1885-28-5

Usage

Appearance

Colorless to pale yellow liquid

Odor

Fruity

Usage

Flavoring agent in food and beverages, production of pharmaceuticals and fragrances, potential insecticidal properties

Health hazards

Skin and eye irritation, harmful if swallowed or inhaled

Physical properties

Sweet, caramel-like aroma

Upstream product

• 32017-76-8 (+/-)-2-(4-bromophenyl)oxirane 
• 105-53-3 diethyl malonate 
• 35656-89-4 4-(4-bromophenyl)butanoic acid 
• 4209-02-3 1-(4-bromophenyl)-2-chloroethan-1-one 
• 30913-86-1 4-(4-bromo-phenyl)-4-oxo-butyric acid methyl ester 
• 80707-14-8 C₁₀H₁₁BrO₃ 
• 106650-98-0 1-(4-bromophenyl)but-3-en-1-ol 
• 1122-91-4 4-bromo-benzaldehyde 
• 94612-95-0 1-(p-bromophenyl)-but-3-yn-1-ol 
• 1356451-44-9 C₁₀H₈Br₂O 
• 6340-79-0 4-oxo-4-(4-bromophenyl)butanoic acid 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 108-24-7 acetic anhydride 

Downstream Products

• 100115-96-6 4-Chlor-4-(4-brom-phenyl)-buttersaeureethylester 
• 1094214-35-3 (E,RS)-5-{4-[2-(2-pyridyl)vinyl]phenyl}dihydrofuran-2(3H)-one 
• 1094214-36-4 (E,RS)-5-{4-[2-(4-pyridyl)vinyl]phenyl}dihydrofuran-2(3H)-one 
• 1094214-31-9 (E)-5-(4-sytrylphenyl)dihydrofuran-2(3H)-one 
• 1094214-37-5 (E,RS)-5-{4-[2-(4-methylthiazol-5-yl)vinyl]phenyl}dihydrofuran-2(3H)-one 
• 1094214-34-2 (E,RS)-5-[4-(4-methoxystyryl)phenyl]dihydrofuran-2(3H)-one 
• 1094213-95-2 lithium (RS)-4-(4-bromophenyl)-4-hydroxybutanoate 
• 1094214-33-1 (E,RS)-5-[4-(3-chlorostyryl)phenyl]dihydrofuran-2(3H)-one 
• 1094214-32-0 (E,RS)-5-[4-(2-chlorostyryl)phenyl]dihydrofuran-2(3H)-one 
• 53582-00-6 ethyl trans-2-(p-bromophenyl)-1-cyclopropanecarboxylate 
• 6142-65-0 trans-(1S,2S)/(1R,2R)-2-(4-bromophenyl)cyclopropanecarboxylic acid 

Relevant academic research and scientific papers

Aniline-Type Hypervalent Iodine(III) for Intramolecular Cyclization via C?H Bond Abstraction of Hydrocarbons Containing N- and O-Nucleophiles

We developed a method for the preparation of (diacetoxyiodo)-2-(N-alkylamido)benzene as an aniline-type hypervalent iodine(III). We also achieved direct cyclizations via C?H bond abstraction, such as the Hofmann-L?ffler-Freytag reaction, a direct amination, and a direct lactonization, using the aniline-type hypervalent iodine(III) to obtain corresponding products in high yields. (Figure presented.).

Efficient hydrogenation of levulinic acid catalysed by spherical NHC-Ir assemblies with atmospheric pressure of hydrogen

A practical, efficient, and mild hydrogenation of levulinic acid (LA) to γ-valerolactone (GVL) under 1 atm H2was realized by single-sited 3D porous self-supported N-heterocyclic carbene iridium catalysts. Quantitative yields and selectivities were achieved at 0.02 mol% catalyst loading, and the catalyst could be reused for 9 runs without obvious loss of selectivity or activity.

Biocatalytic Asymmetric Reduction of γ-Keto Esters to Access Optically Active γ-Aryl-γ-butyrolactones

An efficient stereoselective syntheses of a series of functionalized optically active γ-aryl-γ-butyrolactones is achieved by enzymatic asymmetric reduction of the corresponding sterically demanding γ-keto esters employing wild-type and recombinant alcohol dehydrogenases. The best stereoselectivities for the reduction via hydrogen transfer was obtained with two short chain dehydrogenases (SDRs) of complementary stereospecificity from Aromatoleum aromaticum, namely the Prelog-specific NADH-dependent (S)-1-phenylethanol dehydrogenase [(S)-PED] and the anti-Prelog-specific (R)-1-(4-hydroxyphenyl)-ethanol dehydrogenase [(R)-HPED], respectively.Biotransformations catalyzed by both enzymes, followed by TFA-catalyzed cyclization of the resulting γ-hydroxy esters, furnished the respective (S)- and (R)-configured products with exquisite optical purity (up to >99% ee). The synthetic value was demonstrated on preparative scale for the asymmetric bioreduction of the model compound, methyl 4-oxo-4-phenylbutanoate, affording optically pure (S)-γ-phenyl-γ-butyrolactone (>99% ee) in 67–74% isolated yield at 89–95% conversion depending on the applied scale. (Figure presented.).

