4469-79-8

Basic information

• Product Name: 3-PROPOXY-PHENYLAMINE
• Synonyms: AKOS BC-2544;AKOS BBB/404;3-PROPOXY-PHENYLAMINE;3-propoxybenzenamine
• CAS NO: 4469-79-8
• Molecular Formula: C₉H₁₃NO
• Molecular Weight: 151.21
• Mol File: 4469-79-8.mol

Chemical Properties

• Boiling Point: 266.9°C at 760 mmHg
• Flash Point: 120.9°C
• Appearance: /
• Density: 1.016g/cm³
• Vapor Pressure: 0.00843mmHg at 25°C
• Refractive Index: 1.536
• CAS DataBase Reference: 3-PROPOXY-PHENYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-PROPOXY-PHENYLAMINE(4469-79-8)
• EPA Substance Registry System: 3-PROPOXY-PHENYLAMINE(4469-79-8)

Safety Data

• Hazard Codes: Xi,N,Xn
• Statements: 20/21/22-36/37/38-50/53
• Safety Statements: 26-36/37-61
• HazardClass: IRRITANT
• Hazardous Substances Data: 4469-79-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Propoxy-phenylamine is used as a chemical intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Dye Industry:
It serves as a key component in the production of dyes, enhancing the colorfastness and quality of the final products.
Used in Organic Compounds Synthesis:
3-Propoxy-phenylamine is used as an intermediate in the synthesis of other organic compounds, broadening its applications in the chemical industry.
Used as a Corrosion Inhibitor:
It is employed as a corrosion inhibitor, protecting materials from degradation and extending their service life.
Used in Fragrance Industry:
3-Propoxy-phenylamine is used as a fragrance ingredient, adding unique scents to various products.
Used in Polymer Production:
It plays a role in the production of polymers, contributing to the development of new materials with specific properties.
Used in Medicinal Applications:
Due to its antimicrobial and anti-inflammatory properties, 3-Propoxy-phenylamine is used as a potential candidate for medicinal applications, offering new avenues for treatment and prevention of various conditions.

InChI:InChI=1/C9H13NO/c1-2-6-11-9-5-3-4-8(10)7-9/h3-5,7H,2,6,10H2,1H3

Upstream product

• 106-94-5 propyl bromide 
• 591-27-5 m-Hydroxyaniline 
• 55792-52-4 acetic acid-(3-propoxy-anilide) 
• 554-84-7 meta-nitrophenol 
• 52205-61-5 (3-Propoxy-phenyl)-carbamic acid 2-piperidin-1-yl-ethyl ester; hydrochloride 
• 70599-87-0 (3-nitro-phenyl)-propyl ether 

Downstream Products

• 1138442-32-6 bromo-acetic acid-(3-propoxy-anilide) 
• 1061518-07-7 C₁₇H₂₀N₂O 
• 1442656-58-7 C₁₁H₁₃N₃O₂ 
• 36998-93-3 2-[(3-Propoxy-phenyl)-hydrazono]-propanedioyl dichloride 
• 113501-99-8 2-nitro-5-propoxyaniline 
• 860578-16-1 acetic acid-(4-nitro-3-propoxy-anilide) 
• 130349-21-2 acetic acid-(2-nitro-5-propoxy-anilide) 
• 855839-72-4 Propyl-(6-nitro-3-hydroxy-phenyl)-aether 
• 857591-30-1 4-nitro-3-propoxy-aniline 
• 133071-00-8 2-[2-(5-Bromo-1H-indol-3-yl)-ethyl]-3-(3-propoxy-phenyl)-3H-quinazolin-4-one 
• 98772-19-1 6-Oxo-2-(3-propoxy-phenylamino)-1,6-dihydro-pyrimidine-5-carboxylic acid 
• 14052-88-1 6,6-Dimethyl-1-(3-propoxy-phenyl)-1,6-dihydro-[1,3,5]triazine-2,4-diamine; hydrochloride 
• 128924-33-4 C₁₇H₂₀N₂O₄S 
• 98771-68-7 6-Oxo-2-(3-propoxy-phenylamino)-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester 

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.

[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

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.