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
• Article Data: 6

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

General Description

3-Propoxy-phenylamine is a chemical compound with the molecular formula C9H13NO, and it belongs to the class of organic compounds known as anilines. It is a colorless to light yellow liquid with a faint amine odor, and it is soluble in water. This chemical is commonly used as an intermediate in the synthesis of pharmaceuticals, dyes, and other organic compounds. It is also used as a corrosion inhibitor, a fragrance ingredient, and in the production of polymers. In addition, it has been found to have antimicrobial and anti-inflammatory properties, making it a potential candidate for use in medicinal applications.

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

• 55792-52-4 acetic acid-(3-propoxy-anilide) 
• 1138442-32-6 bromo-acetic acid-(3-propoxy-anilide) 
• 860735-50-8 N,N-dimethyl-3-propoxy-aniline 
• 37054-93-6 2-[(3-Propoxy-phenyl)-hydrazono]-malonic acid 
• 98771-68-7 6-Oxo-2-(3-propoxy-phenylamino)-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester 
• 128924-33-4 C₁₇H₂₀N₂O₄S 
• 14052-88-1 6,6-Dimethyl-1-(3-propoxy-phenyl)-1,6-dihydro-[1,3,5]triazine-2,4-diamine; hydrochloride 
• 857591-30-1 4-nitro-3-propoxy-aniline 
• 855839-72-4 Propyl-(6-nitro-3-hydroxy-phenyl)-aether 
• 130349-21-2 acetic acid-(2-nitro-5-propoxy-anilide) 
• 860578-16-1 acetic acid-(4-nitro-3-propoxy-anilide) 
• 113501-99-8 2-nitro-5-propoxyaniline 
• 1442656-58-7 C₁₁H₁₃N₃O₂ 
• 1061518-07-7 C₁₇H₂₀N₂O 

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 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.

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.