O-Xylene

Last updated
o-Xylene
Skeletal formula Ortho-Xylol - ortho-xylene 2.svg
Skeletal formula
Space-filling model O-xylene-spaceFill.png
Space-filling model
Names
Preferred IUPAC name
1,2-Xylene [1]
Systematic IUPAC name
1,2-Dimethylbenzene [1]
Other names
o-Xylene, [1] o-Xylol
Identifiers
3D model (JSmol)
1815558
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.002.203 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-422-2
67796
KEGG
PubChem CID
RTECS number
  • ZE2450000
UNII
UN number 1307
  • InChI=1S/C8H10/c1-7-5-3-4-6-8(7)2/h3-6H,1-2H3 Yes check.svgY
    Key: CTQNGGLPUBDAKN-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C8H10/c1-7-5-3-4-6-8(7)2/h3-6H,1-2H3
    Key: CTQNGGLPUBDAKN-UHFFFAOYAE
  • CC1=C(C)C=CC=C1
Properties
C8H10
Molar mass 106.168 g·mol−1
AppearanceColorless 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) [2]
Solubility in ethanol very soluble
Solubility in diethyl ether very soluble
Vapor pressure 7 mmHg (20°C) [2]
-77.78·10−6 cm3/mol
1.50545
Viscosity 1.1049 cP at 0 °C
0.8102 cP at 20 °C
Structure
0.64 D [3]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Mildly toxic
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Danger
H225, H226, H304, H305, H312, H315, H319, H332, H335, H412
P210, P233, P240, P241, P242, P243, P261, P264, P271, P273, P280, P301+P310, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P331, P332+P313, P337+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
2
3
0
Flash point 32 °C (90 °F; 305 K)
463 °C (865 °F; 736 K) [4]
Explosive limits 0.9%-6.7% [2]
100 ppm [4] (TWA), 150 ppm [4] (STEL)
Lethal dose or concentration (LD, LC):
4300 mg/kg (rats, orally) [5]
6125 ppm (rat, 12 hr)
6125 ppm (human, 12 hr) [6]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 100 ppm (435 mg/m3) [2]
REL (Recommended)
TWA 100 ppm (435 mg/m3) ST 150 ppm (655 mg/m3) [2]
IDLH (Immediate danger)
900 ppm [2]
Safety data sheet (SDS) External MSDS
Related compounds
m-xylene
p-xylene
toluene
Supplementary data page
O-Xylene (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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 colourless slightly oily flammable liquid. [7]

Contents

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. [7] Related to their easy oxidation, the methyl groups are susceptible to halogenation. When treated with elemental bromine, these groups are brominated, yielding xylylene dibromide: [8]

C6H4(CH3)2 + 2 Br2 → C6H4(CH2Br)2 + 2 HBr

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. [7]

Related Research Articles

Toluene, also known as toluol, is a substituted aromatic hydrocarbon. It is a colorless, water-insoluble liquid with the smell associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a methyl group (CH3) attached to a phenyl group. As such, its systematic IUPAC name is methylbenzene. Toluene is predominantly used as an industrial feedstock and a solvent.

<span class="mw-page-title-main">Xylene</span> Organic compounds with the formula (CH3)2C6H4

In organic chemistry, xylene or xylol are any of three organic compounds with the formula (CH3)2C6H4. They are derived from the substitution of two hydrogen atoms with methyl groups in a benzene ring; which hydrogens are substituted determines which of three structural isomers results. It is a colorless, flammable, slightly greasy liquid of great industrial value.

<span class="mw-page-title-main">1,2-Dibromoethane</span> Chemical compound

1,2-Dibromoethane, also known as ethylene dibromide (EDB), is an organobromine compound with the chemical formula C
2
H
4
Br
2
. Although trace amounts occur naturally in the ocean, where it is formed probably by algae and kelp, it is mainly synthetic. It is a dense colorless liquid with a faint, sweet odor, detectable at 10 ppm, and is a widely used and sometimes-controversial fumigant. The combustion of 1,2-dibromoethane produces hydrogen bromide gas that is significantly corrosive.

