16183-46-3

Basic information

• Product Name: α-Hydroxybutyrophenone
• Synonyms: 1-Phenyl-2-hydroxy-1-butanone;2-Hydroxy-1-phenylbutan-1-one;2-Hydroxybutyrylbenzene
• CAS NO: 16183-46-3
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.2
• Mol File: 16183-46-3.mol

Chemical Properties

• Boiling Point: 251.67°C (rough estimate)
• Appearance: /
• Density: 1.0827
• Refractive Index: 1.5290 (estimate)
• CAS DataBase Reference: α-Hydroxybutyrophenone(CAS DataBase Reference)
• NIST Chemistry Reference: α-Hydroxybutyrophenone(16183-46-3)
• EPA Substance Registry System: α-Hydroxybutyrophenone(16183-46-3)

Safety Data

• Hazardous Substances Data: 16183-46-3(Hazardous Substances Data)

Upstream product

• 93351-19-0 3-ethyl-2-methoxy-2-phenyl-oxirane 
• 877-35-0 2-bromo-1-phenylbutan-1-one 
• 98-88-4 benzoyl chloride 
• 123-38-6 propionaldehyde 
• 613-90-1 benzoyl cyanide 
• 3457-55-4 1-phenyl-1,2-butanedione 
• 108350-39-6 2-iodo-1-phenylbutan-1-one 
• 25438-37-3 phenyl(trimethylsiloxy)acetonitrile 
• 1071009-57-8 C₁₄H₂₁NO₂Si 
• 54034-47-8 1-oxo-1-phenylbutan-2-yl acetate 
• 922186-05-8 phosphoric acid diethyl ester 1-phenyl-but-1-enyl ester 
• 71-23-8 propan-1-ol 
• 100-52-7 benzaldehyde 
• 495-40-9 propiophenone 

Downstream Products

• 108843-02-3 1,1-diphenyl-butane-1,2-diol 
• 17180-71-1 1-phenyl-butane-1,2-dione-bis-(2,4-dinitro-phenylhydrazone) 
• 3457-55-4 1-phenyl-1,2-butanedione 
• 669-32-9 4-ethyl-5-phenyl-1⁽³⁾H-imidazole 
• 103986-08-9 5-ethyl-4-phenyl-3H-oxazol-2-one 

Relevant articles and documents

Aerobic Direct Dioxygenation of Terminal/Internal Alkynes to α-Hydroxyketones by an Fe Porphyrin Catalyst

We herein report a new synthetic method for the preparation of α-hydroxyketones by the dioxygenation of alkynes. The reaction proceeds at room temperature under the action of Fe porphyrin and pinacolborane under air as a green oxidant to produce α-hydroxyketones. The mild reaction conditions allow chemoselective oxidation with functional group tolerance. Terminal alkynes in addition to internal alkynes are applicable, affording unsymmetrical α-hydroxyketones that are difficult to obtain by any reported dioxygenation of unsaturated C?C bonds.

Preparation and Application of α-Imino Ketones through One-Pot Tandem Reactions Based on Heyns Rearrangement

α-Imino ketone is a useful building block for the preparation of α-amino ketones and α-amino alcohols. However, its preparation has been seldomly seen. Herein, a metal-free and operationally simple strategy has been developed to generate α-imino ketones with high regioselectivity. Meanwhile, the method allowed for the preparation of various N,O-ketals with high regioselectivities and diastereoselectivities through cascade reactions in one pot.

Green preparation method α - hydroxyketone

The invention relates to a green preparation method of alpha-hydroxyketone. The method comprises the following steps: adding ketone, iodine, 1,4-diazabicyclo[2.2.2]octane and methanol into a glass reaction bottle in sequence; then stirring and reacting for 14 to 30h at room temperature in an air atmosphere under the irradiation of a 23W compact type fluorescent lamp, so as to obtain a reaction mixture; carrying out silica gel column chromatographic separation to obtain the pure alpha-hydroxyketone. The green preparation method provided by the invention has the characteristics of greenness, high efficiency, simplicity in operation, moderate conditions, wide applicability and easiness for industrialization.

