13664-98-7

Basic information

• Product Name: 2,2-DIBROMO-1-P-TOLYLETHANONE
• Synonyms: 2,2-DIBROMO-1-P-TOLYLETHANONE;2,2-dibromo-1-(4-methylphenyl)ethanone
• CAS NO: 13664-98-7
• Molecular Formula: C₉H₈Br₂O
• Molecular Weight: 291.97
• Mol File: 13664-98-7.mol

Chemical Properties

• Melting Point: 97-98 °C
• Boiling Point: 290.3±25.0 °C(Predicted)
• Appearance: /
• Density: 1.780±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2,2-DIBROMO-1-P-TOLYLETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-DIBROMO-1-P-TOLYLETHANONE(13664-98-7)
• EPA Substance Registry System: 2,2-DIBROMO-1-P-TOLYLETHANONE(13664-98-7)

Safety Data

• Hazardous Substances Data: 13664-98-7(Hazardous Substances Data)

Usage

General Description

2,2-DIBROMO-1-P-TOLYLETHANONE is a chemical compound that belongs to the group of benzyl ketones. It is a white to light yellow crystalline solid with a molecular formula of C9H8Br2O. 2,2-DIBROMO-1-P-TOLYLETHANONE is commonly used in organic synthesis and as a building block for the preparation of other compounds. It is also a useful intermediate in the production of pharmaceuticals, dyes, and other organic substances. 2,2-DIBROMO-1-P-TOLYLETHANONE is a potentially hazardous chemical and should be handled with caution, as it may cause skin and eye irritation and should be stored in a cool, dry place away from direct sunlight and heat sources.

Upstream product

• 122-00-9 para-methylacetophenone 
• 67-66-3 chloroform 
• 7726-95-6 bromine 
• 108-88-3 toluene 
• 766-97-2 4-n-methylphenylacetylene 
• 2089-33-0 4-methylacethophenone oxime 
• 94-08-6 4-methylbenzoic acid ethyl ester 
• 74-95-3 1,1-dibromomethane 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 536-50-5 CH₃C₆H₄CH(CH₃)OH 
• 18103-98-5 3-dimethylamino-1-(4-methyl-phenyl)-2-propen-1-one 
• 7559-36-6 4-methyl-β-nitrostyrene 
• 104-87-0 4-methyl-benzaldehyde 
• 93979-10-3 1-(p-methylphenyl)-2,2,2-tribromoethanol 

Downstream Products

• 86329-49-9 anti-p-tolylglyoxime 
• 62107-95-3 1-p-tolylglyoxal-1-((Z)-oxime )-2-((E)-oxime ) 
• 99-94-5 p-Toluic acid 
• 402578-97-6 dimethyl 1-(4-methylphenyl)-2-bromoethenyl phosphate 
• 122-00-9 para-methylacetophenone 
• 619-41-0 4-(bromoacetyl)toluene 
• 30196-30-6 3,3'-di-p-tolyl-2H,2'H-2,2'-bibenzo[b][1,4]thiazine 
• 140613-81-6 4-methyl-3-p-tolylmorpholin-2-one 
• 1068459-70-0 2-bromo-2-p-tolylpent-4-enal 
• 1194639-53-6 1,1-dimethoxy-2-p-tolylpent-4-en-2-ol 
• 1258309-65-7 2-(4-methylphenyl)-3,3-dibromoacrylonitrile 
• 1320341-22-7 N-(2,4-difluorophenyl)-4-(p-tolyl)thiazol-2-amine 
• 2103-91-5 2-amino-4-(p-methylphenyl)-1,3-thiazole 
• 1284150-89-5 N-(2-(1H-indol-3-yl)ethyl)-2-oxo-2-(p-tolyl)acetamide 

Relevant articles and documents

A H2O2/HBr system-several directions but one choice: oxidation-bromination of secondary alcohols into mono- or dibromo ketones

In this work we found that a H2O2-HBr(aq) system allows synthesis of α-monobromo ketones and α,α′-dibromo ketones from aliphatic and secondary benzylic alcohols with yields up to 91%. It is possible to selectively direct the process toward the formation of mono- or dibromo ketones by varying the amount of hydrogen peroxide and hydrobromic acid. The convenience of application, simple equipment, multifaceted reactivity, and compliance with green chemistry principles make the application of the H2O2-HBr(aq) system very attractive in laboratories and industry. The proposed oxidation-bromination process is selective in spite of known properties of ketones to be oxidized by the Baeyer-Villiger reaction or peroxidated with the formation of compounds with the O-O moiety in the presence of hydrogen peroxide and Bronsted acids.

Access to α,α-dihaloacetophenones through anodic C[dbnd]C bond cleavage in enaminones

We have developed a method to synthesize α,α-dihaloketones under electrochemical conditions. In this reaction, the Cl- or Br- is oxidized to Cl2 or Br2 at the anode, which undergoes two-step addition reactions with the N,N-dimethyl enaminone, and finally breaks C[dbnd]C of the N,N-dimethyl enaminone to generate α,α-dihaloketones. The electrosynthesis reaction can be conveniently carried out in an undivided electrolytic cell at room temperature. In addition, various functional groups are compatible with this green protocol which can be applied simultaneously to the gram scale without significantly lower yield.

