3697-24-3 Usage
Chemical Properties
Three of the listed PAHs (dibenz[a,h]acridine, dibenz[a,j]acridine, and 7H-dibenzo[c,g]carbazole) contain a nitrogen atom as part of a ring and therefore are classified as heterocyclic PAHs. The PAHs can exist as leaflets, plates, needles, or at room temperature and range in color from colorless to yellow, green or blue. All PAHs are soluble in water and slightly soluble in ethanol, acetone or acid; most are soluble in benzene. Physical and chemical properties of the 15 PAHs are listed in the table below. In addition to the properties listed in the table, benzo[a]pyrene has a specific gravity of 1.351 and a vapor density relative to air of 8.7, and dibenzo[a,h]anthracene has a specific gravity of 1.282 (HSDB 2009).
Uses
Different sources of media describe the Uses of 3697-24-3 differently. You can refer to the following data:
1. IARC (1983) reported that no commercial uses or applications were known for dibenzo[a,h]pyrene, dibenzo[a,i]pyrene, and 5-methylchrysene. The remaining twelve listed PAHs are used only in biochemical, biomedical, laboratory, or cancer research (HSDB 2009). At least five of the listed PAHs are present in coal tar, which is used as a fuel in the steel industry in open-hearth and blast furnaces (HSDB 2009). Coal tar is also used in the clinical treatment of skin disorders such as eczema, dermatitis, and psoriasis. Coal tar is distilled to produce a variety of products, including coal-tar pitch and creosote. At least two of the listed PAHs are present in coal-tar pitch, which is used primarily as a binder for aluminum smelting electrodes in the aluminum reduction process. Coal-tar pitch is also used in roofing, in surface coatings, for pitch-coke production, and for a variety of other applications (IARC 1985). At least two of the listed PAHs are found in creosote, which is used to preserve railroad ties, marine pilings, and telephone poles. Some creosote is used for fuel by steel producers (NIOSH 1977). At least three of the listed PAHs are present in bitumens and asphalt, which are used for paving roads, sound- and water-proofing, and coating pipes.
2. 5-Methylchrysene is one of the methylated chrysenes (MeChry), as an aryl hydrocarbon receptor (AhR) agonist. Methylated chrysenes (MeChry) are important cigarette smoke constituents and 5-MeChry has been listed as possibly carcinogenic to humans. 5-Methylchrysene is a possible carcinogenic agent.
General Description
Purple crystals. Water insoluble.
Reactivity Profile
Vigorous reactions, sometimes amounting to explosions, can result from the contact between aromatic hydrocarbons, such as 5-METHYLCHRYSENE, 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.
Safety Profile
Confirmed carcinogen
with experimental carcinogenic,
neoplastigenic, and tumorigenic data.
Mutation data reported. When heated to
decomposition it emits acrid smoke and
irritating fumes.
Carcinogenicity
The 15 individual PAHs are reasonably anticipated to be human carcinogens
based on sufficient evidence of carcinogenicity from studies in experimental animals.
Check Digit Verification of cas no
The CAS Registry Mumber 3697-24-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,6,9 and 7 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 3697-24:
(6*3)+(5*6)+(4*9)+(3*7)+(2*2)+(1*4)=113
113 % 10 = 3
So 3697-24-3 is a valid CAS Registry Number.
InChI:InChI=1/C19H14/c1-13-12-15-7-3-4-8-16(15)18-11-10-14-6-2-5-9-17(14)19(13)18/h2-12H,1H3
3697-24-3Relevant articles and documents
Gold-catalyzed 6-exo-dig cycloisomerization: A versatile approach to functionalized phenanthrenes
Shu, Chao,Li, Long,Chen, Cheng-Bin,Shen, Hong-Cheng,Ye, Long-Wu
, p. 1525 - 1529 (2014/06/09)
A novel gold-catalyzed 6-exo-dig cycloisomerization of o-propargylbiaryls has been developed that provides ready access to functionalized phenanthrenes in largely good to excellent yields. Notable features of this method are readily available starting materials, mild reaction conditions, and broad substrate scope. Golden cat: A novel gold-catalyzed 6-exo-dig cycloisomerization of o-propargylbiaryls has been developed that provides ready access to functionalized phenanthrenes in largely good to excellent yields. Notable features of this method are readily available starting materials, mild reaction conditions, and broad substrate scope.
A new efficient route to the phenolic derivatives of chrysene and 5-methylchrysene, precursors to dihydrodiol and diol epoxide metabolites of chrysene and 5-methylchrysene, through Suzuki cross-coupling reaction
Kumar, Subodh
, p. 3157 - 3161 (2007/10/03)
A new, abbreviated synthesis of 5-methylchrysene (17), 2-hydroxychrysene (16), 8-hydroxy-5-methylchrysene (23), and 2-hydroxy-5-methylchrysene (24) is reported. The phenolic derivatives 16, 23, and 24 can easily be converted to carcinogenic dihydrodiol and diol epoxide metabolites of chrysene and 5-methylchrysene. The method entails the initial Suzuki cross-coupling reaction of naphthalene-2-boronic acid (1) and/or 6-methoxynaphthalene-2-boronic acid (2) with 2-bromo-5-methoxybenzaldehyde (3), methyl 2-bromophenylacetate (4), 2-bromophenylacetone (5), and/or 2-iodo-5-methoxyphenylacetone (6) to produce 2-(2-naphthyl)-5-methoxybenzaldehyde (7), methyl 2-(6-methoxy-2-naphthyl)phenylacetate (8), 2-(2-naphthyl)phenylacetone (9), 2-(2-naphthyl)-5-methoxyphenylacetone (10), and 2-(6-methoxy-2-naphthyl)phenylacetone (11) in 55-98% yields. 2-Methoxychrysene (15) was obtained with high regioselectivity by two different procedures. In the first procedure, the aldehyde function of 7 was elongated with trimethylsulfonium iodide under phase transfer conditions to generate the ethylene oxide 12 which after methanesulfonic acid treatment produced 15. The second procedure involved modification of ester 8 to its aldehyde analogue 14 which was subsequently treated with methanesulfonic acid to produce 15. Phenylacetone 10 was converted by methanesulfonic acid treatment into 8-methoxy-5-methylchrysene (18) with 90% regioselectivity. However, the similar cyclization of phenylacetones 9 and 11 to 5-methylchrysene (17) and 2-methoxy-5-methylchrysene (19) occurred with only 33-50% regioselectivity. The separation of 17 and 19 from their chromatographically similar 6-methylbenz[a]anthracene byproducts 20 and 22 was readily achieved by a chemical method. The methoxy derivatives of chrysene were finally demethylated with boron tribromide to the corresponding phenolic compounds in 90-98% yields.
A NEW SYNTHESIS OF POLYCYCLIC AROMATIC HYDROCARBONS VIA TITANIUM(IV)-CATALYZED ALDOL-TYPE CONDENSATION OF SILYL ENOL ETHERS WITH 2-ARYLACETALDEHYDES
Raddo, Pasquale Di,Harvey, Ronald G.
, p. 3885 - 3886 (2007/10/02)
Anovel one-pot synthesis of angular polycyclic hydrocarbon ring systems involving Ti(IV)-catalyzed aldol-type condensation of silyl enol ethers with 2-arylacetaldehydes and cyclization of the adducts is described.
