2589-71-1

Basic information

• Product Name: 4-Hydroxyvalerophenone
• Synonyms: 1-(4-hydroxyphenyl)-1-pentanon;1-(4-Hydroxyphenyl)-1-pentanone;p-Valerylphenol;Valerophenone, 4'-hydroxy-;P-HYDROXYVALEROPHENONE;4'-HYDROXYPENTANOPHENONE;4'-HYDROXYVALEROPHENONE;4-HYDROXYVALEROPHENONE
• CAS NO: 2589-71-1
• Molecular Formula: C₁₁H₁₄O₂
• Molecular Weight: 178.23
• EINECS: 219-978-7
• Product Categories: C11 to C12;Carbonyl Compounds;Ketones
• Mol File: 2589-71-1.mol

Chemical Properties

• Melting Point: 62-65 °C
• Boiling Point: 182-183 °C/3 mmHg(lit.)
• Flash Point: 137.7 °C
• Appearance: white to light beige powder
• Density: 1.0292 (rough estimate)
• Vapor Pressure: 0.000158mmHg at 25°C
• Refractive Index: 1.5390 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 8.13±0.15(Predicted)
• CAS DataBase Reference: 4-Hydroxyvalerophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxyvalerophenone(2589-71-1)
• EPA Substance Registry System: 4-Hydroxyvalerophenone(2589-71-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-37/39-26
• WGK Germany: 3
• Hazardous Substances Data: 2589-71-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Hydroxyvalerophenone is used as a pharmaceutical intermediate for the preparation of acylphenoxyacetic acid compounds. These compounds are essential in the development of various pharmaceutical products, contributing to their efficacy and therapeutic properties.
Used in Organic Synthesis:
In the field of organic synthesis, 4-Hydroxyvalerophenone serves as an important intermediate. Its unique chemical structure allows it to be a key component in the synthesis of various organic compounds, expanding its applications across different industries.

Preparation

4'-Hydroxyvalerophenone is synthesized from phenol and valeryl chloride. It is a raw material intermediate for liquid crystals.

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 6537, 1994 DOI: 10.1016/S0040-4039(00)78266-9

InChI:InChI=1/C11H14O2/c1-9(12)7-8-11(13)10-5-3-2-4-6-10/h2-6,9,12H,7-8H2,1H3

Upstream product

• 20115-23-5 phenyl valerate 
• 109-52-4 valeric acid 
• 108-95-2 phenol 
• 638-29-9 n-valeryl chloride 
• 109-72-8 n-butyllithium 
• 201230-82-2 carbon monoxide 
• 540-38-5 p-Iodophenol 
• 693-02-7 hex-1-yne 
• 120743-99-9 p-[(tert-butyldimethylsilyl)oxy]benzaldehyde 
• 123-08-0 4-hydroxy-benzaldehyde 
• 96013-81-9 1-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-pentan-1-ol 
• 71-23-8 propan-1-ol 
• 93453-79-3 1-(4-hydroxyphenyl)ethanol 
• 106-51-4 p-benzoquinone 

Downstream Products

• 101888-44-2 1-[4-(2-piperidino-ethoxy)-phenyl]-pentan-1-one 
• 101586-05-4 nicotinic acid-[1-(4-hydroxy-phenyl)-pentylidenehydrazide] 
• 101585-98-2 isonicotinic acid-[1-(4-hydroxy-phenyl)-pentylidenehydrazide] 
• 5408-44-6 1-(3,5-dibromo-4-hydroxy-phenyl)-pentan-1-one 
• 17467-71-9 4-<1-Butylpenten-(1)-yl>-phenol 
• 17404-19-2 4-(1-Butyloct-1-enyl)-phenol 
• 17467-72-0 4-<1-Butylnonen-(1)-yl>-phenol 
• 17404-18-1 4-<1-Butyl-hexen-(1)-yl>-phenol 
• 1671-76-7 p-Methoxyvalerophenon 
• 109720-05-0 1-{4-[2-(4-Methoxy-phenyl)-ethoxy]-phenyl}-pentan-1-one 
• 80417-25-0 4-Propoxy-benzoic acid 4-pentanoyl-phenyl ester 
• 50649-71-3 4-Pentyloxy-benzoic acid 4-pentanoyl-phenyl ester 
• 109720-03-8 1-{4-[2-(4-Hydroxy-phenyl)-ethoxy]-phenyl}-pentan-1-one 
• 14938-35-3 4-n-pentylphenol 

