57009-75-3

Usage

Uses

Used in Pharmaceutical Industry:
2-(4-Fluorophenyl)-1,3-dithiane is utilized as a reagent in the synthesis of biologically active compounds, contributing to the development of new pharmaceuticals. Its unique chemical properties facilitate the creation of complex organic molecules that can be further used in drug discovery and medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, 2-(4-Fluorophenyl)-1,3-dithiane serves as a key intermediate in the synthesis of various agrochemicals, including pesticides and herbicides. Its role in these syntheses helps in developing more effective and targeted agrochemicals for agricultural applications.
Used in Materials Science:
2-(4-Fluorophenyl)-1,3-dithiane has been studied for its potential applications in materials science, where it may contribute to the development of new materials with specific properties, such as improved stability or reactivity, depending on the context of use.
Used as a Building Block in Organic Synthesis:
Beyond its direct applications, 2-(4-Fluorophenyl)-1,3-dithiane is also recognized as a building block in the synthesis of more complex organic molecules. Its structural features and reactivity make it a useful component in the assembly of intricate molecular architectures for a variety of applications in research and industry.

InChI:InChI=1/C10H11FS2/c11-9-4-2-8(3-5-9)10-12-6-1-7-13-10/h2-5,10H,1,6-7H2

Upstream product

• 109-80-8 1.3-propanedithiol 
• 459-57-4 4-fluorobenzaldehyde 
• 628300-14-1 2,4-dichloro-3-(1,3-propylenedithio-methylene)-penta-1,4-diene 
• 55727-23-6 3‐(1,3-dithiane-2-yl)pentane-2,4-dione 
• 682360-46-9 2-(1,3-dithian-2-ylidene)-3-oxobutanoic acid 

Downstream Products

• 144461-86-9 2-(4-fluorophenyl)-2-(α-hydroxy-4-fluorobenzyl)-1,3-dithiane 
• 639821-03-7 2-{2-[2-(4-fluoro-phenyl)-[1,3]dithian-2-yl]-ethyl}-1-methyl-piperidine 
• 725270-43-9 2-(4-fluoro)phenyl-2-triethylsilyl-1,3-dithiane 
• 1043499-07-5 tert-(4R)-4-[2-(4-fluorophenyl)ethyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 1434253-96-9 2-(tert-butyloxycarbonylamino)-3-[2-(4-fluorophenyl)-1,3-dithian-2-yl]propan-1-ol 
• 1434254-20-2 tert-butyl N-[(2R)-4-(4-fluorophenyl)-1-hydroxybutan-2-yl]carbamate 
• 1434254-04-2 3-(tert-butyloxycarbonylamino)-1-(4-fluorophenyl)-4-hydroxybutan-1-one 
• 1434254-12-2 2-(tert-butyloxycarbonylamino)-4-(4-fluorophenyl)-4-oxobutanoic acid 
• 1217624-82-2 (2R)-2-{[(tert-butoxy)carbonyl]amino}-4-(4-fluorophenyl)butanoic acid 

Relevant academic research and scientific papers

Visible-Light-Induced in Situ Generation of Fischer-Type Copper Carbene Complexes from Acylsilanes and Its Application to Catalytic [4 + 1] Cycloaddition with Siloxydienes

A novel methodology for in situ generation of Fischer-type metal–carbene complexes was developed. Photoirradiation to a mixture of an acylsilane and a cationic copper complex cleanly gave a Fischer-type copper–siloxycarbene complex, which was detected by spectroscopic methods. This carbene complex reacted with siloxydienes in a [4 + 1] cycloaddition manner to give cyclopentene derivatives. It is noteworthy that this reaction proceeds with a catalytic amount of copper through in situ generation of a Fischer-type copper–siloxycarbene complex intermediate.

Dehydrative Glycosylation Enabled by a Comproportionation Reaction of 2-Aryl-1,3-dithiane 1-Oxide?

A new dehydrative glycosylation reaction has been established by capitalizing on the comproportionation reaction of 2-aryl-1,3-dithiane 1-oxides promoted by triflic anhydride (Tf2O). By wedding the high potency of thiophilic promoter system with the step efficiency of dehydrative glycosylation, this reagent underwent facile intermolecular oxothio acetalization with C1-hemiacetal donor to install a temporary leaving group, rendering a transient electrophilic center at the remote site to the anomeric position. The sulfenyl triflate tethered at the terminus concomitantly activated the sulfide intramolecularly to afford the oxocarbenium ion, thereby facilitating the title glycosylation. Aside from accommodating broad range functional groups and inactive hemiacetal substrates, the present activation protocol also proved expedient for 1,3-diol protection. Most importantly, this method further provided a fresh perspective for the application of sulfur chemistry to carbohydrate chemistry.