Synthesis of α-heterosubstituted ketones through sulfur mediated difunctionalization of internal alkynes

Synthesis of α-heterosubstituted ketones was achieved through sulfur mediated difunctionalization of internal alkynes in one pot. The reaction design involves: phenyl substituted internal alkyne attacking triflic anhydride activated diphenyl sulfoxide to

Synthesis of α-oxygenated ketones and substituted catechols via the rearrangement of N-enoxy- and N-aryloxyphthalimides

A common approach to the synthesis of α-oxygenated carbonyl compounds and catechols is the treatment of a carbonyl compound or a phenol with an electrophilic oxygen source. As an alternative approach to these important structures, formal [3,3]-rearrangements of N-enoxyphthalimides, N-enoxyisoindolinones, and N-aryloxyphthalimides have been explored. When used in combination with an initial Chan-Lam coupling, these transformations facilitate the dioxygenation of alkenylboronic acids for the synthesis of α-oxygenated ketones and the dioxygenation of arylboronic acids for the synthesis of catechols. The rearrangements of N-enoxyisoindolinones have also been shown to be diastereoselective.

Halogen-bonded iodonium ion catalysis: A route to α-hydroxy ketones: Via domino oxidations of secondary alcohols and aliphatic C-H bonds with high selectivity and control

A domino synthesis of α-hydroxy ketones has been developed from benzylic secondary alcohols employing catalytic iodonium ions stabilized by DMSO. The reaction proceeds through an unprecedented sequential oxidation of alcohols to ketone and its α-hydroxylation in a controlled manner. The spectroscopic evidence establishes the possibility of formation of a stable halogen-bonded adduct between DMSO and iodonium ions.

Α - hydroxy ketone compound low priced high-efficient synthetic method

The invention discloses a cheap and efficient synthesis method of an alpha-hydroxyketone compound. The synthesis method is characterized in that a carbonyl compound undergoes an oxidation hydroxylation reaction at 10-120DEG C under normal pressure with iodine simple substance, N-bromosuccimide, copper bromide, bromine simple substance, hydrogen bromide, N-iodosuccimide or hydrogen iodide as a catalyst, sulfoxide as an oxidant, water or sulfoxide as a hydroxy source and sulfoxide, ethyl acetate, N,N-dimethyl formamide, acetonitrile, toluene, 1,4-dioxane, 1,2-dichloroethane, tetrahydrofuran or H2O as a solvent, and converts into the alpha-hydroxyketone compound in a high selectivity manner. Compared with traditional synthesis methods, the method disclosed in the invention has the advantages of simple operation, high yield, simple conditions, easy purification, small waste discharge amount, simple reaction apparatus, and easy industrial production. The method has wide applicability and can be used for synthesizing various alpha-hydroxyketone compounds.

Green organocatalytic α-hydroxylation of ketones

An efficient and green method for the α-hydroxylation of substituted ketones has been developed. This method includes the in situ conversion of various ketones into the corresponding silyl enol ethers and their oxidation to the corresponding α-hydroxy ketones. Two protocols have been established leading either to protected α-hydroxy carbonyls or free α-hydroxy ketones. Both procedures are easy to follow and lead to good to high yields for a variety of ketones.

Regio- and enantioselective reduction of diketones: Preparation of enantiomerically pure hydroxy ketones catalysed by Candida parapsilosis ATCC 7330

Enantiomerically enriched hydroxy ketones were prepared by the reduction of the corresponding diketones with excellent enantiomeric excess (98%) and in good yields (up to 75%) using whole cells of Candida parapsilosis ATCC 7330. Cyclic diketones, such as 1,2-cyclohexanedione and 1,4-cyclohexanedione, resulted in hydroxy ketones as products. Cyclohexane-1,3-dione and 5,5-dimethylcyclohexane-1,3-dione gave dimerised products, such as 2,2′-(ethane-1,1-diyl)bis(3-hydroxycyclohex-2-enone) and 2,2′-(ethane-1,1-diyl)bis(3-hydroxy-5,5-dimethylcyclohex-2-enone) with acetaldehyde generated in situ from whole cells of Candida parapsilosis ATCC 7330, which is reported here for the first time.

I2- or NBS-catalyzed highly efficient α-hydroxylation of ketones with dimethyl sulfoxide

An efficient method for the direct preparation of high synthetic valuable α-hydroxycarbonyls is described. The simple and readily available I2 or NBS was used as catalyst. DMSO acts as the oxidant, oxygen source, and solvent. A diverse range of tertiary Csp3-H bonds as well as more challenging secondary Csp3-H bonds could be hydroxylated in this transformation. The reaction is mild, less toxic and easy to perform.