M-Cresol

Last updated
m-Cresol
M-Kresol.svg
M-cresol-spaceFill.png
Names
Preferred 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)
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">Phenol</span> Organic compound (C6H5OH)

Phenol 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.

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 methylphenols. 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.

<span class="mw-page-title-main">Diazomethane</span> Simplest diazo compound and methylating agent

Diazomethane is the chemical compound 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.

Dimethylformamide is an organic compound with the formula (CH3)2NC(O)H. Commonly abbreviated as DMF (although this initialism is sometimes used for dimethylfuran, or dimethyl fumarate), 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 a toxic 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.

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.

<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-Dichloroethene, commonly called 1,2-dichloroethylene or 1,2-DCE, is the name for a pair of organochlorine compounds with the molecular formula C2H2Cl2. They are both 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.

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

Isoamyl alcohol is a colorless liquid with the formula C
5
H
12
O
, specifically (H3C–)2CH–CH2–CH2–OH. It is one of several isomers of amyl alcohol (pentanol). It is also known as isopentyl alcohol, isopentanol, or (in the IUPAC recommended nomenclature) 3-methyl-butan-1-ol. An obsolete name for it was isobutyl carbinol.

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

Colobopsis saundersi, synonym Camponotus saundersi, 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 (jaw) gland, many times the size of a normal ant, which produces defense adhesive secretions. 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.

<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">Divinylbenzene</span> Organic compound, C₆H₄(CH=CH₂)₂

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.

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

o-Anisidine (2-anisidine) is an organic compound with the formula CH3OC6H4NH2. A colorless liquid, commercial samples can appear yellow owing to air oxidation. It is one of three isomers of the methoxy-containing aniline derivative.

p-Anisidine (or para-anisidine) is an organic compound with the formula CH3OC6H4NH2. A white solid, commercial samples can appear grey-brown owing to air oxidation. It is one of three isomers of anisidine, methoxy-containing anilines. It is prepared by reduction of 4-nitroanisole.

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.

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.