Names | |||
---|---|---|---|
Preferred IUPAC name 2-Methylphenol | |||
Systematic IUPAC name 2-Methylbenzenol | |||
Other names 2-Cresol o-Cresol ortho-Cresol ortho-Toluenol ortho-Benzol 2-Hydroxytoluene o-Cresylic acid 1-Hydroxy-2-methylbenzene | |||
Identifiers | |||
3D model (JSmol) | |||
3DMet | |||
506917 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.002.204 | ||
EC Number |
| ||
101619 | |||
KEGG | |||
MeSH | 2-Cresol | ||
PubChem CID | |||
RTECS number |
| ||
UNII | |||
UN number | 2076, 3455 | ||
CompTox Dashboard (EPA) | |||
| |||
| |||
Properties | |||
C7H8O | |||
Molar mass | 108.140 g·mol−1 | ||
Appearance | Colorless to white crystals | ||
Odor | sweet, phenolic odor | ||
Density | 1.0465 g cm−3 | ||
Melting point | 31 °C; 88 °F; 304 K | ||
Boiling point | 191 °C; 376 °F; 464 K | ||
31 g dm−3 (at 40 °C) | |||
Solubility | soluble in chloroform, ether, CCl4 | ||
Solubility in ethanol | Miscible (at 30 °C) | ||
Solubility in diethyl ether | Miscible (at 30 °C) | ||
log P | 1.962 | ||
Vapor pressure | 40 Pa (at 20 °C) | ||
Acidity (pKa) | 10.316 | ||
Basicity (pKb) | 3.681 | ||
−72.9×10−6 cm3/mol | |||
Refractive index (nD) | 1.5353 | ||
Viscosity | 35.06 cP (at 45 °C) | ||
Thermochemistry | |||
Heat capacity (C) | 154.56 J K−1 mol−1 | ||
Std molar entropy (S⦵298) | 165.44 J K−1 mol−1 | ||
Std enthalpy of formation (ΔfH⦵298) | −204.3 kJ mol−1 | ||
Std enthalpy of combustion (ΔcH⦵298) | −3.6936 MJ mol−1 | ||
Hazards | |||
GHS labelling: | |||
Danger | |||
H301, H311, H314 | |||
P260, P264, P270, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P361, P363, P405, P501 | |||
NFPA 704 (fire diamond) | |||
Flash point | 81 °C (178 °F; 354 K) | ||
598.9 °C (1,110.0 °F; 872.0 K) | |||
Explosive limits | 1.4%–? (148 °C) [1] | ||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose) | 1350 mg/kg (rat, oral) 121 mg/kg (rat, oral) 344 mg/kg (mouse, oral) [2] | ||
NIOSH (US health exposure limits): | |||
PEL (Permissible) | TWA 5 ppm (22 mg/m3) [skin] [1] | ||
REL (Recommended) | TWA 2.3 ppm (10 mg/m3) [1] | ||
IDLH (Immediate danger) | 250 ppm [1] | ||
Safety data sheet (SDS) | External MSDS | ||
Related compounds | |||
Related phenols | Cresols: | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
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. [3]
o-Cresol is one of the chemical compounds found in castoreum. This compound is gathered from the beaver's castor glands and found in the white cedar consumed by the beaver. [4]
o-Cresol is a constituent of tobacco smoke. [5]
Together with many other compounds, o-cresol is traditionally extracted from coal tar, the volatile materials obtained in the production of coke from coal. A similar source material is petroleum residues. These residue contains a few percent by weight of phenol and isomeric cresols. In addition to the materials derived from these natural sources, about two thirds of the Western world's supply is produced by methylation of phenol using methanol. The alkylation is catalysed by metal oxides:
Over-methylation gives xylenol. Many other production methods have been examined, including oxidative decarboxylation of salicylic acid, oxygenation of toluene, and hydrolysis of 2-chlorotoluene. [3]
o-Cresol is mainly used as a precursor to other compounds. Chlorination and etherification gives members of commercially important herbicides, such as 2-methyl-4-chlorophenoxyacetic acid (MCPA). Nitration gives dinitrocresol, a popular herbicide. Kolbe–Schmitt carboxylation gives o-cresotinic acid, a pharmaceutical intermediate. Carvacrol, essence of oregano, is derived by alkylation of o-cresol with propene. The muscle relaxant mephenesin is an ether derived from o-cresol. [3]
Most exposures to cresols are at very low levels that are not harmful although, like phenols, cresols are skin irritants. When cresols are inhaled, ingested, or applied to the skin at very high levels, they can be harmful. Breathing high levels of cresols for a short time results in irritation of the nose and throat. Aside from these effects, very little is known about the effects of breathing cresols at lower levels over longer times. The acute LD50 for oral ingestion by mice is 344 mg/kg. [3]
Aromatic compounds, also known as "mono- and polycyclic aromatic hydrocarbons", are organic compounds containing one or more aromatic rings. The word "aromatic" originates from the past grouping of molecules based on smell, before their general chemical properties were understood. The current definition of aromatic compounds does not have any relation with their smell.
