o-Cresol

o-Cresol
Systematic name 2-Methylphenol[1]
Other names 2-Hydroxytoluene
Identifiers
CAS number	95-48-7 Y
PubChem	335
UNII	YW84DH5I7U N
EC number	202-423-8
UN number	2076, 3455
KEGG	C01542 N
MeSH	2-Cresol
ChEBI	CHEBI:28054 N
ChEMBL	CHEMBL46931 N
RTECS number	GO6300000
Beilstein Reference	506917
Gmelin Reference	101619
3DMet	B00313
Jmol-3D images	Image 1
SMILES Cc1ccccc1O
InChI InChI=1S/C7H8O/c1-6-4-2-3-5-7(6)8/h2-5,8H,1H3 N Key: QWVGKYWNOKOFNN-UHFFFAOYSA-N N[spiderchem]
Properties
Molecular formula	C7H8O
Molar mass	108.14 g mol−1
Exact mass	108.057514878 g mol-1
Appearance	Colorless crystals
Density	1.0465 g cm-3
Melting point	31 °C, 304 K, 88 °F
Boiling point	191 °C, 464 K, 376 °F
Solubility in water	31 g dm-3 (at 40 °C)
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
Refractive index (nD)	1.5353
Viscosity	35.06 cP (at 45 °C)
Thermochemistry
Std enthalpy of formation ΔfHo298	-204.3 kJ mol-1
Std enthalpy of combustion ΔcHo298	-3.6936 MJ mol-1
Standard molar entropy So298	165.44 J K-1 mol-1
Specific heat capacity, C	154.56 J K-1 mol-1
Hazards
MSDS	External MSDS
EU Index	604-004-00-9
EU classification	T C
R-phrases	R24/25, R34
S-phrases	(S1/2), S36/37/39, S45
NFPA 704	2 3 0
Flash point	81 °C
Autoignition temperature	598.9 °C
Related compounds
Related phenols	m-cresol, p-cresol, phenol
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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

It is an isomer of p-cresol, m-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^[2].

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

• o-CRESOL (ICSC)
• Environmental Science - SMILES Examples Notations

References

1. ^ "2-Cresol - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=335&loc=ec_rcs. 
2. ^ "Lysol Douche Advertisements"