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Cresol
Cresols are organic compoundswhich are methylphenols. They are a widely occurring natural and manufactured group of aromaticorganic compoundswhich are categorized as phenols(sometimes called phenolics). Depending on the temperature, cresols can be solidor liquidsince they have melting pointsnot far from room temperature. Like other types of phenols, they are slowly oxidizedby long exposure to airand the impurities often give cresols a yellowish to brownish red tint. Cresols have an odorcharacteristic to that of other simple phenols, reminiscent to some of a "medicine" smell.
In its chemical structure, a cresol moleculehas a methyl groupsubstituted onto the benzene ringof a phenolmolecule. There are three forms of cresols that are only slightly different in their chemical structure: ortho-cresol (o-cresol), meta-cresol (m-cresol), and para-cresol (p-cresol).
Image:Cresol isomers.PNG
These forms occur separately or as a mixture. They are used to dissolveother chemicals, as disinfectantsand deodorizers, and to make certain chemicals that kill insectpests.
Cresol solutions are used as household cleaners and disinfectants, perhaps most famously under the trade name Lysol. In the past, cresol solutions have been used as antisepticsin surgery, but they have been largely displaced in this role by less toxic compounds. Lysol was also advertised as a disinfecting vaginal douchein mid-twentieth century America.
Cresols are found in many foods and in wood and tobacco smoke, crude oil, coal tar, and in brown mixtures such as creosoteand cresylic acids, which are wood preservatives. Small organisms in soil and water produce cresols when they break down materials in the environment.
Xylenolsare dimethylphenols, or they can be thought of as methylcresols.
| Isomers of Cresol
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| General
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| Common name
| o-cresol
| m-cresol
| p-cresol
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| Systematic name
| 2-methylphenol
| 3-methylphenol
| 4-methylphenol
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| Other names
| ortho-cresol
| meta-cresol
| para-cresol
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| Molecular formula
| C7H8O
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| SMILES
| Oc1c(C)cccc1
| Oc1cc(C)ccc1
| Oc1ccc(C)cc1
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| Molar mass
| 108.14 g/mol
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Appearance at room temperature and pressure
| greasy-looking solid ready to melt on hot day
| thicker liquid
| greasy-looking solid
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| CAS number
| [95-48-7]
| [108-39-4]
| [106-44-5]
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| CAS number for mixture of cresols [1319-77-3]
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| Properties
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| Densityand phase
| 1.05 g/cm3, liquid
| 1.03 g/cm3, liquid
| 1.02 g/cm3, liquid
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Solubilityin pure water at 20-25°C
| 2.5 g/100 ml
| 2.4 g/100 ml
| 1.9 g/100 ml
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| soluble in strongly alkalinewater
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| Melting point
| 29.8 °C (303.0 K)
| 11.8 °C (285.0 K)
| 35.5 °C (309.7 K)
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| Boiling point
| 191.0 °C (464.2 K)
| 202.0 °C (475.2 K)
| 201.9 °C (475.1 K)
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| Acidity(pKa)
| ?
| ?
| ?
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| Viscosity
| solid at 25 °C
| ? cPat 25 °C
| solid at 25 °C
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| Structure
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| Molecular shape
| ?
| ?
| ?
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| Coordination geometry
| ?
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| Crystal structure
| ?
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| Dipole moment
| ? D
| ? D
| ? D
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| Hazards
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| MSDS
| External MSDS
| ?
| ?
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| Main hazards
| flammable, ingestion and inhalation toxicity hazard
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| Flash point
| 81°C c.c.
| 86 °C
| 86°C c.c.
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| R/S statement
| R: 24/25-34 S: (1/2-)36/37/39-45
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| RTECSnumber
| ?
| ?
| ?
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| Supplementary data page
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| Structure & properties
| n, εr, etc.
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| Thermodynamic data
| Phase behaviour Solid, liquid, gas
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| Spectral data
| UV, IR, NMR, MS
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| Related compounds
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| Related phenols
| phenol, xylenols
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| Related compounds
| ?
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Except where noted otherwise, data are given for materials in their standard state (at 25°C, 100 kPa) Infobox disclaimer and references
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Health effects
Most exposures to cresols are at very low levels that are not harmful. When cresols are breathed, ingested, or applied to the skinat very high levels, they can be very harmful. Effects observed in people include irritationand burning of skin, eyes, mouth, and throat; abdominal pain and vomiting; heartdamage; anemia; liverand kidneydamage; facial paralysis; coma; and death.
Breathing high levels of cresols for a short time results in irritation of the noseand throat. Aside from these effects, very little is known about the effects of breathing cresols, for example, at lower levels over longer times.
Ingesting high levels results in kidney problems, mouth and throat burns, abdominal pain, vomiting, and effects on the bloodand nervous system.
Skin contact with high levels of cresols can burn the skin and damage the kidneys, liver, blood, brain, and lungs.
Short-term and long-term studies with animals have shown similar effects from exposure to cresols. No human or animal studies have shown harmful effects from cresols on the ability to have children.
It is not known what the effects are from long-term ingestion or skin contact with low levels of cresols.
References for Table of Properties
- o-CRESOL (ICSC)
- m-CRESOL (ICSC)
- p-CRESOL (ICSC)
- Environmental Science - SMILES Examples Notations
External link
- Lysol advertisements advocating use as a douche, from 1928and 1948de:Kresole
es:Cresol
fr:DNOC
nl:Orthocresol
ja:?????
pl:Krezol
pt:Cresol
tr:Kresol
Categories: Phenols| Antiseptics
This article is licensed under the GNU Free Documentation License. It uses material from the http://en.wikipedia.org/wiki/Cresol Wikipedia article Cresol.
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