Chemical Properties
Grey-brown to rose or red flakes or granules
Uses
3-Diethylaminophenol is used as a reagent in the synthesis of coumarin- and rhodamine-fused deep red fluorescent dyes.
Uses
3-Diethylaminophenol was used as starting reagent for the synthesis of silyloxyaniline. It was used in the synthesis of Nile Red and its hydroxy-derivative.
General Description
Black solid.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
An amine and phenol. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. Phenols do not behave as organic alcohols, as one might guess from the presence of a hydroxyl (-OH) group in their structure. Instead, they react as weak organic acids. Phenols and cresols are much weaker as acids than common carboxylic acids (phenol has Ka = 1.3 x 10^[-10]). These materials are incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Heat is also generated by the acid-base reaction between phenols and bases. Such heating may initiate polymerization of the organic compound. Phenols are sulfonated very readily (for example, by concentrated sulfuric acid at room temperature). The reactions generate heat. Phenols are also nitrated very rapidly, even by dilute nitric acid.
Health Hazard
ACUTE/CHRONIC HAZARDS: 3-Diethylaminophenol may cause irritation on contact.
Fire Hazard
Flash point data are not available for 3-Diethylaminophenol, but 3-Diethylaminophenol is probably combustible.
Flammability and Explosibility
Non flammable
Synthesis
The general procedure for the synthesis of 3-hydroxy-N,N-diethylaniline from diethylamine and resorcinol is as follows: a Raney Ni-catalyzed amination of resorcinol with secondary amines was used. The procedure was as follows: resorcinol (2.2 g, 20 mmol), diethylamine (30 mmol) and Raney Ni catalyst (110 mg) were added to a 100 ml autoclave, and 50 ml of water was added as solvent. The air in the autoclave was replaced with hydrogen three times, followed by maintaining the hydrogen pressure at 0.05 MPa. The reaction mixture was rapidly heated to 200 °C and the reaction was stirred at this temperature for 3 h. The reaction was carried out at a temperature of 0.05 °C. After completion of the reaction, the mixture was cooled to room temperature and extracted with n-butyl acetate. The organic layer was collected, dried with anhydrous magnesium sulfate, filtered and concentrated to obtain the crude product. Finally, the target product 3-hydroxy-N,N-diethylaniline was purified by silica gel fast column chromatography (eluent was petroleum ether/ethyl acetate, 3:1, v/v).
References
[1] Catalysis Communications, 2014, vol. 46, p. 201 - 207
[2] Patent: US2376112, 1942,
