191-24-2 Usage
Description
1,12-Benzoperylene is a colorless to white crystalline solid that is water-insoluble. It is a research chemical derived from industrial and experimental coal gasification operations, where it has been detected in coal tar streams with a maximum concentration of 2.7 mg/m3.
Uses
Used in Research Chemicals Industry:
1,12-Benzoperylene is used as a research chemical for various scientific and experimental purposes, particularly in the field of coal gasification. Its properties and behavior are studied to better understand its potential applications and effects.
Used in Organic Semiconductors:
1,12-Benzoperylene is used as an n-channel organic semiconductor due to its unique electronic properties. This makes it a valuable material in the development of electronic devices and components, such as transistors and solar cells, where its semiconducting properties can be harnessed for improved performance and efficiency.
Used in Industrial Applications:
1,12-Benzoperylene is used in industrial applications, particularly in the coal gasification process. Its presence in coal tar streams indicates its potential role in the production and processing of coal-derived chemicals and materials.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Vigorous reactions, sometimes amounting to explosions, can result from the contact between aromatic hydrocarbons, such as 1,12-BENZOPERYLENE, 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.
Health Hazard
Inhalation of material may be harmful. Contact may cause burns to skin and eyes. Inhalation of Asbestos dust may have a damaging effect on the lungs. Fire may produce irritating, corrosive and/or toxic gases. Some liquids produce vapors that may cause dizziness or suffocation. Runoff from fire control may cause pollution.
Health Hazard
There is very little information available inthe literature on the toxicity of this compound. Benzo[g,h,i]perylene has low oraltoxicity. On the basis of its structural similarities with other carcinogenic polynucleararomatics, this compound is expected to show carcinogenic properties. Such evidence, however, is inadequate at the moment. A histidinereversion–Ames test for mutagenicity gaveinconclusive results.
Fire Hazard
Some may burn but none ignite readily. Containers may explode when heated. Some may be transported hot.
Safety Profile
Questionable carcinogen.Mutation data reported. When heated to decomposition itemits acrid smoke and irritating fumes.
Carcinogenicity
Subcutaneous or dermal administration
(repeated administration and initiation–promotion
protocols) of benzo[ghi]perylene to mice gave negative
results. Intrapulmonary injection into rats gave results considered
to be inadequate for evaluation.
Source
Drinking water standard: No MCLGs or MCLs have been proposed (U.S. EPA, 2000).
Detected in 7 of 8 diesel fuels at concentrations ranging from 0.008 to 0.35 mg/L with a
mean value of 0.113 mg/L (Westerholm and Li, 1994). Identified in Kuwait and South Louisiana
crude oils at concentrations of <1 and 1.6 ppm, respectively (Pancirov and Brown, 1975) and in
fresh motor oil (120 μg/kg) and used motor oil (108.8–289.4 mg/kg) (quoted, Verschueren, 1983).
Detected in asphalt fumes at an average concentration of 22.76 ng/m3 (Wang et al., 2001).
The concentration of benzo[ghi]perylene in coal tar and the maximum concentration reported in
groundwater at a mid-Atlantic coal tar site were 1,200 and 0.002 mg/L, respectively (Mackay and
Gschwend, 2001). Based on laboratory analysis of 7 coal tar samples, benzo[ghi]perylene
concentrations ranged from ND to 1,900 ppm (EPRI, 1990). Benzo[ghi]perylene was reported in a
high-temperature coal tar pitch used in roofing at concentrations ranging from 754 to 3,980 mg/kg
(Malaiyandi et al., 1982).
Nine commercially available creosote samples contained benzo[ghi]perylene at concentrations
ranging from 1 to 45 mg/kg (Kohler et al., 2000).
Schauer et al. (2001) measured organic compound emission rates for volatile organic
compounds, gas-phase semi-volatile organic compounds, and particle-phase organic compounds
from the residential (fireplace) combustion of pine, oak, and eucalyptus. The particle-phase
emission rates of benzo[ghi]perylene were 0.437 mg/kg of pine burned and 0.173 mg/kg of
eucalyptus burned.
Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without
catalytic converters were 0.26 and 10.7 μg/km, respectively (Schauer et al., 2002).
Environmental fate
Biological. Based on aerobic soil die away test data at 10 to 30 °C, the estimated half-lives
ranged from 590 to 650 d (Coover and Sims, 1987).
Groundwater. Based on aerobic soil die away test data at 10 to 30 °C, the estimated half-lives
ranged from 3.23 to 3.56 yr (Coover and Sims, 1987).
