2557-78-0

Basic information

• Product Name: 2-FLUOROTHIOPHENOL
• Synonyms: O-FLUOROBENZENETHIOL;2-FLUOROBENZENETHIOL;2-FLUOROTHIOPHENOL;2-MERCAPTOFLUOROBENZENE;o-Fluoro Thiophenol;o-fluorothiophenol;2-Fluoromercaptobenzene;2-Fluorothiophenol 98%
• CAS NO: 2557-78-0
• Molecular Formula: C₆H₅FS
• Molecular Weight: 128.17
• Product Categories: Phenol&Thiophenol&Mercaptan;Fluorobenzene;Miscellaneous;Aryl Fluorinated Building Blocks;Building Blocks;C6;Chemical Synthesis;Fluorinated Building Blocks;Organic Building Blocks;Organic Fluorinated Building Blocks;Other Fluorinated Organic Building Blocks;Sulfur Compounds;Thiols/Mercaptans;Fluorine series
• Mol File: 2557-78-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 61-62 °C35 mm Hg(lit.)
• Flash Point: 118 °F
• Appearance: clear colorless to light yellow liquid
• Density: 1.2 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.8mmHg at 25°C
• Refractive Index: n20/D 1.557(lit.)
• Storage Temp.: Flammables area
• PKA: 6.00±0.43(Predicted)
• Sensitive: Stench
• BRN: 2039768
• CAS DataBase Reference: 2-FLUOROTHIOPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-FLUOROTHIOPHENOL(2557-78-0)
• EPA Substance Registry System: 2-FLUOROTHIOPHENOL(2557-78-0)

Safety Data

• Hazard Codes: Xi,T
• Statements: 10-36/37/38
• Safety Statements: 16-26-36-36/37/39-27
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 2557-78-0(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to light yellow liquid

Uses

2-Fluorothiophenol was used in the synthesis of 2-bromo-2′-fluorodiphenyl sulfide.

InChI:InChI=1/C6H5FS/c7-5-3-1-2-4-6(5)8/h1-4,8H/p-1

Synthetic route

[Dimethylamino-(2-fluoro-phenylsulfanyl)-methylene]-dimethyl-ammonium; iodide → 2-fluorothiophenol (2557-78-0) + tetramethylurea (632-22-4)

Conditions	Yield
at 20℃; Rate constant; pH=11;

o-Fluorophenylthioglycolic acid (705-02-2) → 2-fluorothiophenol (2557-78-0) + Glyoxilic acid (298-12-4)

Conditions	Yield
With perchloric acid; sodium perborate; acetic acid at 24.9℃; Rate constant; Thermodynamic data; Mechanism; var. temp., ΔH(excit.), ΔS(excit.);

2-Fluoroaniline (348-54-9) → 2-fluorothiophenol (2557-78-0)

Conditions	Yield
(i) NaNO2, aq. H2SO4, (ii) EtOCS2K, Na2B4O7, (iii) KOH, EtOH; Multistep reaction;
Multistep reaction;

o-Fluorophenylthioglycolic acid (705-02-2) → 2-fluorothiophenol (2557-78-0)

Conditions	Yield
With perchloric acid; pyridinium chlorochromate In water; acetic acid at 24.85 - 44.85℃; Kinetics; Oxidation;

2,2-difluoroacetic anhydride (401-67-2) + 2-fluorothiophenol (2557-78-0) → C8H5F3OS

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 2h;	100%

2-fluorothiophenol (2557-78-0) + (2R)-3-bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide (206193-17-1) → C18H14F4N2O2S

Conditions	Yield
Stage #1: 2-fluorothiophenol With sodium hydride In tetrahydrofuran; mineral oil Stage #2: (2R)-3-bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide In tetrahydrofuran; mineral oil at 20℃; for 20h;	100%

