17343-74-7

Usage

Composition

Two bromine atoms, a cyclopropane ring, and two phenyl groups

Usage

Insecticide and acaricide

Target pests

Ants, termites, cockroaches, fleas, and ticks

Mode of action

Disrupts the nervous system of insects, leading to paralysis and death

Environmental impact

Persistent in the environment and can accumulate in the food chain

Health risks

High toxicity and potential risks to human and animal health

Regulatory status

Banned or heavily restricted in many countries due to environmental and health concerns

Alternatives

Safer alternatives have been developed for pest control

InChI:InChI=1/C15H12Br2/c16-15(17)11-14(15,12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10H,11H2

Upstream product

• 530-48-3 1,1-Diphenylethylene 
• 75-25-2 Bromoform 
• 557-95-9 bromodiiodomethane 
• 593-94-2 dibromoiodomethane 
• 98-86-2 acetophenone 
• 108-86-1 bromobenzene 
• 3542-14-1 3,3-diphenylpropene 
• 119-61-9 benzophenone 

Downstream Products

• 17853-44-0 4-(2-bromo-3,3-diphenyl-allyl)-morpholine 
• 14251-57-1 1,1-diphenyl-1,2-propadiene 
• 57719-70-7 2,5-dibromo-1,1,6,6-tetraphenyl-hexa-1,5-diene 
• 3282-18-6 1,1-diphenylcyclopropane 
• 2612-87-5 1-Trimethylsilyl-2.2-diphenyl-cyclopropan 
• 137451-92-4 cis-1-(2',2'-diphenylvinylidene)-2,3-dimethylcyclopropane 
• 137451-94-6 C₂₀H₂₀ 
• 134847-35-1 C₂₁H₂₀ 
• 134847-36-2 C₂₁H₂₀ 
• 7150-12-1 2,2-diphenyl-cyclopropanecarboxylic acid 
• 134847-29-3 1-(2',2'-diphenylethenylidene)-2-vinylcyclopropane 
• 134847-30-6 4-(2',2'-diphenylethenylidene)cyclopent-1-ene 
• 134847-34-0 C₂₁H₂₀ 
• 134847-33-9 C₂₁H₂₀ 

Relevant academic research and scientific papers

Incremental solvation precedes ion-pair separation in enantiomerization of a cyano-stabilized Grignard reagent

Concerted or stepwise? Ion-pair separation is often proposed as a mechanism for enantiomerization of organolithium reagents in ethereal solvents. But what is the timing of the solvation and bond-cleavage events? Are they concerted, or does one precede the

Photoredox-Catalyzed α-Aminoalkylcarboxylation of Allenes with CO2

The photoredox-catalyzed α-aminoalkylcarboxylation of aryl allenes with CO2 and N,N-dimethylanilines is reported for the first time (26 examples, up to 96% yield). In the case of electron-deficient allenes, good regioselectivity was observed (up to 94:6), exclusively generating kinetic products over thermodynamic products. This protocol is a novel synthetic method for highly functionalized β,γ-unsaturated γ-aminobutyric esters.

Synthesis of Quinolines via the Metal-free Visible-Light-Mediated Radical Azidation of Cyclopropenes

We report the synthesis of quinolines using cyclopropenes and an azidobenziodazolone (ABZ) hypervalent iodine reagent as an azide radical source under visible-light irradiation. Multisubstituted quinoline products were obtained in 34-81% yield. The reaction was most efficient for 3-trifluoromethylcyclopropenes, affording valuable 4-trifluoromethylquinolines. The transformation probably proceeds through the cyclization of an iminyl radical formed by the addition of the azide radical on the cyclopropene double bond, followed by ring-opening and fragmentation.

Synthesis of Polycyclic Aromatic Hydrocarbons Decorated by Fluorinated Carbon Acids/Carbanions

The carboarylation reaction of biphenyl-alkynes was successfully triggered by electrophilic attack of 1,1-bis(triflyl)ethylene on the alkyne moiety to give polycyclic aromatic hydrocarbons (PAHs) decorated by superacidic carbon acid functionality. Neutralisation of thus obtained acids with NaHCO3 yielded the corresponding sodium salts, which showed improved solubility in both aqueous and organic solvents.

