147749-67-5

Basic information

• Product Name: 2-bromo-3-methyl-1-phenylbutan-1-one
• CAS NO: 147749-67-5
• Molecular Weight: 241.128
• Mol File: 147749-67-5.mol

Chemical Properties

• CAS DataBase Reference: 2-bromo-3-methyl-1-phenylbutan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-bromo-3-methyl-1-phenylbutan-1-one(147749-67-5)
• EPA Substance Registry System: 2-bromo-3-methyl-1-phenylbutan-1-one(147749-67-5)

Safety Data

• Hazardous Substances Data: 147749-67-5(Hazardous Substances Data)

Upstream product

• 56813-82-2 (Z)-(1-bromo-3-methylbut-1-enyl)benzene 
• 100-47-0 benzonitrile 
• 71-43-2 benzene 
• 108-12-3 isopentanoyl chloride 
• 618-31-5 benzylidene dibromide 
• 78-84-2 isobutyraldehyde 
• 26464-05-1 2-bromo-3-methyl-butyryl bromide 
• 582-62-7 3-methyl-1-phenylbutan-1-one 

Downstream Products

• 101594-59-6 3-methyl-2-phenoxy-1-phenylbutan-1-one 
• 312307-42-9 2-(1-benzoyl-2-methyl-propyl)-malononitrile 
• 1321959-79-8 N-(3,5-dimethylphenyl)-5-isopropyl-4-phenylthiazol-2-amine 
• 1321959-61-8 5-isopropyl-N,4-diphenylthiazol-2-amine 
• 7332-95-8 3-methyl-1-phenylbutane-1,2-dione 
• 118299-64-2 2-Azido-3-methyl-1-phenyl-butan-1-one 
• 1025901-58-9 N-(1-Benzoyl-2-methyl-propyl)-N-[3-(3-methyl-2-nitro-phenoxy)-propyl]-formamide 
• 147749-71-1 N-(2-iodobenzyl)-α-isopropyl-N-methylphenacylamine 
• 582-62-7 3-methyl-1-phenylbutan-1-one 
• 5650-07-7 3-methyl-1-phenyl-but-2-en-1-one 
• 1427727-88-5 C₁₆H₁₆N₂OS₂ 

Relevant articles and documents

Iodine(III)-Mediated Oxidative Hydrolysis of Haloalkenes: Investigation of the Effect of Iodine(III) Reagents

The iodine(III)-mediated oxidative transposition of vinyl halides to the corresponding α-halo ketones has been recently reported. The method is high yielding and offers good substrate scope. The investigation of other iodine(III) reagents to promote this

Aldol-Tishchenko Reaction of α-Oxy Ketones: Diastereoselective Synthesis of 1,2,3-Triol Derivatives

α-Oxy ketones, easily accessible by conventional routes, can be selectively deprotonated generating an enolate intermediate, which upon treatment with paraformaldehyde undergoes an aldol-Tishchenko reaction, leading to relevant 1,2,3-triol fragments in a totally diastereoselective manner. The excellent stereocontrol in the generation of a quaternary stereocenter is attributed to stereoelectronic effects in the Evans intermediate. This methodology allows overcoming some limitations of our previously reported strategy, based on the reaction of α-lithiobenzyl ethers with esters and paraformaldehyde, broadening the scope of the obtained polyols. Synthetic applications of this process include the preparation of a new dilignol model and some functionalized oxetanes.

Synthesis of α,β-dibromo ketones by photolysis of α-bromo ketones with N-bromosuccinimide: Photoinduced β-bromination of α-bromo ketones

Irradiation of α-bromopropiophenones in the presence of NBS results in the formation of α,β-dibromopropiophenones, which can be viewed as β-bromination of α-bromopropiophenones. The reaction is believed to go through a series of reactions; photoinduced C–Br bond cleavage, elimination of HBr to give α,β-unsaturated ketone intermediates, and addition of Br2, which are formed by the reaction between HBr and NBS. From mechanistic studies of the reaction, we have also found a very convenient method for α-debromination of the α,β-dibromopropiophenones which is by simple irradiation of the dibromo ketones in acetone or 2-propanol without the use of any additives. Our results demonstrate that bromine can be added into or eliminated from the alpha, beta, or both positions to the carbonyl group by photochemical methods, which make synthetic options of bromine containing carbonyl compounds versatile.

