2270-20-4

Basic information

• Product Name: 5-Phenylvaleric acid
• Synonyms: 5-phenyl-valericaci;benzenepentanoicacid;Benzenepentanoic-acid-;gamma-phenylvalericacid;Phenylpentanoic acid;phenylpentanoicacid;Phenylvaleric acid;Valeric acid, 5-phenyl-
• CAS NO: 2270-20-4
• Molecular Formula: C₁₁H₁₄O₂
• Molecular Weight: 178.23
• EINECS: 218-872-8
• Product Categories: API intermediates;C11 to C12;Building Blocks;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks
• Mol File: 2270-20-4.mol

Chemical Properties

• Melting Point: 58-60 °C(lit.)
• Boiling Point: 177-178 °C13 mm Hg(lit.)
• Flash Point: 176-178°C/12mm
• Appearance: white crystals.
• Density: 1.0292 (rough estimate)
• Vapor Pressure: 0.000293mmHg at 25°C
• Refractive Index: 1.4920 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: pKa 4.59 ± 0.02(H2O,t =25±0.5,I=0.015(KCl)) (Uncertain)
• Water Solubility: 1.777g/L(30 oC)
• BRN: 2049062
• CAS DataBase Reference: 5-Phenylvaleric acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Phenylvaleric acid(2270-20-4)
• EPA Substance Registry System: 5-Phenylvaleric acid(2270-20-4)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: YV7816000
• Hazardous Substances Data: 2270-20-4(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
5-Phenylvaleric acid is used as an organic intermediate for the synthesis of various chemical compounds. Its unique structure allows it to serve as a building block in the creation of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-Phenylvaleric acid is used as a key intermediate in the development of drugs targeting specific medical conditions. Its chemical properties make it a valuable component in the synthesis of new therapeutic agents.
Used in Agrochemical Industry:
5-Phenylvaleric acid is also utilized in the agrochemical industry for the production of various pesticides and other agricultural chemicals. Its role as an intermediate allows for the creation of effective solutions to protect crops and enhance agricultural productivity.
Used in Specialty Chemicals:
5-Phenylvaleric acid finds application in the production of specialty chemicals, such as additives, coatings, and polymers. Its unique properties contribute to the development of innovative materials with specific characteristics tailored to various industrial needs.

Synthesis Reference(s)

Tetrahedron, 48, p. 9531, 1992 DOI: 10.1016/S0040-4020(01)88320-4

InChI:InChI=1/C11H14O2/c12-11(13)9-5-4-8-10-6-2-1-3-7-10/h1-3,6-7H,4-5,8-9H2,(H,12,13)/p-1

Upstream product

• 542-28-9 3,4,5,6-tetrahydro-2H-pyran-2-one 
• 71-43-2 benzene 
• 996-82-7 sodium diethylmalonate 
• 637-59-2 1-Bromo-3-phenylpropane 
• 28010-12-0 5-phenylpenta-2,4-dienoic acid 
• 7726-45-6 5-phenylvaleronitrile 
• 676551-01-2 2-((Z)-3-Phenyl-allylidene)-malonic acid 
• 17920-83-1 5-phenyl-4-pentenoic acid 
• 24271-22-5 5-phenylpent-2-enoic acid 
• 14171-89-2 1-phenyl-5-hexanone 
• 78905-97-2 (E)-5-phenylpent-3-enoic acid 
• 857976-04-6 4,4-bis-ethanesulfonyl-5-phenyl-valeric acid 
• 1501-05-9 5-oxo-5-phenylvaleric acid 
• 1119-46-6 5-chloro-valeric acid 

Downstream Products

• 6308-43-6 4-[4-(4-ethoxycarbonyl-butyl)-phenyl]-4-oxo-butyric acid 
• 100388-80-5 5-(4-chloromethyl-phenyl)-valeric acid 
• 102472-04-8 4-phenylbutyl 5-phenylpentanoate 
• 20492-10-8 5-(4'-nitrophenyl)pentanoic acid 
• 5962-88-9 5-cyclohexylvaleric acid 
• 35511-91-2 1,8-diphenyloctane 
• 17734-38-2 ethyl 5-phenylpentanoate 
• 116680-98-9 5-(4-iodophenyl)pentanoic acid 
• 806600-26-0 5-(2-amino-phenyl)-valeric acid 
• 103856-01-5 5-(4-aminophenyl)pentanoic acid 
• 332-58-1 5-(4-fluorosulfonyl-phenyl)-valeric acid 
• 611-73-4 Benzoylformic acid 
• 826-73-3 1-Benzosuberone 
• 20371-41-9 5-phenylvaleric acid chloride 

Relevant articles and documents

Homoenolic radical derived from propionic acid: A versatile reagent for the radical version of the Michael reaction

The homoenolic radical, derived from 3-iodopropionic acid (1) by reaction with in situ generated tributyltin hydride, undergoes clean carbon-carbon forming reaction with electrophilic olefins (2) yielding functionalized acids (3).

Pd-Catalyzed Regioselective Branched Hydrocarboxylation of Terminal Olefins with Formic Acid

A regioselective Pd-catalyzed hydrocarboxylation of terminal olefins with HCOOH is described. A wide variety of branched carboxylic acids can readily be obtained with high regioselectivities under mild reaction conditions. The reaction is operationally simple and requires no handling of toxic CO. The ligand and LiCl are important factors for reaction reactivity and selectivity.