Ynamide Smiles Rearrangement Triggered by Visible-Light-Mediated Regioselective Ketyl-Ynamide Coupling: Rapid Access to Functionalized Indoles and Isoquinolines

In the past decades, significant advances have been made on radical Smiles rearrangement. However, the eventually formed radical intermediates in these reactions are limited to the amidyl radical, except for the few examples initiated by a N-centered radical. Here, a novel and practical radical Smiles rearrangement triggered by photoredox-catalyzed regioselective ketyl-ynamide coupling is reported, which represents the first radical Smiles rearrangement of ynamides. This method enables facile access to a variety of valuable 2-benzhydrylindoles with broad substrate scope in generally good yields under mild reaction conditions. In addition, this chemistry can also be extended to the divergent synthesis of versatile 3-benzhydrylisoquinolines through a similar ketyl-ynamide coupling and radical Smiles rearrangement, followed by dehydrogenative oxidation. Moreover, such an ynamide Smiles rearrangement initiated by intermolecular photoredox catalysis via addition of external radical sources is also achieved. By control experiments, the reaction was shown to proceed via key ketyl radical and α-imino carbon radical intermediates.

Rhodium-Catalyzed Intermolecular Cyclopropanation of Benzofurans, Indoles, and Alkenes via Cyclopropene Ring Opening

The generation of metal carbenoids via ring opening of cyclopropenes by transition metals offers a simple entry into highly reactive intermediates. Herein, we describe a diastereoselective intermolecular rhodium-catalyzed cyclopropanation of heterocycles and alkenes using cyclopropenes as carbene precursors with a low loading of a commercially available rhodium catalyst. The reported method is scalable and could be performed with catalyst loadings as low as 0.2 mol %, with no impact to the reaction yield or selectivity.

Stereoselective Synthesis of Vinylcyclopropa[ b]indolines via a Rh-Migration Strategy

A mild rhodium catalytic system has been developed to synthesize vinylcyclopropa[b]indolines through cyclopropanation of indoles with vinyl carbenoids generated from ring opening of cyclopropenes in situ. By employing a Rh-migration strategy, the products can be obtained with good to excellent E:Z ratios (≤99:1) and complete diastereoselectivity (≤99:1). This method is easy, has a low catalyst loading, and works for a broad range of functionalities.

Visible-Light-Driven N-Heterocyclic Carbene Catalyzed γ- and ?-Alkylation with Alkyl Radicals

The merging of photoredox catalysis and N-heterocyclic carbene (NHC) catalysis for γ- and ?-alkylation of enals with alkyl radicals was developed. The alkylation reaction of γ-oxidized enals with alkyl halides worked well for the synthesis γ-multisubstituted-α,β-unsaturated esters, including those with challenging vicinal all-carbon quaternary centers. The synthesis of ?-multisubstituted-α,β-γ,δ-diunsaturated esters by an unprecedented NHC-catalyzed ?-functionalization was also established.

A convenient access to allylic triflones with allenes and triflyl chloride in the presence of (EtO)2P(O)H

A simple method for the preparation of allylic triflones from allenes and triflyl chloride in the presence of (EtO)2P(O)H has been developed. The features of this reaction are catalyst-free and simple starting substrates. This method tolerates diverse functional groups and substituted allylic triflones are obtained in moderate to good yields.

Synthesis of Functionalized α-Vinyl Aldehydes from Enaminones

An efficient RhII-catalyzed synthesis of functionalized α-vinyl aldehydes with high E/Z stereoselectivity was developed. The reaction mediates the cyclopropanation of enaminones with vinyl carbenoids that are generated from cyclopropenes in situ to give the aminocyclopropane intermediates. Selective C?C bond cleavage of the cyclopropane intermediates leads to formation of α-vinyl aldehyde derivatives with high E/Z selectivity. This method proceeds at room temperature under very mild reaction conditions and works with a broad substrate scope.