Photolytic. The atmospheric half-life was estimated to range from 0.321 to 3.21 h (Atkinson,
1987). Behymer and Hites (1985) determined the effect of different substrates on the rate of
photooxidation of benzo[ghi]perylene using a rotary photoreactor. The photolytic half-lives of
benzo[ghi]perylene using silica gel, alumina, and fly ash were 7.0, 22, and 29 h, respectively.
Chemical/Physical. At influent concentrations of 1.0, 0.1, 0.01, and 0.001 mg/L, the GAC
adsorption capacities were 10.7, 4.6, 2.0, and 0.85 mg/g, respectively (Dobbs and Cohen, 1980).
Purification Methods
It forms light green crystals on recrystallisation from *C6H6 or xylene and sublimes at 320-340o/0.05mm [UV: Hopff & Schweizer Helv Chim Acta 42 2315 1959, Clar Chem Ber 65 846 1932, Fluoresc. Spectrum: Bowen & Brocklehurst J Chem Soc 3875 1954]. It also recrystallises from propan-1-ol [Altman & Ginsburg J Chem Soc 466 1959]. The 1,3,5-Trinitrobenzene complex has m 310-313o (deep red crystals from *C6H6), the picrate has m 267-270o (dark red crystals from *C6H6), and the styphnate (2,4,6-trinitroresorcinol complex) has m 234o (wine red crystals from *C6H6). [Beilstein 5 IV 2766.]
Check Digit Verification of cas no
The CAS Registry Mumber 191-24-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,9 and 1 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 191-24:
(5*1)+(4*9)+(3*1)+(2*2)+(1*4)=52
52 % 10 = 2
So 191-24-2 is a valid CAS Registry Number.
InChI:InChI=1/C22H12/c1-3-13-7-9-15-11-12-16-10-8-14-4-2-6-18-17(5-1)19(13)21(15)22(16)20(14)18/h1-12H
191-24-2Relevant articles and documents
Scholz et al.
, p. 665 (1967)
REDUCTIVE RING CLOSURE OF HELICENES
Ayalon, Ari,Rabinovitz, Mordecai
, p. 2395 - 2398 (1992)
Reduction of -helicene (1) by alkali metal in THF yields a closed condensed polycyclic dianion i.e. benzoperylene dianion (3=).The ring closure reaction takes place via dihydro intermediate (2=).
Probing Diels-Alder reactivity on a model CNT sidewall
Jackson, Evan P.,Sisto, Thomas J.,Darzi, Evan R.,Jasti, Ramesh
, p. 3754 - 3758 (2016)
We have synthesized a cycloparaphenylene containing a perylene motif that is a model for a carbon nanotube sidewall. The reactivity of the sidewall model towards a Diels-Alder reaction using a masked acetylene was examined and similar reactivity was observed between the macrocyclic and planar substrate. This study suggests that a Diels-Alder reaction is a viable method for carbon nanotube growth using an appropriate template.
ORGANIC COMPOUND, THREE-DIMENSIONAL ORGANIC FRAMEWORK FORMED BY USING ORGANIC COMPOUND, SEPARATION SIEVE AND OPTICAL LAYER, WHICH COMPRISE ORGANIC FRAMEWORK, AND OPTICAL DEVICE COMPRISING OPTICAL LAYER AS OPTICAL AMPLIFICATION LAYER
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Paragraph 0356; 0359; 0360, (2019/02/13)
An organic compound, a three-dimensional organic structure formed by using the organic compound, a separation sieve and an optical layer having the organic structure, and an optical device having the optical layer as an optical amplification layer are provided. The organic structure includes a plurality of organic molecules self-assembled by non-covalent bonding. Each of the unit organic molecules has an aromatic ring, a first pair of substituents being connected to immediately adjacent positions of substitutable positions of the aromatic ring, and a second pair of substituents being connected to immediately adjacent positions of remaining substitutable positions of the aromatic ring. The unit organic molecules are self-assembled by van der Waals interaction, London dispersion interaction or hydrogen bonding between the first and the second pairs of the substituents and by pi-pi interactions between the aromatic rings.
Facile photochemical synthesis of 5,10-disubstituted [5]helicenes by removing molecular orbital degeneracy
Ito, Natsuki,Hirose, Takashi,Matsuda, Kenji
supporting information, p. 2502 - 2505 (2014/05/20)
Photocyclodehydrogenation is a key reaction to synthesize helicenes; however, because of overannulation, it is not applicable to the synthesis of [5]helicene. Introduction of a cyano group was found to remove the orbital degeneracy of the low-lying unoccupied MOs; consequently, the lowest excitation comprises a single transition involving the C2-antisymmetric MO. Therefore, the problematic overannulation can be effectively suppressed. Moreover, in combination with the Knoevenagel reaction, a one-pot synthesis of 5,10-dicyano[5]helicene with 67% yield was accomplished.