Mesitylene or 1,3,5-trimethylbenzene is a derivative of benzene with three methyl substituents positioned symmetrically around the ring. The other two isomeric trimethylbenzenes are 1,2,4-trimethylbenzene (pseudocumene) and 1,2,3-trimethylbenzene (hemimellitene). All three compounds have the formula C6H3(CH3)3, which is commonly abbreviated C6H3Me3. Mesitylene is a colorless liquid with sweet aromatic odor. It is a component of coal tar, which is its traditional source. It is a precursor to diverse fine chemicals. The mesityl group (Mes) is a substituent with the formula C6H2Me3 and is found in various other compounds.

<span class="mw-page-title-main">Ethylbenzene</span> Hydrocarbon compound; precursor to styrene and polystyrene

Ethylbenzene is an organic compound with the formula C6H5CH2CH3. It is a highly flammable, colorless liquid with an odor similar to that of gasoline. This monocyclic aromatic hydrocarbon is important in the petrochemical industry as an reaction intermediate in the production of styrene, the precursor to polystyrene, a common plastic material. In 2012, more than 99% of ethylbenzene produced was consumed in the production of styrene.

<i>p</i>-Xylene Chemical compound

p-Xylene (para-xylene) is an aromatic hydrocarbon. It is one of the three isomers of dimethylbenzene known collectively as xylenes. The p- stands for para-, indicating that the two methyl groups in p-xylene occupy the diametrically opposite substituent positions 1 and 4. It is in the positions of the two methyl groups, their arene substitution pattern, that it differs from the other isomers, o-xylene and m-xylene. All have the same chemical formula C6H4(CH3)2. All xylene isomers are colorless and highly flammable. The odor threshold of p-xylene is 0.62 parts per million (ppm).

<i>m</i>-Xylene Chemical compound

m-Xylene (meta-xylene) is an aromatic hydrocarbon. It is one of the three isomers of dimethylbenzene known collectively as xylenes. The m- stands for meta-, indicating that the two methyl groups in m-xylene occupy positions 1 and 3 on a benzene ring. It is in the positions of the two methyl groups, their arene substitution pattern, that it differs from the other isomers, o-xylene and p-xylene. All have the same chemical formula C6H4(CH3)2. All xylene isomers are colorless and highly flammable.

1,2,4-Trimethylbenzene, also known as pseudocumene, is an organic compound with the chemical formula C6H3(CH3)3. Classified as an aromatic hydrocarbon, it is a flammable colorless liquid with a strong odor. It is nearly insoluble in water but soluble in organic solvents. It occurs naturally in coal tar and petroleum (about 3%). It is one of the three isomers of trimethylbenzene.

<span class="mw-page-title-main">Crotonaldehyde</span> Chemical compound

Crotonaldehyde is a chemical compound with the formula CH3CH=CHCHO. The compound is usually sold as a mixture of the E- and Z-isomers, which differ with respect to the relative position of the methyl and formyl groups. The E-isomer is more common (data given in Table is for the E-isomer). This lachrymatory liquid is moderately soluble in water and miscible in organic solvents. As an unsaturated aldehyde, crotonaldehyde is a versatile intermediate in organic synthesis. It occurs in a variety of foodstuffs, e.g. soybean oils.

<span class="mw-page-title-main">1,2-Dichlorobenzene</span> Chemical compound

1,2-Dichlorobenzene, or orthodichlorobenzene (ODCB), is an organic compound with the formula C6H4Cl2. This colourless liquid is poorly soluble in water but miscible with most organic solvents. It is a derivative of benzene, consisting of two adjacent chlorine atoms.

