13466-40-5

Basic information

• Product Name: 5-phenylpenta-2,4-dienal
• Synonyms: 5-phenylpenta-2,4-dienal;5-Phenyl-2,4-pentadienal
• CAS NO: 13466-40-5
• Molecular Formula: C₁₁H₁₀O
• Molecular Weight: 158.1965
• EINECS: 236-718-8
• Mol File: 13466-40-5.mol

Chemical Properties

• Melting Point: 42.5°C
• Boiling Point: 243.28°C (rough estimate)
• Flash Point: 109.2°C
• Appearance: /
• Density: 0.9887 (rough estimate)
• Vapor Pressure: 0.00108mmHg at 25°C
• Refractive Index: 1.5472 (estimate)
• CAS DataBase Reference: 5-phenylpenta-2,4-dienal(CAS DataBase Reference)
• NIST Chemistry Reference: 5-phenylpenta-2,4-dienal(13466-40-5)
• EPA Substance Registry System: 5-phenylpenta-2,4-dienal(13466-40-5)

Safety Data

• Hazardous Substances Data: 13466-40-5(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
5-Phenylpenta-2,4-dienal is used as a flavoring agent for its strong, sweet, floral, and slightly spicy odor, contributing to the unique scents of perfumes, soaps, and other scented products. Its ability to impart a distinct aroma makes it a sought-after ingredient in this industry.
Used in Food Industry:
In the food industry, 5-phenylpenta-2,4-dienal is utilized as a flavoring agent, particularly in baked goods and confectionery. Its aromatic properties enhance the taste and smell of these food products, providing a more appealing sensory experience for consumers.
Used in Pharmaceutical Industry:
5-Phenylpenta-2,4-dienal has potential applications in the pharmaceutical industry, where it may be used in the development of new drugs or as a component in existing formulations. Its chemical properties could be harnessed to create innovative treatments or improve the efficacy of current medications.
Used in Cosmetic Industry:
In the cosmetic industry, 5-phenylpenta-2,4-dienal may be used for its fragrance properties, adding a pleasant scent to various cosmetic products. Its ability to enhance the sensory experience of these products can make them more appealing to consumers.
Used as an Intermediate in Organic Synthesis:
5-Phenylpenta-2,4-dienal is a versatile intermediate in organic synthesis processes. Its chemical structure allows it to be a key component in the production of a wide range of compounds, making it valuable in the field of organic chemistry.

InChI:InChI=1/C11H10O/c12-10-6-2-5-9-11-7-3-1-4-8-11/h1-10H/b6-2+,9-5+

Upstream product

• 100-52-7 benzaldehyde 
• 123-73-9 crotonaldehyde 
• 75-07-0 acetaldehyde 
• 104-55-2 3-phenyl-propenal 
• 54668-02-9 4-Benzoyl-1-methylmercapto-1cis-buten-⁽¹⁾-in-⁽³⁾ 
• 73224-97-2 (1E,4E)-1-tert-Butylsulfanyl-5-phenyl-penta-1,4-dien-3-one 
• 2798-73-4 1-methoxy-buten-3-yne 
• 56118-04-8 (E)-5-Methoxy-5-phenyl-pent-2-enal 
• 58506-33-5 5-phenylpenta-2,4-dien-1-ol 
• 110905-37-8 (E)-(4-Oxo-2-butenyl)phosphonsaeure-diethylester 
• 135386-73-1 2-Phenyl-3-cinnamal-5-hydroxyisoxazolidine 
• 495-48-7 azoxybenzene 
• 110-89-4 piperidine 
• 14371-10-9 (E)-3-phenylpropenal 

Downstream Products

• 6460-62-4 7-phenyl-hepta-2,4,6-trienoic acid 
• 88842-99-3 5-fluoren-9-ylidene-1t-phenyl-penta-1,3t-diene 
• 7508-19-2 (5t-phenyl-penta-2t,4-dienylidene)-malonic acid 
• 3029-42-3 1,12-diphenyl-dodeca-1,3,5,7,9,11-hexaene 
• 28010-12-0 5-phenylpenta-2,4-dienoic acid 
• 55284-09-8 N-(5-phenyl-penta-2,4-dienyliden)-p-anisidine 
• 6460-63-5 7-phenyl-hepta-2,4,6-trienal 
• 56110-22-6 (E)-N-((2E,4E)-5-phenylpenta-2,4-dienylidene)aniline 
• 35328-83-7 1,7-diphenyl-hepta-2,4,6-trien-1-one 
• 93845-04-6 ethyl 5-phenyl-4-pentenoate 
• 3893-10-5 (1E,3E,5E)-1-(p-methoxyphenyl)-6-phenyl-1,3,5-hexatriene 
• 20264-90-8 1-Phenyl-6-<4-Nitro-phenyl>-hexatrien-(1,3,5) 
• 36288-12-7 1-Fluoro-4-((1E,3E,5E)-6-phenyl-hexa-1,3,5-trienyl)-benzene 
• 36288-10-5 1-Phenyl-6--hexatrien-(1trans.3trans.5trans) 

