18979-72-1

Basic information

• Product Name: 4-N-BUTOXYPHENOL
• Synonyms: butoxyphenol;HYDROQUINONE MONO-N-BUTYL ETHER;HYDROQUINONE MONOBUTYL ETHER;4-NORMAL-BUTOXYPHENOL;4-N-BUTYLOXYPHENOL;4-BUTYLOXYPHENOL;3-BUTOXYPHENOL;P-BUTOXYPHENOL
• CAS NO: 18979-72-1
• Molecular Formula: C₁₀H₁₄O₂
• Molecular Weight: 166.22
• EINECS: 204-583-4
• Mol File: 18979-72-1.mol

Chemical Properties

• Melting Point: 65-66 °C(lit.)
• Boiling Point: 269 °C
• Flash Point: 132.4°C
• Appearance: /
• Density: 1,05 g/cm3
• Refractive Index: 1.5230-1.5260
• Storage Temp.: 2-8°C
• PKA: 9.61±0.10(Predicted)
• Water Solubility: 1.37g/L(30 oC)
• CAS DataBase Reference: 4-N-BUTOXYPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-N-BUTOXYPHENOL(18979-72-1)
• EPA Substance Registry System: 4-N-BUTOXYPHENOL(18979-72-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-40-41-43-52/53
• Safety Statements: 26-36/37/39-61
• RIDADR: 1760
• WGK Germany: 3
• Hazardous Substances Data: 18979-72-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-N-BUTOXYPHENOL is used as a key intermediate in the synthesis of various organic compounds. Its versatile chemical structure allows it to be a valuable building block in the production of a range of chemical products.
Used in Antimicrobial Applications:
4-N-BUTOXYPHENOL is used as an antibacterial agent, particularly effective against oral bacteria. Its inhibitory action on these bacteria makes it a promising candidate for use in oral care products and other applications where controlling bacterial growth is essential.
Used in the Synthesis of 3BOP-daC12 Benzoxazine:
4-N-BUTOXYPHENOL is used as a starting material in the synthesis of 3BOP-daC12 Benzoxazine, a novel compound with potential applications in various industries, such as materials science and pharmaceuticals.
Used in the Synthesis of 2-Butoxy-6-Benzyloxybenzaldehyde:
4-N-BUTOXYPHENOL is also utilized in the synthesis of 2-Butoxy-6-Benzyloxybenzaldehyde, an organic compound with potential applications in the fragrance and flavor industries, as well as in the development of new pharmaceutical agents.

Synthesis

1)Stir a solution of 1,5-dihydroxybenzene (5 mmol ) and cerium trifluoromethanesulfonate (0.1 mmol ) in 1-butanol (10 mmol, 5.4 mL) at 130 °C for 5 days in round bottom flask.2)Quench the mixture with water (20 mL).3)Extract the reaction mixture three times with dichloromethane (3 x10 mL).4)Wash the combined organic layers with brine (15 mL).5)Dry the combined organic layers over MgSO4.6)Concentrate the combined organic layers.7)Purify the crude product by column chromatography (Cyclohexane-ethyl acetate 99/1) to obtain 3-butoxyphenol.

Upstream product

• 778-28-9 butyl para-toluenesulfonate 
• 54494-87-0 resorcinol; sodium-compound 
• 109-89-7 diethylamine 
• 109-65-9 1-bromo-butane 
• 108-46-3 recorcinol 
• 2492-36-6 n-butyl radical 
• 24856-47-1 3-hydroxy-phenyloxyl 
• 71-36-3 butan-1-ol 
• 161006-18-4 3-((tert-butyldimethylsilyl)oxy)phenol 

Downstream Products

• 6329-30-2 3-Butyloxy-phenylessigsaeure 
• 4475-79-0 diethyl-carbamic acid-(3-butoxy-phenyl ester) 
• 135360-33-7 5-(3-Butoxy-phenoxy)-pentanoic acid methyl ester 
• 135360-21-3 2-(3-Butoxy-phenoxy)-1-(4-isobutyl-phenyl)-ethanone 
• 135360-28-0 (3-Butoxy-phenoxy)-acetic acid methyl ester 
• 135360-22-4 2-(3-Butoxy-phenoxy)-1-phenyl-ethanone 
• 91561-01-2 1-(2-bromo-ethoxy)-3-butoxy-benzene 
• 1359756-86-7 4-(3-butoxyphenoxy)benzonitrile 
• 1359764-02-5 3-(3-butoxyphenyloxy)benzonitrile 
• 763868-64-0 C₁₀H₁₅NO₂ 
• 1005005-61-7 2-allyl-3-butoxy phenol 
• 1005005-60-6 2-allyl-5-butoxy phenol 
• 1005005-97-9 1-allyloxy-3-butoxybenzene 