<span class="mw-page-title-main">Tolidine</span> Chemical compound

2-Tolidine (orthotolidine, o-tolidine; not to be confused with o-toluidine) is an organic compound with the chemical formula (C6H4(CH3)NH2)2. Several isomers are known; the 3-tolidine derivative is also important commercially. It is a colorless compound although commercial samples are often colored. It is slightly soluble in water. It forms salts with acids, such as the hydrochloride, which is commercially available.

<span class="mw-page-title-main">Benzene</span> Hydrocarbon compound consisting of a 6-sided ring

Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, benzene is classed as a hydrocarbon.

<span class="mw-page-title-main">Terphenyl</span> Chemical compound

Terphenyls are a group of closely related aromatic hydrocarbons. Also known as diphenylbenzenes or triphenyls, they consist of a central benzene ring substituted with two phenyl groups. There are three substitution patterns: ortho-terphenyl, meta-terphenyl, and para-terphenyl. Commercial grade terphenyl is generally a mixture of the three isomers. This mixture is used in the production of polychlorinated terphenyls, which were formerly used as heat storage and transfer agents.

ortho-Cresol (IUPAC name: 2-methylphenol, also known as 2-hydroxytoluene or ortho-Toluenol) is an organic compound with the formula CH3C6H4(OH). It is a colourless solid that is widely used intermediate in the production of other chemicals. It is a derivative of phenol and is an isomer of p-cresol and m-cresol.

Dinitro-<i>ortho</i>-cresol Chemical compound

Dinitro-ortho-cresol (DNOC) is an organic compound with the structural formula CH3C6H2(NO2)2OH. It is a yellow solid that is only slightly soluble in water. DNOC and some related derivatives have been used as herbicides.

1,2,3-Trimethylbenzene is an organic compound with the chemical formula C6H3(CH3)3. Classified as an aromatic hydrocarbon, it is a flammable colorless liquid. It is nearly insoluble in water but soluble in organic solvents. It occurs naturally in coal tar and petroleum. It is one of the three isomers of trimethylbenzene. It is used in jet fuel, mixed with other hydrocarbons, to prevent the formation of solid particles which might damage the engine.

4-Nitrotoluene or para-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is a pale yellow solid. It is one of three isomers of nitrotoluene.

2-Nitrotoluene or ortho-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is pale yellow liquid that crystallizes in two forms, called α (−9.27 °C) and β (−3.17 °C). It is mainly a precursor to o-toluidine, which is an intermediate in the production of various dyes.

Tetrabromo-<i>o</i>-xylene Chemical compound

α,α,α',α'-Tetrabromo-o-xylene is an organobromine compound with the formula C6H4(CHBr2)2. Three isomers of α,α,α',α'-Tetrabromoxylene exist, but the ortho derivative is most widely studied. It is an off-white solid. The compound is prepared by the photochemical reaction of o-xylene with elemental bromine:

<span class="mw-page-title-main">Xylylene dibromide</span> Chemical compound

Xylylene dibromide is an organic compound with the formula C6H4(CH2Br)2. It is an off-white solid that, like other benzyl halides, a strong lachrymator. It is a useful reagent owing to the convenient reactivity of the two C-Br bonds. Two other isomers are known, para- and meta-xylylene dibromide.

References

  1. 1 2 3 Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 121, 139, 653. doi:10.1039/9781849733069. ISBN   978-0-85404-182-4.
  2. 1 2 3 4 5 6 NIOSH Pocket Guide to Chemical Hazards. "#0668". National Institute for Occupational Safety and Health (NIOSH).
  3. 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.
  4. 1 2 3 "o-Xylene". International Chemical Safety Cards. ICSC/NIOSH. July 1, 2014.
  5. O-xylene toxicity
  6. "Xylene (o-, m-, p-isomers)". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  7. 1 2 3 Fabri, Jörg; Graeser, Ulrich; Simo, Thomas A. (2000). "Xylenes". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a28_433.
  8. Emily F. M. Stephenson (1954). "o-Xylylene Dibromide". Organic Syntheses. 34: 100. doi:10.15227/orgsyn.034.0100.