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3-Diethylaminophenol

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3-Diethylaminophenol Basic information
Product Name:3-Diethylaminophenol
Synonyms:3-DIETHYLAMINOPHENOL;3-(N,N'-DIETHYLAMINO)PHENOL;1-(DIETHYLAMINO)-3-HYDROXYBENZENE;M-DIETHYLAMINOPHENOL;m-N,N-Diethylaminophenol;3-DIETHYLAMINOPHENOL GRANULATED;3-(DIETHYLAMINO)PHENOL / 3-HYDROXY-N,N-DIETHYLANILINE;3-HYDROXY-N,N-DIETHYLANILINE, 99+%
CAS:91-68-9
MF:C10H15NO
MW:165.23
EINECS:202-090-9
Product Categories:Organic Building Blocks;Oxygen Compounds;Dye Intermediate;Phenols;bc0001
Mol File:91-68-9.mol
3-Diethylaminophenol Structure
3-Diethylaminophenol Chemical Properties
Melting point 69-72 °C (lit.)
Boiling point 170 °C/15 mmHg (lit.)
density 1.0203 (rough estimate)
vapor pressure 0.345Pa at 25℃
refractive index 1.4820 (estimate)
Fp 141 °C
storage temp. Inert atmosphere,Room Temperature
solubility 4.087g/L in organic solvents at 20 ℃
pka10.08±0.10(Predicted)
form Flakes or Granules
color Gray-brown to rose or red
Water Solubility <0.1 g/100 mL at 20.5 ºC
BRN 908212
Cosmetics Ingredients FunctionsHAIR DYEING
InChI1S/C10H15NO/c1-3-11(4-2)9-6-5-7-10(12)8-9/h5-8,12H,3-4H2,1-2H3
InChIKeyWAVOOWVINKGEHS-UHFFFAOYSA-N
SMILESCCN(CC)c1cccc(O)c1
LogP0.929 at 23℃
CAS DataBase Reference91-68-9(CAS DataBase Reference)
NIST Chemistry ReferencePhenol, 3-(diethylamino)-(91-68-9)
EPA Substance Registry Systemm-(Diethylamino)phenol (91-68-9)
Safety Information
Hazard Codes T,Xi
Risk Statements 25-36/37/38
Safety Statements 36/37/39-45-22-26-36-24/25
RIDADR UN 2512 6.1/PG 3
WGK Germany 2
RTECS SL0550500
TSCA TSCA listed
HazardClass 6.1
HS Code 29222900
Storage Class6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects
Hazard ClassificationsAcute Tox. 3 Oral
MSDS Information
ProviderLanguage
3-Diethylaminophenol English
SigmaAldrich English
ACROS English
ALFA English
3-Diethylaminophenol Usage And Synthesis
Chemical PropertiesGrey-brown to rose or red flakes or granules
Uses3-Diethylaminophenol is used as a reagent in the synthesis of coumarin- and rhodamine-fused deep red fluorescent dyes.
Uses3-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 DescriptionBlack solid.
Air & Water ReactionsInsoluble in water.
Reactivity ProfileAn 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.
HazardSee phenol.
Health HazardACUTE/CHRONIC HAZARDS: 3-Diethylaminophenol may cause irritation on contact.
Fire HazardFlash point data are not available for 3-Diethylaminophenol, but 3-Diethylaminophenol is probably combustible.
Flammability and ExplosibilityNon flammable
Synthesis
Diethylamine

109-89-7

Resorcinol

108-46-3

3-Diethylaminophenol

91-68-9

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,
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