7205-91-6

Usage

Uses

Used in Pharmaceutical Synthesis:
CHLOROMETHYL PHENYL SULFIDE is used as a reagent for the high-yield thiomethylation of O-silylated lactone and ester enolates. This application is crucial in the synthesis of α-methylene lactones and esters, which are important building blocks in the development of various pharmaceutical compounds. The use of CHLOROMETHYL PHENYL SULFIDE in this process enhances the efficiency and yield of the desired products, contributing to the advancement of drug discovery and development.
Used in Chemical Reactions:
In the field of organic chemistry, CHLOROMETHYL PHENYL SULFIDE is utilized as a reagent for the thiomethylation of O-silylated lactone and ester enolates. This reaction is significant in the synthesis of α-methylene lactones and esters, which are key intermediates in the production of various chemicals and materials. The employment of CHLOROMETHYL PHENYL SULFIDE in these reactions improves the overall yield and efficiency, making it an essential tool for chemists and researchers in the chemical industry.

Purification Methods

Dissolve the sulfide in CH2Cl2 or CCl4 and dry it (CaCl2), or pass it through a tube of CaCl2 and distil it using a fractionating column. Harmful vapours. It gives the sulfone [7205-98-3] (b 130o/1mm and m 53o from EtOH) [Beilstein 6 IV 1507] on oxidation with permonophthalic acid. [B.hme et al. Justus Liebigs Ann Chem 563 54 64 1949.] [Beilstein 6 III 1002.]

InChI:InChI=1/C7H7ClS/c8-6-9-7-4-2-1-3-5-7/h1-5H,6H2

Upstream product

• 100-68-5 methyl-phenyl-thioether 
• 1193-82-4 racemic methyl phenyl sulfoxide 
• 26905-22-6 hydroxymethyl phenyl sulfide 
• 50-00-0 formaldehyd 
• 108-98-5 thiophenol 
• 17873-08-4 (phenylsulfanylmethyl)trimethylsilane 
• 74-97-5 chlorobromomethane 
• 56814-31-4 (phenylseleno)methyl phenyl sulfide 
• 701-65-5 (trichloromethylthio)benzene 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 541-41-3 chloroformic acid ethyl ester 
• 54086-42-9 (phenylsulfinylmethyl)-tri-n-butyltin 
• 930-69-8 sodium thiophenolate 
• 7790-99-0 Iodine monochloride 

Downstream Products

• 56772-75-9 {[(methylsulfanyl)methyl]sulfanyl}benzene 
• 52094-80-1 (3-Methyl-1-methylsulfanyl-but-3-enylsulfanyl)-benzene 
• 91012-49-6 S-Phenylthiomethyl-L-cystein 
• 53097-28-2 (E/Z)-1-(phenylthio)buta-1,3-diene 
• 65597-71-9 (1-Ethylsulfanyl-but-3-enylsulfanyl)-benzene 
• 65597-75-3 (2,2-Dimethyl-1-methylsulfanyl-but-3-enylsulfanyl)-benzene 
• 71309-72-3 ethyl 2-phenylthiomethyl-butanoate 
• 37987-30-7 (o-tolylmethylene)bis(phenylsulfane) 
• 37987-31-8 3,3-dimethyl-4,4-bis-phenylsulfanyl-but-1-ene 
• 65597-80-0 C₂₆H₂₂S₂ 
• 65597-79-7 orthobenzylbenzaldehyde diphenylthioacetal 
• 65597-77-5 4,4-dimethyl-5,5-bis-phenylsulfanyl-pent-2-ene 
• 65597-78-6 1-(Bis-phenylsulfanyl-methyl)-2-ethyl-benzene 
• 16627-79-5 (E) 3-methyl-1,3-butadienyl phenyl sulfide 

Relevant academic research and scientific papers

Novel process for synthesizing 2 -fluorocyclopropylamine with high selectivity and asymmetric synthesis

A novel highly selective asymmetric synthesis process of 2 -fluorocyclopropylamine (Structural I). The method provided by the invention uses 1 - fluorine -1 - benzene (propylene) sulfonyl methane and chiral epichlorohydrin to construct chiral cyclopropane under basic conditions, and a new synthetic route not only achieves a special cis-trans selectivity, but also has a highly specific stereoselectivity. The synthesis route is efficient, the reaction condition is mild, the method is suitable for large industrial production in a green environment, 2 -fluorocyclopropylamine production cost is greatly reduced.

