149733-71-1

Basic information

• Product Name: 2-FLUOROCINNAMALDEHYDE
• Synonyms: 2-FLUOROCINNAMALDEHYDE;2-PROPENAL, 3-(2-FLUOROPHENYL)-,(2E);2-Propenal,3-(2-fluorophenyl)-,(2E)-(9CI);(E)-3-(2-Fluorophenyl)-2-propenal;(E)-3-(2-fluorophenyl)acrylaldehyde
• CAS NO: 149733-71-1
• Molecular Formula: C₉H₇FO
• Molecular Weight: 150.15
• Product Categories: HALIDE
• Mol File: 149733-71-1.mol

Chemical Properties

• Boiling Point: 245.6 °C at 760 mmHg
• Flash Point: 91.3 °C
• Appearance: /
• Density: 1.138 g/cm³
• Vapor Pressure: 0.0284mmHg at 25°C
• Refractive Index: 1.554
• CAS DataBase Reference: 2-FLUOROCINNAMALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-FLUOROCINNAMALDEHYDE(149733-71-1)
• EPA Substance Registry System: 2-FLUOROCINNAMALDEHYDE(149733-71-1)

Safety Data

• Hazardous Substances Data: 149733-71-1(Hazardous Substances Data)

Usage

Uses

Used in Flavoring and Fragrance Industry:
2-Fluorocinnamaldehyde is utilized as a flavoring agent and fragrance ingredient in the food and cosmetics industries, leveraging its sweet, floral scent to enhance the sensory experience of products.
Used in Pharmaceutical and Synthetic Chemistry:
In the pharmaceutical and synthetic chemistry sectors, 2-Fluorocinnamaldehyde serves as a building block for the synthesis of various organic compounds, contributing to the development of new drugs and chemical products.
Used in Perfumery:
2-Fluorocinnamaldehyde is employed in the creation of perfumes and other aromatic products, where its strong and distinctive aroma adds depth and complexity to fragrances.
Synthesis:
2-Fluorocinnamaldehyde is synthesized through the reaction of fluorobenzaldehyde with acetaldehyde, a process that highlights its potential applications across different fields due to its unique chemical properties.

InChI:InChI=1/C9H7FO/c10-9-6-2-1-4-8(9)5-3-7-11/h1-7H/b5-3+

Upstream product

• 3054-95-3 acrylaldehyde diethyl acetal 
• 348-52-7 1-Fluoro-2-iodobenzene 
• 2343-61-5 1-(2-fluoro-phenyl)prop-2-yn-1-ol 
• 446-52-6 2-Fluorobenzaldehyde 
• 1008753-16-9 1-(2-fluorophenyl)butadiene 
• 75-07-0 acetaldehyde 
• 2136-75-6 (triphenylphosphoranylidene)acetaldehyde 
• 201230-82-2 carbon monoxide 
• 766-49-4 (2-fluorophenyl)acetylene 
• 76727-24-7 3-(2-fluorophenyl)propan-1-ol 
• 807369-87-5 (E)-3-(2-fluorophenyl)-prop-2-en-1-ol 

Downstream Products

• 1015486-72-2 3-(2-fluoro-phenyl)-oxirane-2-carbaldehyde 
• 1308401-11-7 (R)-3,3-bis(4-(dimethylamino)phenyl)-2-(2-fluorobenzyl)propanal 
• 1314236-51-5 (1'S,2'S,3'R)-ethyl 2''-fluoro-2'-formyl-5'-hydroxy-1',2',3',6'-tetrahydro-[1,1':3',1''-terphenyl]-4'-carboxylate 
• 1314236-63-9 C₁₃H₁₅FO₃ 
• 1314236-61-7 (E)-ethyl 5-(2-fluorophenyl)-3-oxopent-4-enoate 
• 1314236-57-1 (1S,2R,3R)-ethyl 2'-fluoro-2-formyl-3-(furan-2-yl)-5-hydroxy-1,2,3,6-tetrahydro-[1,1'-biphenyl]-4-carboxylate 
• 1637759-13-7 N-tert-butyl-4-(2-fluorophenyl)-2-oxo-4-phenylbutanamide 
• 1637758-28-1 (E)-N-tert-butyl-4-(2-fluorophenyl)-2-oxobut-3-enamide 
• 1637758-66-7 (R)-N-tert-butyl-4-(2-fluorophenyl)-2-oxo-4-phenylbutanamide 
• 1637758-86-1 C₁₄H₁₈FNO₂ 
• 807369-87-5 (E)-3-(2-fluorophenyl)-prop-2-en-1-ol 

