5883-81-8

Usage

Physical State

Pale yellow solid

Common Uses

Intermediate in pharmaceutical synthesis
Intermediate in dye synthesis
Intermediate in organic compound synthesis
Building block in organic chemistry
Catalyst in chemical reactions
Precursor in fragrance and flavoring production

Chemical Functionality

Aromatic ketone (acetophenone)
Aniline (phenylamine)

Versatility

Used in preparation of heterocyclic compounds
Used in preparation of complex molecules

Toxicity

Considered of moderate toxicity

Safety Precautions

Proper handling required
Adherence to safety protocols necessary

Upstream product

• 62-53-3 aniline 
• 70-11-1 α-bromoacetophenone 
• 105-36-2 ethyl bromoacetate 
• 98-86-2 acetophenone 
• 4636-16-2 iodoacetophenone 
• 1074-12-0 phenylglyoxal hydrate 
• 98-88-4 benzoyl chloride 
• 20718-17-6 2-(dimethyl(oxo)-λ⁶-sulfaneylidene)-1-phenylethan-1-one 
• 99433-31-5 Na⁽¹⁺⁾*C₈H₇O₅S^(1-) 
• 3282-32-4 2-diazo-acetophenone 
• 7647-01-0 hydrogenchloride 
• 112537-84-5 phenacyl m-nitrobenzenesulphonate 
• 110143-20-9 α-(p-chlorobenzenesulfonyloxy)acetophenone 
• 98475-06-0 α-phenylsulfonyloxyacetophenone 

Downstream Products

• 495-71-6 phenacylacetophenone 
• 41120-12-1 N,N-diphenacylaniline 
• 948-65-2 2-phenyl-indole 
• 59541-82-1 7-methyl-2-phenyl-1H-indole 
• 1197040-29-1 phenyl isocyanate 
• 62-53-3 aniline 
• 65-85-0 benzoic acid 
• 79220-94-3 1,4-diphenyl-1,3-dihydro-imidazole-2-thione 
• 51118-10-6 2-anilino-1-phenyl-ethanone (Z)-oxime 
• 51118-09-3 2-anilino-1-phenyl-ethanone-⁽¹⁾-seqtrans-oxime 
• 50650-62-9 3-acetyl-1,4-diphenyl-1,3-dihydro-pyrrol-2-one 
• 13228-36-9 5-methyl-2-phenyl-1H-indole 
• 7397-17-3 phenylglyoxal oxazone 
• 155014-69-0 1-(2-methyl-1,4-diphenyl-1H-pyrrol-3-yl)ethanone 

Relevant academic research and scientific papers

Visible-Light-Induced Oxidative α-Alkylation of Glycine Derivatives with Ethers under Metal-Free Conditions

In this work, a visible-light-induced oxidative α-alkylation of glycine derivatives with ethers has been developed in the presence of catalytic Eosin Y. Under the blue light of a 3 W LED, a range of α-etherized glycine derivatives, including α-amino esters, α-amino ketones and α-amino amides, were achieved with good to excellent yields and functional group tolerance with tert-butyl hydroperoxide (TBHP) as oxidant at ambient temperature. The operationally easy procedure provides an economical, metal-free, and mild alternative for the synthesis of the α-etherized glycine derivatives.

Phosphine-Catalyzed Synthesis of Chiral N-Heterocycles through (Asymmetric) P(III)/P(V) Redox Cycling

Phosphine-catalyzed tandem Michael addition/intramolecular Wittig reactions have been developed for the synthesis of chiral 2,5-dihydro-1H-pyrrole and tetrahydropyridine derivatives. These processes have been rendered catalytic in phosphine, thanks to the in situ reduction of phosphine oxide by phenylsilane. Furthermore, catalytic and asymmetric P(III)/P(V) processes were implemented using enantiopure chiral phosphines.

