2,5-Dimethylphenol

Chemical properties

WHITE TO CREAM COLORED CRYSTALS

Chemical properties

2,5-Xylenol has a creosote, sweet, medicinal taste.

Occurrence

Reported found in coffee, smoked fatty fish, processed lean fish, malt whiskey, Scotch blended whiskey, katsuobushi (dried bonito) and kumazasa (Sasa albo-marginata).

The Uses of 2,5-Dimethylphenol

Used to make phenolic resins and (in isomeric mixtures) as an antioxidant for lubricating oils, gasoline, and elastomers. Also used as perfuming agents.

Definition

ChEBI: 2,5-xylenol is a member of the class of phenols that phenol substituted by methyl groups at positions 2 and 5. It has a role as a volatile oil component and an animal metabolite. It derives from a hydride of a p-xylene.

Aroma threshold values

Detection: 400 ppb

Taste threshold values

Taste characteristics at 10 ppm: musty, chemical, stringent and phenolic.

General Description

Colorless to off-white crystalline solid. Odor threshold concentration 0.4 mg/L. Taste threshold concentration 0.5 mg/L.

Air & Water Reactions

2,5-Dimethylphenol is hygroscopic. Insoluble in water.

Reactivity Profile

2,5-Dimethylphenol is incompatible with bases, acid chlorides, acid anhydrides and oxidizing agents. 2,5-Dimethylphenol corrodes steel, brass, copper and copper alloys.

Health Hazard

Symptoms of exposure to this compound may include severe irritation and burns of the skin and eyes; irritation of the respiratory tract, dizziness, stomach pain, exhaustion, coma and damage to the liver or kidneys. Other symptoms include headache, nausea and vomiting. It may cause corrosion of the tissues of the mucous membranes and upper respiratory tract, eyes and skin. Inhalation may result in burning sensation, coughing, wheezing, laryngitis and shortness of breath. Inhalation may be fatal as a result of spasm, inflammation and edema of the larynx and bronchi; chemical pneumonitis and pulmonary edema. Symptoms of exposure to this class of compounds include skin sensitization, profuse sweating, painless blanching or erythema of the skin, intense thirst, diarrhea, cyanosis from methemoglobinemia, hyperactivity, stupor, blood pressure fall, hyperpnea, abdominal pain, hemolysis and convulsions. If death from respiratory failure is not immediate, jaundice and oliguria or anuria may occur.

Fire Hazard

Flash point data for 2,5-Dimethylphenol are not available. 2,5-Dimethylphenol is probably combustible.

Safety Profile

Poison by ingestion. Moderately toxic by an unspecified route. When heated to decomposition it emits acrid smoke and irritating fumes. Questionable carcinogen with experimental tumorigenic data. Used in disinfectants, solvents, pharmaceuticals, plasticizers, and wetting agents. See also other xylenol entries.

Purification Methods

Crystallise 2,5-xylenol from EtOH/ether. [Beilstein 6 IV 3164.]