Relevant articles and documents

Substrate-Controlled Chemo-/Enantioselective Synthesis of α-Benzylated Enals and Chiral Cyclopropane-Fused 2-Chromanone Derivatives

Substrate-controlled cascade reactions between α,β-unsaturated aldehydes or their analogues and 2,4-dinitrobenzyl chloride in the presence of a chiral secondary amine as the catalyst and base were developed, to obtain a broad spectrum of α-benzylated enals and enantioenriched cyclopropane-fused chroman-2-one derivatives. The cyclopropane-tethered iminium ion clearly served as a key intermediate in these reactions to trigger stereochemical outcomes, one of which was supported by a control experiment. (Figure presented.).

Biocatalytic Asymmetric Cyclopropanations via Enzyme-Bound Iminium Ion Intermediates

Cyclopropane rings are an important structural motif frequently found in many natural products and pharmaceuticals. Commonly, biocatalytic methodologies for the asymmetric synthesis of cyclopropanes rely on repurposed or artificial heme enzymes. Here, we engineered an unusual cofactor-independent cyclopropanation enzyme based on a promiscuous tautomerase for the enantioselective synthesis of various cyclopropanes via the nucleophilic addition of diethyl 2-chloromalonate to α,β-unsaturated aldehydes. The engineered enzyme promotes formation of the two new carbon-carbon bonds with excellent stereocontrol over both stereocenters, affording the desired cyclopropanes with high diastereo- and enantiopurity (d.r. up to 25:1; e.r. up to 99:1). Our results highlight the usefulness of promiscuous enzymes for expanding the biocatalytic repertoire for non-natural reactions.

Potent Inhibition of Nicotinamide N-Methyltransferase by Alkene-Linked Bisubstrate Mimics Bearing Electron Deficient Aromatics

Nicotinamide N-methyltransferase (NNMT) methylates nicotinamide (vitamin B3) to generate 1-methylnicotinamide (MNA). NNMT overexpression has been linked to a variety of diseases, most prominently human cancers, indicating its potential as a therapeutic target. The development of small-molecule NNMT inhibitors has gained interest in recent years, with the most potent inhibitors sharing structural features based on elements of the nicotinamide substrate and the S-adenosyl-l-methionine (SAM) cofactor. We here report the development of new bisubstrate inhibitors that include electron-deficient aromatic groups to mimic the nicotinamide moiety. In addition, a trans-alkene linker was found to be optimal for connecting the substrate and cofactor mimics in these inhibitors. The most potent NNMT inhibitor identified exhibits an IC50 value of 3.7 nM, placing it among the most active NNMT inhibitors reported to date. Complementary analytical techniques, modeling studies, and cell-based assays provide insights into the binding mode, affinity, and selectivity of these inhibitors.

Selective Rhodium-Catalyzed Hydroformylation of Terminal Arylalkynes and Conjugated Enynes to (Poly)enals Enabled by a π-Acceptor Biphosphoramidite Ligand

The hydroformylation of terminal arylalkynes and enynes offers a straightforward synthetic route to the valuable (poly)enals. However, the hydroformylation of terminal alkynes has remained a long-standing challenge. Herein, an efficient and selective Rh-catalyzed hydroformylation of terminal arylalkynes and conjugated enynes has been achieved by using a new stable biphosphoramidite ligand with strong π-acceptor capacity, which affords various important E-(poly)enals in good yields with excellent chemo- and regioselectivity at low temperatures and low syngas pressures.

