621-33-0

Basic information

• Product Name: 3-Ethoxyaniline
• Synonyms: M-PHENETIDINE;3'-AMINOPHENETOL;3-ETHOXYBENZENAMINE;3-ETHOXYANILINE;AKOS BBB/405;m-Ethoxyaniline;META-PHENETIDINE;LABOTEST-BB LTBB000784
• CAS NO: 621-33-0
• Molecular Formula: C₈H₁₁NO
• Molecular Weight: 137.18
• EINECS: 210-680-2
• Product Categories: Phenetole;Amines
• Mol File: 621-33-0.mol

Chemical Properties

• Melting Point: 204 °C
• Boiling Point: 248 °C(lit.)
• Flash Point: >230 °F
• Appearance: Clear brown/Liquid
• Density: 1.032 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0209mmHg at 25°C
• Refractive Index: n20/D 1.566(lit.)
• Storage Temp.: Store below +30°C.
• PKA: 4.18(at 25℃)
• Water Solubility: 0.1-0.5 g/100 mL at 20 ºC
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents, acids, acid chlorides, acid anhydrides. Sensitive to prolonged e
• BRN: 971028
• CAS DataBase Reference: 3-Ethoxyaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Ethoxyaniline(621-33-0)
• EPA Substance Registry System: 3-Ethoxyaniline(621-33-0)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25-33
• Safety Statements: 28-36/37/39-45-36/37-28A
• RIDADR: UN 2311 6.1/PG 3
• WGK Germany: 3
• RTECS: SI5400000
• F: 8-10-23
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 621-33-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Ethoxyaniline is used as a starting reagent for the synthesis of 1,2,3,4-tetrahydroacridinylhydrazides, which are important compounds in the pharmaceutical industry. These hydrazides have potential applications as therapeutic agents, particularly in the development of drugs targeting various diseases and conditions.
Used in Chemical Synthesis:
Due to its unique chemical structure, 3-Ethoxyaniline serves as a valuable intermediate in the synthesis of a wide range of organic compounds. Its ability to participate in various chemical reactions, such as substitution, addition, and condensation, makes it a useful building block for creating complex molecules with diverse applications in different industries.
Used in Dye and Pigment Industry:
The light yellow to dark red color of 3-Ethoxyaniline makes it a potential candidate for use in the dye and pigment industry. Its color properties can be exploited to create a variety of dyes and pigments for use in textiles, plastics, and other materials.
Used in Research and Development:
3-Ethoxyaniline's versatile chemical properties also make it a valuable compound for research and development purposes. Scientists and researchers can use it to explore new reaction pathways, develop novel synthetic methods, and create new compounds with potential applications in various fields, such as medicine, agriculture, and materials science.

Air & Water Reactions

Slightly soluble in water.

Reactivity Profile

3-Ethoxyaniline neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Fire Hazard

3-Ethoxyaniline is probably combustible.

Safety Profile

Mutation data reported. When heated to decomposition it emits toxic vapors of NOx.

Upstream product

• 591-33-3 3-ethoxyacetanilide 
• 621-52-3 1-ethoxy-3-nitrobenzene 
• 55792-09-1 (3-Ethoxy-phenyl)-carbamic acid 2-piperidin-1-yl-ethyl ester; hydrochloride 
• 64-17-5 ethanol 
• 7647-01-0 hydrogenchloride 
• 90434-59-6 (3-ethoxy-phenyl)-hydrazine 
• 588-02-3 3,3'-diethoxyazobenzene 
• 621-42-1 meta-hydroxyacetanilide 
• 554-84-7 meta-nitrophenol 
• 74-96-4 ethyl bromide 
• 591-27-5 m-Hydroxyaniline 
• 75-00-3 chloroethane 

