14804-59-2

Basic information

• Product Name: 2-Propenal, 3-bromo-3-phenyl-
• CAS NO: 14804-59-2
• Molecular Formula: C9H7BrO
• Molecular Weight: 211.058
• Mol File: 14804-59-2.mol

Chemical Properties

• CAS DataBase Reference: 2-Propenal, 3-bromo-3-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenal, 3-bromo-3-phenyl-(14804-59-2)
• EPA Substance Registry System: 2-Propenal, 3-bromo-3-phenyl-(14804-59-2)

Safety Data

• Hazardous Substances Data: 14804-59-2(Hazardous Substances Data)

Usage

Physical properties

yellow to brown liquid with a pungent odor

Uses

raw material in pharmaceutical and organic compound synthesis, flavoring agent in food industry

Health effects

mild skin and eye irritant, respiratory irritation upon prolonged exposure

Safety precautions

hazardous if ingested or inhaled, handle with care in well-ventilated area

Upstream product

• 2579-22-8 Phenylpropargyl aldehyde 
• 68-12-2 N,N-dimethyl-formamide 
• 536-74-3 phenylacetylene 
• 98-86-2 acetophenone 
• 75-15-0 carbon disulfide 
• 10035-10-6 hydrogen bromide 
• 64-19-7 acetic acid 

Downstream Products

• 57200-23-4 3-phenyl-2(5H)-furanone 
• 6831-89-6 1,5-diphenyl-1H-pyrazole 
• 1207436-01-8 (E)-ethyl 5-oxo-3-phenyl-2-styryl-2,5-dihydrofuran-2-carboxylate 
• 1423718-53-9 C₂₃H₁₈N₂ 
• 1423718-70-0 C₄₂H₅₁N₂OP 
• 1423718-71-1 C₂₃H₃₀N₂ 
• 26029-32-3 4,4-dimethyl-3-phenyl-cyclopent-2-enone 
• 26274-35-1 2,4-diphenylpyridine 
• 1449578-22-6 methyl 2-(3-phenyl-1H-pyrrol-2-yl)acetate 
• 18714-17-5 methyl 4-phenylpyridine-2-carboylate 
• 64516-59-2 (2Z,4E)-3,5-Diphenyl-penta-2,4-dienal 
• 1449578-11-3 C₁₃H₁₂O₃ 

Relevant articles and documents

Conceptual approach to the synthesis of symmetrical 1,3-diynes from β-bromo vinyl carboxylic acids

Abstract: A conceptual route has been developed for the synthesis of 1,3-diyne from β-bromo vinyl carboxylic acids. The reaction of the β-bromo vinyl carboxylic acid with palladium catalyst is conceptually similar to the decomposition of 2-diazoniumbenzoic acid to benzyne. In the presence of palladium catalyst, the β-bromo vinyl carboxylic acid undergoes a fragmentation to generate terminal alkyne. The terminal alkyne undergoes dimerisation in the presence of palladium catalysts to produce the product 1,3-diyne. Graphic abstract: A conceptual route has been developed for the synthesis of 1,3-diyne from β-bromo vinyl carboxylic acids. To the best of our knowledge, we are the first ones reporting the synthesis of 1,3-diyne in a catalytic way without the requirement of any prefunctionalized alkyne unit(s).[Figure not available: see fulltext.]

Copper and Rhodium Relay Catalysis for Selective Access to cis-2,3-Dihydroazepines

A new catalytic protocol to access synthetically challenging cis-2,3-dihydroazepines is reported. The reaction starts with readily available dienals, alkynes, and sulfonyl azides as the substrates and employs copper and rhodium as relay catalysts. Key steps include a copper-catalyzed reaction between an alkyne and a sulfonyl azide to form a triazole intermediate. The subsequent activation of this triazole intermediate by a rhodium catalyst, followed by a reaction with the dienal substrate, eventually leads to the dihydroazepine product. The regio- and stereochemistries of the products are believed to be controlled through a stereospecific conrotatory 8π-electrocyclization process against a possible competing 6π-electrocyclization process.

