2491-32-9

Basic information

• Product Name: BENZYL 4-HYDROXYPHENYL KETONE
• Synonyms: 1-(4-Hydroxy-phenyl)-2-phenyl-ethanone;4-Hydroxydesoxybenzoin;Acetophenone, 4'-hydroxy-2-phenyl-;Benzyl p-hydroxyphenyl ketone;p-(Phenylacetyl)phenol;4'-HYDROXY-2-PHENYLACETOPHENONE;4-HYDROXYPHENYL BENZYL KETONE;4'-HYDROXYDEOXYBENZOIN
• CAS NO: 2491-32-9
• Molecular Formula: C₁₄H₁₂O₂
• Molecular Weight: 212.24
• EINECS: 219-654-5
• Mol File: 2491-32-9.mol
• Article Data: 21

Chemical Properties

• Melting Point: 148-151 °C(lit.)
• Boiling Point: 403.3 °C at 760 mmHg
• Flash Point: 172.2 °C
• Appearance: /
• Density: 1.178 g/cm³
• Vapor Pressure: 4.42E-07mmHg at 25°C
• Refractive Index: 1.612
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 8.12±0.15(Predicted)
• CAS DataBase Reference: BENZYL 4-HYDROXYPHENYL KETONE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL 4-HYDROXYPHENYL KETONE(2491-32-9)
• EPA Substance Registry System: BENZYL 4-HYDROXYPHENYL KETONE(2491-32-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 2491-32-9(Hazardous Substances Data)

Usage

Chemical Properties

Cream crystalline powder

Preparation

– Obtained by reaction of phenylacetic acid with phenol, ? in the presence of zinc chloride (Nencki reaction), ? in the presence of zinc chloride and phosphorous oxychloride for 24 h at r.t. (75%) ; ? in the presence of polyphosphoric acid in a boiling water bath for 15 min (28%) or at 100° (19%) ; ? in the presence of boron trifluoride at 80° for 2 h (87%) ; ? in the presence of boron trifluoride etherate under argon on a water bath for 1.5 h (75%).

InChI:InChI=1/C14H12O2/c15-13-8-6-12(7-9-13)14(16)10-11-4-2-1-3-5-11/h1-9,15H,10H2

Upstream product

• 1023-17-2 4-methoxyphenyl benzyl ketone 
• 722-01-0 phenyl phenylacetate 
• 33555-64-5 2-hydroxy-5-phenylacetyl-benzoic acid 
• 103-80-0 phenylacetyl chloride 
• 108-95-2 phenol 
• 103-82-2 phenylacetic acid 
• 2491-31-8 2-hydroxy-deoxybenzoin 
• 73049-07-7 bibenzyl-4,α-diol 
• 7446-70-0 aluminium trichloride 
• 540-38-5 p-Iodophenol 
• 100-44-7 benzyl chloride 
• 100-66-3 methoxybenzene 
• 62673-31-8 benzyl(bromo)zinc 
• 13939-06-5 molybdenum hexacarbonyl 

Downstream Products

• 63187-05-3 1-(4-hydroxy-phenyl)-2,3-diphenyl-3-piperidino-propan-1-one 
• 32599-27-2 1-(4-hydroxy-phenyl)-2-phenyl-3-piperidin-1-yl-propan-1-one 
• 102156-36-5 4-hydroxy-3-piperidinomethyl-deoxybenzoin 
• 63192-19-8 1-(4-butoxyphenyl)-2-phenylethanone 
• 38495-73-7 1-(4-ethoxyphenyl)-2-phenylethanone 
• 69342-32-1 1-(4-isopropoxyphenyl)-2-phenylethanone 
• 857562-76-6 4-(2-butoxy-ethoxy)-deoxybenzoin 
• 79838-57-6 2-phenyl(4-diethylaminoethoxyphenyl)ethan-1-one 
• 6335-83-7 4-(2-phenylethyl)phenol 
• 855242-75-0 2,3-bis-(4-hydroxy-phenyl)-1,4-diphenyl-butane-2,3-diol 
• 34544-90-6 4,α-diacetoxy-stilbene 
• 14293-14-2 4-(benzyloxy)phenyl benzyl ketone 
• 61078-33-9 1-(4-hydroxy-phenyl)-3-(4-methoxy-phenyl)-2-phenyl-propenone 
• 63192-18-7 4-propoxy-deoxybenzoin 

Relevant articles and documents

Versatile and base-free copper-catalyzed α-arylations of aromatic ketones using diaryliodonium salts

A ligand and base-free copper catalyzed synthetic method for the efficient α-arylation of aromatic ketones is described. In order to avoid strong bases, ketone-derived silyl enol ethers were employed. Their reaction with diaryliodonium salts as aryl source provided the intermolecular C–C coupling displaying good functional group tolerance and requiring low catalyst loading.

PtO2/PTSA system catalyzed regioselective hydration of internal arylalkynes bearing electron withdrawing groups

A highly efficient PtO2/PTSA catalyst system for the hydration of a wide array of alkynes was developed. This method proved to be compatible with a large range of functional groups and the ketone products were obtained in high yields. The scope of this methodology was also extended to the synthesis of 3-Aryl-isochromenones,-indoles and-benzofurans.

Diarylated ethanones from Mo(CO)6-mediated and microwave-assisted palladium-catalysed carbonylative Negishi cross-couplings

Two protocols for palladium-catalysed carbonylative Negishi cross-couplings were developed for aryl iodides and aryl bromides. The two main breakthroughs were that molybdenum hexacarbonyl [Mo(CO)6] could be used as a solid in situ source of CO, and that controlled microwave irraditaion could be used for heating. Consequently, the reactions were safe (in contrast to when CO gas was used) and fast (in comparison to when conventional heating was used). The carbonylative cross-coupling reactions were carried out using commercially available benzylzinc bromide in closed vials (90-120°C for 0.5-1 h) to give a set of diarylated ethanones, a common pharmacophore found in several pharmaceuticals, in moderate to high isolated yields (47-84 %). The mild three-component carbonylation protocol presented here is operationally simple, safe, and rapid, and the formation of the carbonylative Negishi cross-coupling product is favoured over the product of Negishi cross-coupling. Copyright