40150-92-3

Usage

Uses

Used in Pharmaceutical Industry:
(1-HYDROXYETHYL)-4-(2-METHYLPROPYL)BENZENE is used as a cytotoxic agent for its ability to exhibit cytotoxicity activity. This property makes it a promising candidate for the development of new drugs or therapies targeting cancer cells or other harmful cell types.
Used in Environmental Applications:
As a photodegradation product of Ibuprofen, (1-HYDROXYETHYL)-4-(2-METHYLPROPYL)BENZENE can be studied for its role in the breakdown and environmental impact of pharmaceutical compounds. This knowledge can be applied to develop strategies for reducing the ecological footprint of pharmaceutical waste and improving water treatment processes.
Used in Chemical Research:
(1-HYDROXYETHYL)-4-(2-METHYLPROPYL)BENZENE's unique structure and properties make it an interesting subject for further research in the field of chemistry. It can be used as a starting material for the synthesis of new compounds or as a model to study various chemical reactions and mechanisms.

Preparation

1-(4-Isobutylphenyl)ethanol synthesis: A solution of p-isobutylacetophenone (1.20mL), methanol (3.00mL), and sodium borohydride (0.2509g) was mixed in a separatory funnel and allowed to sit for 10min. After the standing time period, a 10 % HCl solution (10.0 mL) was added to remove any unreacted sodium borohydride, and the product was extracted using petroleum ether. 1-(4-Isobutylphenyl)ethanol product (1.002g, 87.2%) was collected and dried using anhydrous sodium sulfate.1HNMR (300MHz, CDCl3): δ7.281 (2H, m, J = 4.0 Hz), δ7.174 (2H, m, J = 4.0 Hz), δ4.855 (1H, s, J =0.92Hz), δ2.714 (3H, q, J =2.2Hz), δ2.554 (2H, t, J = 2.8 Hz), δ1.795 (1H, q, J = 2.7 Hz), δ1.484 (1H, m, J =2.8Hz), δ0.976 (6H, q, J =6.1Hz). 13C NMR (300 MHz, CDCl3): 143.325, 140.684, 129.143, 125.357, 70.034, 45.196, 30.343, 25.076, 22.725, 22.465.

InChI:InChI=1/C12H18O/c1-9(2)8-11-4-6-12(7-5-11)10(3)13/h4-7,9-10,13H,8H2,1-3H3

Upstream product

• 38861-78-8 1-(4-isobutyl-phenyl)-ethanone 
• 51407-46-6 2-(4-isobutylphenyl)propionaldehyde 
• 15687-27-1 ibuprofen 
• 75-69-4 trichlorofluoromethane 
• 152360-64-0 1-(1,1-Dimethoxy-ethyl)-4-isobutyl-benzene 
• 538-93-2 1-phenyl-2-methylpropane 
• 99-90-1 para-bromoacetophenone 
• 1191-15-7 diisobutylaluminium hydride 
• 138948-58-0 (RS)-p-isobutyl-1-phenylethanol acetate 
• 59512-17-3 benzeneacetamide-α-methyl-4-(2-methylpropyl) 
• 144-62-7 oxalic acid 
• 10442-39-4 tetra-n-butylammonium cyanide 
• 62049-65-4 S-(-)-1-(-)-[4-isobutylphenyl]-chloroethane 

Downstream Products

• 125653-69-2 Acetic acid (S)-1-(4-isobutyl-phenyl)-ethyl ester 
• 125653-69-2 (R)-p-isobutyl-1-phenylethanol acetate 
• 63444-56-4 p-isobutylstyrene 
• 62049-65-4 S-(-)-1-(-)-[4-isobutylphenyl]-chloroethane 
• 15687-27-1 ibuprofen 
• 65322-85-2 3-(4'-isobutylphenyl)propionic acid 
• 125653-66-9 (S)-(-)-1-(4-isobutylphenyl)ethanol 
• 448961-59-9 2,3-dimethyl-4-[1-(4-isobutylphenyl)ethoxy]benzonitrile 
• 608119-56-8 1-[(4-isobutylphenyl)ethyl] thioacetate 
• 1025963-03-4 (E)-2-(4-Isobutyl-phenyl)-ethenesulfonyl chloride 
• 38861-78-8 1-(4-isobutyl-phenyl)-ethanone 
• 51146-56-6 (S)-ibuprofen 
• 51146-57-7 (R)-ibuprofene 
• 133868-69-6 (S)-(-)-2-(4-isobutylphenyl)propionitrile 

Relevant academic research and scientific papers

Evaluation of Oxetan-3-ol, Thietan-3-ol, and Derivatives Thereof as Bioisosteres of the Carboxylic Acid Functional Group

The oxetane ring serves as an isostere of the carbonyl moiety, suggesting that oxetan-3-ol may be considered as a potential surrogate of the carboxylic acid functional group. To investigate this structural unit, as well as thietan-3-ol and the corresponding sulfoxide and sulfone derivatives, as potential carboxylic acid bioisosteres, a set of model compounds has been designed, synthesized, and evaluated for physicochemical properties. Similar derivatives of the cyclooxygenase inhibitor, ibuprofen, were also synthesized and evaluated for inhibition of eicosanoid biosynthesis in vitro. Collectively, the data suggest that oxetan-3-ol, thietan-3-ol, and related structures hold promise as isosteric replacements of the carboxylic acid moiety.

Synthesis of Ibuprofen intermediate using alcoholic silver nanoparticles and its kinetics: A greener approach towards drug synthesis

Silver nanoparticles (AgNPs) were prepared and tested for the activity in the catalytic reduction of 4-nitrophenol to 4-aminophenol showing to be exceptionally active. Further, using AgNPs we catalytically synthesized 1-(4-isobutylphenyl)ethanol which is

Heterogeneous selective catalytic hydrogenation of aryl ketones to alcohols without additives

A selective hydrogenation of different aryl ketones can be obtained by using a heterogeneous copper catalyst under very mild experimental conditions, namely 90°C and 1 atm of hydrogen, without using any kind of additive or poisoning agent.

