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
• Article Data: 18

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

Chemical Properties

white to light beige powder

Uses

4'-Hydroxyvalerophenone is an organic intermediate and pharmaceutical intermediate for the preparation of acylphenoxyacetic acid compounds.

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

Downstream Products

• 101586-05-4 nicotinic acid-[1-(4-hydroxy-phenyl)-pentylidenehydrazide] 
• 101585-98-2 isonicotinic acid-[1-(4-hydroxy-phenyl)-pentylidenehydrazide] 
• 80417-29-4 4-Butoxy-benzoic acid 4-pentanoyl-phenyl ester 
• 1026542-50-6 2-Bromo-1-(4-triisopropylsilanyloxy-phenyl)-pentan-1-one 
• 1026076-93-6 2-(4-Benzyl-4-hydroxy-piperidin-1-yl)-1-(4-triisopropylsilanyloxy-phenyl)-pentan-1-one 
• 938077-66-8 [2-(4-hydroxyphenyl)-1-hexene-1,1-diyl]dibenzene-4,1-diyl bis(2,2-dimethylpropanoate) 
• 42018-03-1 ethyl [(4-pentanoylphenyl)oxy]acetate 
• 101888-44-2 1-[4-(2-piperidino-ethoxy)-phenyl]-pentan-1-one 

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.

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.

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.