Design and discovery of new antiproliferative 1,2,4-triazin-3(2H)-ones as tubulin polymerization inhibitors targeting colchicine binding site

Thirty-five new colchicine binding site inhibitors have been designed and synthesized based on the 1,2,4-triazin-3(2H)-one nucleus. Such molecules were synthesized through a cascade reaction between readily accessible α-amino ketones and phenyl carbazate

BF3·Et2O as a metal-free catalyst for direct reductive amination of aldehydes with amines using formic acid as a reductant

A versatile metal- and base-free direct reductive amination of aldehydes with amines using formic acid as a reductant under the catalysis of inexpensive BF3·Et2O has been developed. A wide range of primary and secondary amines and diversely substituted aldehydes are compatible with this transformation, allowing facile access to various secondary and tertiary amines in high yields with wide functional group tolerance. Moreover, the method is convenient for the late-stage functionalization of bioactive compounds and preparation of commercialized drug molecules and biologically relevant N-heterocycles. The procedure has the advantages of simple operation and workup and easy scale-up, and does not require dry conditions, an inert atmosphere or a water scavenger. Mechanistic studies reveal the involvement of imine activation by BF3and hydride transfer from formic acid.

Iodine-mediated C-N and N-N bond formation: A facile one-pot synthetic approach to 1,2,3-triazoles under metal-free and azide-free conditions

A novel strategy towards the synthesis of 1,4-disubstituted 1,2,3-triazoles via C-N and N-N bond formation has been demonstrated under transition metal-free and azide-free conditions. These 1,2,3-triazoles were obtained in a regioselective manner from commercially available anilines, aryl alkenes/aryl alkynes and N-tosylhydrazines using I2 under O2 atmosphere. Broad substrate scope, milder reaction conditions, good to moderate yields and clean protocol are the notable features of the method. Moreover, this protocol is amenable for the generation of a library of medicinally important key building blocks.

Regioselective Synthesis of 2-Arylindoles via Palladium-Catalyzed Cyclization of Phenylglyoxal and 2-Anilinoacetophenones with Anilines

A versatile route has been developed for the synthesis of 2-arylindoles using a Pd-catalyzed tandem process. Under reductive conditions, different 2-arylindoles were synthesized from phenylglyoxal and aniline. This synthetic methodology involves a tandem reaction of four steps with high regioselectivity. Alternatively, 2-anilinoacetophenones intermediates also can be using to give access to the corresponding 2-arylindoles.

A one-pot and three-component synthetic approach for the preparation of asymmetric and multi-substituted 1,4-dihydropyrazines

An efficient, one-pot and three-component synthesis of a new series of 2-acyl-3,4,6-triaryl-1,4-dihydropyrazines is described. This two-step strategy involves treatment of phenacyl bromides and anilines to give the nucleophilic substitution intermediate f

Synthesis of (Z)-nitroalkene derivatives through oxidative dehydrogenation coupling of α-aminocarbonyl compounds with nitromethane by copper catalysis

A novel copper-catalyzed cross-dehydrogenative coupling reaction of α-amino carbonyl compounds with nitromethane to synthesis of (Z)-nitroalkene derivatives has been established. (Z)-Nitroalkene derivatives are achieved through the cleavage of sp3 CsbndH bonds and formation of CsbndC double bond, with mild reaction conditions and excellent stereoselectivity.

Chiral Ion-Pair Organocatalyst-Promoted Efficient Enantio-selective Reduction of α-Hydroxy Ketones

The enantioselective reduction of α-hydroxy ketones with catecholborane has been developed employing 5 mol% of an 1,1′-bi-2-naphthol (BINOL)-derived ion-pair organocatalyst. This methodology provides a straightforward access to the corresponding aromatic 1,2-diols in high yields (up to 90%) with excellent enantioselectivities (up to 97%). Furthermore, the α-amino ketones also could be reduced with moderate ee values under mild reaction condition. (Figure presented.).

Copper-catalyzed oxidative cross-coupling of α-aminocarbonyl compounds with primary amines toward 2-oxo-acetamidines

A general and mild method for the construction of a carbon-nitrogen bond via copper-catalyzed oxidative cross-coupling of amines with α-aminocarbonyl compounds was achieved. Amines, either aliphatic primary amines, aromatic primary amines or secondary amines can be used as the starting materials. When R2 was different from R3, two isomers would be observed. Therefore, this reaction system has a broad substrate scope and provides a facile pathway for the synthesis of 2-oxo-acetamidines.