Relevant articles and documents

Structural Basis for Developing Multitarget Compounds Acting on Cysteinyl Leukotriene Receptor 1 and G-Protein-Coupled Bile Acid Receptor 1

G-protein-coupled receptors (GPCRs) are the molecular target of 40% of marketed drugs and the most investigated structures to develop novel therapeutics. Different members of the GPCRs superfamily can modulate the same cellular process acting on diverse pathways, thus representing an attractive opportunity to achieve multitarget drugs with synergic pharmacological effects. Here, we present a series of compounds with dual activity toward cysteinyl leukotriene receptor 1 (CysLT1R) and G-protein-coupled bile acid receptor 1 (GPBAR1). They are derivatives of REV5901-the first reported dual compound-with therapeutic potential in the treatment of colitis and other inflammatory processes. We report the binding mode of the most active compounds in the two GPCRs, revealing unprecedented structural basis for future drug design studies, including the presence of a polar group opportunely spaced from an aromatic ring in the ligand to interact with Arg792.60 of CysLT1R and achieve dual activity.

Synthesizing method of 3-butoxyphenol

The invention discloses a synthesizing method of 3-butoxyphenol, and belongs to the technical field of chemical synthesis. The method comprises the following steps: adding resorcinol, potassium carbonate and n-butyl bromide into an acetonitrile solvent and mechanically stirring the mixture, so as to obtain a mixed solution; putting the mixed solution into a constant temperature magnetic stirrer, heating the mixed solution for reacting for 24h and performing rotary evaporation, so as to obtain a reaction liquid; adding dichloromethane into the reaction liquid, adjusting the mixed solution to beacidic with hydrochloric acid, respectively performing extraction and layering with dichloromethane, 50-DEG C water, diethyl ether and sodium hydroxide solution and performing rotary evaporation on the obtained black brown solution, so as to obtain the 3-butoxyphenol. The synthesizing method of the 3-butoxyphenol is simple in steps and low in production cost and is operated under normal pressure.Therefore, the synthesizing method has the advantages of being high in product yield and being capable of achieving industrial production.

Phthalocyanine-based discotic liquid crystals switching from a molten alkyl chain type to a flying-seed-like type

We have synthesised a series of phthalocyanine-based discotic liquid crystals, (m-CnOPhO)8PcCu (n = 1-20: 2a-o), and investigated their mesomorphism by using a polarizing optical microscope (POM), a differential scanning calorimeter (DSC) and a temperature-dependent small angle X-ray diffractometer. We found that each of the derivatives 2a-o shows mesomorphism. However, the mesomorphism of the (m-CnOPhO)8PcCu derivatives strongly depends on the alkoxy chain length (n). The mesomorphism of the short chain-substituted derivatives 2a-e for n = 1-5 is a flying-seed-like type induced by flip-flop of the peripheral bulky substituents, whereas the mesomorphism of the long chain-substituted derivatives 2j-o for n = 10-20 is a conventional molten alkyl chain type induced by melting of the long alkyl chains. The moderately long chain derivatives (2f-i) for n = 6-9 in between show both types of mesophases. The detailed temperature-dependent X-ray diffraction measurements were carried out for three representative derivatives, 2b (n = 2 for n = 1-5), 2h (n = 8 for n = 6-9), and 2o (n = 20 for n = 10-20). As a result, we revealed that the Colro(P2m) mesophase in 2b (n = 2) gave a halo denoted as Haloarom. at d ? 5.2 ? due to flip-flop of the bulky aromatic substituents, and that the Colho mesophase in 2o (n = 20) gave a halo denoted as Haloalkyl at d ? 4.6-4.8 ? due to melting of the long alkyl chains. Therefore, we can distinguish the type of mesophase from Haloarom. and Haloalkyl. Very interestingly, the (m-C8OPhO)8PcCu (2h) derivative having moderately long alkyl chains gave Haloalkyl at about 4.8 ? in the lower temperature mesophase of Colho, but Haloarom. at about 5.2 ? in the higher temperature mesophase of Colro(P21/a). This means that melting of the alkyl chains induces the Colho phase in the lower temperature region, but that flip-flop of the bulky aromatic substituents induces the Colro(P21/a) phase in the higher temperature region. This unusual reverse phase transition sequence from a higher symmetry of the Colh mesophase to a lower symmetry of the Colr mesophase on a heating stage is attributable to such a unique stepwise melting of these two different types of substituents. To the best of our knowledge, this mesogen (2h) is the first example switching mesomorphism from the molten alkyl chain type to the flying-seed-like type in a discotic liquid crystal.