A 2 - substituted - 1, 3 - dithiane derivative of the preparation method

The invention provides a preparation method of a 2-substituted-1,3-dithiane derivative. The preparation method comprises the following steps: adding 1,3-dithiane (CAS:505-23-7) and 1,2-dichloroethane (DCE) or dichloromethane (DCM) into a reaction bottle, adding N-chlorosuccinimide (NCS) under ice-bath condition, and stirring for 0.5-1 h to prepare a 2-chloro-1,3-dithiane solution; and adding an aldehyde or ketone compound and a lewis acid catalyst into the above solution, and reacting to prepare the 2-substituted-1,3-dithiane derivative. By using the 1,3-dithiane solid and different types of aldehyde and keto-carbonyl compounds as raw material and using one or more of ferric trichloride, boron trifluoride diethyl etherate, methanesulfonic acid, aluminum trichloride, ferrous chloride and nickel chloride as catalysts, preparation of the 2-substituted-1,3-dithiane derivative is realized. The catalysts used in the invention are cheap and easily available, dosage of the catalysts is low and pollution of the catalysts is little. The solid raw materials used in the invention can avoid use of fetid toxic 1,3-dimercaptopropane with strong volatility, and the purpose of protecting an experimenter's body and reducing environmental pollution is realized. In addition, the preparation method has advantages of mild reaction condition, high yield, simple operation and the like.

Synthesis of Chiral α-Aminosilanes through Palladium-Catalyzed Asymmetric Hydrogenation of Silylimines

The asymmetric hydrogenation of silylimines was first developed by using a palladium complex of a P-stereogenic diphosphine ligand as the catalyst, affording the valuable chiral α-aminosilanes with quantitative conversions and excellent enantioselectiviti

Nickel-Catalyzed Synthesis of Silanes from Silyl Ketones

An unprecedented nickel-catalyzed decarbonylative silylation via CO extrusion intramolecular recombination fragment coupling of unstrained and nondirecting group-Assisted silyl ketones is described. The inexpensive and readily available catalyst performs

Preparing method of 2-substituted-1,3-dithiane derivative

The invention belongs to the technical field of organic synthesis, and particularly discloses a preparing method of a 2-substituted-1,3-dithiane derivative. The preparing method comprises the following steps of adding substrate aldehyde, 1,3-dimercaptopro

Visible-light promoted dithioacetalization of aldehydes with thiols under aerobic and photocatalyst-free conditions

A novel photocatalyst-free visible-light-mediated dithioacetalization of aldehydes and thiols has been developed. This protocol is operationally simple, mild and atom-economical, which provides an environmental benign access to dithioacetals at room temperature under aerobic conditions.

Pot-economy autooxidative condensation of 2-Aryl-2-lithio-1,3-dithianes

The autoxidative condensation of 2-aryl-2-lithio-1,3-dithianes is here reported. Treatment of 2-aryl-1,3-dithianes with n-BuLi in the absence of any electrophile leads to condensation of three molecules of 1,3-dithianes and formation of highly functionalized α-thioether ketones orthothioesters in 51-89% yields upon air exposure. The method was further expanded to benzaldehyde dithioacetals, affording corresponding orthothioesters and α-thioether ketones in 48-97% yields. The experimental results combined with density functional theory studies support a mechanism triggered by the autoxidation of 2-aryl-2-lithio-1,3-dithianes to yield a highly reactive thioester that undergoes condensation with two other molecules of 2-aryl-2-lithio-1,3-dithiane.

Lewis Acid-Assisted Photoinduced Intermolecular Coupling between Acylsilanes and Aldehydes: A Formal Cross Benzoin-Type Condensation

Intermolecular carbon–carbon bond-forming reaction between readily available acylsilanes and aldehydes was achieved under photoirradiation conditions with assistance of a catalytic amount of Lewis acid. Nucleophilic addition of photochemically generated s

Sulfur-Directed Ligand-Free C-H Borylation by Iridium Catalysis

An iridium-catalyzed ortho C-H borylation reaction directed by cyclic dithioacetal moiety is disclosed. A series of borylation products were obtained in moderate to good yields under mild conditions in exclusive mono- and ortho-regioselectivity. Thus, the 1,3-dithiane or 1,3-dithiolane group serves as a remarkable effective directing group for C-H borylation without any ligand assistance. The further transformations of the borylation products are also carried out to change boryl group to other functional groups.