Downstream Products

• 105974-01-4 (3-ethoxy-phenyl)-[2]pyridyl-amine 
• 109688-62-2 (3-ethoxy-phenyl)-(6-methyl-[2]pyridyl)-amine 
• 26117-42-0 N-(3-ethoxy-phenyl)-phthalimide 
• 591-33-3 3-ethoxyacetanilide 
• 13140-68-6 N-(3-ethoxy-phenyl)-N'-phenyl-thiourea 
• 13256-74-1 N-(3-ethoxy-phenyl)-N'-p-tolyl-urea 
• 20041-28-5 N-propyl-m-phenetidine 
• 106270-46-6 N'-(3-ethoxy-phenyl)-N,N-dimethyl-ethylenediamine 
• 82745-08-2 N-(3-ethoxy-phenyl)-N'-methyl-thiourea 
• 17641-12-2 chloro-acetic acid m-phenetidide 
• 17765-38-7 3-chloro-propionic acid m-phenetidide 
• 1864-91-1 3-ethoxy-N,N-dimethylaniline 
• 14255-74-4 N-(3-ethoxy-phenyl)-N'-allyl-thiourea 
• 17722-29-1 N,N'-bis-(3-ethoxy-phenyl)-malonamide 

Relevant articles and documents

Investigation of hydro-lipophilic properties of n-alkoxyphenylhydroxynaphthalenecarboxamides ?

The evaluation of the lipophilic characteristics of biologically active agents is indispensable for the rational design of ADMET-tailored structure–activity models. N-Alkoxy-3-hydroxynaphthalene-2-carboxanilides, N-alkoxy-1-hydroxynaphthalene-2-carboxanilides, and N-alkoxy-2-hydroxynaphthalene-1-carboxanilides were recently reported as a series of compounds with antimycobacterial, antibacterial, and herbicidal activity. As it was found that the lipophilicity of these biologically active agents determines their activity, the hydro-lipophilic properties of all three series were investigated in this study. All 57 anilides were analyzed using the reversed-phase high-performance liquid chromatography method for the measurement of lipophilicity. The procedure was performed under isocratic conditions with methanol as an organic modifier in the mobile phase using an end-capped non-polar C18 stationary reversed-phase column. In the present study, a range of software lipophilicity predictors for the estimation of clogP values of a set of N-alkoxyphenylhydroxynaphthalenecarboxamides was employed and subsequently cross-compared with experimental parameters. Thus, the empirical values of lipophilicity (logk) and the distributive parameters (π) were compared with the corresponding in silico characteristics that were calculated using alternative methods for deducing the lipophilic features. To scrutinize (dis)similarities between the derivatives, a PCA procedure was applied to visualize the major differences in the performance of molecules with respect to their lipophilic profile, molecular weight, and violations of Lipinski’s Rule of Five.

Synthesis method of m-phenetidine by one-pot reaction

The invention discloses a synthesis method of m-phenetidine by a one-pot reaction. The method comprises the following steps: m-aminophenol, alkali and a solvent are thrown into a reaction vessel, and then only an alkylating agent or a catalyst and an alkylating agent are added at the same time, after materials are added, the reaction vessel is enclosed, and stirring is carried out for 0.5-1 hour at room temperature; the temperature is raised to 40-80 DEG C, a reaction is carried out for 1-8 hours, after the reaction, obtained reaction solution is cooled to room temperature and filtered, and filtrate is obtained; reduced pressure distillation for the filtrate is carried out, and m-phenetidine is obtained. The synthesis method of m-phenetidine has the characteristics of low reaction temperature, high safety performance, convenient operation, high purity and high yield of the product, etc.

[Cp?RhCl2]2-catalyzed alkyne hydroamination to 1,2-dihydroquinolines

[Cp?RhCl2]2 catalyzes the formation of 1,2-dihydroquinolines from the reaction of two terminal alkynes and an aniline. This reaction is believed to proceed via an alkyne hydroamination followed by an alkyne insertion.

Synthesis and Biological Evaluation of N-Alkoxyphenyl-3-hydroxynaphthalene-2-carboxanilides