Synthesis of Carboxylic Acids by Palladium-Catalyzed Hydroxycarbonylation

The synthesis of carboxylic acids is of fundamental importance in the chemical industry and the corresponding products find numerous applications for polymers, cosmetics, pharmaceuticals, agrochemicals, and other manufactured chemicals. Although hydroxycarbonylations of olefins have been known for more than 60 years, currently known catalyst systems for this transformation do not fulfill industrial requirements, for example, stability. Presented herein for the first time is an aqueous-phase protocol that allows conversion of various olefins, including sterically hindered and demanding tetra-, tri-, and 1,1-disubstituted systems, as well as terminal alkenes, into the corresponding carboxylic acids in excellent yields. The outstanding stability of the catalyst system (26 recycling runs in 32 days without measurable loss of activity), is showcased in the preparation of an industrially relevant fatty acid. Key-to-success is the use of a built-in-base ligand under acidic aqueous conditions. This catalytic system is expected to provide a basis for new cost-competitive processes for the industrial production of carboxylic acids.

Strategic Approach to the Metamorphosis of γ-Lactones to NH γ-Lactams via Reductive Cleavage and C-H Amidation

A new approach has elaborated on the conversion of γ-lactones to the corresponding NH γ-lactams that can serve as γ-lactone bioisosteres. This approach consists of reductive C-O cleavage and an Ir-catalyzed C-H amidation, offering a powerful synthetic tool for accessing a wide range of valuable NH γ-lactam building blocks starting from γ-lactones. The synthetic utility was further demonstrated by the late-stage transformation of complex bioactive molecules and the asymmetric transformation.

Pd-Catalyzed Highly Chemo- And Regioselective Hydrocarboxylation of Terminal Alkyl Olefins with Formic Acid

An efficient Pd-catalyzed hydrocarboxylation of alkenes with HCOOH is described. A wide variety of linear carboxylic acids bearing various functional groups can be obtained with excellent chemo- and regioselectivities under mild reaction conditions. The reaction process is operationally simple and requires no handling of toxic CO.

Synthetic method of terminal carboxylic acid

The invention discloses a synthetic method of a terminal carboxylic acid. The synthetic method is characterized by comprising the steps of adding an olefin represented by a formula (3) shown in the description, formic acid, acetic anhydride, Pd(OAc)2 and a monophosphorus ligand TFPP into an organic solvent in a proportion, carrying out hydrogen carbonylation reaction on the olefin represented by the formula (3) shown in the description, formic acid and acetic anhydride at 80-90 DEG C for 48h-72h under the catalysis of the metal palladium salt Pd(OAc)2 and the monophosphorus ligand TFPP so as to obtain the terminal carboxylic acid represented by a formula shown in the description, and separating a target product, namely the terminal carboxylic acid after the reaction is finished, wherein olefin represented by the formula (3) is selected from cycloolefins, or linear olefins of which the R1 is electron donating groups. By virtue of the method disclosed by the invention, corresponding terminal carboxylic acid and a derivative thereof can be prepared through the reaction under mild conditions of low temperature and no high pressure; and the steps of the synthetic method are simple and convenient, the operation is convenient, the yield is high, the energy source can be greatly saved, and the synthetic efficiency can be greatly improved.

Carbonylative Transformation of Allylarenes with CO Surrogates: Tunable Synthesis of 4-Arylbutanoic Acids, 2-Arylbutanoic Acids, and 4-Arylbutanals

In this Communication, procedures for the selective synthesis of 4-arylbutanoic acids, 2-arylbutanoic acids, and 4-arylbutanals from the same allylbenzenes have been developed. With formic acid or TFBen as the CO surrogate, reactions proceed selectively and effectively under carbon monoxide gas-free conditions.

CATALYTIC CARBOXYLATION OF ACTIVATED ALKANES AND/OR OLEFINS

The present invention relates to a method of reacting starting materials with an activating group, namely alkanes carrying a leaving group and/or olefins, with carbon dioxide under transition metal catalysis to give carboxyl group-containing products. It is a special feature of the method of the present invention that the carboxylation predominantly takes place at a preferred position of the molecule irrespective of the position of the activating group. The carboxylation position is either an aliphatic terminus of the molecule or it is a carbon atom adjacent to a carbon carrying an electron withdrawing group. The course of the reaction can be controlled by appropriately choosing the reaction conditions to yield the desired regioisomer.

Site-Selective Catalytic Carboxylation of Unsaturated Hydrocarbons with CO2 and Water

A catalytic protocol that reliably predicts and controls the site-selective incorporation of CO2 to a wide range of unsaturated hydrocarbons utilizing water as formal hydride source is described. This platform unlocks an opportunity to catalytically repurpose three abundant, orthogonal feedstocks under mild conditions.

Hydrogen-transfer reduction of α,β-unsaturated carbonyl compounds catalyzed by naphthyridine-functionalized N-heterocyclic carbene complexes

Substitution of silver complex of 2-chloro-7-(mesitylimidazolylidenylmethyl)naphthyridine (NpNHC) with palladium(II), rhodium(I) and iridium(I) metal precursors provided [Pd(C,N-NpNHC)(η3-allyl)](BF4) (5), RhCl(COD)(C-NpNHC) (6a) and IrCl(COD)(C-NpNHC) (6b), respectively. Abstraction of chloride from 6a and 6b with AgBF4 provided the chelation complexes [Rh(COD)(C,N-NpNHC)](BF4) (7a) and Ir(COD)(C,N-NpNHC)(BF4) (7b), respectively. All complexes were characterized using NMR and elemental analyses and the structural details of 5 and 6a were further confirmed using X-ray crystallography. In catalytic activity studies, complex 5 was found to be an effective catalyst in the hydrogen-transfer reduction of α,β-unsaturated carbonyl compounds into the corresponding saturated carbonyl compounds.