Electrochemical Oxidative Functionalization of Arylalkynes: Access to α,α-Dibromo Aryl Ketones

A general and effective protocol to synthesize α,α-dibromo aryl ketones has been developed via an electrochemical oxidative method. The reaction proceeds smoothly at room temperature in an undivided cell without the addition of external oxidants. In the reaction process, LiBr acts as both bromine source and supporting electrolyte. This electrooxidation strategy has good substrate applicability and functional group compatibility. Moreover, the reaction could be scaled up efficiently in a continuous flow cell. The target product could undergo further functionalization for the synthesis of some useful heterocyclic compounds. (Figure presented.).

Reactivity of substrates with multiple competitive reactive sites toward NBS under neat reaction conditions promoted by visible light

Regioselectivity of visible-light-induced transformations of a range of (hetero)aryl alkyl-substituted ketones bearing several competitive reactive sites (α-carbonyl, benzyl and aromatic ring) with N-bromosuccinimide (NBS) was studied under solvent-free reaction conditions (SFRC) and in the absence of inert-gas atmosphere, radical initiators and catalysts. An 8-W energy-saving household lamp was used for irradiation. Heterogeneous reaction conditions were dealt with throughout the study. All substrates were mono- or dibrominated at the α-carbonyl position, and additionally, some benzylic or aromatic bromination was observed in substrates with benzylic carbon atoms or electron-donating methoxy groups, respectively. Surprisingly, ipso-substitution of the acyl group with a bromine atom took place with (4-methoxynaphthyl) alkyl ketones. While the addition of the radical scavenger TEMPO (2,2,6,6-tetramethylpiperidin-1-yloxy) decreased the extent of α- and ring bromination, it completely suppressed the benzylic bromination and α,α-dibromination with NBS under SFRC.

Switchable Synthesis of α,α-Dihalomethyl and α,α,α-Trihalomethyl Ketones by Metal-Free Decomposition of Enaminone C=C Double Bond

The novel free radical-based cleavage of the enaminone C=C double bond is realized by using N-halosuccinimides (NXS) in the presence of benzoyl peroxide (BPO) with mild heating, enabling the tunable synthesis of α,α-dihalomethyl ketones and α,α,α-trihalomethyl ketones under different reaction conditions. The formation of these divergent products involving featured C=C double bond cleavage requires no any metal reagent, and represents one more practical example on the synthesis of poly halogenated methyl ketones via the functionalization of carbon?carbon bond. (Figure presented.).

α,α-Dibromoketone precursors in the synthesis of some new thiazole derivatives: Thiazol-2-yl hydrazonobutanoates, thiazol-2-yl pyrazole-4-carboxylates and acids

In the present study, α,α-dibromoacetophenones are used as efficient precursors for the facile synthesis of several new hydrazonothiazoles, ethyl 3-((4-arylthiazol-2-yl)hydrazono)butanoates, which undergo Vilsmeier-Haack cyclization to obtain thiazolylpyrazole esters, ethyl 3-methyl-1-(4-arylthiazol-2-yl)-1H-pyrazole-4-carbxylates, basic hydrolysis of which gives the corresponding acids, 3-methyl-1-(4-arylthiazol-2-yl)-1H-pyrazole-4-carbxylic acids. All these compounds are tested for antibacterial activity against Gram-positive bacteria Staphylococcus aureus and Bacillus subtilis; Gram-negative bacteria Escherichia coli and Pseudomonas aeruginosa and antifungal activity against Saccharomyces cerevisiae and Candida albicans.

Method for preparing alpha,alpha-dihalogenated acetophenone compound

The invention belongs to the technical field of organic synthesis and in particular relates to a method for preparing an alpha,alpha-dihalogenated acetophenone compound. The preparation method provided by the invention comprises the following steps: in an alcohol solvent, enabling nitroalkenes, electrophilic halogen reagents and sodium hydride to react at 55-65 DEG C under a heating condition for5-10 hours, cooling the components to the room temperature, adding a diluted acid solution, and performing continue stirring for 2-5 hours, so as to obtain a target compound, namely alpha,alpha-dihalogenated acetophenone. The method for preparing the alpha,alpha-dihalogenated acetophenone compound, which is provided by the invention, is simple and efficient, mild in condition, easy in raw materialobtaining, green and environment-friendly and simple and convenient to operate, and as a synthesis intermediate, the obtained alpha,alpha-dihalogenated acetophenone compound has the potential of being widely used in fields such as medicine chemical engineering.

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.

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.

Selective Debromination of α,α,α-Tribromomethylketones with HBr–H2O Reductive Catalytic System

A debromination of α,α,α-tribromomethylketones is developed for chemoselective synthesis of α-mono- and α,α-dibromomethylketones with high selectivity under H2O–HBr reductive conditions. This method offers an efficient and direct way to synthesize α-mono or α,α-dibromomethylketone compounds in high to excellent yields through the process of HBr self-circulation in water.