Relevant articles and documents

Iridium Complexes as Efficient Catalysts for Construction of α-Substituted Ketones via Hydrogen Borrowing of Alcohols in Water

Ketones are of great importance in synthesis, biology, and pharmaceuticals. This paper reports an iridium complexes-catalyzed cross-coupling of alcohols via hydrogen borrowing, affording a series of α-alkylated ketones in high yield (86 %–95 %) and chemoselectivities (>99 : 1). This methodology has the advantages of low catalyst loading (0.1 mol%) and environmentally benign water as the solvent. Studies have shown the amount of base has a great impact on chemoselectivities. Meanwhile, deuteration experiments show water plays an important role in accelerating the reduction of the unsaturated ketones intermediates. Remarkably, a gram-scale experiment demonstrates this methodology of iridium-catalyzed cross-coupling of alcohols has potential application in the practical synthesis of α-alkylated ketones.

Rhodium-Catalyzed Deoxygenation and Borylation of Ketones: A Combined Experimental and Theoretical Investigation

The rhodium-catalyzed deoxygenation and borylation of ketones with B2pin2 have been developed, leading to efficient formation of alkenes, vinylboronates, and vinyldiboronates. These reactions feature mild reaction conditions, a broad substrate scope, and excellent functional-group compatibility. Mechanistic studies support that the ketones initially undergo a Rh-catalyzed deoxygenation to give alkenes via boron enolate intermediates, and the subsequent Rh-catalyzed dehydrogenative borylation of alkenes leads to the formation of vinylboronates and diboration products, which is also supported by density functional theory calculations.

Visible Light-Mediated [2 + 2] Cycloaddition Reactions of 1,4-Quinones and Terminal Alkynes

A single-step synthesis of 4-hydroxy-functionalized bi-aryl and aryl/alkyl ketones via oxidative coupling of terminal alkynes with benzoquinones is reported. Furthermore, with naphthoquinones, owing to the cross-resonance of carbonyl with the aromatic ring, alkene-alkyne cycloaddition is more favored to give four-membered carbocyclic adducts, thereby precluding the requirement of preactivated alkynes.

Visible Light Copper Photoredox-Catalyzed Aerobic Oxidative Coupling of Phenols and Terminal Alkynes: Regioselective Synthesis of Functionalized Ketones via C C Triple Bond Cleavage

Direct oxidative coupling of phenols and terminal alkynes was achieved at room temperature by a visible-light-mediated copper-catalyzed photoredox process. This method allows regioselective synthesis of hydroxyl-functionalized aryl and alkyl ketones from simple phenols and phenylacetylene via C C triple bond cleavage. 47 examples were presented. From a synthetic perspective, this protocol offers an efficient synthetic route for the preparation of pharmaceutical drugs, such as pitofenone and fenofibrate.

THIOSEMICARBAZONES INHIBITORS OF LYSOPHOSPHATIDIC ACID ACYLTRANSFERASE AND USES THEREOF

Lysophosphatidic acid acyltransferase-beta (LPAAT-β) catalyzes the production of phosphatidic acid (PA) from lysophosphatidic acid (LPA). The lipid cofactor PA contributes to the activation of c-Raf, BRAF, mTOR and PKC-ζ. LPAAT-β expression is a prognostic factor in gynecologic malignancies and is being investigated as a therapeutic target in a variety of tumor types. A class of thiosemicarbazones was identified as inhibitors of LPAAT-β from a screen of a library of small molecules. A focused library of thiosemicarbazones derivatives was prepared and led to the development of compounds which potently inhibit LPAAT-β and inhibit the growth of MiaPaCa2 human pancreatic cancer cells.