Solvent free, light induced 1,2-bromine shift reaction of α-bromo ketones

Photolysis of α-bromopropiophenones in acetonitrile results in formation of β-bromopropiophenones with good product selectivity, which can be coined as 1,2-Br shift reaction. The product selectivity increases when the reaction is done in neat or solid state, where only the 1,2-Br shift product is formed in some cases. The reaction is suggested to proceed by C–Br bond homolysis to give a radical pair, followed by disproportionation and conjugate addition of HBr to the α,β-unsaturated ketone intermediate. When the unsaturated intermediate is stabilized by an extra conjugation, the reaction stops at the stage, in which the unsaturated ketone becomes a major product. The synthetic method described in this research fits in a category of eco-friendly organic synthesis nicely since the reaction does not use volatile organic solvents and any other additives such as acid, base or metal catalysts, etc. Besides, the method fits into perfect atom economy, which does not give any side products. The synthetic method should find much advantage over other alternative methods to obtain β-bromo carbonyl compounds.

Unexpected Role of p-Toluenesulfonylmethyl Isocyanide as a Sulfonylating Agent in Reactions with α-Bromocarbonyl Compounds

The reactions of p-toluenesulfonylmethyl isocyanide (TosMIC) with α-bromocarbonyl compounds leading efficiently to α-sulfonated ketones, esters, and amides were reported, in which an explicit new role of TosMIC as the sulfonylating agent was uncovered for the first time. Mechanistic study by control experiments and DFT calculations suggested that the reaction is initiated by Cu(OTf)2-catalyzed hydration of TosMIC to form a formamide intermediate, which undergoes facile C-S bond cleavage under the mediation of a Cs2CO3 additive.

Iodine(III)-Mediated Oxidative Hydrolysis of Haloalkenes: Access to α-Halo Ketones by a Release-and-Catch Mechanism

An unprecedented iodine(III)-mediated oxidative transposition of vinyl halides has been accomplished. The products obtained, α-halo ketones, are useful and polyvalent synthetic precursors. There are only a handful of reported examples of the direct conversion of vinyl halides to their corresponding α-halo carbonyl compounds. Insights into the mechanism and demonstration that this synthetic transformation can be done under enantioselective conditions are reported.

Copper-catalyzed 1,2-addition of α-carbonyl iodides to alkynes

β,γ-Unsaturated ketones are an important class of organic molecules. Herein, copper catalysis has been developed for the synthesis of β-γ-unsaturated ketones through 1,2-addition of α-carbonyl iodides to alkynes. The reactions exhibit wide substrate scope and high functional group tolerance. The reaction products are versatile synthetic intermediates to complex small molecules. The method was applied for the formal synthesis of (±)-trichostatin A, a histone deacetylase inhibitor.

Substituted 2-aminothiazoles are exceptional inhibitors of neuronal degeneration in tau-driven models of Alzheimer's disease

A novel series of 2-aminothiazoles with strong protection in an Alzheimer's disease (AD) model comprising tau-induced neuronal toxicity is disclosed. These derivatives can be synthesized in one-pot and a small SAR of the substitution within these series afforded several compounds that counteracted tau-induced cell toxicity at nanomolar concentrations. These congeners therefore have strong potential as possible treatment for Alzheimer's disease and other related tauopathies.

Acid-mediated cyclization of 3-benzoyl-2-cyanobutyronitrile to 2-amino-4-methyl-5-phenylfuran-3-carbonitrile

Cyclization of 3-benzoyl-2-cyanobutyronitrile to 2-amino-4-methyl-5-phenylfuran-3-carbonitrile was effected under acidic conditions, rather than the basic conditions previously reported. Since treatment with trifluoroacetic acid (TFA) at room temperature is very mild, 2-amino-4-methyl-5-phenylfuran-3-carbonitriles containing various functional groups can be accessed via this route.

N-aminoimidazole derivatives inhibiting retroviral replication via a yet unidentified mode of action

The synthesis of a series of N-aminoimidazoles (NAIMs) with an uncommon spectrum of antiretroviral activity is described. From a group of 60 closely related molecules, we were able to subdivide the molecules in different groups based on their anti-HIV and anti-SIV activity in vitro: (i) molecules acting on a new, immediate postintegration step, (ii) molecules acting on both postintegration and HIV-1 reverse transcriptase (RT) as NNRTI, and (iii) molecules that mainly act at the HIV-1 RT according to an NNRTI-type mode of action.