51407-46-6

Basic information

• Product Name: 2-(4-isobutylphenyl)propionaldehyde
• Synonyms: A-METHYL-4-(2-METHYLPROPYL)BENZENEACETALDEHYDE;2-(4-Isobutylphenyl)propanal;α-Methyl-4-(2-methylpropyl)benzeneacetaldehyde;2-[4-(2-Methylpropyl)phenyl]propanal;p-(2-Methylpropyl)hydratropaldehyde;α-Methyl-4-isobutylbenzeneacetaldehyde;alpha-Methyl-4-(2-Methylpropyl)benzeneacetaldehyde;2-(4-isobutylphenyl)propionaldehyde
• CAS NO: 51407-46-6
• Molecular Formula: C₁₃H₁₈O
• Molecular Weight: 190.28142
• EINECS: 257-180-0
• Mol File: 51407-46-6.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 276.865°C at 760 mmHg
• Flash Point: 126.026°C
• Appearance: /
• Density: 0.937g/cm³
• Vapor Pressure: 0.005mmHg at 25°C
• Refractive Index: 1.497
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: 2-(4-isobutylphenyl)propionaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-isobutylphenyl)propionaldehyde(51407-46-6)
• EPA Substance Registry System: 2-(4-isobutylphenyl)propionaldehyde(51407-46-6)

Safety Data

• Hazardous Substances Data: 51407-46-6(Hazardous Substances Data)

Usage

Uses

2-(4-Isobutylphenyl)propanal is an impurity of the drug Ibuprofen (I140000), a selective cyclooxygenase inhibitor that also inhibits PGH synthase-1 and PGH synthase-2 with comparable potency.

InChI:InChI=1/C13H18O/c1-10(2)8-12-4-6-13(7-5-12)11(3)9-14/h4-7,9-11H,8H2,1-3H3

Upstream product

• 60-29-7 diethyl ether 
• 7664-93-9 sulfuric acid 
• 59771-01-6 1-(para-isobutyl phenyl)-1-bromoethane 
• 201230-82-2 carbon monoxide 
• 63444-56-4 p-isobutylstyrene 
• 1424343-26-9 2-(4-isobutylphenyl)prop-2-en-1-ol 
• 38861-78-8 1-(4-isobutyl-phenyl)-ethanone 
• 34352-86-8 1-isobutyl-4-(prop-1-en-2-yl)benzene 
• 1246302-53-3 N-methoxy-N-methyl-2-(4-isobutylphenyl)propanamide 
• 538-93-2 1-phenyl-2-methylpropane 
• 623-53-0 ethyl methyl carbonate 
• 56374-24-4 (R/S)-4-isobutyl-α-methylstyrene oxide 
• 36039-36-8 2-(4-isobutylphenyl)propan-1-ol 
• 110773-62-1 S-2-(p-isobutylphenyl)propionaldehyde 

Downstream Products

• 89539-10-6 2-(4-isobutylphenyl)propanal dimethyl acetal 
• 114937-30-3 (2S)-2-<4-(2-Methylpropyl)phenyl>propan-1-ol 
• 15687-27-1 ibuprofen 
• 60601-66-3 2-cyclohexylmethyl-1-[2-(4-isobutylphenyl)propyl]piperidine 
• 38861-78-8 1-(4-isobutyl-phenyl)-ethanone 
• 159850-44-9 (S)-2-(4-isobutylphenyl)-1,2-propanediol 
• 171417-12-2 (R)-2-(p-isobutylphenyl)-1,2-propanediol 
• 41343-01-5 2-(p-isobutylphenyl)-1,2-propanediol 
• 182816-19-9 2-fluoro-2-(4-isobutylphenyl)propanol 
• 58609-73-7 2-(4-isobutylphenyl)propanenitrile 
• 58609-72-6 2-(para-isobutylphenyl)propionoxime 
• 93673-13-3 (2R)-2-<4-(2-methylpropyl)phenyl>propan-1-ol 

Relevant articles and documents

Synthesis of rac-ɑ-aryl propionaldehydes via branched-selective hydroformylation of terminal arylalkenes using water-soluble Rh-PNP catalyst

This work detailed the preparation of a class of water-soluble PNP ligands that differed by the nature of the substitute on phenyl ring of ligands. These ligands were incorporated into water-soluble rhodium-PNP complex catalysts that were used to regioselective hydroformylation of a series of terminal arylalkenes, providing efficient access to rac-α-aryl propionaldehydes in good to excellent yield (up to 97%) and branched-regioselectivity (up to 40:1 b/l ratio). Furthermore, gram-scale and diverse synthetic transformation demonstrated synthetic application of this methodology for non-steroidal antiinflammatory drugs.

METHODS OF ACYLATION WITH AN IONIC LIQUID CATALYZING MEDIUM

Described herein are methods of acylating an aryl substrate comprising combining a substituted aryl substrate with an acylating agent in the presence of a catalyzing medium, thereby acylating the substituted aryl substrate in the para position, wherein the catalyzing medium is an ionic liquid comprising at least one cation and at least one metal halide anion.

Iron Catalyzed Hydroformylation of Alkenes under Mild Conditions: Evidence of an Fe(II) Catalyzed Process

Earth abundant, first row transition metals offer a cheap and sustainable alternative to the rare and precious metals. However, utilization of first row metals in catalysis requires harsh reaction conditions, suffers from limited activity, and fails to tolerate functional groups. Reported here is a highly efficient iron catalyzed hydroformylation of alkenes under mild conditions. This protocol operates at 10-30 bar syngas pressure below 100 °C, utilizes readily available ligands, and applies to an array of olefins. Thus, the iron precursor [HFe(CO)4]-[Ph3PNPPh3]+ (1) in the presence of triphenyl phosphine catalyzes the hydroformylation of 1-hexene (S2), 1-octene (S1), 1-decene (S3), 1-dodecene (S4), 1-octadecene (S5), trimethoxy(vinyl)silane (S6), trimethyl(vinyl)silane (S7), cardanol (S8), 2,3-dihydrofuran (S9), allyl malonic acid (S10), styrene (S11), 4-methylstyrene (S12), 4-iBu-styrene (S13), 4-tBu-styrene (S14), 4-methoxy styrene (S15), 4-acetoxy styrene (S16), 4-bromo styrene (S17), 4-chloro styrene (S18), 4-vinylbenzonitrile (S19), 4-vinylbenzoic acid (S20), and allyl benzene (S21) to corresponding aldehydes in good to excellent yields. Both electron donating and electron withdrawing substituents could be tolerated and excellent conversions were obtained for S11-S20. Remarkably, the addition of 1 mol % acetic acid promotes the reaction to completion within 16-24 h. Detailed mechanistic investigations revealed in situ formation of an iron-dihydride complex [H2Fe(CO)2(PPh3)2] (A) as an active catalytic species. This finding was further supported by cyclic voltammetry investigations and intermediacy of an Fe(0)-Fe(II) species was established. Combined experimental and computational investigations support the existence of an iron-dihydride as the catalyst resting state, which then follows a Fe(II) based catalytic cycle to produce aldehyde.