Synthesis, biochemical evaluation and rationalisation of a series of 3,5- dibromo derivatives of 4-hydroxyphenyl ketone-based compounds as probes of the active site of type 3 of 17β-hydroxysteroid dehydrogenase (17β-hsd3) and the role of hydrogen bonding interaction in the inhibition of 17β-HSD3

We report the synthesis, evaluation and rationalisation of the inhibitory activity of a series of 3,5-dibromo derivatives of 4-hydroxyphenyl ketone as probes of the active site of the type 3 of 17β-hydroxysteroid dehydrogenase (17β-HSD3). The results support the important role of hydrogen bonding interaction in the inhibition of 17β-HSD3.

Comparisons of O-acylation and Friedel-Crafts acylation of phenols and acyl chlorides and Fries rearrangement of phenyl esters in trifluoromethanesulfonic acid: Effective synthesis of optically active homotyrosines

Reactions involving phenol derivatives and acyl chlorides have to be controlled for competitive O-acylations and C-acylations (Friedel-Crafts acylations and Fries rearrangements) in acidic condition. The extent for these reactions in trifluoromethanesulfonic acid (TfOH), which is used as catalyst and solvent, is examined. Although diluted TfOH was needed for effective O-acylation, concentrated TfOH was required for effective C-acylations in mild condition. These results have been applied to the novel synthesis of homotyrosine derivatives. Both Fries rearrangement of N-TFA-Asp(OBn)-OMe and Friedel-Crafts acylation of phenol with N-TFA-Asp(Cl)-OMe in TfOH afforded the homotyrosine skeleton, followed by reduction and deprotection afforded homotyrosines maintaining stereochemistry of Asp as an optically pure form.

Synthesis and biochemical evaluation of a series of trifluoromethanesulfonate derivatives of 4 hydroxyphenyl ketones - Probes of the active site of type 1 and 3 of the 17β-hydroxysteroid dehydrogenase family of enzymes

In an effort to aid the design of 'dual-inhibitors' of types 1 and 3 of the 17β-hydroxysteroid dehydrogenase (17β-HSD), we report the synthesis, biochemical evaluation and rationalisation of the inhibitory activity of trifluoromethanesulfonate derivatives of 4-hydroxyphenyl ketone-based compounds which were found to be weak inhibitors of types 1 and 3.

Synthesis, biochemical evaluation and rationalisation of the inhibitory activity of a series of 4-hydroxyphenyl ketones as potential inhibitors of 17β-hydroxysteroid dehydrogenase type 3 (17β-HSD3)

We report the preliminary results of the synthesis and biochemical evaluation of a number of 4-hydroxyphenyl ketones as inhibitors of the isozyme of the enzyme 17β-hydroxysteroid dehydrogenase (17β-HSD) responsible for the conversion of androstenedione (AD) to testosterone (T), more specifically type 3 (17β-HSD3). The results of our study suggest that we have synthesised compounds which are, in general, potent inhibitors of 17β-HSD3, in particular, we discovered that 1-(4-hydroxy-phenyl)-nonan-1-one (8) was the most potent (IC50 = 2.86 ± 0.03 μM). We have therefore provided good lead compounds in the synthesis of novel non-steroidal inhibitors of 17β-HSD3.

Pd-catalyzed carbonylative cross-coupling reactions by triorganoindiums: Highly efficient transfer of organic groups attached to indium under atmospheric pressure

(Matrix presented) A highly atom-efficient synthetic method of unsymmetrical ketones was developed by using trialkyl- and triarylindiums, which could be employed as effective cross-coupling partners in Pd-catalyzed carbonylative cross-coupling reactions with a variety of organic electrophiles. The present method produced unsymmetrical ketones and 1,4-diacylbenzenes in good yields with highly efficient transfer of almost all the organic groups attached to the indium under atmospheric pressure of CO gas in THF at 66°C.