Catalytic Redox Chain Ring Opening of Lactones with Quinones to Synthesize Quinone-Containing Carboxylic Acids

Catalytic ring opening of five- to eight-membered lactones with quinones is achieved through a redox chain mechanism. With low loading of a simple metal triflate Lewis acid catalyst and a chain initiator, C-H bonds of many quinones were efficiently functionalized with carboxylic acid-containing side chains. This method also features 100% atom economy and wide substrate scope. A novel route to the anti-asthma drug Seratrodast was developed. Mechanism study suggests that the redox chain reaction likely undergoes a carbocation intermediate.

Indium-Catalyzed Direct Conversion of Lactones into Thiolactones and Selenolactones in the Presence of Elemental Sulfur and Selenium

The direct conversion of lactones into thiolactones with elemental sulfur (S 8) catalyzed by InCl 3 /PhSiH 3 in a one-pot reaction is described. This catalytic system was successfully applied to the novel preparation of selenolactones from lactones and selenium.

Asymmetric Organocatalytic One-Pot, Two-Step Sequential Process to Synthesize Chiral Acetal-Containing Polycyclic Derivatives from Cyclic Hemiacetals and Enones

We have developed an efficient one-pot, two-step sequential process to synthesize biologically and synthetically important chiral acetal-containing polycyclic derivatives. This novel protocol had been proved to proceed via Michael-lactolization-oxocarbenium ion ring-closing sequence, which was initiated by a key reactive enamine intermediate and interrupted the previously established reaction pathway of two different enones used in this work, and generated the corresponding cycloadducts with excellent stereoselectivity bearing up to seven continuous stereocenters. Both chiral and racemic starting cyclic hemiacetals worked well in this strategy. The synthetic applications of the obtained polycyclic products have also been demonstrated.

Nucleo-Palladation-Triggering Alkene Functionalization: A Route to γ-Lactones

An unprecedented strategy for the highly effective synthesis of γ-lactones from homoallylic alcohols was achieved by palladium catalysis in one step. The protocol affords aryl, alkyl, and spiro γ-lactones directly from readily available homoallylic alcohols in good yields with excellent functional group tolerance and high chemoselectivity under mild conditions.

Efficient Hydrogenation of Biomass Oxoacids to Lactones by Using NHC–Iridium Coordination Polymers as Solid Molecular Catalysts

A series of NHC–iridium coordination polymers have proven to be robust, efficient and recyclable solid molecular catalysts toward the hydrogenation of biomass levulinic acid (LA) to γ-valerolactone. Along with quantitative yields attained at 0.01 mol % catalyst loading under 50 atm of H2, the solid molecular catalyst was readily recovered and reused for 12 runs without obvious loss of the selectivity and activity. Remarkably, up to 1.2×105 TON, an unprecedented value could be achieved in this important transformation. In addition, a number of LA homologues, analogues and derivatives were well tolerated to deliver various intriguing and functional lactones in good to excellent yields, which further confirmed the feasibility of the solid molecular catalysts.

(HMe 2 SiCH 2) 2: A Useful Reagent for B(C 6 F 5) 3 -Catalyzed Reduction-Lactonization of Keto Acids: Concise Syntheses of (-)- cis -Whisky and (-)- cis -Cognac Lactones

(HMe 2 SiCH 2) 2 has been utilized as a useful reagent for B(C 6 F 5) 3 -catalyzed reduction-lactonization of keto acids to synthesize γ- and δ-lactones. The process led concisely to (-)- cis -whisky and (-)- cis -cognac lactones in respective overall yields of 32% and 36%.

Copper-Catalyzed Oxidative Cyclization of Carboxylic Acids

A method for converting C-H to C-O bonds through oxidative cyclization of carboxylic acids to generate lactone products is described. The reaction employs catalytic amounts of Cu(OAc)2 and potassium persulfate as the terminal oxidant and is performed open to air in an aqueous acetic acid solvent system. Preliminary mechanistic studies suggest that substrate oxidation likely proceeds by sulfate radical anion and that the Cu catalyst has no influence on the product-determining step. These conclusions differ from related investigations that propose the intermediacy of a carboxylate radical.