Phenol, or Benzenol, is an aromatic organic compound with the molecular formula C6H5OH. It is a white crystalline solid that is volatile. The molecule consists of a phenyl group bonded to a hydroxy group. Mildly acidic, it requires careful handling because it can cause chemical burns.
Creosote is a category of carbonaceous chemicals formed by the distillation of various tars and pyrolysis of plant-derived material, such as wood, or fossil fuel. They are typically used as preservatives or antiseptics.
Butanone, also known as methyl ethyl ketone (MEK) or ethyl methyl ketone, is an organic compound with the formula CH3C(O)CH2CH3. This colorless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in nature only in trace amounts. It is partially soluble in water, and is commonly used as an industrial solvent. It is an isomer of another solvent, tetrahydrofuran.
Cresols are a group of aromatic organic compounds. They are widely-occurring phenols which may be either natural or manufactured. They are also categorized as methyl phenols. Cresols commonly occur as either solids or liquids because their melting points are generally close to room temperature. Like other types of phenols, they are slowly oxidized by exposure to air, and the resulting impurities often give the samples a yellow to brownish red tint. Cresols have an odor characteristic to that of other simple phenols, reminiscent to some of a "coal tar" smell. The name "cresol" is an adduct of phenol and their traditional source, creosote.
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.
In organic chemistry, dihydroxybenzenes (benzenediols) are organic compounds in which two hydroxyl groups are substituted onto a benzene ring. These aromatic compounds are classed as phenols. There are three structural isomers: 1,2-dihydroxybenzene is commonly known as catechol, 1,3-dihydroxybenzene is commonly known as resorcinol, and 1,4-dihydroxybenzene is commonly known as hydroquinone.
Hydroquinone, also known as benzene-1,4-diol or quinol, is an aromatic organic compound that is a type of phenol, a derivative of benzene, having the chemical formula C6H4(OH)2. It has two hydroxyl groups bonded to a benzene ring in a para position. It is a white granular solid. Substituted derivatives of this parent compound are also referred to as hydroquinones. The name "hydroquinone" was coined by Friedrich Wöhler in 1843.
Phosphorus trichloride is an inorganic compound with the chemical formula PCl3. A colorless liquid when pure, it is an important industrial chemical, being used for the manufacture of phosphites and other organophosphorus compounds. It is toxic and reacts readily with water to release hydrogen chloride.
tert-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as t-BuOH). Its isomers are 1-butanol, isobutanol, and butan-2-ol. tert-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor. It is miscible with water, ethanol and diethyl ether.
para-Cresol, also 4-methylphenol, 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 o-cresol and m-cresol.
meta-Cresol, also 3-methylphenol, is an organic compound with the formula CH3C6H4(OH). It is a colourless, viscous liquid that is used as an intermediate in the production of other chemicals. It is a derivative of phenol and is an isomer of p-cresol and o-cresol.
Xylenols are organic compounds with the formula (CH3)2C6H3OH. They are volatile colorless solids or oily liquids. They are derivatives of phenol with two methyl groups at various positions relative to the hydroxyl group. Six isomers exist, of which 2,6-xylenol with both methyl groups in an ortho position with respect to the hydroxyl group is the most important. The name xylenol is a portmanteau of the words xylene and phenol.
2,6-Xylenol is a chemical compound which is one of the six isomers of xylenol. It is also commonly known as 2,6-dimethylphenol (DMP). It is a colorless solid.
2,4-Dimethyl-6-tert-butylphenol is the organic compound with the formula Me2(tert-Bu)C6H2OH (Me = methyl, tert-Bu = tertiary butyl). It is a colorless oil that is classified as an alkylated phenol.
Tricresyl phosphate (TCP), is a mixture of three isomeric organophosphate compounds most notably used as a flame retardant. Other uses include as a plasticizer in manufacturing for lacquers and varnishes and vinyl plastics and as an antiwear additive in lubricants. Pure tricresyl phosphate is a colourless, viscous liquid, although commercial samples are typically yellow. It is virtually insoluble in water, but easily soluble in organic solvents like toluene, hexane, and diethylether among others. It was synthesized by Alexander Williamson in 1854 upon reacting phosphorus pentachloride with cresol, though today's manufacturers can prepare TCP by mixing cresol with phosphorus oxychloride or phosphoric acid as well. TCP, especially the all-ortho isomer, is the causative agent in a number of acute poisonings. Its chronic toxicity is also of concern. The ortho-isomer is rarely used on its own outside of laboratory studies that require isomeric purity, due to its extremely toxic nature, and is generally excluded from commercial products where TCP is involved.
Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, benzene is classed as a hydrocarbon.
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.
EPN is an insecticide of the phosphonothioate class. It is used against pests such as European corn borer, rice stem borer, bollworm, tobacco budworm, and boll weevil.
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.