14204-27-4

Basic information

• Product Name: N-(PHENYLTHIO)PHTHALIMIDE
• Synonyms: 2-(Phenylthio)-1,3-isoindolinedione;2-(Phenylthio)isoindoline-1,3-dione;N-(Phenylthio)phthalimide;N-(PHENYLTHIO)PHTHALIMIDE
• CAS NO: 14204-27-4
• Molecular Formula: C₁₄H₉NO₂S
• Molecular Weight: 255.29
• Product Categories: N-Substituted Phthalimides;Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry;Organic Building Blocks;Others;Sulfur Compounds;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfur Compounds;N-Substituted Maleimides, Succinimides & Phthalimides
• Mol File: 14204-27-4.mol
• Article Data: 20

Chemical Properties

• Melting Point: 160-163 °C(lit.)
• Boiling Point: 432.2°C at 760 mmHg
• Flash Point: 215.2°C
• Appearance: /
• Density: 1.42g/cm³
• Vapor Pressure: 1.13E-07mmHg at 25°C
• Refractive Index: 1.723
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO: soluble25mg/mL, clear, yellow
• PKA: -3.05±0.20(Predicted)
• CAS DataBase Reference: N-(PHENYLTHIO)PHTHALIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(PHENYLTHIO)PHTHALIMIDE(14204-27-4)
• EPA Substance Registry System: N-(PHENYLTHIO)PHTHALIMIDE(14204-27-4)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 14204-27-4(Hazardous Substances Data)

Usage

Preparation

(a) Preparation of benzenesulfenyl chloride. To a stirred solution of 55 gm (0.5 mole) of benzene thiol in 300 ml of η -pentane at 0°C is added chlorine gas until an assay (GC) of the resulting red-orange solution shows quantitative conversion to the sulfenyl chloride. The reaction usually re-quires about 39 gm (0.6 mole) of chlorine. (b) Reaction of benzenesulfenyl chloride with phthalimide. To a stirred solution of 73.5 gm (0.5 mole) of phthalimide in 200 ml of dimethylforma-mide is first added 60 gm (0.6 mole) of triethylamine. Then the sulfenyl chloride solution from (a) is slowly added dropwise. The reaction mixture is stirred for \ hr, poured into 2 liters of cold water, filtered, and dried to afford 121 gm (95%), m.p. 160-161°C (recrystallized from ethanol). Complex imides such as camphorimide and 9,10-dihydroanthracene-9,10-endo-a,/3-succinimide have been alkylated in methylene dichloride with alkyl halides, using tetrabutylammonium bromide as a phase-transfer catalyst and aqueous potassium hydroxide as a base.

InChI:InChI=1/C14H9NO2S/c16-13-11-8-4-5-9-12(11)14(17)15(13)18-10-6-2-1-3-7-10/h1-9H

Upstream product

• 1212-08-4 S-Phenyl benzenethiosulfonate 
• 1146-42-5 p-methoxyphenylsulfonothioic phenyl ester 
• 136918-14-4 phthalimide 
• 108-98-5 thiophenol 
• 931-59-9 benzenesulfenyl chloride 
• 882-33-7 diphenyldisulfane 
• 108-86-1 bromobenzene 
• 54974-07-1 phthalimidesulfenyl chloride 
• 7764-30-9 2,2'-disulfanediylbis(isoindoline-1,3-dione) 
• 3481-09-2 N-chlorophthalimide 
• 1142-97-8 phenyl 4-chlorobenzenethiosulfonate 

Downstream Products

• 63633-99-8 1-(4-chlorophenyl)-4-(phenylthio)piperazine 
• 63633-93-2 1-phenylsulfanyl-4-o-tolyl-piperazine 
• 63633-91-0 1-(4-methoxy-phenyl)-4-phenylsulfanyl-piperazine 
• 129762-13-6 (E)-1-fluoro-1-phenyl-2-(phenylthio)propene 
• 129110-59-4 trans-1-fluoro-2-(phenylthio)cyclooctane 
• 128787-42-8 (E)-4-fluoro-3-(phenylthio)-hex-3-ene 
• 128787-43-9 (E)-4-fluoro-5-(phenylthio)oct-4-ene 
• 113450-71-8 (E)-2-fluoro-1-(phenylthio)hex-1-ene 
• 97231-52-2 trans-1-fluoro-2-(phenylthio)cyclohexane 
• 216244-37-0 1-{trans-4-[2-fluoro-3-(phenylthio)propyl]cyclohexyl}-trans-4-pentylcyclohexane 
• 216244-41-6 1-{trans-4-[3-fluoro-4-(phenylthio)butyl]cyclohexyl}-trans-4-pentylcyclohexane 
• 216244-32-5 1-{trans-4-[3-fluoro-4-(phenylthio)butyl]cyclohexyl}-trans-4-(3,4-difluorophenyl)cyclohexane 
• 136918-14-4 phthalimide 
• 6954-27-4 (1,1'-biphenyl)-4,4'-dithiol 

Relevant articles and documents

Catalytic enantioselective oxysulfenylation ofo-vinylanilides

Tf2NH-assisted BINAM-derived thiophosphoramide catalysis has been accomplished for the enantioselective oxysulfenylation ofo-vinylanilides withN-(aryl/alkylthio)imides. The developed reaction offers access to diverse substituted aryl/alkylthio

A Unified Strategy for Arylsulfur(VI) Fluorides from Aryl Halides: Access to Ar-SOF3 Compounds

A convenient protocol to selectively access various arylsulfur(VI) fluorides from commercially available aryl halides in a divergent fashion is presented. Firstly, a novel sulfenylation reaction with the electrophilic N-(chlorothio)phthalimide (Cl-S-Phth) and arylzinc reagents afforded the corresponding Ar-S-Phth compounds. Subsequently, the S(II) atom was selectively oxidized to distinct fluorinated sulfur(VI) compounds under mild conditions. Slight modifications on the oxidation protocol permit the chemoselective installation of 1, 3, or 4 fluorine atoms at the S(VI) center, affording the corresponding Ar-SO2F, Ar-SOF3, and Ar-SF4Cl. Of notice, this strategy enables the effective introduction of the rare and underexplored -SOF3 moiety into various (hetero)aryl groups. Reactivity studies demonstrate that such elusive Ar-SOF3 can be utilized as a linchpin for the synthesis of highly coveted aryl sulfonimidoyl fluorides (Ar-SO(NR)F).

Photochemical, Metal-Free Sigmatropic Rearrangement Reactions of Sulfur Ylides

Sigmatropic rearrangement reactions constitute one of the most fundamental reactions of carbenes. While state-of-the-art synthetic methods require the use of expensive precious metal catalysts, the application of visible light for the photolysis of α-aryldiazoacetates is much less investigated and provides an operationally simple entry to carbenes under mild reaction conditions. Herein, we report on blue-light induced sigmatropic rearrangement reactions of sulfur compounds with α-aryldiazoacetates. This process, depending on the substitution pattern of the sulfide, opens up formal insertion reactions of carbenes into S?N, S?C, or C?H bonds.