4469-81-2

Basic information

• Product Name: 2-BUTOXYANILINE
• Synonyms: 2-BUTOXY-PHENYLAMINE;2-BUTOXYANILINE;AKOS BC-2531;AKOS BBB/406;NSC 55075;o-Butoxyaniline;2-Butoxybenzenamine
• CAS NO: 4469-81-2
• Molecular Formula: C₁₀H₁₅NO
• Molecular Weight: 165.23
• Mol File: 4469-81-2.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 266.5°C at 760 mmHg
• Flash Point: 114.2°C
• Appearance: /
• Density: 0.999g/cm³
• Vapor Pressure: 0.0086mmHg at 25°C
• Refractive Index: 1.53
• PKA: 4.49±0.10(Predicted)
• CAS DataBase Reference: 2-BUTOXYANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BUTOXYANILINE(4469-81-2)
• EPA Substance Registry System: 2-BUTOXYANILINE(4469-81-2)

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: 4469-81-2(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthetic Communications, 24, p. 945, 1994 DOI: 10.1080/00397919408020769

InChI:InChI=1/C10H15NO/c1-2-3-8-12-10-7-5-4-6-9(10)11/h4-7H,2-3,8,11H2,1H3

Upstream product

• 7252-51-9 n-butyl o-nitrophenyl ether 
• 65347-85-5 (2-Butoxy-phenyl)-carbamic acid 2-morpholin-4-yl-ethyl ester 
• 109-69-3 n-Butyl chloride 
• 95-55-6 2-amino-phenol 
• 88-75-5 2-hydroxynitrobenzene 
• 1493-27-2 ortho-nitrofluorobenzene 
• 109-65-9 1-bromo-butane 
• 532-09-2 acetic acid-(2-butoxy-anilide) 
• 614-80-2 2-(acetylamino)phenol 

Downstream Products

• 500334-19-0 1-iodo-2-butoxybenzene 
• 72635-76-8 2-butoxy-5-nitro-aniline 
• 101584-26-3 benzoic acid-(2-butoxy-anilide) 
• 41240-82-8 chloro-acetic acid-(2-butoxy-anilide) 
• 57836-96-1 2-(2-Butoxy-phenylamino)-propionic acid methyl ester 
• 55792-33-1 2-n-Butyloxyphenylisocyanat 
• 98771-58-5 ethyl 1,6-dihydro-2-(2-butoxyanilino)-6-oxo-5-pyrimidinecarboxylate 
• 78406-69-6 2,3-Dibromo-N-(2-butoxy-phenyl)-propionamide 
• 106476-37-3 1-(o-butoxyphenyl)piperazine 
• 101862-70-8 N-2-Hydroxyaethyl-2-butoxy-anilin 
• 108012-30-2 N_.N-Bis-(2-hydroxyaethyl)-2-butoxy-anilin 
• 215810-76-7 N-(o-butoxyphenyl)maleimide 
• 98772-04-4 1,6-dihydro-2-(2-butoxyanilino)-6-oxo-5-pyrimidinecarboxylic acid 
• 114559-79-4 1-(2-Butoxy-phenyl)-3-((1R,3R,5S)-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-urea 

Relevant articles and documents

A simple preparation of O-substituted o-aminophenols

A simple and not protective method, phase transfer catalysis (PTC) in solvent-free conditions, to prepare the title compounds is described.

Determination of critical micellar concentration of homologous 2-alkoxyphenylcarbamoyloxyethyl-morpholinium chlorides

The critical micellar concentrations of selected alkyloxy homologues of local anesthetic 4-(2-[(2-alkoxyphenyl)carbamoyl]oxy ethyl)morpholin-4-ium chloride with nc = 2, 4, 5, 6, 7, 8, and 9 carbons in alkyloxy tail were determined by absorption spectroscopy in the UV–vis spectral region with the use of a pyrene probe. Within the homologous series of the studied amphiphilic compounds, the ln(cmc) was observed to be dependent linearly on the number of carbon atoms nc in the hydrophobic tail: ln(cmc) = 0.705–0.966 nc. The Gibbs free energy, necessary for the transfer of the methylene group of the alkoxy chain from the water phase into the inner part of the micelle at the temperature of 25?C and pH ≈ 4.5–5.0, was found to be ?2.39 kJ/mol. The experimentally determined cmc values showed good correlations with the predicted values of the bulkiness of the alkoxy tail expressed as the molar volume of substituent R, as well as with the surface tension of the compounds.

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.