A series of fifteen new N-alkoxyphenylanilides of 3-hydroxynaphthalene-2-carboxylic acid was prepared and characterized. Primary in vitro screening of the synthesized compounds was performed against Staphylococcus aureus, three methicillin-resistant S. aureus strains, Mycobacterium tuberculosis H37Ra and M. avium subsp. paratuberculosis. Some of the tested compounds showed antibacterial and antimycobacterial activity against the tested strains comparable with or higher than that of the standards ampicillin or rifampicin. 3-Hydroxy-N-(2-propoxyphenyl)naphthalene-2-carboxamide and N-[2-(but-2-yloxy)-phenyl]-3-hydroxynaphthalene-2-carboxamide had MIC = 12 μM against all methicillin-resistant S. aureus strains; thus their activity is 4-fold higher than that of ampicillin. The second mentioned compound as well as 3-hydroxy-N-[3-(prop-2-yloxy)phenyl]-naphthalene-2-carboxamide had MICs = 23 μM and 24 μM against M. tuberculosis respectively. N-[2-(But-2-yloxy)phenyl]-3-hydroxynaphthalene-2-carboxamide demonstrated higher activity against M. avium subsp. paratuberculosis than rifampicin. Screening of the cytotoxicity of the most effective antimycobacterial compounds was performed using THP-1 cells, and no significant lethal effect was observed for the most potent compounds. The compounds were additionally tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. N-(3-Ethoxyphenyl)-3-hydroxynaphthalene-2-carboxamide (IC50 = 4.5 μM) was the most active PET inhibitor. The structure-activity relationships are discussed.

Design, synthesis, and anticonvulsant activity evaluation of 4-(3-Alkoxy-phenyl)-2,4-dihydro-[1,2,4]triazol-3-ones

A series of 4-(3-alkoxy-phenyl)-2,4-dihydro-[1,2,4]triazol-3-ones were synthesized using the appropriate synthetic route and evaluated experimentally in the maximal electroshock test; their neurotoxicities were evaluated by the rotarod neurotoxicity test. The structures of these compounds were confirmed by IR, MS, 1H-NMR, and elementary analysis. All target compounds exhibited anticonvulsant activity to varying degrees in the maximal electroshock test. 4-(3-Benzyloxy-phenyl)-2,4-dihydro-[1,2,4]triazol-3-one (4i) was the most promising compound with an ED50 value of 30.5 mg/kg and a protective index (PI) of 18.63, showing a higher safety than the standard carbamazepine (PI = 6.45). In addition, the potency of compound 4i against seizures induced by pentylenetetrazole and 3-mercaptopropionic acid suggested its broad-spectrum activity, and the mechanisms of action including inhibition of voltage-gated ion channels and modulation of GABAergic activity might be involved in its anticonvulsant activity. Copyright

Hydrogenative cleavage of azo compounds catalyzed by commercial zinc dust using ammonium acetate

Addition of ammonium acetate followed by commercial zinc dust to the solution of azo compounds in methanol appears to offer a general and convenient means for reducing both symmetrical and unsymmetrical azo compounds to the corresponding amine/s at ambient temperature. Many other reducible and hydrogenolysable groups like -OCH3, -OH, -COOH, -CH3, -COCH3 and halogens are tolerated. The reduction is fast, clean, high yielding and inexpensive compared to earlier methods.

Facile Transfer Hydrogenation of Azo Compounds to Hydrazo Compounds and Anilines by Using Raney Nickel and Hydrazinium Monoformate

Azo compounds are conveniently reduced to either partially reduced hydrazo compounds or completely reduced anilines by employing Raney nickel in presence of hydrazinium monoformate depending upon reaction conditions. The other reducible moieties like -COOH and halogens are tolerated. The reduction process is selective, rapid and high yielding.

Rapid cleavage of azo compounds to amine/s using Raney nickel and ammonium formate or formic acid

Azo compounds, both symmetrical and unsymmetrical are cleaved to amine/s by using Raney nickel and ammonium formate or formic acid in methanol at room temperature. The reductive cleavage is very fast, clean, cost effective and high yielding as compared to earlier methods and many other functionality such as -OH, -CH3 -OCH3, -COOH, -COCH3 and halogen remained unaffected.

KINETICS OF ALKALINE HYDROLYSIS AND CORRELETION STUDIES OF m- AND p-SUBSTITUTED PIPERIDINOETHYL PHENYLCARBAMATES

Kinetics of alkaline hydrolysis have been studied with a series of 15 m- and p-substituted piperidinoethyl phenylcarbamates.The rate constants have been determined at 70, 60, 50, and 40 deg C and the activation parameters have been calculated.These values have been correlated with the substituent constants ?, , , F, R, ?.Validity of the Hammett equation and the Swain-Lupton equation has been confirmed in the series studied and for the p-derivatives, respectively.The lipophilicity parameter ? does not correlate with the values found.