50807-17-5

Usage

Physical state

White crystalline solid

Uses

Intermediate in the production of various pharmaceuticals and agrochemicals

Chemical stability

High degree of chemical stability, relatively non-reactive under normal conditions

Toxicity

Toxic, may cause irritation to the skin, eyes, and respiratory system upon exposure

Safety precautions

Follow proper safety protocols and use protective equipment when working with 2,2-dichloro-1-[4-(1,1-dimethylethyl)phenyl]ethan-1-one.

InChI:InChI=1/C12H14Cl2O/c1-12(2,3)9-6-4-8(5-7-9)10(15)11(13)14/h4-7,11H,1-3H3

Upstream product

• 943-27-1 4'-t-butylacetophenone 
• 79-36-7 dichloroacethyl chloride 
• 253185-03-4 tert-butylbenzene 
• 51326-37-5 1-[4-(tert-butyl)phenyl]-2,2,2-trichloroethan-1-one 
• 100-58-3 phenylmagnesium bromide 
• 16002-63-4 phenylmagnesium iodide 
• 122-04-3 4-nitro-benzoyl chloride 
• 772-38-3 4-tert-Butylphenylacetylene 
• 75-09-2 dichloromethane 
• 208188-23-2 N-methoxy-N-methyl-4-(2-methyl-2-propanyl)benzamide 

Relevant academic research and scientific papers

Modular and Chemoselective Strategy for Accessing (Distinct) α,α-Dihaloketones from Weinreb Amides and Dihalomethyllithiums

The selective transfer of diversely functionalized dihalomethyllithiums (LiCHBrCl, LiCHClI, LiCHBrI, LiCHCl2, LiCHBr2, LiCHFI) to Weinreb amides for preparing gem-dihaloketones in one synthetic operation is reported. The capability of these amides as acylating agents and, the wide availability of dihalomethanes as pronucleophiles, enable a straightforward route to the title compounds under full chemocontrol. No racemization phenomena were evidenced in the case of optically active materials. Additionally, tolerance to sensitive functional groups (esters, amides, halogens, olefins etc.) was uniformly noticed, thus making this conceptually intuitive strategy flexible and tunable by the operator. (Figure presented.).

Electrochemical synthesis of α,α-dihaloacetophenones from terminal alkyne derivatives

By virtue of electrochemistry, a series of α,α-dihaloacetophenones were easily obtained with good to excellent yields. This electrochemical procedure was taken in a divided cell with constant current in aqueous media. The reaction can be carried out smoothly at room temperature under metal and oxidant free condition, which provides an eco-friendly synthesis for the α,α-dihaloacetophenone derivatives.

Electrochemical Oxidative Oxydihalogenation of Alkynes for the Synthesis of α,α-Dihaloketones

An electrochemical oxydihalogenation of alkynes has been developed for the first time. Using this sustainable protocol, a variety of α,α-dihaloketones can be prepared with readily available CHCl3, CH2Cl2, ClCH2CH2Cl, and CH2Br2 as the halogen source under electrochemical conditions at room temperature.

Iodine-DMSO-promoted divergent reactivities of arylacetylenes

An unprecedented set of efficient, economical, atom-economic and exceedingly selective I2-DMSO-promoted methods is described for the generation of different structures. The reaction represents the first of its kind, involving the use of different iodine concentrations, temperatures, acids and salt to adjust the selectivity for the synthesis of different alkenes, α-functionalized ketones and α-ketomethylthioesters.

Visible-light-promoted oxidative halogenation of alkynes

In nature, halogenation promotes the biological activity of secondary metabolites, especially geminal dihalogenation. Related natural molecules have been studied for decades. In recent years, their diversified vital activities have been explored for treating various diseases, which call for efficient and divergent synthetic strategies to facilitate drug discovery. Here we report a catalyst-free oxidative halogenation achieved under ambient conditions (halide ion, air, water, visible light, room temperature, and normal pressure). Constitutionally, electron transfer between the oxygen and halide ion is shuttled via simple conjugated molecules, in which phenylacetylene works as both reactant and catalyst. Synthetically, it provides a highly compatible late-stage transformation strategy to build up dihaloacetophenones (DHAPs).

Grignard-mediated reduction of 2,2,2-trichloro-1-arylethanones

2,2,2-Trichloro-1-aryl-ethanones can be reduced by RMgX to the corresponding 2,2-dichloro-1-arylethen-1-olates and trapped with a range of electrophiles resulting in either reduction, reduction/aldol, reduction/Claisen condensation or reduction/aldol-Tishchenko products. In addition we demonstrate that 2,2-dichloro-1-arylethen-1-olates undergo counter-ion controlled Darzens condensations, which can be followed by a thermal rearrangement as a route to 1,3-diaryl-3-chloropropane-1,2-diones.

Reduction of 2,2,2-trichloro-1-arylethanones by RMgX: Mechanistic investigation and the synthesis of substituted α,α-dichloroketones

2,2,2-Trichloro-1-arylethanones undergo high yielding reductions to the corresponding 2,2-dichloro-1-arylethanones in the presence of RMgX. A single electron transfer mechanism for the reaction is proposed based on trapping experiments. Reaction of the intermediate enolates with a range of electrophiles is described, providing a convenient route to substituted α,α- dichloro-β-hydroxyketones and related molecules. The Royal Society of Chemistry 2013.

A convenient and efficient synthesis of 1-aryl-2,2-dichloroethanones

1-Arylethanones are readily chlorinated with an aqueous HCl-H 2O2 system using ethanol as a cosolvent. The reaction prceeds rapidly and results in selective conversion of 1-arylethanones into 1-aryl-2,2-dichloroethanones in yields of 48-89%, depending on the nature of the substituent in the aryl group.

P-tert-butyl-diphenylalkane insecticides

1,1-Diphenylalkanes having a p-tert-butyl and a p'-alkoxy group substituted thereon are a novel class of compounds having a broad range of insecticidal activity.

P-Tert-butyl-diphenylalkane insecticides

1,1-Diphenylalkanes having a p-tert-butyl and a p'-alkyl group substituted thereon are a new class of compounds possessing a broad range of insecticidal activity.