16251-77-7

Basic information

• Product Name: 3-PHENYLBUTYRALDEHYDE
• Synonyms: beta-methyl-benzenepropana;R,S-3-Phenyl-butyraldehyde;Trifernal;3-Phenylbutylraldehyde;Benzenepropanal, .beta.-methyl-;3-Phenylbutyraldehyd;TRIFERNAL, FIRMENICH;PHENYLBUTYRALDEHYDE(3-)
• CAS NO: 16251-77-7
• Molecular Formula: C₁₀H₁₂O
• Molecular Weight: 148.2
• EINECS: 240-362-9
• Product Categories: Aldehydes;C10 to C21;Carbonyl Compounds
• Mol File: 16251-77-7.mol

Chemical Properties

• Boiling Point: 93-94 °C16 mm Hg(lit.)
• Flash Point: 206 °F
• Appearance: /
• Density: 0.997 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.206mmHg at 25°C
• Refractive Index: n20/D 1.5179(lit.)
• Water Solubility: 2g/L at 20℃
• CAS DataBase Reference: 3-PHENYLBUTYRALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-PHENYLBUTYRALDEHYDE(16251-77-7)
• EPA Substance Registry System: 3-PHENYLBUTYRALDEHYDE(16251-77-7)

Safety Data

• WGK Germany: 2
• Hazardous Substances Data: 16251-77-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Phenylbutyraldehyde is used as a reactant for studying the kinetics of certain reactions involving hydrogen peroxide and aromatic aldehydes with cytochrome P450BM3-F87G. This research is significant in understanding the enzyme's role in drug metabolism and detoxification processes, which can lead to the development of new drugs and therapies.
Used in Chemical Research:
3-Phenylbutyraldehyde serves as a valuable compound in chemical research, particularly in the synthesis of various organic molecules and the study of reaction mechanisms. Its unique structure allows for further functionalization and modification, making it a versatile building block in organic chemistry.
Used in Flavor and Fragrance Industry:
Due to its distinct aromatic properties, 3-phenylbutyraldehyde can be used as a component in the flavor and fragrance industry. It can contribute to the creation of unique scents and flavors in various consumer products, such as perfumes, cosmetics, and the food industry.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C10H12O/c1-9(7-8-11)10-5-3-2-4-6-10/h2-6,8-9H,7H2,1H3

Upstream product

• 28084-55-1 α-methylbenzyl vinyl ether 
• 14371-10-9 (E)-3-phenylpropenal 
• 82263-47-6 (2S,3R,4S,5R)-3,4-Dimethyl-5-phenyl-2-((E)-styryl)-oxazolidine 
• 86296-02-8 (2S,4S,5R)-3,4-Dimethyl-5-phenyl-2-(2-phenyl-propyl)-oxazolidine 
• 2031-46-1 (R)-3-phenylbutanol 
• 772-14-5 (R)-3-phenylbutyric acid 
• 1196-67-4 (E)-β-methylcinnamaldehyde 
• 544-97-8 dimethyl zinc(II) 
• 104-55-2 3-phenyl-propenal 
• 100-58-3 phenylmagnesium bromide 
• 123-73-9 crotonaldehyde 
• 1196-67-4 (Z)-3-Phenyl-but-2-en-1-al 
• 917-54-4 methyllithium 
• 82215-31-4 (2S,4S,5R)-3,4-dimethyl-5-phenyl-2-(2-phenylvinyl)-1,3-oxazolidine 

Downstream Products

• 27395-21-7 2-Formylamino-4-phenyl-pentanoic acid amide 
• 119092-11-4 (4S,5S)-1,3-Dimethyl-4,5-diphenyl-2-(2-phenyl-propyl)-imidazolidine 
• 133420-72-1 (E)-4-phenyl-1-(phenylsulfonyl)-1-penten-3-ol 
• 704-79-0 (Z)-3-phenylbut-2-enoic acid 
• 704-80-3 (E)-3-phenyl-2-butenoic acid 
• 4593-90-2 3-phenylbutyric acid 
• 78999-43-6 C₂₀H₂₄ 
• 16251-77-7 3-Phenyl-butyraldehyde 
• 16251-77-7 3-Phenyl-butyraldehyde 
• 80691-79-8 2-methylene-3-phenylbutyraldehyde 
• 1072275-32-1 (E)-2-nitro-5-phenyl-2-hexene 
• 1160858-31-0 C₁₄H₁₈O₃ 

Relevant articles and documents

Highly active rhodium/phosphorus catalytic system for the hydroformylation of α-methylstyrene

Rhodium catalyzed hydroformylation of α-methylstyrene was investigated in the presence of monodentate phosphine ligands L1-L6. We found that the phosphine with good π-acceptability could efficiently improve the activity of the α-methylstyrene hydroformylation. The big steric hindrance of α-C in α-methylstyrene enhanced the regioselectivity towards the linear aldehyde, which resulted in 3-phenylbutanal as the predominant product (>99.0%). When tris(N-pyrrolyl)phosphine (L1) modified Rh(acac)(CO)2 was employed as the catalyst, the TOF could reach up to 5786 h-1 in the α-methylstyrene hydroformylation at relatively mild conditions (110 °C, 6 MPa).

Pd-Catalyzed Arylation of 1,2-Amino Alcohol Derivatives via β-Carbon Elimination

Herein, we describe a Pd-catalyzed arylation of 1,2-amino alcohols with aryl halides enabled by a retroallylation manifold. This protocol constitutes a new entry point to β-arylated aldehydes via the intermediacy of in situ generated enamine intermediates. The protocol is characterized by its exquisite regioselectivity profile and broad substrate scope including challenging substrate combinations even in an enantioselective manner.