O-Alkylation of phenol derivatives via a nucleophilic substitution

The alkylation of phenol derivatives can be achieved in good yield via Lewis or Bronsted acid. The only by-product of the reaction is water and the catalyst can be recycled when using Bronsted acid.

Dialkoxybenzene and dialkoxyallylbenzene feeding and oviposition deterrents against the cabbage looper, trichoplusia ni: Potential insect behavior control agents

The antifeedant, oviposition deterrent, and toxic effects of individual dialkoxybenzene compounds/sets and of hydroxy- or alkoxy-substituted allylbenzenes, obtained through Claisen rearrangement of substituted allyloxybenzenes, were assessed against the cabbage looper, Trichoplusia ni, in laboratory bioassays. Most of the compounds/sets strongly deterred larval feeding, with some exhibiting mild toxic and oviposition deterrent effects as well. Some of the compounds/sets were more active than the commercial insect repellent, DEET (N,N-diethyl-m-toluamide), as both feeding and oviposition deterrents against the cabbage looper. On the basis of the obtained oviposition data a general hypothesis was proposed regarding the oviposition sites: one binding mode with the alkyl and allyl groups on the same side of the benzene ring resulted in deterrence, the other with alkyl and allyl groups on opposite sides of the benzene ring resulted in stimulation. The results suggest some structure-activity relationships useful in improving the efficacy of the compounds and designing new, nontoxic insect control agents for agriculture.

Zinc-catalyzed Williamson ether synthesis in the absence of base

A zinc-catalyzed Williamson ether synthesis is described with microwave heating in the presence of DMF or stirring in an oil-bath using THF as solvent and in the absence of base. Zinc powder was found to be a highly efficient catalyst for the synthesis of aromatic ethers using microwave heating in the presence of N,N-dimethylformamide as well as under stirring in an oil-bath using tetrahydrofuran as solvent without any inorganic base. This method can be used for selective mono-, di- or tri-O-alkylations.

Diphenol radical cations and semiquinone radicals as direct products of the free electron transfer from catechol, resorcinol and hydroquinone to parent solvent radical cations

In the pulse radiolysis of solutions of catechol, resorcinol and hydroquinone in n-butylchloride, dihydroxybenzene radical cations (40%) as well as semiquinone radicals (60%) are observed as direct synchronously formed products of the electron transfer from the solvent parent ions to the solute. This is explained in terms of free electron transfer succeeding in nearly every encounter of the reactants, which in the case of the studied dihydroxybenzenes involves femtosecond molecular dynamics effects. The rotation of the C-OH bond causes cycling of the molecule through transient conformations also exhibiting different electron distributions. From the more chemical point of view, the diphenol radical cations represent the first and till now unknown intermediates of oxidative semiquinone radical formation.

[(3-alkoxy-phenoxy)-ethyl]-dialkylamine derivatives and their use as local anaesthetics

There is provided compounds of formula I, wherein R1represents C3-5alkyl; and R2and R3independently represent C1-3alkyl; provided that when R2and R3both represent ethyl, then R1does not represent n-butyl, i-butyl or n-pentyl; or a pharmaceutically acceptable salt thereof, which are useful as anaesthetics, in particular local anaesthetics and especially topically applied local anaesthetics.

Selective etherification of polyhydroxybenzenes using PEG 200 as solvent or cosolvent

The monoalkylation of hydroquinone is performed using PEG 200 as a solvent or a cosolvent.The effect on the selectivity of the base strength, the temperature, and the percentage of cosolvent are discussed.The substituted phenols were found to behave differently upon etherification.When a carboxylic function is present in the ring, the hydroxybenzoic acids were selectively etherified using pure PEG and sodium hydroxyde as a base.Substituted diphenols were selectively etherified using a mixture of PEG and dioxan and potassium hydrogencarbonate as a base.Keywords - etherification / selectivity / polyhydroxybenzenes / polyethylene glycol