91-68-9

Basic information

• Product Name: 3-Diethylaminophenol
• Synonyms: 3-Diethylaminophenol,99%;3-DiethylaMinophenol, 99% 100GR;3-(diethylamino)-pheno;3-Hydroxy-N,N-diethylaniline;diethylaminophenol;m-(diethylamino)-pheno;m-Hydroxydiethylaniline;N,N-Diethyl-3-hydroxyaniline
• CAS NO: 91-68-9
• Molecular Formula: C₁₀H₁₅NO
• Molecular Weight: 165.23
• EINECS: 202-090-9
• Product Categories: Dye Intermediate;Organic Building Blocks;Oxygen Compounds;Phenols
• Mol File: 91-68-9.mol
• Article Data: 18

Chemical Properties

• Melting Point: 69-72 °C(lit.)
• Boiling Point: 170 °C15 mm Hg(lit.)
• Flash Point: 141 °C
• Appearance: Gray-brown to rose or red/Flakes or Granules
• Density: 1.0203 (rough estimate)
• Vapor Pressure: 0.00259mmHg at 25°C
• Refractive Index: 1.4820 (estimate)
• Storage Temp.: Refrigerator
• Solubility: 4.087g/L in organic solvents at 20 ℃
• PKA: 10.08±0.10(Predicted)
• Water Solubility: <0.1 g/100 mL at 20.5℃
• BRN: 908212
• CAS DataBase Reference: 3-Diethylaminophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Diethylaminophenol(91-68-9)
• EPA Substance Registry System: 3-Diethylaminophenol(91-68-9)

Safety Data

• Hazard Codes: T,Xi
• 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
• Hazardous Substances Data: 91-68-9(Hazardous Substances Data)

Usage

Chemical Properties

Grey-brown to rose or red flakes or granules

Uses

Different sources of media describe the Uses of 91-68-9 differently. You can refer to the following data:
1. 3-Diethylaminophenol is used as a reagent in the synthesis of coumarin- and rhodamine-fused deep red fluorescent dyes.
2. 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.

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.

Hazard

See phenol.

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

Nonflammable

InChI:InChI=1/C10H15NO/c1-3-11(4-2)9-6-5-7-10(12)8-9/h5-8,12H,3-4H2,1-2H3

Upstream product

• 60-29-7 diethyl ether 
• 95-56-7 2-hydroxybromobenzene 
• 816-43-3 lithium diethylamide 
• 64-17-5 ethanol 
• 51-81-0 3-aminophenol hydrochloride 
• 26513-20-2 N,N-diethyl-1,3-benzenediamine 
• 660-68-4 diethyl amine hydrochloride 
• 109-89-7 diethylamine 
• 108-46-3 recorcinol 
• 91-66-7 N,N-diethylaniline 
• 97-20-1 3-diethylamino-benzenesulfonic acid 
• 95-57-8 2-monochlorophenol 
• 108-43-0 3-monochlorophenol 
• 75-03-6 ethyl iodide 

Downstream Products

• 5809-23-4 2'-Carboxy-4-diethylamino-2-hydroxybenzophenon 
• 40445-22-5 2,3,4,5-tetrachloro-6-(4-(diethylamino)-2-hydroxybenzoyl)benzoic acid 
• 18997-95-0 3-(diethylamino)phenyl acetate 
• 91-44-1 7-diethylamino-4-methylcoumarin 
• 41681-29-2 N,N-diethyl-3-(2-dimethylamino-ethoxy)-aniline 
• 2631-26-7 3-(N,N-diethylamino)phenyl-N'-methylcarbamate 
• 17754-90-4 4-(Diethylamino)salicylaldehyde 
• 92-18-2 N,N-diethyl-3-methoxyaniline 
• 19026-53-0 N,N-diethyl-3-((oxiran-2-yl)methoxy)aniline 
• 65883-15-0 2-[3-(diethylamino)phenoxy]ethanol 
• 6274-83-5 5,5'-bis-diethylamino-2,2'-methanediyl-di-phenol 
• 1864-92-2 N,N-diethyl-3-ethoxyaniline 
• 51716-97-3 diethyl-(7-phenylimino-7H-phenoxazin-3-yl)-amine 

Relevant articles and documents

Mechanism study on Raney nickel-catalyzed amination of resorcinol

Amination of resorcinol catalyzed by Raney nickel has been examined with good yield. Using the first principle density functional theory, some detailed mechanism of the amination of resorcinol on the Ni(111) surface is explored. The resorcinol is adsorbed on the Ni surface at the hollow site to form ketone by isomerization. The isomerization has a barrier of 122.1 kJ/mol. Ketone can couple with secondary amine mediated by resorcinol to afford hemiaminal. For the formation of hemiaminal, the steric effect of the alkyl group of secondary amine is obvious. Hemiaminal undergoes dehydration to get final product, which occurs by the preferred adsorption in the bridge site, cleavage of CO bond initially, followed by subsequent cleavage of CH bond.

A inter-b-aminophenol preparation method

The invention belongs to organic synthesis and chemical raw material preparation technical field, and in particular relates to inter-b-aminophenol and intermediate preparation method, inter-b-aminophenol of the preparation method, comprises the steps of: (1) dinitrobenzene substituted benzyl alcohol generated by the reaction with 1 - benzyloxy - 3 - nitrophenyl; (2) 1 - benzyloxy - 3 - nitrobenzene with acetaldehyde in the foaming PH to acid substituted in the reaction solution, or 1 - benzyloxy - 3 - nitrobenzene with acetaldehyde to replace after the recovery of the solvent of the reaction solution dissolved in the dissolving of the re-dissolved solution in organic solvent, by reducing amination and catalytic debenzylation of hydrogenation generating inter-b-aminophenol. 1 - Benzyloxy - 3 - nitrophenyl without separation and purification, directly with the aldehyde and hydrogen reduction amination and debenzylation of hydrogenation reaction. The method is simple, mild condition, equipment strength requirement is low, not produce waste, environment friendly, easily available raw materials, high yield, is suitable for the large-scale generation.

A benzothiazole-rhodol based luminophor: ESIPT-induced AIE and an application for detecting Fe2+ ion

Herein, we designed and synthesized a luminophor, Rh-F, which is an intergrant of rhodol and 2-hydroxy benzothiazole by introducing a benzothiazole unit onto the ortho-position of the phenolic hydroxy of rhodol. Rh-F exhibited excellent fluorescence properties such as a large Stokes shift (>180 nm) and the synergistic effect of aggregation-induced emission (AIE) and an excited state intramolecular proton transfer (ESIPT) feature. The AIE/ESIPT mechanism was thoroughly explored using X-ray single-crystal structures and photophysical determinations. Furthermore, Rh-F showed a sensitive fluorescence response to Fe2+ with low detection limits of 115.2 nM and high selectivity. Studies of its sensing mechanism indicated that the Fe2+-induced blue-green fluorescence-quenched at 525 nm originates from an irreversible Fe2+ chelate with the oxygen atom of the hydroxyl group and the N atom of the benzothiazole moiety. This blocked the ESIPT process of Rh-F which resulted in the quenching of the fluorescence sensor for Rh-F.