Relevant articles and documents

Electronic absorption and fluorescence properties of 2,5-diarylidene-cyclopentanones

Spectroscopic properties for a series of 2,5-diarylidene-cyclopentanones are reported. Electronic absorption and fluorescence spectra have been measured for the all-E configurations of 2,5-dibenzylidene-cyclopentanone (1), 2,5-bis-(3-phenyl-allylidene)-cyclopentanone (2), and 2,5-bis-(5-phenyl-penta-2,4-dienylidene)-cyclopentanone (3). The absorption spectra have been assigned with the aid of INDO/S calculations. Molecular structures used for the INDO/S calculations were computed with the PM3 Hamiltonian. Agreement between absorption spectra obtained in cyclohexane at room temperature and the theoretical predictions is good. For 1, 2, and 3 the general features of the spectra are similar. The transition to S1 (weak) is assigned as n → π* (A2 ← A1), to S2 (strong) as π → π* (B2 ← A1), and to S3 (moderate) as π → π* (A1 ← A1). The energy gap between S1 and S2 is seen to decrease as the length of the polyene chain increases in going from 1 to 3. Fluorescence is not observed for 1 in any of the solvents studied (protic and aprotic). Fluorescence is observed for 2 in protic solvents only. For 3, fluorescence is observed in a number of protic and aprotic solvents. Solvents which are able to induce fluorescence are believed to do so by inverting the order of 1(nπ*) and 1(ππ*) states. The influence of hydrogen bonding on the excitation spectra of 2 and 3 is discussed. Solvent-induced shifts in the absorption and fluorescence spectra of 3 in combination with the PM3 calculated ground-state dipole moment (2.8 D) are used to determine the excited-state dipole moment of 3 (6.4 D/protic solvents; 6.6 D/aprotic solvents). Fluorescence quantum yields in different solvents for 3 vary as the fluorescence maxima shift in these solvents, going through a maximum in the mid-frequency range. The variation in quantum yields with different solvents is primarily attributed to changes in the nonradiative rate of decay from S1. Excitation, polarized excitation, and fluorescence spectra have been measured for 2 and 3 at 77 K in ethanol/ methanol glass. Vibronic features not observed in the broad spectra obtained in alcohols at room temperature become clearly resolved at 77 K. Evidence is provided that indicates that 2 and 3 undergo excited-state proton-transfer reactions in acetic acid at room temperature.

Four- and eight-carbon homologation of benzaldehyde by (1Z,3Z)- butyltelluro-1,3-butadiene: Synthesis of navenone B: Alarm pheromone of the mollusk navanax inermis

Four- and eight-carbon homologation of benzaldehydes is described. The hydrotel-luration of (Z)-1-methoxy-but-1-en-3-ynes 1 afforded (1Z,3Z)-1-butyltelluro-4-methoxy-1,3-butadiene 2, this compound 2 underwent a Te=Li exchange reaction, and the butadienyl-lithium 3 obtained reacted with benzaldehyde to form the corresponding allylic alcohol 4 with total retention of configuration. The allylic alcohol 4a formed underwent acidic hydrolysis, resulting in 5-phenyl-(2E,4E)-dienal 5 (four-carbon homologation of benzaldehyde). Product 5 reacted with the butadienyllithium 3, affording the alcohol 9-phenyl-(1-Z,3Z,6E,8E)-1-methoxy-5-hydroxy-nonatetraene 6, which was hydrolyzed or spontaneously transformed into 9-phenyl-(2E,4E,6E,8E)-tetraenal 7, completing the eight-carbon homologation of benzaldehyde. Reaction of 9-phenyl-nona-(2E,4E,6E,8E)-tetraenal 7 with methyllithium in tetrahydrofuran afforded (3E,5E,7E, 9E)-10-phenyl-deca-3,5,7,9-tetraen-2-ol 8. The product of the reaction described was employed in the synthesis of (3E,5E,7E,9E)-10-phenyl- deca-3,5,7,9-tetraen-2-one 9, which is known as navenone B, an alarm pheromone of the mollusk Navanax inermis. Taylor & Francis Group, LLC.

