1638-22-8

Usage

Uses

Used in Liquid Crystals Industry:
4-Butylphenol is used as an intermediate in the synthesis of liquid crystals. Liquid crystals are unique materials that exhibit properties between those of conventional liquids and solid crystals. They have a wide range of applications, particularly in display technologies, such as liquid crystal displays (LCDs) found in televisions, computer monitors, and smartphones.
As an intermediate, 4-butylphenol plays a crucial role in the production of various liquid crystal compounds, which are then utilized to create the display panels. The liquid crystal molecules align in specific orientations when subjected to an electric field, allowing for the manipulation of light and the creation of images on the screen.

Safety Profile

A poison. Questionable carcinogen with experimental tumorigenic v v data. When heated to decomposition it emits acrid smoke and irritating fumes. See also PHENOL and other butyl phenols.

Potential Exposure

Butylphenols may be used as intermediates in manufacturing varnish and lacquer resins; as a germicidal agent in detergent disinfectants; as a pour point depressant, in motor-oil additives; de-emulsifier for oil; soap-antioxidant, plasticizer, fumigant, and insecticide

Shipping

UN2430 Alkylphenols, solid, n.o.s. (including C2-C12 homologues), Hazard class: 8; Labels: 8— Corrosive material

Incompatibilities

Vapors may form explosive mixture with air. These phenol/cresol materials can react with oxidizers; reaction may be violent. Incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may cause the gas to ignite and explode. Heat is also generated by the acid-base reaction with bases; such heating may initiate polymerization of the organic compound. React with boranes, alkalies, aliphatic amines, amides, nitric acid, sulfuric acid. Phenols are sulfonated very readily (for example, by concentrated sulfuric acid at room temperature). These reactions generate heat. Phenols are also nitrated very rapidly, even by dilute nitric acid and can explode when heated. Many phenols form metal salts that may be detonated by mild shock

InChI:InChI=1/C10H14O/c1-2-3-4-9-5-7-10(11)8-6-9/h5-8,11H,2-4H2,1H3

Upstream product

• 18272-84-9 4-n-butylanisole 
• 4731-84-4 1,1-bis(4-hydroxyphenyl)-n-butane 
• 123-72-8 butyraldehyde 
• 108-95-2 phenol 
• 1009-11-6 1-(4-hydroxyphenyl)-butan-1-one 
• 72653-47-5 α-chlorobutyl phenyl sulfide 
• 7446-70-0 aluminium trichloride 
• 71-36-3 butan-1-ol 
• 7647-01-0 hydrogenchloride 
• 106-98-9 1-butylene 
• 104-51-8 1-butylbenzene 
• 20651-67-6 4-butyliodobenzene 
• 145240-28-4 4-butylphenylboronic acid 
• 109-65-9 1-bromo-butane 

Downstream Products

• 109368-14-1 succinic acid mono-(4-butyl-phenyl ester) 
• 109496-40-4 glutaric acid mono-(4-butyl-phenyl ester) 
• 103156-50-9 adipic acid bis-(4-butyl-phenyl ester) 
• 5530-30-3 4-butyl-2,6-di-tert-butylphenol 
• 92863-76-8 methacrylic acid-(4-butyl-phenyl ester) 
• 35684-15-2 4-n-Butyl-4'-methoxy-diphenylether 
• 35684-14-1 4-n-Butyl-phenyl-4'-anisoyl-carbonat 
• 59748-22-0 4-(4-n-pentylphenyl)-benzoic acid 4'-n-butylphenyl ester 
• 61733-18-4 4-(4-n-hexylphenyl)-benzoic acid 4'-butylphenyl ester 
• 61733-22-0 4-(4-n-heptylphenyl)-benzoic acid 4'-n-butylphenyl ester 
• 61305-69-9 2,4,6-Trichlor-4-butyl-cyclohexa-2,5-dienon 
• 35840-23-4 4-n-Butyl-phenyl-4'-anisoat 
• 98741-97-0 3,4-Dichlor-benzyl-thiocarbamidsaeure-<4-butyl-phenyl-ester> 
• 98147-45-6 3.4-Dichlor-thiocarbanilsaeure-<4-butyl-phenyl-ester> 

Relevant academic research and scientific papers

Stable isotope characterization of raspberry ketone extracted from Taxus baccata and obtained by oxidation of the accompanying alcohol (betuligenol)

The natural abundance 2H NMR characterization of raspberry ketone 1 extracted from himalayan Taxus baccata and of the accompanying (R) carbinol 2 is performed and compared with that of samples of 1 obtained from 2 by oxidation with Candida boidinii and CrO3, respectively. The determination of the δ(13C) and/or δ(18O) values of the above extractive products and of benzoic acid (6) and 4-butylphenol (10), obtained from natural of synthetic 1, and of 4-phenylbutan-2-ol (8), prepared from extractive 2, allows a description of the labeling pattern of this set of products. A graph of (D/H)3/(D/H)2 vs (D/H)5/(D/H)4 (Figure 3) of the presently examined samples and of those previously characterized in the laboratory, including three commercial samples sold as natural, defines three areas, containing (a) the material of botanical origin and that produced from extractive 2 by biooxidation, (b) those produced by bioreduction of the unsaturated ketone 3, and (c) the synthetic samples.