Method for preparing aldehyde/ketone by breaking C-C key

The invention discloses a method for preparing aldehyde/ketone by breaking C-C bonds, and the method comprises the following steps of anaerobic condition. In an organic solvent system, an alcohol is used as a reaction raw material, and the C-C bond is selectively broken under the common action of an iron catalyst, an organic base and an additive to obtain aldehyde/ketone. The method is low in cost, easy to obtain, wide in substrate range, simple and product in post-treatment and high in purity, a new synthetic route and a method are developed for an aldehyde ketone compound, and the method has good application potential and research value.

Iron-Catalyzed C-C Single-Bond Cleavage of Alcohols

An iron-catalyzed deconstruction/hydrogenation reaction of alcohols through C-C bond cleavage is developed through photocatalysis, to produce ketones or aldehydes as the products. Tertiary, secondary, and primary alcohols bearing a wide range of substituents are suitable substrates. Complex natural alcohols can also perform the transformation selectively. A investigation of the mechanism reveals a procedure that involves chlorine radical improved O-H homolysis, with the assistance of 2,4,6-collidine.

Highly Selective Hydrogenation of C═C Bonds Catalyzed by a Rhodium Hydride

Under mild conditions (room temperature, 80 psi of H2) Cp*Rh(2-(2-pyridyl)phenyl)H catalyzes the selective hydrogenation of the C═C bond in α,β-unsaturated carbonyl compounds, including natural product precursors with bulky substituents in the β position and substrates possessing an array of additional functional groups. It also catalyzes the hydrogenation of many isolated double bonds. Mechanistic studies reveal that no radical intermediates are involved, and the catalyst appears to be homogeneous, thereby affording important complementarity to existing protocols for similar hydrogenation processes.

Intermetallic Nanocatalyst for Highly Active Heterogeneous Hydroformylation

Hydroformylation is an imperative chemical process traditionally catalyzed by homogeneous catalysts. Designing a heterogeneous catalyst with high activity and selectivity in hydroformylation is challenging but essential to allow the convenient separation and recycling of precious catalysts. Here, we report the development of an outstanding catalyst for efficient heterogeneous hydroformylation, RhZn intermetallic nanoparticles. In the hydroformylation of styrene, it shows three times higher turnover frequency (3090 h-1) compared to the benchmark homogeneous Wilkinson's catalyst (966 h-1), as well as a high chemoselectivity toward aldehyde products. RhZn is active for a variety of olefin substrates and can be recycled without a significant loss of activity. Density functional theory calculations show that the RhZn surfaces reduce the binding strength of reaction intermediates and have lower hydroformylation activation energy barriers compared to pure Rh(111), leading to more favorable reaction energetics on RhZn. The calculations also predict potential catalyst design strategies to achieve high regioselectivity.

Selective Production of Linear Aldehydes and Alcohols from Alkenes using Formic Acid as Syngas Surrogate

Performing carbonylation without the use of carbon monoxide for high-value-added products is an attractive yet challenging topic in sustainable chemistry. Herein, effective methods for producing linear aldehydes or alcohols selectively with formic acid as both carbon monoxide and hydrogen source have been described. Linear-selective hydroformylation of alkenes proceeds smoothly with up to 88 % yield and >30 regioselectivity in the presence of single Rh catalyst. Strikingly, introducing Ru into the system, the dual Rh/Ru catalysts accomplish efficient and regioselective hydroxymethylation in one pot. The present processes utilizing formic acid as syngas surrogate operate simply under mild condition, which opens a sustainable way for production of linear aldehydes and alcohols without the need for gas cylinders and autoclaves. As formic acid can be readily produced via CO2 hydrogenation, the protocols represent indirect approaches for chemical valorization of CO2.

Linear Selective Hydroformylation of 2-Arylpropenes Using Water-Soluble Rh-PNP Complex: Straightforward Access to 3-Aryl-Butyraldehydes

Straightforward access to 3-aryl-butyraldehydes was developed through the aqueous biphasic Rh-catalyzed hydroformylation of 2-arylpropenes using a water-soluble PNP ligand. This protocol accommodates broad substrate scope with high yields (up to 95 %) and excellent linear selectivity (>99 : 1 b/l ratio). The synthesis of rac-ar-turmerone and the gram-scale hydroformylation further demonstrated the practical nature of this method.

Optimized iminium-catalysed 1,4-reductions inside the resorcinarene capsule: achieving >90% ee with proline as catalyst

In previous work, we demonstrated that iminium-catalysed 1,4-reductions inside the supramolecular resorcinarene capsule display increased enantioselectivities as compared to their regular solution counterparts. Utilizing proline as the chiral catalyst, enantioselectivities remained below 80% ee. In this study, the reaction conditions were optimized by determining the optimal capsule loading and HCl content. Additionally, it was found that alcohol additives increase the enantioselectivity of the capsule-catalysed reaction. As a result, we report enantioselectivities of up to 92% ee for iminium-catalysed 1,4-reductions relying on proline as the sole chiral source. This is of high interest, as proline is unable to deliver high enantioselectivities for 1,4-reductions in a regular solution setting. Investigations into the role of the alcohol additive revealed a dual role: it not only slowed down the background reaction but also increased the capsule-catalysed reaction rate.

Catalyst for catalyzing hydroformylation reaction of gem-disubstituted aromatic olefin and preparation method and application of catalyst

The invention provides a catalyst for catalyzing a hydroformylation reaction of gem-disubstituted aromatic olefin and a preparation method and application of the catalyst. The catalyst is a complex, aprecursor of the complex comprises rhodium salt, and a ligand comprises a phosphoramidite ligand. When the catalyst is used for catalyzing the hydroformylation reaction of gem-disubstituted aromaticolefin, the efficiency is high, and the reaction conditions are mild.