75321-85-6

Usage

Uses

Used in Pharmaceutical Industry:
2-(2-Fluorophenyl)acetaldehyde is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and reactivity make it a valuable component in the development of new drugs with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, 2-(2-Fluorophenyl)acetaldehyde is employed as a precursor for the production of various agrochemicals, including pesticides and herbicides. Its incorporation into these products enhances their effectiveness in controlling pests and weeds, thereby contributing to improved crop yields and agricultural productivity.
Used in Organic Synthesis:
2-(2-Fluorophenyl)acetaldehyde is utilized as a building block in organic synthesis, allowing chemists to construct a wide range of complex organic molecules. Its reactivity and functional group compatibility make it a useful component in the synthesis of various organic compounds for research and industrial applications.
Safety Precautions:
When working with 2-(2-Fluorophenyl)acetaldehyde, it is essential to take appropriate protective measures to avoid skin and eye irritation, as well as inhalation and ingestion hazards. Proper handling and storage of 2-(2-FLUOROPHENYL)ACETALDEHYDE are crucial to ensure the safety of individuals and the environment.

InChI:InChI=1/C8H7FO/c9-8-4-2-1-3-7(8)5-6-10/h1-4,6H,5H2

Upstream product

• 50919-06-7 2-(2-fluorophenyl)ethanol 
• 394-46-7 2-fluorostyrene 
• 54533-38-9 1-fluoro-2-(2-methoxyvinyl)benzene 
• 451-82-1 (2-fluorophenyl)acetic acid 
• 584-74-7 o-fluorophenylacetic acid ethyl ester 
• 766-49-4 (2-fluorophenyl)acetylene 
• 446-52-6 2-Fluorobenzaldehyde 
• 74249-17-5 (S)-2-(2-fluorophenyl)oxirane 
• 57486-67-6 methyl o-fluorophenylacetate 

Downstream Products

• 46322-12-7 C₉H₁₁FN₄ 
• 1219025-78-1 (E/Z)-4-(2-fluorophenyl)-2-methylbut-2-enol 
• 1219025-80-5 4-(2-fluorophenyl)-2-methylbutanol 
• 1219025-82-7 4-(2-fluorophenyl)-2-methylbromobutane 
• 1219025-84-9 8-(2-fluorophenyl)-2,2,6-trimethyl-4-(1H-1,2,4-triazol-1-yl)-octan-3-one 
• 1338349-48-6 N-[2-ethyl-2-(4-fluorophenyl)butyl]-1-[2-(2-fluorophenyl)ethyl]piperidine-4-carboxamide oxalate 
• 1361045-75-1 1-(2-fluorobenzyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol 
• 1374667-39-6 2-(2-fluorophenyl)-2-oxo-N,N'-di(p-tolyl)acetimidamide 
• 1249529-29-0 C₁₁H₁₁FO 
• 1571070-56-8 1-(2-fluorophenyl)-4-methyl-1H-quinolizin-2(9aH)-one 
• 1571071-17-4 C₁₁H₉FO 
• 89346-49-6 3-(2-fluorophenyl)pyridine 
• 52721-69-4 [2-(2-fluorophenyl)ethyl]amine 

Relevant academic research and scientific papers

Stereoselective synthesis of 3,4-di-substituted mercaptolactones via photoredox-catalyzed radical addition of thiophenols

A visible light mediated radical addition of thiophenols on 4-phenylbut-3-enoic acids to give diastereoselective synthesis of 3,4-disubstituted γ-lactones is reported. The reaction precludes the conventional prerequisite of conjugate addition. Furthermore, the lactones were successfully utilized in the synthesis of γ-ketoamides.

Novel Hypoxia-Inducible Factor 1α (HIF-1α) Inhibitors for Angiogenesis-Related Ocular Diseases: Discovery of a Novel Scaffold via Ring-Truncation Strategy

Ocular diseases featuring pathologic neovascularization are the leading cause of blindness, and anti-VEGF agents have been conventionally used to treat these diseases. Recently, regulating factors upstream of VEGF, such as HIF-1α, have emerged as a desirable therapeutic approach because the use of anti-VEGF agents is currently being reconsidered due to the VEGF action as a trophic factor. Here, we report a novel scaffold discovered through the complete structure-activity relationship of ring-truncated deguelin analogs in HIF-1α inhibition. Interestingly, analog 6i possessing a 2-fluorobenzene moiety instead of a dimethoxybenzene moiety exhibited excellent HIF-1α inhibitory activity, with an IC50 value of 100 nM. In particular, the further ring-truncated analog 34f, which showed enhanced HIF-1α inhibitory activity compared to analog 2 previously reported by us, inhibited in vitro angiogenesis and effectively suppressed hypoxia-mediated retinal neovascularization. Importantly, the heteroatom-substituted benzene ring as a key structural feature of analog 34f was identified as a novel scaffold for HIF-1α inhibitors that can be used in lieu of a chromene ring.

Manganese-Catalyzed Dual-Deoxygenative Coupling of Primary Alcohols with 2-Arylethanols

Reported herein is a general and efficient dual-deoxygenative coupling of primary alcohols with 2-arylethanols catalyzed by a well-defined Mn/PNP pincer complex. This reaction is the first example of the catalytic dual-deoxygenation of alcohols using a non-noble-metal catalyst. Both deoxygenative homocoupling of 2-arylethanols (17 examples) and their deoxygenative cross-coupling with other primary alcohols (20 examples) proceeded smoothly to form the corresponding alkenes by a dehydrogenation and deformylation reaction sequence.