Consecutive C1-Homologation / Displacement Strategy for Converting Thiosulfonates into O,S-Oxothioacetals

A conceptually intuitive synthesis of oxothioacetals is reported starting from thiosulfonates as electrophilic sulfur donors. The installation of a reactive CH2Cl motif with a homologating carbenoid reagent, followed by the immediate nucleophilic displacement with alcoholic groups [(hetero)-aromatic, aliphatic] offer a convenient access to the title compounds. Genuine chemoselectivity is uniformly observed in the case of multi-functionalized systems. (Figure presented.).

A Manganese N-Heterocyclic Carbene Catalyst for Reduction of Sulfoxides with Silanes

The first reduction of sulfoxides catalysed by a well-defined manganese complex is described. A variety of sulfoxides are reduced to the corresponding sulfides in high yields using phenylsilane, diphenylsilane, and the economically feasible 1,1,3,3-tetramethyldisiloxane (TMDS) as reducing agents in the presence of a Mn-NHC complex. The reaction is performed under air and without the need of any additive. The involvement of radicals in the catalytic reaction is probed by spin-trap experiments.

An electrophilic reagent for the synthesis of OCHFMe-containing molecules

Herein the synthesis of a novel and bench stable electrophilic reagent to construct the OCFHMe motif from O-nucleophiles has been described. This sulfonium salt, readily obtained in 5 steps, reacted with various phenols and alcohols. The resulting products, including complex molecules, were obtained in good yields. This reagent was also used for the functionalization of thiol derivatives.

Systematic Evaluation of Sulfoxides as Catalysts in Nucleophilic Substitutions of Alcohols

Herein, a method for the nucleophilic substitution (SN) of benzyl alcohols yielding chloro alkanes is introduced that relies on aromatic sulfoxides as Lewis base catalysts (down to 1.5 mol-%) and benzoyl chloride (BzCl) as reagent. A systematic screening of various sulfoxides and other sulfinyl containing Lewis bases afforded (2-methoxyphenyl)methyl sulfoxide as optimal catalyst. In contrast to reported formamide catalysts, sulfoxides also enable the application of plain acetyl chloride (AcCl) as reagent. In addition, it was demonstrated that weakly electrophilic carboxylic acid chlorides like BzCl promote Pummerer rearrangement of sulfoxides already at room temperature. This side-reaction also provided the explanation, why sulfoxide catalyzed SN-reactions of alcohols do not allow the effective production of aliphatic and electron deficient chloro alkanes. Comparison experiments provided further insight into the reaction mechanism.

CURABLE COMPOUND WITH HIGH REFRACTIVE INDEX, ADHESIVE COMPOSITION FOR OPTICAL MEMBER COMPRISING THE SAME AND COMPOSITION FOR OPTICAL SHEET COMPRISING THE SAME

Provided is a compound which is represented by chemical formula 1, an adhesive composition for optical members including the same, and a composition for optical sheets including the same. More specifically, the purpose of the present invention is to provide a compound which is curable and has a high refractive index.COPYRIGHT KIPO 2016

Bromomethyllithium-mediated chemoselective homologation of disulfides to dithioacetals

An efficient, chemoselective homologation of disulfides and diselenides to the corresponding dithio- and diselenoacetals has been developed via the addition of bromomethyllithium. Chemoselectivity is fully preserved in the presence of concomitant electrophilic sites decorating the substrates. The synthetic potential of selected dithioacetals has been evaluated in Feringa-Fa?anas-Mastral-type Pd-catalyzed coupling with an organolithium and in the unusual 1,4-addition to a Weinreb amide.

