almost never found by itself, chrysene is found in gasoline and diesel exhaust as well as in cigarette smoke; and in coal tar; coal tar pitch; creosote. It is used in organic synthesis. | [Fire Hazard]
Some may burn but none ignite readily. Containers may explode when heated. Some may be transported hot. | [First aid]
If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit. | [Shipping]
UN3077 Environmentally Hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required. | [Incompatibilities]
Contact with strong oxidizers may cause fire and explosion hazard | [Chemical Properties]
Chrysene is a combustible, white (when pure), red, or blue, fluorescent crystalline solid. Odorless. Chrysene 859 Polycyclic aromatic hydrocarbons (PAHs) are compounds containing multiple benzene rings and are also called polynuclear aromatic hydrocarbons | [Chemical Properties]
crystalline powder | [Waste Disposal]
Chrysene may be destroyed by permanganate oxidation, by high-temperature incinerator with scrubbing equipment; or by microwave plasma treatment. | [Physical properties]
Orthorhombic, bipyramidal plates from benzene exhibiting strong reddish-blue fluorescence under
UV light | [Definition]
ChEBI: Chrysene is an ortho-fused polycyclic arene found commonly in the coal tar. It has a role as a plant metabolite. | [Synthesis Reference(s)]
Tetrahedron Letters, 29, p. 3865, 1988 DOI: 10.1016/S0040-4039(00)82136-X | [Carcinogenicity]
The IARC has determined that there is
limited evidence that chrysene is carcinogenic
to experimental animals.ACGIH has classified
chrysene as a confirmed animal carcinogen
with unknown relevance to humans; a numerical
threshold limit value (TLV) is not
recommended. | [Source]
Identified in Kuwait and South Louisiana crude oils at concentrations of 6.9 and 17.5
ppm, respectively (Pancirov and Brown, 1975). Also present in high octane gasoline (6.7 mg/kg),
bitumen (1.64–5.14 ppm), gasoline exhaust (27–318 μg/m3), cigarette smoke (60 μg/1,000
cigarettes), and South Louisiana crude oil (17.5 ppm) (quoted, Verschueren, 1983). Also detected
in fresh motor oil (56 mg/L), used motor oil (10.17 mg/L) (Pasquini and Monarca, 1093).
Detected in groundwater beneath a former coal gasification plant in Seattle, WA at a
concentration of 10 μg/L (ASTR, 1995). The concentration of chrysene in coal tar and the
maximum concentration reported in groundwater at a mid-Atlantic coal tar site were 3,600 and 0.0063 mg/L, respectively (Mackay and Gschwend, 2001). Based on laboratory analysis of 7 coal
tar samples, chrysene concentrations ranged from 620 to 5,100 ppm (EPRI, 1990). Chrysene was
also detected in 9 commercially available creosote samples at concentrations ranging from 19 to
620 mg/kg (Kohler et al., 2000).
Identified in high-temperature coal tar pitches used in roofing operations at concentrations
ranging from 2,600 to 88,000 mg/kg (Arrendale and Rogers, 1981; Malaiyandi et al., 1982).
Chrysene was detected in asphalt fumes at an average concentration of 115.67 ng/m3 (Wang et
al., 2001).
Under atmospheric conditions, a low rank coal (0.5–1 mm particle size) from Spain was burned
in a fluidized bed reactor at seven different temperatures (50 °C increments) beginning at 650 °C.
The combustion experiment was also conducted at different amounts of excess oxygen (5 to 40%)
and different flow rates (700 to 1,100 L/h). At 20% excess oxygen and a flow rate of 860 L/h, the
amount of chrysene emitted ranged from 127.9 ng/kg at 950 °C to 1,186.0 ng/kg at 750 °C. The
greatest amount of PAHs emitted were observed at 750 °C (Mastral et al., 1999). | [Environmental Fate]
Biological. When chrysene was statically incubated in the dark at 25 °C with yeast extract and
settled domestic wastewater inoculum, significant biodegradation with varied adaptation rates was
observed. At concentrations of 5 and 10 mg/L, 59 and 38% biodegradation, respectively, were
observed after 28 d (Tabak et al., 1981).
