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2-Methylnaphthalene

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2-Methylnaphthalene Basic information

Product Name:
2-Methylnaphthalene
CAS:
91-57-6
MF:
C11H10
MW:
142.2
EINECS:
202-078-3
Mol File:
91-57-6.mol
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2-Methylnaphthalene Chemical Properties

Melting point:
34-36 °C(lit.)
Boiling point:
241-242 °C(lit.)
Density 
1.01
vapor pressure 
5.4 (extrapolated, Mackay et al., 1982)
refractive index 
1.6019
Flash point:
208 °F
storage temp. 
2-8°C
solubility 
0.025g/l
form 
Crystalline Low Melting Solid
form 
Solid
color 
White
Water Solubility 
0.00246 g/100 mL
FreezingPoint 
34.5℃
BRN 
906859
Henry's Law Constant
6.13 at 25 °C (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999)
Stability:
Stable. Incompatible with strong oxidizing agents.
InChIKey
QIMMUPPBPVKWKM-UHFFFAOYSA-N
CAS DataBase Reference
91-57-6(CAS DataBase Reference)
NIST Chemistry Reference
Naphthalene, 2-methyl-(91-57-6)
EPA Substance Registry System
2-Methylnaphthalene (91-57-6)
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Safety Information

Hazard Codes 
Xn,N,T
Risk Statements 
22-36/37/38-51/53-63-43-23/24/25-45-20/21/22-67-40
Safety Statements 
26-37/39-61-36/37-24/25-23-53-36-29
RIDADR 
UN 3077 9/PG 3
WGK Germany 
2
RTECS 
QJ9635000
TSCA 
Yes
HazardClass 
9
PackingGroup 
III
HS Code 
29029080
Hazardous Substances Data
91-57-6(Hazardous Substances Data)
Toxicity
Acute oral LD50 for rats 1,630 mg/kg (quoted, RTECS, 1985).

MSDS

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2-Methylnaphthalene Usage And Synthesis

Chemical Properties

Solid. Insoluble inwater; soluble in alcohol and ether. Combustible.

Uses

Organic synthesis, insecticides.

Definition

ChEBI: A methylnaphthalene carrying a methyl substituent at position 2.

Production Methods

Alkylnaphthalenes are formed as pyrolysis products in cigarette smoke. Some have been identified in commercial carbon paper. They are also the major components of the C10–C13 alkylnaphthalene concentrate fraction, which distills at 400–500F. A C11–C12 petroleum mixture of reformates that contained about 23% alkylnaphthalenes caused skin and eye effects. The toxicity of the alkylnaphthalenes to marine species is greater than that of the alkylbenzenes (85). The toxicity and the bioaccumulation increase with molecular weight. Nocardia cultures, isolated from soil, preferentially oxidized alkylnaphthalenes when methylated in the two positions. Methylnaphthalene can occur as the 1- or 2-, the alpha or the beta isomer. 1-Naphthalene, a flammable solid, has also been identified in the wastewater of coking operations, and in textile processing plants. Methylnaphthalene is used as a component in slow-release insecticides and in mole repellents. Workplace exposures to 18–32 mg/m3 for 2-methylnaphthalene have been reported.

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 2142, 1989 DOI: 10.1021/jo00270a024
Synthesis, p. 1036, 1982
Tetrahedron Letters, 36, p. 6051, 1995

General Description

White crystalline solid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2-Methylnaphthalene is incompatible with strong oxidizing agents. 2-Methylnaphthalene is also incompatible with peroxides and oxygen.

Hazard

Lower respiratory tract irritant and lungdamage. Questionable carcinogen.

Fire Hazard

2-Methylnaphthalene is combustible.

Carcinogenicity

The carcinogenic potential of 1- and 2-methyl was investigated in B6C3F1 mice. Female and male mice were given methylnaphthalene in their diets for 81 weeks. The results indicated that 1-methyl was a possible weak carcinogen in the lung of male but not female mice whereas 2-methyl did not possess unequivocal carcinogenic potential in these mice.

