M-Cresol

Last updated
m-Cresol
M-Kresol.svg
M-cresol-spaceFill.png
Names
IUPAC name
3-methylphenol
Other names
3-Cresol
m-Cresol
3-Hydroxytoluene
m-Cresylic acid
1-Hydroxy-3-methylbenzene
3-Methylbenzenol
Identifiers
3D model (JSmol)
506719
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.253 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-39-4
101411
KEGG
PubChem CID
RTECS number
  • GO6125000
UNII
  • InChI=1S/C7H8O/c1-6-3-2-4-7(8)5-6/h2-5,8H,1H3 X mark.svgN
    Key: RLSSMJSEOOYNOY-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C7H8O/c1-6-3-2-4-7(8)5-6/h2-5,8H,1H3
    Key: RLSSMJSEOOYNOY-UHFFFAOYAJ
  • Cc1cc(O)ccc1
Properties
C7H8O
Molar mass 108.14 g/mol
Appearancecolorless liquid to yellowish liquid
Density 1.034 g/cm3, liquid at 20 °C
Melting point 11 °C (52 °F; 284 K)
Boiling point 202.8 °C (397.0 °F; 475.9 K)
2.35 g/100 ml at 20 °C
5.8 g/100 ml at 100 °C
Solubility in ethanol miscible
Solubility in diethyl ether miscible
Vapor pressure 0.14 mmHg (20 °C) [1]
−72.02×10−6 cm3/mol
1.5398
Viscosity 6.1 cP at 40 °C
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
May cause serious burns. Very destructive of mucous membranes. Harmful if inhaled. Toxic in contact with the skin or if swallowed.
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-skull.svg GHS-pictogram-silhouette.svg
Danger
H227, H301, H311, H314, H351, H370, H372, H373, H401
P201, P202, P210, P260, P264, P270, P273, P280, P281, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P308+P313, P310, P312, P314, P321, P322, P330, P361, P363, P370+P378, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
2
0
Flash point 86 °C
Explosive limits 1.1%–? (149 °C) [1]
Lethal dose or concentration (LD, LC):
242 mg/kg (oral, rat, 1969)
2020 mg/kg (oral, rat, 1944)
828 mg/kg (oral, mouse) [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
o-cresol, p-cresol, phenol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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. [3]

Contents

Production

Together with many other compounds, m-cresol is traditionally extracted from coal tar, the volatile materials obtained in the production of coke from (bituminous) coal. This residue contains a few percent by weight of phenol and isomeric cresols. In the cymene–cresol process, toluene is alkylated with propylene to give isomers of cymene, which can be oxidatively dealkylated analogous to the cumene process. Another method, involves carbonylation of a mixture of methallyl chloride and acetylene in the presence of nickel carbonyl. [3]

Applications

m-Cresol is a precursor to numerous compounds. Important applications include:

C7H8O + C3H6 ⇌ C10H14O

Natural occurrences

m-Cresol is a component found in temporal glands secretions during musth in male African elephants (Loxodonta africana). [7]

m-Cresol is a constituent of tobacco smoke. [8]

m-Cresol is a component found in secretions from the ant Colobopsis saundersi during Autothysis. [9] [10]

See also

Related Research Articles

<span class="mw-page-title-main">Octane</span> Hydrocarbon compound with the formula C8H18

Octane is a hydrocarbon and an alkane with the chemical formula C8H18, and the condensed structural formula CH3(CH2)6CH3. Octane has many structural isomers that differ by the location of branching in the carbon chain. One of these isomers, 2,2,4-trimethylpentane (commonly called iso-octane), is used as one of the standard values in the octane rating scale.

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

Heptane or n-heptane is the straight-chain alkane with the chemical formula H3C(CH2)5CH3 or C7H16. When used as a test fuel component in anti-knock test engines, a 100% heptane fuel is the zero point of the octane rating scale (the 100 point is 100% iso-octane). Octane number equates to the anti-knock qualities of a comparison mixture of heptane and iso-octane which is expressed as the percentage of iso-octane in heptane, and is listed on pumps for gasoline (petrol) dispensed globally.

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.

Cyclohexene is a hydrocarbon with the formula (CH2)4C2H2. It is an example of a cycloalkene. At room temperature, cyclohexene is a colorless liquid with a sharp odor. It has few practical applications.

Dimethylformamide is an organic compound with the chemical formula HCON(CH3)2. Its structure is HC(=O)−N(−CH3)2. Commonly abbreviated as DMF, this colourless liquid is miscible with water and the majority of organic liquids. DMF is a common solvent for chemical reactions. Dimethylformamide is odorless, but technical-grade or degraded samples often have a fishy smell due to impurity of dimethylamine. Dimethylamine degradation impurities can be removed by sparging samples with an inert gas such as argon or by sonicating the samples under reduced pressure. As its name indicates, it is structurally related to formamide, having two methyl groups in the place of the two hydrogens. DMF is a polar (hydrophilic) aprotic solvent with a high boiling point. It facilitates reactions that follow polar mechanisms, such as SN2 reactions.

<span class="mw-page-title-main">Catechol</span> Organic compound (C6H4(OH)2); benzene with two adjacent –OH groups

Catechol, also known as pyrocatechol or 1,2-dihydroxybenzene, is an organic compound with the molecular formula C6H4(OH)2. It is the ortho isomer of the three isomeric benzenediols. This colorless compound occurs naturally in trace amounts. It was first discovered by destructive distillation of the plant extract catechin. About 20,000 tonnes of catechol are now synthetically produced annually as a commodity organic chemical, mainly as a precursor to pesticides, flavors, and fragrances. Small amounts of catechol occur in fruits and vegetables.

