Cresols

Cresols
	about : m : n :
	about : m : n :
Isomers
Are common
Systematic name	o : 2-methylphenol m : 3-methylphenol p : 4-methylphenol
Traditional names	about : ortho- cresol m : meta- cresol n : steam- cresol
Chem. formula	C 7 H 8 O
Physical properties
Molar mass	108.14 g / mol
Density	o : 1.05 g / cm³ m : 1.03 g / cm³ n : 1.02 g / cm³
Thermal properties
T. melt.	about : 29.8 ℃ m : 11.8 ℃ n : 35.5 ℃
T. bale.	about : 191 ℃ m : 202 ℃ n : 201.9 ℃
Chemical properties
Solubility in water	o : 2.5 g / 100 ml m : 2.4 g / 100 ml p : 1.9 g / 100 ml
Structure
Dipole moment	o : 1.35 D m : 1.61 D p : 1.58 D
Classification
CAS Number
EINECS Number	215-293-2
Chebi	25399
Drugbank
Smiles
	about : Oc1c (C) cccc1 m : Oc1cc (C) ccc1 n : Oc1ccc (C) cc1
Security
R phrases	R24 / 25 , R34
S-phrases	S36 / 37/39 , S45
GHS icons
	Data is provided for standard conditions (25 ℃, 100 kPa) , unless otherwise indicated.

Cresols (methylphenols, hydroxytoluene) - There are ortho-, meta- and para-isomers - colorless crystals or liquids. Cresols are readily soluble in ethanol , diethyl ether , benzene , chloroform , acetone ; soluble in water, alkali solutions (with the formation of cresolate salts). Like phenol , cresols are weak acids .

Content

Chemical Properties

Cresols easily enter into reactions of electrophilic substitution, condensation , for example with aldehydes . Para-cresol is oxidized by oxides of Pb , Mn, or Fe to para-hydroxybenzoic acid, and by stronger oxidizing agents to quinone or hydroquinone . During catalytic reduction, it turns into methylcyclohexanols and methylcyclohexanones.

When mixed with chlorine water in the presence of NH ₃ , cresol isomers form colored compounds: ortho-cresol gives a yellow-brown color, turning into greenish, meta -cresol gives green, turns into dark yellow, para-cresol gives a dark yellow, turning into yellow orange or red.

The technical mixture of ortho-, meta- and para-cresol is called tricresol .

Application

Used as solvents and as intermediates in organic synthesis.

Cresols are used in the production or laboratory preparation of aromatic compounds , antiseptics , dyes , synthetic rubbers , fuels and lubricants , phenol-formaldehyde and other resins, insecticides , fungicides and herbicides and medicines ^[1] .

It is also a potent broad-acting antiseptic . It is used mainly in the form of soap solutions for general disinfection (See Lysol ). In small concentrations, it is sometimes used as a preservative for injection solutions. They are part of the preparations Feresol (tricresol) and Verrucacid (metacresol), which are used as a local necrotizing and mummifying agent to remove papillomas and some other skin neoplasms ^[2] .

Effects on the body

Cresol solutions irritate the skin and, when ingested, corrode the mucous surfaces that they come into contact with, causing pain, nausea and vomiting ^[2] .

Cresol steam enters the body through the lungs. Liquid cresols can enter the body through the gastric tract, mucous membranes, and skin. After ingestion, cresols are distributed in tissues and organs in which they can be detected 12-14 hours after absorption. The action of cresols on the body is similar to the action of phenol. However, the irritating and cauterizing effect of cresols on the skin is more pronounced than that of phenols.

Notes

↑ Tricresol description on the website of TPK EI-Resource LLC
↑ ¹ ² Medical Encyclopedia (inaccessible link)