O-Cresol

Chembox new
Name = "o"-cresol
ImageFile = O-Kresol.svg
ImageSize = 120px
ImageName = o-cresol
ImageFile1 = Ortho-cresol-3D-vdW.png ImageSize1 = 150px
ImageName1 = 3D model of o-cresol
OtherNames = 2-Hydroxytoluene "ortho"-cresol
IUPACName = 2-Methylphenol
Section1 = Chembox Identifiers
CASNo = 95-48-7
RTECS = GO6300000
SMILES = Cc1ccccc1O
Section2 = Chembox Properties
Appearance = colorless crystals or liquid
Formula = C₇H₈O
MolarMass = 108.14 g/mol
Density = 1.0465 g/cm³, liquid at 20 °C
Solubility = 3.1 g/100 ml at 40 °C
5.6 g/100 ml at 100 °C
Solubility1 = fully miscible at > 30 °C
Solvent1 = ethanol
Solubility2 = fully miscible at > 30 °C
Solvent2 = diethyl ether
MeltingPt = 29.8 °C
BoilingPt = 191.5 °C
RefractIndex = 1.5353
Viscosity = 35.06 cP at 45 °C
pKa = 10.26
Section7 = Chembox Hazards
MainHazards = Highly toxic. May be fatal if inhaled, swallowed or absorbed through skin. Experimental neoplastigen. Human mutagenic data. Readily absorbed through the skin. Very destructive of mucous membranes. Causes burns. Inhalation may cause spasm. Severe skin and eye irritant.
ExternalMSDS = [http://www.sciencelab.com/msds.php?msdsId=9923570 External MSDS]
FlashPt = 81 °C
RPhrases = R24 R25 R34
SPhrases = S37 S39 S45
NFPA-H = 3
NFPA-F = 2
NFPA-R = 0
NFPA-O =
Section8 = Chembox Related
Function = phenols
OtherFunctn = m-cresol, p-cresol, phenol

"ortho"-Cresol, also 2-methylphenol, is a phenol, with formula (CH₃)C₆H₄(OH).

It is an isomer of "p"-cresol, "o"-cresol and anisole

Chemistry

Cresols are organic compounds which are methylphenols. They are a widely occurring natural and manufactured group of aromatic organic compounds which are categorized as phenols (sometimes called "phenolics"). Depending on the temperature, cresols can be solid or liquid because they have melting points not far from room temperature. Like other types of phenols, they are slowly oxidized by long exposure to air and the impurities often give cresols a yellowish to brownish red tint. Cresols have an odor characteristic to that of other simple phenols, reminiscent to some of a "medicine" smell.

In its chemical structure, a cresol molecule has a methyl group substituted onto the benzene ring of a phenol molecule. 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). These forms occur separately or as a mixture.

Applications

Cresols are used to dissolve other chemicals, as disinfectants and deodorizers, and to make specific chemicals that kill insect pests.

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 antiseptics in surgery, but they have been largely displaced in this role by less toxic compounds. Lysol was also advertised as a disinfecting vaginal douche in mid-twentieth century America [ [http://www.flickr.com/photos/mrbill/sets/834100/ "Lysol Douche Advertisements"] ] .

Cresols are found in many foods and in wood and tobacco smoke, crude oil, coal tar, and in brown mixtures such as creosote, cresolene and cresylic acids, which are wood preservatives. Small organisms in soil and water produce cresols when they break down materials in the environment.

Health effects

Most exposures to cresols are at very low levels that are not harmful. When cresols are breathed, ingested, or applied to the skin at very high levels, they can be very harmful. Effects observed in people include irritation and burning of skin, eyes, mouth, and throat; abdominal pain and vomiting; heart damage; anemia; liver and kidney damage; facial paralysis; coma; and death.

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, 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 blood and 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.

External links

* [http://www.inchem.org/documents/icsc/icsc/eics0030.htm o-CRESOL (ICSC)]
* [http://www.syrres.com/esc/smiles_ex_notations.htm Environmental Science - SMILES Examples Notations]

References