Soil. The reported half-lives for chrysene in a Kidman sandy loam and McLaurin sandy loam
are 371 and 387 d, respectively (Park et al., 1990).
Surface Water. In a 5-m deep surface water body, the calculated half-lives for direct
photochemical transformation at 40 °N latitude, in the midsummer during midday were 13 h and
68 d with and without sediment-water partitioning, respectively (Zepp and Schlotzhauer, 1979).
Photolytic. Based on structurally related compounds, chrysene may undergo photolysis to yield
quinones (U.S. EPA, 1985) and/or hydroxy derivatives (Nielsen et al., 1983). The atmospheric
half-life was estimated to range from 0.802 to 8.02 h (Atkinson, 1987). Behymer and Hites (1985)
determined the effect of different substrates on the rate of photooxidation of chrysene using a
rotary photoreactor. The photolytic half-lives of chrysene using silica gel, alumina, and fly ash
were 100, 78, and 38 h, respectively. | [storage]
Color Code—Green: General storage may be used.Prior to working with chrysene you should be trained on itsproper handling and storage. A regulated, marked areashould be established where this chemical is handled, used,or stored in compliance with OSHA Standard 1910.1045.Store in tightly closed containers in a cool, well-ventilatedarea away from oxidizers. Sources of ignition, such assmoking and open flames, are prohibited where this chemical is used, handled, or stored in a manner that could createa potential fire or explosion hazard. | [Purification Methods]
Purify chrysene by chromatography on alumina from pet ether in a darkened room. Its solution in *C6H6 is passed through a column of decolorising charcoal, then crystallised by concentrating the eluate. It has also been purified by crystallising from *C6H6 or *C6H6/pet ether, and by zone refining. [Gorman et al. J Am Chem Soc 107 4404 1985]. It is freed from 5H-benzo[b]carbazole by dissolving it in N,N-dimethylformamide and successively adding small portions of alkali and iodomethane until the fluorescent colour of the carbazole anion no longer appears when alkali is added. The chrysene (and alkylated 5H-benzo[b]carbazole) separate on addition of water. Final purification is by crystallisation from ethylcyclohexane and/or from 2-methoxyethanol [Bender et al. Anal Chem 36 1011 1964]. It can be sublimed in a vacuum. [Beilstein 5 IV 2554.] | [Toxicity evaluation]
Generally, disposal of PAH from the industrial plants, accidental
release from the containers, smoke from plant,
combustion, or automobile exhaust causes chrysene and other
PAHs to enter the environment. Because of the poor water
solubility and low vapor pressure, chrysene has limited chance
to get washed away or evaporate in the environment. Therefore,
it remains immobile in soils. If exposed to water, it gets
absorbed on the particulate matters and either float or sediment
on the riverbed. The rate of biodegradation in soil ranges
from 77 to 387 days depending on the soil type.Chrysene does
not undergo hydrolysis due to the lack of hydrolyzable functional
groups. However, it undergoes photochemical oxidations
when exposed to the environment. Dihydrodiol is the
common degradation product of chrysene. Half-life of degradation of chrysene, absorbed to soot particles and
exposed to sunlight in air containing 10 ppm nitrogen oxides is
26 days. The National Research Council (NRC 1983) noted
that the PAHs adsorbed to soot particles are more resistant to
photochemical reactions than pure compounds. |
| Questions And Answer | Back Directory | [Description]
Chrysene is a polycyclic aromatic hydrocarbon (PAH) consisting of four fused benzene rings. Some of its derivatives such as electroluminescent 3, 6, 9, 12-tetrasubstituted chrysenes are useful in electroluminescent applications such as being used in the organic light emitting dioxide (OLED). They are also relates to electronic devices in which the active layer includes such a chrysene composition. Chrysene is a potential carcinogen.
| [Sources]
Tokito, Shizuo, et al. Applied Physics Letters 77.2(2000):160-162.
Gao, Weiying, D. T. Deibler, and V. Rostovtsev. "Chrysene derivative host materials." US, US8932733. 2015.
Ionkin, Alex Sergey. "Tetra-substituted chrysenes for luminescent applications." US, US8115378. 2012.
https://en.wikipedia.org/wiki/Chrysene
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