o-Xylene

o-Xylene
Skeletal formula	Space-filling model
Names
	Preferred IUPAC name 1,2-Xylene
	Systematic IUPAC name 2-Methyltoluene
	Other names ortho-Xylene
Identifiers
CAS Number	95-47-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28063 ;
ChEMBL	ChEMBL45005 ;
ChemSpider	6967 ;
DrugBank	DB03029 ;
ECHA InfoCard	100.002.203
KEGG	C07212 ;
RTECS number	ZE2450000;
UNII	Z2474E14QP ;
CompTox Dashboard (EPA)	DTXSID3021807 ;
	InChI InChI=1S/C8H10/c1-7-5-3-4-6-8(7)2/h3-6H,1-2H3 Key: CTQNGGLPUBDAKN-UHFFFAOYSA-N ; InChI=1/C8H10/c1-7-5-3-4-6-8(7)2/h3-6H,1-2H3 Key: CTQNGGLPUBDAKN-UHFFFAOYAE;
	SMILES CC1=C(C)C=CC=C1;
Properties
Chemical formula	C8H10
Molar mass	106.168 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)
Solubility in water	0.02% (20°C)[1]
Solubility in ethanol	very soluble
Solubility in diethyl ether	very soluble
Vapor pressure	7 mmHg (20°C)[1]
Magnetic susceptibility (χ)	-77.78·10−6 cm3/mol
Refractive index (nD)	1.50545
Viscosity	1.1049 cP at 0 °C; 0.8102 cP at 20 °C
Structure
Dipole moment	0.64 D [2]
Hazards
Safety data sheet	See: data page; External MSDS
EU classification (DSD) (outdated)	Harmful (Xn) Flammable (F)
R-phrases (outdated)	R11 R20 R21 R38
S-phrases (outdated)	S25
NFPA 704 (fire diamond)	3 2 0
Flash point	32 °C (90 °F; 305 K)
Autoignition; temperature	463 °C (865 °F; 736 K)[3]
Explosive limits	0.9%-6.7%[1]
Threshold limit value (TLV)	100 ppm[3] (TWA), 150 ppm[3] (STEL)
	Lethal dose or concentration (LD, LC):
LCLo (lowest published)	6125 ppm (rat, 12 hr); 6125 ppm (human, 12 hr)[4]
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 100 ppm (435 mg/m3)[1]
REL (Recommended)	TWA 100 ppm (435 mg/m3) ST 150 ppm (655 mg/m3)[1]
IDLH (Immediate danger)	900 ppm[1]
Related compounds
Related aromatic hydrocarbons	m-xylene; p-xylene; toluene
Supplementary data page
Structure and; properties	Refractive index (n),; Dielectric constant (εr), etc.
Thermodynamic; data	Phase behaviour; solid–liquid–gas
Spectral data	UV, IR, NMR, MS
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[5]

Production and use

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.[5]

Toxicity and exposure

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 effects.[5]

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References

NIOSH Pocket Guide to Chemical Hazards. "#0668". National Institute for Occupational Safety and Health (NIOSH).
Rudolph, H.D.; Walzer, K.; Krutzik, Irmhild (1973). "Microwave spectrum, barrier for methyl rotation, methyl conformation, and dipole moment of ortho-xylene". Journal of Molecular Spectroscopy. 47 (2): 314. Bibcode:1973JMoSp..47..314R. doi:10.1016/0022-2852(73)90016-7.
"o-Xylene". International Chemical Safety Cards. ICSC/NIOSH. July 1, 2014.
"Xylene (o-, m-, p-isomers)". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
Fabri, Jörg; Graeser, Ulrich; Simo, Thomas A. (2000). "Xylenes". Xylenes]. Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a28_433. ISBN 3527306730.

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[PGCH-1] NIOSH Pocket Guide to Chemical Hazards. "#0668". National Institute for Occupational Safety and Health (NIOSH).

[2] Rudolph, H.D.; Walzer, K.; Krutzik, Irmhild (1973). "Microwave spectrum, barrier for methyl rotation, methyl conformation, and dipole moment of ortho-xylene". Journal of Molecular Spectroscopy. 47 (2): 314. Bibcode:1973JMoSp..47..314R. doi:10.1016/0022-2852(73)90016-7.

[ICSC-3] "o-Xylene". International Chemical Safety Cards. ICSC/NIOSH. July 1, 2014.

[4] "Xylene (o-, m-, p-isomers)". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[Ullmann-5] Fabri, Jörg; Graeser, Ulrich; Simo, Thomas A. (2000). "Xylenes". Xylenes]. Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a28_433. ISBN 3527306730.