832-69-9 Usage
Description
1-Methylphenanthrene, also known as 1-methylphenanthrene, is a member of the class of phenanthrenes that is phenanthrene substituted by a methyl group at position 1. It is a polycyclic aromatic hydrocarbon (PAH) that has been found in particulate matter from small-scale biomass combustion from both old and modern technologies.
Uses
Used in Environmental Research:
1-Methylphenanthrene is used as a biomarker for [identifying the presence of particulate matter from small-scale biomass combustion] in environmental studies. Its presence in samples can indicate exposure to pollutants from combustion processes.
Used in Toxicological Studies:
1-Methylphenanthrene is used as a test compound for [studying the effects of polycyclic aromatic hydrocarbons on biological systems] in toxicological research. It has been found to cause acute systemic and lung inflammation in mice after intratracheal aspiration, providing valuable insights into the potential health risks associated with exposure to PAHs.
Synthesis Reference(s)
The Journal of Organic Chemistry, 45, p. 2009, 1980 DOI: 10.1021/jo01298a054Tetrahedron Letters, 6, p. 359, 1965
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-METHYLPHENANTHRENE, 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. 1-METHYLPHENANTHRENE is sensitive to excessive heat and light.
Fire Hazard
Flash point data for 1-METHYLPHENANTHRENE are not available. 1-METHYLPHENANTHRENE is probably combustible.
Source
Detected in 8 diesel fuels at concentrations ranging from 0.10 to 210 mg/L with a mean
value of 44.33 mg/L (Westerholm and Li, 1994). Identified in a South Louisiana crude oil at a
concentration of 111 ppm (Pancirov and Brown, 1975). Schauer et al. (1999) reported 1-
methylphenanthrene in diesel fuel at a concentration of 28 μg/g and in a diesel-powered mediumduty
truck exhaust at an emission rate of 17.0 μg/km.
California Phase II reformulated gasoline contained 1-methylphenathrene at a concentration of
3.91 g/kg. Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without
catalytic converters were approximately 1.63 and 122 μg/km, respectively (Schauer et al., 2002).
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 respective gas-phase
and particle-phase emission rates of 1-methylphenanthrene were 2.22 and 0.579 mg/kg of pine
burned and 1.04 and 0.050 mg/kg of oak burned. The gas-phase emission rate was 0.720 mg/kg of
eucalyptus burned.
Check Digit Verification of cas no
The CAS Registry Mumber 832-69-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,3 and 2 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 832-69:
(5*8)+(4*3)+(3*2)+(2*6)+(1*9)=79
79 % 10 = 9
So 832-69-9 is a valid CAS Registry Number.
InChI:InChI=1/C15H12/c1-11-5-4-8-15-13(11)10-9-12-6-2-3-7-14(12)15/h2-10H,1H3
832-69-9Relevant articles and documents
Deno,Chafetz
, p. 449 (1960)
Alumina-Mediated π-Activation of Alkynes
Akhmetov, Vladimir,Amsharov, Konstantin,Feofanov, Mikhail,Sharapa, Dmitry I.
, p. 15420 - 15426 (2021/09/30)
The ability to induce powerful atom-economic transformation of alkynes is the key feature of carbophilic π-Lewis acids such as gold- and platinum-based catalysts. The unique catalytic activity of these compounds in electrophilic activations of alkynes is explained through relativistic effects, enabling efficient orbital overlapping with π-systems. For this reason, it is believed that noble metals are indispensable components in the catalysis of such reactions. In this study, we report that thermally activated γ-Al2O3activates enynes, diynes, and arene-ynes in a manner enabling reactions that were typically assigned to the softest π-Lewis acids, while some were known to be triggered exclusively by gold catalysts. We demonstrate the scope of these transformations and suggest a qualitative explanation of this phenomenon based on the Dewar-Chatt-Duncanson model confirmed by density functional theory calculations.
Construction of Phenanthrenes and Chrysenes from β-Bromovinylarenes via Aryne Diels-Alder Reaction/Aromatization
Singh, Vikram,Verma, Ram Subhawan,Khatana, Anil K.,Tiwari, Bhoopendra
, p. 14161 - 14167 (2019/10/28)
A highly efficient transition-metal-free general method for the synthesis of polycyclic aromatic hydrocarbons like phenanthrenes and chrysenes (and tetraphene) from β-bromovinylarenes and arynes has been developed. The reactions proceed via an aryne Diels-Alder (ADA) reaction, followed by a facile aromatization. This is the first report on direct construction of chrysenes (and tetraphene) using the ADA approach. Unlike the literature method which is limited to only 9/10-substituted derivatives, this method gives access to a wide variety of functionalized phenanthrenes.
Regioselective Synthesis of Polycyclic and Heptagon-embedded Aromatic Compounds through a Versatile π-Extension of Aryl Halides
Fu, Wai Chung,Wang, Zheng,Chan, Wesley Ting Kwok,Lin, Zhenyang,Kwong, Fuk Yee
supporting information, p. 7166 - 7170 (2017/06/13)
A versatile π-extension reaction was developed based on the three-component cross-coupling of aryl halides, 2-haloarylcarboxylic acids, and norbornadiene. The transformation is driven by the direction and subsequent decarboxylation of the carboxyl group, while norbornadiene serves as an ortho-C?H activator and ethylene synthon via a retro-Diels–Alder reaction. Comprehensive DFT calculations were performed to account for the catalytic intermediates.