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 | ||
EC Number |
| ||
67796 | |||
KEGG | |||
PubChem CID | |||
RTECS number |
| ||
UNII | |||
UN number | 1307 | ||
CompTox Dashboard (EPA) | |||
| |||
| |||
Properties | |||
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) | ||
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 | |||
Refractive index (nD) | 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: | |||
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) | |||
Flash point | 32 °C (90 °F; 305 K) | ||
463 °C (865 °F; 736 K) [4] | |||
Explosive limits | 0.9%-6.7% [2] | ||
Threshold limit value (TLV) | 100 ppm [4] (TWA), 150 ppm [4] (STEL) | ||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose) | 4300 mg/kg (rats, orally) [5] | ||
LCLo (lowest published) | 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 | |||
Related aromatic hydrocarbons | 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). |
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]
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]
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]
Toluene, also known as toluol, is a substituted aromatic hydrocarbon with the chemical formula C6H5CH3, often abbreviated as PhCH3, where Ph stands for phenyl group. It is a colorless, water-insoluble liquid with the odor associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a methyl group (CH3) attached to a phenyl group by a single bond. As such, its systematic IUPAC name is methylbenzene. Toluene is predominantly used as an industrial feedstock and a solvent.
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.
Phthalic anhydride is the organic compound with the formula C6H4(CO)2O. It is the anhydride of phthalic acid. Phthalic anhydride is a principal commercial form of phthalic acid. It was the first anhydride of a dicarboxylic acid to be used commercially. This white solid is an important industrial chemical, especially for the large-scale production of plasticizers for plastics. In 2000, the worldwide production volume was estimated to be about 3 million tonnes per year.
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).
Dimethyl sulfate (DMS) is a chemical compound with formula (CH3O)2SO2. As the diester of methanol and sulfuric acid, its formula is often written as (CH3)2SO4 or Me2SO4, where CH3 or Me is methyl. Me2SO4 is mainly used as a methylating agent in organic synthesis. Me2SO4 is a colourless oily liquid with a slight onion-like odour. Like all strong alkylating agents, Me2SO4 is toxic. Its use as a laboratory reagent has been superseded to some extent by methyl triflate, CF3SO3CH3, the methyl ester of trifluoromethanesulfonic acid.
There are three isomers of toluidine, which are organic compounds. These isomers are o-toluidine, m-toluidine, and p-toluidine, with the prefixed letter abbreviating, respectively, ortho; meta; and para. All three are aryl amines whose chemical structures are similar to aniline except that a methyl group is substituted onto the benzene ring. The difference between these three isomers is the position where the methyl group (–CH3) is bonded to the ring relative to the amino functional group (–NH2); see illustration of the chemical structures below.
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.
Divinylbenzene (DVB) is an organic compound with the chemical formula C6H4(CH=CH2)2 and structure H2C=CH−C6H4−HC=CH2. It is related to styrene by the addition of a second vinyl group. It is a colorless liquid manufactured by the thermal dehydrogenation of isomeric diethylbenzenes. Under synthesis conditions, o-divinylbenzene converts to naphthalene and thus is not a component of the usual mixtures of DVB.
Durene, or 1,2,4,5-tetramethylbenzene, is an organic compound with the formula C6H2(CH3)4. It is a colourless solid with a sweet odor. The compound is classified as an alkylbenzene. It is one of three isomers of tetramethylbenzene, the other two being prehnitene (1,2,3,4-tetramethylbenzene) and isodurene (1,2,3,5-tetramethylbenzene). Durene has an unusually high melting point (79.2 °C), reflecting its high molecular symmetry.
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.
Mononitrotoluene or nitrotoluene (MNT or NT), is any of three organic compounds with the formula C6H4(CH3)(NO2). They can be viewed as nitro derivatives of toluene or as methylated derivatives of nitrobenzene.
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-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. It is extremely toxic to humans and was previously used as a herbicide and insecticide.
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.
In organic chemistry, a xylylene (sometimes quinone-dimethide) is any of the constitutional isomers having the formula C6H4(CH2)2. These compounds are related to the corresponding quinones and quinone methides by replacement of the oxygen atoms by CH2 groups. ortho- and para-xylylene are best known, although neither is stable in solid or liquid form. The meta form is a diradical. Certain substituted derivatives of xylylenes are however highly stable, such as tetracyanoquinodimethane and the xylylene dichlorides.
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.
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:
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.