Names | |||
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Preferred IUPAC name 1,2,3-Trimethylbenzene | |||
Other names Hemellitol; Hemimellitol, Hemimelithol; Hemimellitine; Hemimellitene | |||
Identifiers | |||
3D model (JSmol) | |||
1903410 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.007.633 | ||
EC Number |
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326517 | |||
PubChem CID | |||
RTECS number |
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UNII | |||
UN number | 1993 | ||
CompTox Dashboard (EPA) | |||
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Properties | |||
C9H12 | |||
Molar mass | 120.195 g·mol−1 | ||
Appearance | Colorless liquid [1] | ||
Density | 0.89 g/mL [1] | ||
Melting point | −25 °C (−13 °F; 248 K) [1] | ||
Boiling point | 176 °C (349 °F; 449 K) [1] | ||
0.006% (20°C) [2] | |||
Vapor pressure | 1 mmHg (16.7°C) [2] | ||
Hazards | |||
Occupational safety and health (OHS/OSH): | |||
Main hazards | Flammable [3] | ||
GHS labelling: | |||
Warning | |||
H226, H315, H319, H335 | |||
P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501 | |||
Flash point | 11 °C; 51 °F; 284 K [1] | ||
243 °C; 470 °F; 516 K [1] | |||
Explosive limits | 0.8%-6.6% [2] | ||
NIOSH (US health exposure limits): | |||
PEL (Permissible) | none [2] | ||
REL (Recommended) | TWA 25 ppm (125 mg/m3) [2] | ||
IDLH (Immediate danger) | N.D. [2] | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
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.
The compound 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.
German chemist Oscar Jacobsen first prepared the hydrocarbon in 1882 and designated it hemellitol as a reference to the trivial name of hexamethylbenzene. [4] Four years later he also discovered it in the coal tar. [5]
Industrially, it is isolated from the C9 aromatic hydrocarbon fraction during petroleum distillation. It is also generated by methylation of toluene and xylenes. [6]
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.
Furfural is an organic compound with the formula C4H3OCHO. It is a colorless liquid, although commercial samples are often brown. It has an aldehyde group attached to the 2-position of furan. It is a product of the dehydration of sugars, as occurs in a variety of agricultural byproducts, including corncobs, oat, wheat bran, and sawdust. The name furfural comes from the Latin word furfur, meaning bran, referring to its usual source. Furfural is only derived from dried biomass. In addition to ethanol, acetic acid, and sugar, furfural is one of the oldest organic chemicals available readily purified from natural precursors.
Phenanthrene is a polycyclic aromatic hydrocarbon (PAH) with formula C14H10, consisting of three fused benzene rings. It is a colorless, crystal-like solid, but can also appear yellow. Phenanthrene is used to make dyes, plastics, pesticides, explosives, and drugs. It has also been used to make bile acids, cholesterol and steroids.
Diazomethane is an organic chemical compound with the formula CH2N2, discovered by German chemist Hans von Pechmann in 1894. It is the simplest diazo compound. In the pure form at room temperature, it is an extremely sensitive explosive yellow gas; thus, it is almost universally used as a solution in diethyl ether. The compound is a popular methylating agent in the laboratory, but it is too hazardous to be employed on an industrial scale without special precautions. Use of diazomethane has been significantly reduced by the introduction of the safer and equivalent reagent trimethylsilyldiazomethane.
Resorcinol (or resorcin) is a phenolic compound. It is an organic compound with the formula C6H4(OH)2. It is one of three isomeric benzenediols, the 1,3-isomer (or meta-isomer). Resorcinol crystallizes from benzene as colorless needles that are readily soluble in water, alcohol, and ether, but insoluble in chloroform and carbon disulfide.
Stibine (IUPAC name: stibane) is a chemical compound with the formula SbH3. A pnictogen hydride, this colourless, highly toxic gas is the principal covalent hydride of antimony, and a heavy analogue of ammonia. The molecule is pyramidal with H–Sb–H angles of 91.7° and Sb–H distances of 170.7 pm (1.707 Å). The smell of this compound from usual sources (like from reduction of antimony compounds) is reminiscent of arsine, i.e. garlic-like.
The Bischler–Möhlau indole synthesis, also often referred to as the Bischler indole synthesis, is a chemical reaction that forms a 2-aryl-indole from an α-bromo-acetophenone and excess aniline; it is named after August Bischler and Richard Möhlau .
Aziridine is an organic compound consisting of the three-membered heterocycle C2H5N. It is a colorless, toxic, volatile liquid that is of significant practical interest. Aziridine was discovered in 1888 by the chemist Siegmund Gabriel. Its derivatives, also referred to as aziridines, are of broader interest in medicinal chemistry.
Friedrich Karl Johannes Thiele was a German chemist and a prominent professor at several universities, including those in Munich and Strasbourg. He developed many laboratory techniques related to isolation of organic compounds. In 1907 he described a device for the accurate determination of melting points, since named Thiele tube after him.
Indene is an aromatic, polycyclic hydrocarbon with chemical formula C9H8. It is composed of a benzene ring fused with a cyclopentene ring. This flammable liquid is colorless although samples often are pale yellow. The principal industrial use of indene is in the production of indene/coumarone thermoplastic resins. Substituted indenes and their closely related indane derivatives are important structural motifs found in many natural products and biologically active molecules, such as sulindac.
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.
Diisopropylamine is a secondary amine with the chemical formula (Me2CH)2NH (Me = methyl). Diisopropylamine is a colorless liquid with an ammonia-like odor. Its lithium derivative, lithium diisopropylamide, known as LDA is a widely used reagent.
Mellitic anhydride, the anhydride of mellitic acid, is an organic compound with the formula C12O9.
Roland Heinrich Scholl was a Swiss chemist who taught at various European universities. Among his most notable achievements are the synthesis of coronene, the co-development of the Bally-Scholl synthesis, and various discoveries about polycyclic aromatic hydrocarbons.
3-Nitrotoluene or meta-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is one of three isomers of nitrotoluene. A yellow liquid, it is used in the manufacture of meta-toluidine, which is an intermediate in the production of various dyes.
Spiropentane is a hydrocarbon with formula C5H8. It is the simplest spiro-connected cycloalkane, a triangulane. It took several years after the discovery in 1887 until the structure of the molecule was determined. According to the nomenclature rules for spiro compounds, the systematic name is spiro[2.2]pentane. However, there can be no constitutive isomeric spiropentanes, hence the name is unique without brackets and numbers.
Alexander Ellinger was a German chemist and pharmacologist.
Acetyl nitrate is the organic compound with the formula CH3C(O)ONO2. It is classified as the mixed anhydride of nitric and acetic acids. It is a colorless explosive liquid that fumes in moist air.
Alexander Nikolaus Franz Naumann was a Prussian and German physical chemist and a professor at the University of Giessen. He was a pioneer of chemical thermodynamics and proposed that molecules reacted when their energy levels exceeded a certain critical level which could be achieved through the provision of heat.
Karl Ludwig Reimer was a German chemist and industrialist. He's responsible for the cheap synthesis of the chemical compound Vanillin, having discovered the Reimer-Tiemann Reaction.