Description
2, 5-dimethylphenol (also known as 2, 5-xylenol, or p-xylenol, chemical formula: (CH3)2C6H3OH.) is a chemical compound as one of the six isomers of xylenol. It is found in alcoholic beverages, coffee and whisky. It is a kind of flavoring agent belonging to the family of Ortho Cresols. One of its applications is for the synthesis of Mexilethine. It has important industrial importance, e.g. for the manufacture of antioxidants. It is also a monomer for the poly (p-phenylene oxide) engineering resins through carbon-oxygen oxidative coupling. It is traditionally extracted from the coal tar.
References
https://en.wikipedia.org/wiki/2,6-Xylenol
https://en.wikipedia.org/wiki/Xylenol
https://pubchem.ncbi.nlm.nih.gov/compound/2_5-dimethylphenol#section=Top
Chemical Properties
2,5-Xylenol has a creosote, sweet, medicinal taste.
Chemical Properties
WHITE TO CREAM COLORED CRYSTALS
Occurrence
Reported found in coffee, smoked fatty fish, processed lean fish, malt whiskey, Scotch blended whiskey, katsuobushi
(dried bonito) and kumazasa (Sasa albo-marginata).
Uses
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.]