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

Hydrogen selenide is an inorganic compound with the formula H2Se. This hydrogen chalcogenide is the simplest and most commonly encountered hydride of selenium. H2Se is a colorless, flammable gas under standard conditions. It is the most toxic selenium compound with an exposure limit of 0.05 ppm over an 8-hour period. Even at extremely low concentrations, this compound has a very irritating smell resembling that of decayed horseradish or "leaking gas", but smells of rotten eggs at higher concentrations.

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

Isobutanol (IUPAC nomenclature: 2-methylpropan-1-ol) is an organic compound with the formula (CH3)2CHCH2OH (sometimes represented as i-BuOH). This colorless, flammable liquid with a characteristic smell is mainly used as a solvent either directly or as its esters. Its isomers are 1-butanol, 2-butanol, and tert-butanol, all of which are important industrially.

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

Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately 500,000 tonnes produced in 1998. Ethylenediamine is the first member of the so-called polyethylene amines.

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

Cumene (isopropylbenzene) is an organic compound that contains a benzene ring with an isopropyl substituent. It is a constituent of crude oil and refined fuels. It is a flammable colorless liquid that has a boiling point of 152 °C. Nearly all the cumene that is produced as a pure compound on an industrial scale is converted to cumene hydroperoxide, which is an intermediate in the synthesis of other industrially important chemicals, primarily phenol and acetone.

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

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.

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

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.

1,2-Dichloroethylene or 1,2-DCE is the name for a pair of organochlorine compounds with the molecular formula C2H2Cl2. The two compounds are isomers, each being colorless liquids with a sweet odor. It can exist as either of two geometric isomers, cis-1,2-dichloroethene or trans-1,2-dichloroethene, but is often used as a mixture of the two. They have modest solubility in water. These compounds have some applications as a degreasing solvent. In contrast to most cis-trans compounds, the Z isomer (cis) is more stable than the E isomer (trans) by 0.4 kcal/mol.

<i>Colobopsis saundersi</i> Ant species capable of suicidal altruism

Colobopsis saundersi, also called the Malaysian exploding ant, is a species of ant found in Malaysia and Brunei, belonging to the genus Colobopsis. A worker can explode suicidally and aggressively as an ultimate act of defense, an ability it has in common with several other species in this genus and a few other insects. The ant has an enormously enlarged mandibular gland, many times the size of other ants, which produces adhesive secretions for defense. According to a 2018 study, this species forms a species complex and is probably related to C. explodens, which is part of the C. cylindrica group.

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

Disulfur dichloride is the inorganic compound of sulfur and chlorine with the formula S2Cl2. It is an amber oily liquid.

<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 aryl chloride and isomer of dichlorobenzene 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.

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.

<span class="mw-page-title-main">2-Nitropropane</span> Chemical compound

2-Nitropropane (2-NP) is an organic compound with the formula (CH3)2CH(NO2). It is used as a solvent. It is a colorless liquid and is classified as a nitro compound.

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.

References

  1. 1 2 3 4 5 NIOSH Pocket Guide to Chemical Hazards. "#0155". National Institute for Occupational Safety and Health (NIOSH).
  2. ↑ "Cresol (o, m, p isomers)". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  3. 1 2 3 Helmut Fiege (2007). "Cresols and Xylenols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_025. ISBN   978-3527306732.
  4. ↑ Alan G. MacDiarmid and Arthur J. Epstein. 1995. "Secondary Doping in Polyaniline" Synthetic Metals 69 (85-92).
  5. ↑ Stroh, R.; Sydel, R.; Hahn, W. (1963). Foerst, Wilhelm (ed.). Newer Methods of Preparative Organic Chemistry, Volume 2 (1st ed.). New York: Academic Press. p. 344. ISBN   9780323150422.
  6. ↑ Asim Kumar Mukhopadhyay (2004). Industrial Chemical Cresols and Downstream Derivatives. New York: CRC Press. pp. 99–100. ISBN   9780203997413.
  7. ↑ Some chemical constituents of the secretion from the temporal gland of the African elephant (Loxodonta africana). Jack Adams, Alexander Garcia and Christopher S. Foote, Journal of Chemical Ecology, 1978, Volume 4, Number 1, 17-25, doi : 10.1007/BF00988256
  8. ↑ Talhout, Reinskje; Schulz, Thomas; Florek, Ewa; Van Benthem, Jan; Wester, Piet; Opperhuizen, Antoon (2011). "Hazardous Compounds in Tobacco Smoke". International Journal of Environmental Research and Public Health. 8 (12): 613–628. doi: 10.3390/ijerph8020613 . ISSN   1660-4601. PMC   3084482 . PMID   21556207.
  9. ↑ Jones, T. H.; Clark, D. A.; Edwards, A. A.; Davidson, D. W.; Spande, T. F.; Snelling, Roy R. (2004). "The chemistry of exploding ants, Camponotus spp. (cylindricus complex)". Journal of Chemical Ecology . 30 (8): 1479–1492. doi:10.1023/B:JOEC.0000042063.01424.28. PMID   15537154. S2CID   23756265.
  10. ↑ Betz, Oliver (2010). "Adhesive Exocrine Glands in Insects: Morphology, Ultrastructure, and Adhesive Secretion". In von Byern, Janek; Grunwald, Ingo (eds.). Biological Adhesive Systems . pp.  111–152. doi:10.1007/978-3-7091-0286-2_8. ISBN   978-3-7091-0141-4.
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