A Strategy To Obtain o-Naphthoquinone Methides: Ag(I)-Catalyzed Cyclization of Enynones for the Synthesis of Benzo[ h]chromanes and Naphthopyryliums

A new strategy to obtain o-NQM intermediates through a ring-formation strategy by Ag(I)-catalyzed cyclization of 2-alkenylphenyl alkynyl ketones and its [4 + 2] annulations with styrenes has been developed. This reaction features high efficiency, mild reaction conditions, as well as flexible substitutions and atom economy. The obtained benzo[h]chromane products were further oxidized to naphthopyryliums, which displayed tunable photophysical properties.

Exploiting Hydrazones to Improve the Efficiency of 6π-Electrocyclization Reactions of 1-Azatrienes

The greater geometric lability of hydrazones compared to that of oxime ethers is used as a basis to overcome the reluctance of Z-oxime ether azatrienes to undergo electrocyclization toward the synthesis of borylated (heteroaromatic) pyridines and ring-fused analogues. Such hydrazones now allow access to previously inaccessible tri- and tetrasubstituted 3-borylpyridines in high yields.

Atroposelective Arene Formation by Carbene-Catalyzed Formal [4+2] Cycloaddition

Atroposelective arene formation is an efficient method to build axially chiral molecules with multi-substituted arenes. Reported here is an organocatalyzed atroposelective arene formation reaction by an N-heterocyclic carbene (NHC) catalyzed formal [4+2] cycloaddition of conjugated dienals and α-aryl ketones. This study expands the synthetic potential of NHC organocatalysis and provides a competitive pathway for the synthesis of axially chiral ligands, catalysts, and other functional molecules.

Biocatalysis with the milk protein β-lactoglobulin: Promoting retroaldol cleavage of α,β-unsaturated aldehydes

Enzymes with a hydrophobic binding site and an active site lysine have been suggested to be promiscuous in their catalytic activity. β-Lactoglobulin (BLG), the principle whey protein found in milk, possesses a central calyx that binds non-polar molecules. Here, we report that BLG can catalyze the retro-aldol cleavage of α,β-unsaturated aldehydes making it a naturally occurring protein capable of catalyzing retro-aldol reactions on hydrophobic substrates. Retroaldolase activity was seen to be most effective on substrates with phenyl or naphthyl side-chains. Use of a brominated substrate analogue inhibitor increases the product yield by a factor of three. BLG's catalytic activity and its ready availability make it a prime candidate for the development of commercial biocatalysts.

Intramolecular cascade rearrangements of enynamine derived ketenimines: Access to acyclic and cyclic amidines

Copper-catalyzed reaction of enynamines with sulfonylazides provides acyclic and cyclic amidines. Nucleophilic addition of the tethered amino group on the in situ generated ketenimine forms a six-membered cyclic zwitterionic intermediate which facilitates

Gold-Catalyzed Ring Expansion of Enyne-Lactone: Generation and Transformation of 2-Oxoninonium

An efficient gold-catalyzed ring-expansion reaction of enyne-lactones to form 2-oxoninonium intermediates is reported. The 2-oxoninonium generated in this work could undergo further 6π electrocyclization and aromatization reaction to produce different aromatic compounds.

Stitching Oxindoles and Ynones in a Domino Process: Access to Spirooxindoles and Application to a Short Synthesis of Spindomycin B

A general, transition-metal-free, one-pot, domino Michael-SNAr or AdNE substitution protocol was devised for spiroannulation of oxindoles with ortho-bromoaryl ynones, β-bromoalkenyl ynones, and β-bromoalkenyl enones in a convenient a

Silver Tetrafluoroborate-Catalyzed Oxa-Diels-Alder Reaction between Electrically Neutral Dienes and Aldehydes

Chemoselective oxa-Diels-Alder reactions between electrically neutral 1,3-dienes and various aldehydes were achieved using the commercially available silver tetrafluoroborate (AgBF4) as catalyst. This catalytic process has high functional group tolerance. Heteroatoms at the β-position of the aryl aldehydes can greatly promote the reactivity of the substrates even with heterocyclic aldehydes that were previously believed to be unreactive for the oxa-Diels-Alder reaction. In addition, acroleins with β-heteroatom substitution are also good substrates. High chemoselectivity and regioselectivity were achieved at room temperature for the oxa-Diels-Alder reaction between acroleins and stoichiometric simple 1,3-dienes.