Biocatalytic Formal Anti-Markovnikov Hydroamination and Hydration of Aryl Alkenes

Biocatalytic anti-Markovnikov alkene hydroamination and hydration were achieved based on two concepts involving enzyme cascades: epoxidation-isomerization-amination for hydroamination and epoxidation-isomerization-reduction for hydration. An Escherichia coli strain coexpressing styrene monooxygenase (SMO), styrene oxide isomerase (SOI), ω-transaminase (CvTA), and alanine dehydrogenase (AlaDH) catalyzed the hydroamination of 12 aryl alkenes to give the corresponding valuable terminal amines in high conversion (many ≥86%) and exclusive anti-Markovnikov selectivity (>99:1). Another E. coli strain coexpressing SMO, SOI, and phenylacetaldehyde reductase (PAR) catalyzed the hydration of 12 aryl alkenes to the corresponding useful terminal alcohols in high conversion (many ≥80%) and very high anti-Markovnikov selectivity (>99:1). Importantly, SOI was discovered for stereoselective isomerization of a chiral epoxide to a chiral aldehyde, providing some insights on enzymatic epoxide rearrangement. Harnessing this stereoselective rearrangement, highly enantioselective anti-Markovnikov hydroamination and hydration were demonstrated to convert α-methylstyrene to the corresponding (S)-amine and (S)-alcohol in 84-81% conversion with 97-92% ee, respectively. The biocatalytic anti-Markovnikov hydroamination and hydration of alkenes, utilizing cheap and nontoxic chemicals (O2, NH3, and glucose) and cells, provide an environmentally friendly, highly selective, and high-yielding synthesis of terminal amines and alcohols.

Synthesis of 3-Arylpyridines via Palladium/Copper-Catalyzed Annulation of Allylamine/1,3-Propanediamine and Aldehydes

A novel and efficient method for the synthesis of 3-arylpyridines from allylamine/propanediamine and aldehydes by palladium/copper-catalyzed oxidative tandem cyclization has been developed. With this reaction, a series of desired 3-arylpyridines was synthesized in moderate yields via C-C/C-N bond formation and 6-endo/exo-trig cyclization.

Catalysed anti-Markovnikov oxidation of terminal aryl alkenes to aldehydes and transformation of methyl aryl tertiary amines to formamides with H2O2 as a terminal oxidant

Anti-Markovnikov oxidation of terminal aryl alkenes to aldehydes and transformation of N-methyl aryl tertiary amines to formamides with H2O2 as a terminal oxidant under mild conditions have been achieved with moderate to good product yields using [FeIII(TF4DMAP)OTf] as catalyst. This journal is

Broad-spectrum catalysts for the ambient temperature anti-Markovnikov hydration of alkynes

Anti-Markovnikov alkyne hydration provides a valuable route to aldehydes. Half-sandwich ruthenium complexes ligated by 5,5′-bis(trifluoromethyl)-2, 2′-bipyridine are remarkably active for this transformation. In the presence of 2 mol % metal, a wide range of functionalized aliphatic and aromatic alkynes are hydrated in high yield at ambient temperature. Alkyne hydration: Half-sandwich ruthenium complexes derived from 5,5′-bis(trifluoromethyl)- 2,2′-bipyridine show a high activity for the anti-Markovnikov hydration of terminal alkynes (see picture). A wide array of alkynes are efficiently hydrated to aldehydes using 2 mol % metal loadings at 25 °C within 8-24 h.

Temporal separation of catalytic activities allows anti-Markovnikov reductive functionalization of terminal alkynes

There is currently great interest in the development of multistep catalytic processes in which one or several catalysts act sequentially to rapidly build complex molecular structures. Many enzymes - often the inspiration for new synthetic transformations - are capable of processing a single substrate through a chain of discrete, mechanistically distinct catalytic steps. Here, we describe an approach to emulate the efficiency of these natural reaction cascades within a synthetic catalyst by the temporal separation of catalytic activities. In this approach, a single catalyst exhibits multiple catalytic activities sequentially, allowing for the efficient processing of a substrate through a cascade pathway. Application of this design strategy has led to the development of a method to effect the anti-Markovnikov (linear-selective) reductive functionalization of terminal alkynes. The strategy of temporal separation may facilitate the development of other efficient synthetic reaction cascades.

A continuous flow solution to achieving efficient aerobic anti-Markovnikov Wacker oxidation

An aerobic anti-Markovnikov Wacker oxidation for the flow-synthesis of arylacetaldehydes is reported. In the process, flow chemistry techniques have provided a means to control and minimise the over-oxidation of sensitive products. The reaction showed general applicability to various functionalised styrenes and provided a process capable of a multi-gram scale. Copyright

Biocatalytic production of tetrahydroisoquinolines

The promiscuity of the enzyme norcoclaurine synthase is described. This biocatalyst yielded a diverse array of substituted tetrahydroisoquinolines by cyclizing dopamine with various acetaldehydes in a Pictet-Spengler reaction. This enzymatic reaction may provide a biocatalytic route to a range of tetrahydroisoquinoline alkaloids.