Orthoxylene
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| Names | |||
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Preferred IUPAC name
1,2-Xylene
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Systematic IUPAC name
1,2-Dimethylbenzene
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| Other names
o-Xylene
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| Identifiers | |||
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3D model (JSmol)
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| ChEBI | |||
| ChemSpider | |||
| DrugBank | |||
| ECHA InfoCard | 100.002.203 | ||
| KEGG | |||
| RTECS number | ZE2450000 | ||
| UNII | |||
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| Properties | |||
| C8H10 | |||
| Molar mass | 106.17 g·mol−1 | ||
| Appearance | Colorless liquid | ||
| Density | 0.88 g/ml | ||
| Melting point | −24 °C (−11 °F; 249 K) | ||
| Boiling point | 144.4 °C (291.9 °F; 417.5 K) | ||
| 0.02% (20°C) | |||
| Solubility in ethanol | very soluble | ||
| Solubility in diethyl ether | very soluble | ||
| Vapor pressure | 7 mmHg (20°C) | ||
| -77.78·10−6 cm3/mol | |||
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Refractive index (nD)
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1.50545 | ||
| Viscosity | 1.1049 cP at 0 °C 0.8102 cP at 20 °C |
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| Structure | |||
| 0.64 D | |||
| Hazards | |||
| Safety data sheet |
See: data page External MSDS |
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EU classification (DSD) (outdated)
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Harmful (Xn) Flammable (F) | ||
| R-phrases (outdated) | R11 R20 R21 R38 | ||
| S-phrases (outdated) | S25 | ||
| NFPA 704 | |||
| Flash point | 32 °C (90 °F; 305 K) | ||
| 463 °C (865 °F; 736 K) | |||
| Explosive limits | 0.9%-6.7% | ||
| 100 ppm (TWA), 150 ppm (STEL) | |||
| Lethal dose or concentration (LD, LC): | |||
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LCLo (lowest published)
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6125 ppm (rat, 12 hr) 6125 ppm (human, 12 hr) |
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| US health exposure limits (NIOSH): | |||
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PEL (Permissible)
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TWA 100 ppm (435 mg/m3) | ||
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REL (Recommended)
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TWA 100 ppm (435 mg/m3) ST 150 ppm (655 mg/m3) | ||
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IDLH (Immediate danger)
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900 ppm | ||
| Related compounds | |||
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Related aromatic hydrocarbons
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m-xylene p-xylene toluene |
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| Supplementary data page | |||
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Refractive index (n), Dielectric constant (εr), etc. |
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Thermodynamic
data |
Phase behaviour solid–liquid–gas |
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| UV, IR, NMR, MS | |||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| Infobox references | |||
o-Xylene (ortho-xylene) is an aromatic hydrocarbon with the formula C6H4(CH3)2. with two methyl substituents bonded to adjacent carbon atoms of a benzene ring (the ortho configuration). It is a constitutional isomer of m-xylene and p-xylene, the mixture being called xylene or xylenes. o-Xylene is a colorless slightly oily flammable liquid.
Petroleum contains about one weight percent xylenes. Most o-xylene is produced by cracking petroleum, which affords a distribution of aromatic compounds, including xylene isomers. m-Xylene is isomerized to o-xylene. Net production was approximately 500,000 tons in the year 2000.
o-Xylene is largely used in the production of phthalic anhydride, which is a precursor to many materials, drugs, and other chemicals.
Xylenes are not acutely toxic, for example the LD50 (rat, oral) is 4300 mg/kg. Effects vary with animal and xylene isomer. Concerns with xylenes focus on narcotic efffects.
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