Tandem oxidation-dehydrogenation of (hetero)arylated primary alcohols via perruthenate catalysis

Tandem oxidative-dehydrogenation of primary alcohols to give a,b-unsaturated aldehydes in one pot are rare transformations in organic synthesis, with only two methods currently available. Reported herein is a novel method using the bench-stable salt methyltriphenylphosphonium perruthenate (MTP3), and a new co-oxidant NEMO&middoPF6 (NEMO = N-ethyl-N-hydroxymorpholinium) which provides unsaturated aldehydes in low to moderate yields. The Ley-Griffith oxidation of (hetero)arylated primary alcohols with N-oxide co-oxidants NMO (NMO = N-methylmorpholine N-oxide)/NEMO, is expanded by addition of the N-oxide salt NEMO&middoPF6 to convert the intermediate saturated aldehyde into its unsaturated counterpart. The discovery, method development, reaction scope, and associated challenges of this method are highlighted. The conceptual value of late-stage dehydrogenation in natural product synthesis is demonstrated via the synthesis of a polyene scaffold related to auxarconjugatin B.

Palladium-Catalyzed [5 + 2] Annulation of Vinylethylene Carbonates with Barbiturate-Derived Alkenes

A palladium/XantPhos-catalyzed [5 + 2] annulation of VECs with electron-deficient alkenes having an isolated carbon-carbon double bond has been developed to afford spirobarbiturate-tetrahydrooxepines. This study provides an expedient assembly of biologically interesting spirobarbiturate-tetrahydrooxepines. The easy scalability and versatile transformability of the reaction products were also exhibited.

Iron(III)/O2-Mediated Regioselective Oxidative Cleavage of 1-Arylbutadienes to Cinnamaldehydes

A simple, efficient, and environmentally benevolent regioselective oxidative cleavage of 1-arylbutadienes to cinnamaldehydes mediated by iron(III) sulfate/O2 has been developed. The reaction offered good yields and excellent regioselectivity and showed good functional group tolerance (31 examples). The method is important, as few reports with limited substrate scope are available for such excellent oxidative cleavage of conjugated dienes.

Vinylogous Reactivity of Cyclic 2-Enones: Organocatalysed Asymmetric Addition to 2-Enals to Synthesize Fused Carbocycles

A method for asymmetric and site selective annulations at the γ and γ′ positions of cyclic 2-enones with α,β-unsaturated aldehydes has been developed. The organocatalysed [3+3]-annulations proceed with high levels of regio-, diastereo-, and enantioselectivity, affording a series of high value fused carbocycles. Further elaboration gave key lactones (both bridged and fused).

Highly γ-Regioselective 1,2-Addition of α,β-Unsaturated Oxime Ethers with Allylzinc Bromides: A Straightforward Approach for the Synthesis of Homoallylic Amines

A highly regioselective reaction between allylzinc bromide reagents and α,β-unsaturated oxime ethers for the one-step synthesis of the homoallylic amines is reported. This process is a regioselective 1,2-addition reaction providing a new γ-position with carbon-carbon bond formation. Furthermore, the reaction substrates are widely applicable and can be produced in a high yield.

Discovery of novel piperonyl derivatives as diapophytoene desaturase inhibitors for the treatment of methicillin-, vancomycin- and linezolid-resistant Staphylococcus aureus infections

Inhibition of S. aureus diapophytoene desaturase (CrtN) could serve as an alternative approach for addressing the tricky antibiotic resistance by blocking the biosynthesis of carotenoid pigment which shields the bacterium from host oxidant killing. In this study, we designed and synthesized 44 derivatives with piperonyl scaffold targeting CrtN and the structure-activity relationships (SARs) were examined extensively to bring out the discovery of 21b with potent efficacy and better hERG safety profile compared to the first class CrtN inhibitor benzocycloalkane derivative 2. Except the excellent pigment inhibitory activity against wild-type S. aureus, 21b also showed excellent pigment inhibition against four pigmented MRSA strains. In addition, H2O2 killing and human whole blood killing assays proved 21b could sensitize S. aureus to be killed under oxidative stress conditions. Notably, the murine study in vivo validated the efficacy of 21b against pigmented S. aureus Newman, vancomycin-intermediate S. aureus Mu50 and linezolid-resistant S. aureus NRS271.