Deoxygenation of sulfoxides to sulfides with thionyl chloride and triphenylphosphine: Competition with the Pummerer reaction

Although a number of methods have been developed to reduce sulfoxides to sulfides, many of these processes are limited by side reactions, low yields, poorly available reagents, or harsh reaction conditions. We recently studied the reaction of various sulfoxides with SOCl2 and Ph3P. We were able to obtain the corresponding sulfides in excellent yields (>90%) when aliphatic and aromatic sulfoxides were treated with SOCl2 as a catalyst and Ph3P in THF at room temperature.

ELECTROPHILIC REAGENTS FOR MONOHALOMETHYLATION,THEIR PREPARATION AND THEIR USES

The invention provides a compound of formula A, B, C or D, methods for making them, intermediates therefor, and their use in making organic biologically active compounds: (Formula (A)). Wherein: ? X = F, CI, Br, I, sulfonate esters, phosphate esters or another leaving group ? R1, R2, R3, R4, R5, R6, R7, R8, R9, R1O are each individually selected from H, alkyl, aryl, alkynyl, alkenyl, cycloalkyl, cycloalkenyl, alkoxy, nitro, halogen or amino; or are selected from H, C1C10 alkyl, aryl, C1C10 alkynyl, C1C10 alkenyl, C1C10 cycloalkyl, C1C10 cycloalkenyl, C1C10 alkoxy, nitro, halogen or amino ? R11 = tetrafluoroborate, triflate, halogen, perclorate, sulfates, phosphates or carbonates ? Excluding the case when: X = F and R1= R2 = R3 = R4= R5 = H and R6 R8 = R9 = methyl, R10 = H and R11 = triflate or tetrafluoroborate; or (Formula (B)). Wherein: X = F, CI, Br, I, sulfonate esters, phosphate esters or other another leaving group; and R1, R2, R3, R4, R5 are each individually selected from H, alkyl, aryl, alkynyl, alkenyl, cycloalkyl, cycloalkenyl, alkoxy, nitro, halogen or amino; or are selected from H, C1C10 alkyl, aryl, C1C10 alkynyl, C1C10 alkenyl, C1C10 cycloalkyl, C1C10 cycloalkenyl, C1C10 alkoxy, nitro, halogen or amino and R11 = tetrafluoroborate, triflate, halogen, perclorate, sulfates, phosphates or carbonates; and R12 = resin, naphthalene or substituted naphthalene Excluding the case when: X = F and R1= R2 = R3 = R4= R5 = H and R6 = R7 = R8 = R9 = methyl, R10 = H and R11 = triflate or tetrafluoroborate and when X = F and R1= R2 = R3 = R4= R5 = H and R12 = poly(styrene-co- divinylbenzene) and R11 = triflate or tetrafluoroborate; or (Formula (C)). Wehrein ? X = F, CI, Br, I, sulfonate esters, phosphate esters or another leaving group ? R13 = naphthalene or substituted naphthalene ? R6, R7, R8, R9, R10 are each individually selected from H, alkyl, aryl, alkynyl, alkenyl, cycloalkyl, cycloalkenyl, alcoxy, nitro, halogen or amino; or are selected from H, C1C10 alkyl, aryl, C1C10 alkynyl, C1C10 alkenyl, C1C10 cycloalkyl, C1C10 cycloalkenyl, C1C10 alkoxy, nitro, halogen or amino ? R11 = tetrafluoroborate, triflate, halogen, perclorate, sulfates, phosphates or carbonates: or (Formula (D)) X = F, CI, Br, I, sulfonate esters, phosphate esters or another leaving group R13 = naphthalene or substituted naphthalene R11 = tetrafluoroborate, triflate, halogen, perclorate, sulfates, phosphates carbonates R12 = resin, naphthalene or substituted naphthalene.