Source

Detected in distilled water-soluble fractions of No. 2 fuel oil (0.42 mg/L), jet fuel A (0.17 mg/L), diesel fuel (0.27 mg/L), military jet fuel JP-4 (0.07 mg/L) (Potter, 1996), new motor oil (0.42 to 0.66 μg/L), and used motor oil (46 to 54 μg/L) (Chen et al., 1994). Present in diesel fuel and corresponding aqueous phase (distilled water) at concentrations of 3.5 to 9.0 g/L and 180 to 340 μg/L, respectively (Lee et al., 1992). Schauer et al. (1999) reported 2-methylnaphthalene in diesel fuel at a concentration of 980 μg/g and in a diesel-powered medium-duty truck exhaust at an emission rate of 511 μg/km.
Thomas and Delfino (1991) equilibrated contaminant-free groundwater collected from Gainesville, FL with individual fractions of three individual petroleum products at 24–25 °C for 24 h. The aqueous phase was analyzed for organic compounds via U.S. EPA approved test method 625. Average 2-methylnaphthalene concentrations reported in water-soluble fractions of unleaded gasoline, kerosene, and diesel fuel were 256, 354, and 267 μg/L, respectively.
California Phase II reformulated gasoline contained 2-methylnaphthalene at a concentration of 1.33 g/kg. Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without catalytic converters were approximately 1.00 and 50.0 mg/km, respectively (Schauer et al., 2002).
Based on laboratory analysis of 7 coal tar samples, 2-methylnaphthalene concentrations ranged from 680 to 42,000 ppm (EPRI, 1990). Detected in 1-yr aged coal tar film and bulk coal tar at concentrations of 25,000 and 26,000 mg/kg, respectively (Nelson et al., 1996). A high-temperature coal tar contained 2-methylnaphthalene at an average concentration of 1.23 wt % (McNeil, 1983).
Lee et al. (1992a) equilibrated eight coal tars with distilled water at 25 °C. The maximum concentration of 2-methylnaphthalene observed in the aqueous phase is 1.4 mg/L.
Detected in wood-preserving creosotes at a concentration of 3.0 wt % (Nestler, 1974).
Typical concentration of 2-methylnaphthalene in a heavy pyrolysis oil is 7.4 wt % (Chevron Phillips, May 2003).
An impurity identified in commercially available acenaphthene (Marciniak, 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 gas-phase emission rates of 2-methylnaphthalene were 15.0 mg/kg of pine burned, 9.61 mg/kg of oak burned, and 5.69 mg/kg of eucalyptus burned.

Environmental Fate

Biological. 2-Naphthoic acid was reported as the biooxidation product of 2-methylnaphthalene by Nocardia sp. in soil using n-hexadecane as the substrate (Keck et al., 1989). Dutta et al. (1998) investigated the degradation of 2-methylnaphthalene using a bacterial strain of Sphingomonas paucimobilis grown on phenanthrene. Degradation products identified using GC-MS were 4- methylsalicylate, 2-methylnaphthoate, and 1-hydroxy-2-methylnaphthoate.
Estimated half-lives of 2-methylnaphthalene (0.6 μg/L) from an experimental marine mesocosm during the spring (8–16 °C), summer (20–22 °C), and winter (3–7 °C) were 11, 1.0, and 13 d, respectively (Wakeham et al., 1983).
Photolytic. Fukuda et al. (1988) studied the photodegradation of 2-methylnaphthalene and other alkylated naphthalenes in distilled water and artificial seawater using a high-pressure mercury lamp. Based upon an experimentally rate constant of 0.042/h, the photolytic half-life of 2- methylnaphthalene in water is 16.4 h.
Phousongphouang and Arey (2002) investigated gas-phase reaction of naphthalene with OH radicals in a 7-L Teflon chamber at 25 °C and 740 mmHg containing 5% humidity. The rate constant for this reaction was 4.86 x 10-11 cm3/molecule?sec.
Chemical/Physical. An aqueous solution containing chlorine dioxide in the dark for 3.5 d at room temperature oxidized 2-methylnaphthalene into the following: 1-chloro-2-methylnaphthalene, 3-chloro-2-methylnaphthalene, 1,3-dichloro-2-methylnaphthalene, 3-hydroxymethylnaphthalene, 2-naphthaldehyde, 2-naphthoic acid, and 2-methyl-1,4-naphthoquinone (Taymaz et al., 1979).

Purification Methods

Fractionally crystallise repeatedly from its melt, then fractionally distil under reduced pressure. It has been crystallised from *benzene and dried under vacuum in an Abderhalden pistol. It can be purified via its picrate (m 114-115o) or better via the 1,3,5-trinitrobenzene complex as for 1-methylnaphthalene (above). [Beilstein 5 IV 1693.]

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