CONTINUOUS FLOW SYNTHESIS OF IBUPROFEN

This disclosure generally relates to methods of making ibuprofen, naproxen, and derivatives thereof. This disclosure also generally relates to compounds made by the disclosed methods. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

Preparation method of aryl propionic acid compound

The invention provides a preparation method of an aryl propionic acid compound, wherein the preparation method comprises the following steps: carrying out acetylation reaction on substituted aryl benzene to obtain aryl acetophenone; carrying out hydrogenation reduction reaction on alpha-substituted aryl ethyl ketone to obtain alpha-substituted aryl ethanol; and in an acidic solution, introducing carbon monoxide gas into the alpha-substituted aryl ethanol, and carrying out a carbonylation reaction under the co-catalytic action of a main catalyst and a cocatalyst to obtain the aryl propionic acid compound, wherein the cocatalyst has the following structural formula described in the specification, R1 is one of hydrogen and a substituted carboxylic acid group, and R2 is one of hydrogen, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C6 alkoxy, substituted or unsubstituted C3-C12 naphthenic base, substituted carbonyl containing C6-C24 aryl or substitutedaryl, substituted carbonyl containing C3-C12 heterocyclic radical or substituted heterocyclic radical, phenyl, substituted phenyl, naphthyl and substituted naphthyl.

Pyridine mediated transition-metal-free direct alkylation of anilines using alcohols: via borrowing hydrogen conditions

Herein, we report pyridine and other similar azaaromatics as efficient biomimetic hydrogen shuttles for a transition-metal-free direct N-alkylation of aryl and heteroaryl amines using a variety of benzylic and straight chain alcohols. Mechanistic studies including deuterium labeling and the isolation of dihydro-intermediates of the benzannulated pyridine confirmed the role of pyridine and a borrowing hydrogen process operating in these reactions. In addition, we have extended this methodology for the development of dehydrogenative synthesis of quinolines and indoles, as well as the transfer hydrogenation of ketones. This journal is

One-pot method for the synthesis of 1-aryl-2-aminoalkanol derivatives from the corresponding amides or nitriles

We have identified a novel one-pot method for the synthesis of β-amino alcohols, which is based on C-H bond hydroxylation at the benzylic α-carbon atom with a subsequent nitrile or amide functional group reduction. This cascade process uses molecular oxygen as an oxidant and sodium bis(2-methoxyethoxy)aluminum hydride as a reductant. The substrate scope was examined on 30 entries and, although the respective products were provided in moderate yields only, the above simple protocol may serve as a direct and powerful entry to the sterically congested 1,2-amino alcohols that are difficult to prepare by other routes. The plausible mechanistic rationale for the observed results is given and the reaction was applied to a synthesis of a potentially bioactive target. This journal is

A General Method for Photocatalytic Decarboxylative Hydroxylation of Carboxylic Acids

A general and practical method for decarboxylative hydroxylation of carboxylic acids was developed through visible light-induced photocatalysis using molecular oxygen as the green oxidant. The addition of NaBH4 to in situ reduce the unstable peroxyl radical intermediate much broadened the substrate scope. Different sp3 carbon-bearing carboxylic acids were successfully employed as substrates, including phenylacetic acid-type substrates, as well as aliphatic carboxylic acids. This transformation worked smoothly on primary, secondary, and tertiary carboxylic acids.

Pyridine-Stabilized Rhodium Nanoparticles in Ionic Liquids as Selective Hydrogenation and Transfer Hydrogenation Catalysts

Rhodium nanoparticles (RhNPs) stabilized with pyridine-based ligands in the ionic liquid [BMIM][BF4] (RhNPs-I to III) were synthesized from the organometallic precursor [Rh(μ-OMe)COD]2 under dihydrogen pressure. The pyridine-stabilized RhNPs showed smaller size compared to the ligand free RhNPs-V and presented higher activity and selectivity in the hydrogenation of acetophenone to 1-phenylethanol. In the case of pyridine-capped RhNPs-I, the system was reused for several runs without loss of activity and selectivity. Nitrobenzene was reduced to aniline with dihydrogen in the presence of RhNPs-I with moderate activity. When the hydrogen source was formic acid-Et3N azeotrope (transfer hydrogenation) the reaction was completed within minutes with high selectivity. Under transfer hydrogenation conditions, it was possible to apply the catalytic system RhNPs-I in multistep processes for the generation of substituted arylic amines through the reductive N-alkylation of nitrobenzene and benzaldehyde; and the synthesis of substituted pyrroles through the nitroarene reduction/Paal-Knorr condensation.

Enantiocomplementary decarboxylative hydroxylation combining photocatalysis and whole-cell biocatalysis in a one-pot cascade process

Designing a green, highly efficient and stereoselective catalytic system to generate valuable enantioenriched products is a long-standing goal in green chemistry. Here, we report a one-pot cascade combining photocatalysts with (R)- or (S)-selective ketoreductases for the decarboxylative carbonylation of carboxylic acids and the subsequent bioreduction to generate valuable chiral alcohols. Using this approach, various chiral alcohols with complementary (R)- or (S)-configurations were prepared with good yields (up to 93%) and excellent stereoselectivity (up to 99% ee). Such a photochemo-enzymatic one-pot whole-cell process combines the advantages of both photocatalysts and enzyme catalysts and provides a mild, green, metal-free and highly stereoselective alternative in asymmetric decarboxylative hydroxylation reactions.