832-69-9 Usage
Uses
1-Methylphenanthrene is a polycyclic aromatic hydrocarbon that has been found in particulate matter from small-scale biomass combustion from old and modern technologies and that has caused acute systemic and lung inflammation in mice after intratracheal aspiration.
Definition
ChEBI: A member of the class of phenanthrenes that is phenanthrene substituted by a methyl group at position 1.
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.