Addition of carbon nucleophiles to aldehyde tosylhydrazones of aromatic and heteroaromatic-compounds: Total synthesis of piperine and its analogs

Addition of carbon nucleophiles to aldehyde tosylhydrazones of aromatic and heteroaromatic compounds is reported. New observations have been made wherein alkylative reduction is observed in some cases whereas alkylative fragmentation is noticed in others. These findings are exploited in the synthesis of the useful alkaloid piperine and its analogs. (C) 2000 Elsevier Science Ltd.

A new and easy route to (2E,4E)-dienals by four-carbon homologation of aldehydes

A new synthetic method of (2E,4E)-dienals by four-carbon homologation of aldehydes is described. γ-trimethylsilyl crotonaldimine 2 , easily generated from N-ter-butyl-crotonaldimine 1, LDA and ClSiMe3, reacts with aldehydes in the presence of catalytic CsF in DMSO at rt → 100°C to afford homologous aldehydes 3 in good yields and with excellent (E,E)-selectivities.

Derives silyles issus d'aldimines α,β-insaturees: preparations et applications en synthese

The preparation of silylated N-tert-butyl α,β-unsaturated aldimines is reported.The disilylated reagent 3a derived from crotonaldimine is used for the conversion of aromatic aldehydes into conjugated dienals in one-pot reaction.

Two-Carbon Homologation of Aldehydes. Synthesis of trans-α,β-Unsaturated Aldehydes

2-tri-n-Butylstannylvinyl ethers are useful synthetic equivalents of acetaldehyde in 2-carbon homologation reactions.When reacted with aldehydes in the presence of BF3-OEt2 the corresponding trans-α,β-unsaturated aldehydes are obtained in high yield.

Aldehydes α-silyles: preparation et properties nouvelles

t-Butyldimethylsilyl acetaldehyde (3) is obtained from the hydrolysis of the (Z)-β-silylenoxysilane (2), prepared from (Z)-1-bromo-2-(trimethylsiloxy)ethylene by reaction with t-butyllithium followed by condensation with t-butyldimethylsilyl triflate.The lithium enolate of aldehyde 3 is prepared direct by reaction with lithium diisopropylamide or lithium hexamethyldisilazane; its condensation with trimethylchlorosilane leads to the (E)-β-silylenoxysilane (2) and with aldehydes, to α,β-ethylenic aldehydes (4).

Tandem Addition of Phosphite Nucleophiles Across Unsaturated Nitrogen-Containing Systems: Mechanistic Insights on Regioselectivity

The addition of phosphite nucleophiles across linear unsaturated imines is a powerful and atom-economical methodology for the synthesis of aminophosphonates. These products are of interest from both a biological and a synthetic point of view: they act as amino acid transition state analogs and Horner-Wadsworth-Emmons reagents, respectively. In this work the reaction between dialkyl trimethylsilyl phosphites and α,β,γ,δ-diunsaturated imines was evaluated as a continuation of our previous efforts in the field. As such, the first conjugate 1,6-addition of a phosphite nucleophile across a linear unsaturated N-containing system is reported herein. Theoretical calculations were performed to rationalize the observed regioselectivites and to shed light on the proposed mechanism.

Application of (2E,4E)-5-bromo-2,4-pentadienal in palladium catalyzed cross-coupling: Easy access to (2E,4E)-2,4-dienals

Palladium catalyzed cross-coupling reactions of (2E,4E)-5-bromo-2,4-pentadienal 1 with organozinc reagents gives an easy access to the corresponding (2E,4E)-2,4-dienals. The improved preparation of all trans 1 by isomerization of its (2E,4Z) isomer is reported.

Synthesis of conjugated multiunsaturated thioesters via one-pot TiCl4-promoted aldol condensation

TiCl4-promoted aldol condensations of S-4-chlorophenyl thioesters with enals or dienals led to the production of dienyl or trienyl thioesters in good yields. Due to good crystallinity, products with high E/Z ratios were obtained by simple filtr