Selective hydrodeoxygenation of hydroxyacetophenones to ethyl-substituted phenol derivatives using a FeRu?SILP catalyst

The selective hydrodeoxygenation of hydroxyacetophenone derivatives is achieved opening a versatile pathway for the production of valuable substituted ethylphenols from readily available substrates. Bimetallic iron ruthenium nanoparticles immobilized on an imidazolium-based supported ionic liquid phase (Fe25Ru75?SILP) show high activity and stability for a broad range of substrates without acidic co-catalysts. This journal is

Synthesis of 4 - n-alkyl substituted phenol method

The invention discloses a synthesis method of 4-n-alkyl substituted phenol. Under the catalysis of zinc chloride, aniline and n-alkyl alcohol with the carbon number being 4-30 react in methylbenzene or xylene to obtain the 4-n-alkyl substituted aniline, and then the 4-n-alkyl substituted aniline reacts with sodium nitrite and acid to obtain the 4-n-alkyl substituted phenol. The synthesis method is easy to implement, an intermediate directly enters the next reaction without being separated or purified, and therefore the reaction efficiency is improved. The final product is high in purity and is good in depth of parallelism when reappearing, and technological conditions are suitable for mass production.

Photoredox-Assisted Reductive Cross-Coupling: Mechanistic Insight into Catalytic Aryl-Alkyl Cross-Couplings

Here, we describe a photoredox-assisted catalytic system for the direct reductive coupling of two carbon electrophiles. Recent advances have shown that nickel catalysts are active toward the coupling of sp3-carbon electrophiles and that well-controlled, light-driven coupling systems are possible. Our system, composed of a nickel catalyst, an iridium photosensitizer, and an amine electron donor, is capable of coupling halocarbons with high yields. Spectroscopic studies support a mechanism where under visible light irradiation the Ir photosensitizer in conjunction with triethanolamine are capable of reducing a nickel catalyst and activating the catalyst toward cross-coupling of carbon electrophiles. The synthetic methodology developed here operates at low 1 mol % catalyst and photosensitizer loadings. The catalytic system also operates without reaction additives such as inorganic salts or bases. A general and effective sp2-sp3 cross-coupling scheme has been achieved that exhibits tolerance to a wide array of functional groups.

Synthesis and catalytic activity of monobridged bis(cyclopentadienyl)rhenium carbonyl complexes

Thermal treatment of three monobridged biscyclopentadienes (C5H5)R(C5H5) [R?=?C(CH3)2 (1), C(CH2)5 (2), Si(CH3)2 (3)] with Re2(CO)10 in refluxing mesitylene gave the corresponding complexes [(η5-C5H4)2R][Re(CO)3]2 [R?=?C(CH3)2 (4), C(C5H10) (5), Si(CH3)2 (6)], which were separated by chromatography, and characterized by elemental analysis, IR, and 1H NMR spectroscopy. The molecular structures of complexes 5 and 6 were characterized by X-ray crystal diffraction analysis and show that both are monobridged bis(cyclopentadienyl)rhenium carbonyl complexes in which the molecule consists of two [(η5-C5H4)Re(CO)3] moieties linked by a single bridge, in which each of the two Re(CO)3 units is coordinated to the cyclopentadienyl ring in an η5 mode. All three of these monobridged bis(cyclopentadienyl)rhenium carbonyl complexes have good catalytic activities in Friedel–Crafts alkylation reactions.

Sustainable oxidations with air mediated by gallic acid: Potential applicability in the reutilization of grape pomace

Gallic acid converts atmospheric oxygen into hydrogen peroxide, which is able to oxidize arylboronic acids as a proof of concept of sustainable oxidations. Moreover, tannic acid and grape pomace extract are also able to perform oxidations with air. Therefore this work unleashes an alternative method for reutilization and valorization of bio-wastes rich in tannins.

Oxidation with air by ascorbate-driven quinone redox cycling

Transition metal-free oxidation with air at room temperature has been achieved by simply using ascorbate (vitamin C) and catalytic amounts of menadione (vitamin K3). A combination of the mentioned vitamins transforms atmospheric oxygen into hydrogen peroxide, which is able to oxidize arylboronic acids and other chemical moieties. This journal is

Computational and Experimental Studies of Phthaloyl Peroxide-Mediated Hydroxylation of Arenes Yield a More Reactive Derivative, 4,5-Dichlorophthaloyl Peroxide

The oxidation of arenes by the reagent phthaloyl peroxide provides a new method for the synthesis of phenols. A new, more reactive arene oxidizing reagent, 4,5-dichlorophthaloyl peroxide, computationally predicted and experimentally determined to possess enhanced reactivity, has expanded the scope of the reaction while maintaining a high level of tolerance for diverse functional groups. The reaction proceeds through a novel "reverse-rebound" mechanism with diradical intermediates. Mechanistic insight was achieved through isolation and characterization of minor byproducts, determination of linear free energy correlations, and computational analysis of substituent effects of arenes, each of which provided additional support for the reaction proceeding through the diradical pathway.

Heterogeneous copper-catalyzed hydroxylation of aryl iodides under air conditions

In this work, the ligand-free heterogeneous copper Cu-g-C3N 4 was synthesized and used for the hydroxylation of aryl iodides to synthesize phenols using cheap bases. The catalyst was conveniently prepared, air-tolerant, reusable and scalable, and is very efficient for a wide range of substrates. The synthesis of substituted phenols can be carried out under air conditions and has great potential for practical applications. This journal is the Partner Organisations 2014.

CYCLIC PEROXIDE OXIDATION OF AROMATIC COMPOUND PRODUCTION AND USE THEREOF

The present invention provides a method for converting an aromatic hydrocarbon to a phenol by providing an aromatic hydrocarbon comprising one or more aromatic C-H bonds and one or more activated C-H bonds in a solvent; adding a phthaloyl peroxide to the solvent; converting the phthaloyl peroxide to a di-radical; contacting the di-radical with the one or more aromatic C-H bonds; oxidizing selectively one of the one or more aromatic C-H bonds in preference to the one or more activated C-H bonds; adding a hydroxyl group to the one of the one or more aromatic C-H bonds to form one or more phenols; and purifying the one or more phenols.