832-69-9

Basic information

• Product Name: 1-METHYLPHENANTHRENE
• Synonyms: 1-METHYLPHENANTHRENE;1-methyl-phenanthren;PHENANTHRENE,1-METHYL-;1-Methylphenanthrene 100mg [832-69-9];NSC 146583
• CAS NO: 832-69-9
• Molecular Formula: C₁₅H₁₂
• Molecular Weight: 192.26
• EINECS: 212-622-1
• Mol File: 832-69-9.mol
• Article Data: 26

Chemical Properties

• Melting Point: 123°C
• Boiling Point: 353.25°C (rough estimate)
• Flash Point: 157.5 °C
• Appearance: /
• Density: 1.0561 (estimate)
• Vapor Pressure: 7.27E-05mmHg at 25°C
• Refractive Index: 1.6031 (estimate)
• Storage Temp.: Room Temperature
• Solubility: Soluble in alcohol (Weast, 1986)
• Water Solubility: 269ug/L(25 oC)
• CAS DataBase Reference: 1-METHYLPHENANTHRENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYLPHENANTHRENE(832-69-9)
• EPA Substance Registry System: 1-METHYLPHENANTHRENE(832-69-9)

Safety Data

• Hazardous Substances Data: 832-69-9(Hazardous Substances Data)

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.

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

Upstream product

• 917-64-6 methyl magnesium iodide 
• 107620-55-3 1,2,3,4,4a,9,10,10a-octahydro-1-oxo-phenanthren 
• 483-65-8 Retene 
• 6314-07-4 2-Isopropyl-8-methyl-[3]phenanthrol 
• 5947-49-9 podocarpic acid 
• 514-10-3 abietic acid 
• 93987-66-7 1-methyl-1,2,3,4,4a,10a-hexahydro-phenanthrene 
• 111589-13-0 8-methylphenanthren-3-ol 
• 97277-92-4 1,2,3,4-tetrahydro-1,1-dimethylphenanthrene 
• 854649-66-4 1-cyclohexyl-3-(2-methyl-cyclopentyl)-propane 
• 2883-13-8 1-(2-methyl-cyclopentyl)-3-phenyl-propane 
• 132649-61-7 1,1-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene 
• 408318-61-6 1-methyl-3,4-dihydro-phenanthrene 
• 17058-00-3 1-methyl-tetrahydrophenanthrene 

Downstream Products

• 217-37-8 benzo[c]picene 
• 42155-49-7 1-Phenanthreneacetonitrile 
• 42050-08-8 5(4H)-Acephenanthrylenone 
• 2531-84-2 2-methylphenathrene 
• 832-71-3 3-methylphenathrene 
• 883-20-5 9-methylphenanthrene 
• 85-01-8 phenanthrene 

Relevant articles and documents

Palladium-Catalyzed Sequential Vinyl C–H Activation/Dual Decarboxylation: Regioselective Synthesis of Phenanthrenes and Cyclohepta[1,2,3-de]naphthalenes

The application of a C(vinyl), C(aryl)-palladacycle from vinyl-containing substrates is challenging due to the interference of a reactive double bond in palladium catalysis. This Letter describes a [4 + 2] or [4 + 3] cyclization based on a C(vinyl), C(aryl)-palladacycle by employing α-oxocarboxylic acids as the insertion units under a palladium/air system. The reaction proceeded through the key vinyl C–H activation and dual decarboxylation sequence, forming phenanthrenes and cyclohepta[1,2,3-de]naphthalenes regioselectively in good yields. The synthetic versatility of this protocol is highlighted by the gram-scale synthesis and synthesizing functional material molecule.

Construction of Phenanthrenes and Chrysenes from β-Bromovinylarenes via Aryne Diels-Alder Reaction/Aromatization

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.

Systematic investigations on fused π-system compounds of seven benzene rings prepared by photocyclization of diphenanthrylethenes

We studied the photoproducts of 1-(n-phenanthryl)-2-(m-phenanthryl)ethenes (nEm; n, m = 1, 3 and 9) for understanding photocyclization patterns based on NMR spectroscopy. The crystal structures of the photoproducts were analyzed by X-ray crystallography, and the photophysical features of the photocyclized molecules were investigated based on emission and transient absorption measurements. Phenanthrene derivatives substituted at the 1- and 3-positions were prepared for synthesizing nEm by photocyclization of stilbene derivatives. We obtained four types of primary photoproducts (n@m) from the corresponding nEm. Two of them were found to have racemic molecular structures in the single crystal determined by X-ray crystallography. Besides the primary photoproducts, two types of secondary photoproducts (n@mPP) were isolated. Fluorescence quantum yields and lifetimes of the obtained photoproducts were determined in solution whereas the definite fluorescence quantum yields were obtained in the powder. Observation of the triplet-triplet absorption spectra in solution by laser photolysis techniques showed that intersystem crossing to the triplet state competes with the fluorescence process.