2-fluorothiophenol (2557-78-0) → bis(2-fluorophenyl) disulfide (14135-38-7)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; oxygen; eosin y In ethanol for 0.333333h; Irradiation;	99%
With (bis(2,1-phenylene)bis(azanediyl)bis(methylene)diphenol)diselenide In acetonitrile at 20℃; for 7h;	89%
With sodium perborate In methanol; water for 2h; Ambient temperature;	82%

cyclohexenone (930-68-7) + 2-fluorothiophenol (2557-78-0) → (S)-3-(2-fluorophenylthio)cyclohexanone (1215843-23-4)

Conditions	Yield
With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methyl)urea In toluene at 20℃; for 5h; Michael addition; optical yield given as %ee; enantioselective reaction;	99%

methyl 1-((2-acetoxyethoxy)methyl)-5-bromo-1H-1,2,4-triazole-3-carboxylate (934281-62-6) + 2-fluorothiophenol (2557-78-0) → C15H16FN3O5S (1237741-60-4)

Conditions	Yield
With potassium carbonate In acetonitrile at 100℃; for 0.5h; Inert atmosphere; Microwave irradiation;	99%

2-fluorothiophenol (2557-78-0) + 2-aminoacetonitrile hydrochloride (6011-14-9) → 2-((2-fluorophenyl)thio)acetonitrile (61081-27-4)

Conditions	Yield
Stage #1: 2-aminoacetonitrile hydrochloride With FeCl(tiprp); sodium nitrite In toluene at 55℃; Inert atmosphere; Flow reactor; Stage #2: 2-fluorothiophenol In toluene at 20℃; for 3h; Inert atmosphere;	99%

2-fluorothiophenol (2557-78-0) + benzenesufonyl hydrazide (80-17-1) → S-(2-fluorophenyl) benzenesulfonothioate (1394124-47-0)

Conditions	Yield
With tert.-butylhydroperoxide; sodium iodide In acetonitrile at 20℃; for 12h;	99%

2-fluorothiophenol (2557-78-0) → 2-fluorobenzenesulfenyl chloride

Conditions	Yield
With sulfuryl dichloride In dichloromethane at 0 - 20℃; for 16h;	98%
With thionyl chloride In dichloromethane at 0℃; for 1h;
With sulfuryl dichloride In dichloromethane at 0℃;	7.94 g

2-fluorothiophenol (2557-78-0) + 1-(tert-butoxycarbonyl)piperidin-4-yl methanesulfonate (141699-59-4) → tert-butyl 4-((2-fluorophenyl)thio)piperidine-1-carboxylate

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃;	98%
With potassium carbonate In acetonitrile at 80℃;	98%
With potassium carbonate In acetonitrile at 80℃;	98%

1-ethynylnaphthalene (15727-65-8) + 2-fluorothiophenol (2557-78-0) → C18H13FS

Conditions	Yield
With pyridine; eosin y In N,N-dimethyl-formamide at 40℃; for 6h; Irradiation; regioselective reaction;	98%

2-fluorothiophenol (2557-78-0) + 2-chloro-5-(trifluoromethyl)benzaldehyde (82386-89-8) → 2-(2-Fluorophenylthio)-5-trifluoromethylbenzaldehyde (83986-21-4)

Conditions	Yield
With sodium hydroxide In N,N,N,N,N,N-hexamethylphosphoric triamide at 100℃; for 6h;	97%

1-methylindole (603-76-9) + formaldehyd (50-00-0) + 2-fluorothiophenol (2557-78-0) → 3-(((2-fluorophenyl)thio)methyl)-1-methyl-1H-indole

Conditions	Yield
With ethylenediamine In water at 130℃; for 4h; Green chemistry;	97%

methanesulfonic acid 2-[1-(4-methoxy-phenyl)-3-methyl-5-oxo-1,5-dihydro-[1,2,4]triazol-4yl]-ethyl ester (1001077-60-6) + 2-fluorothiophenol (2557-78-0) → 4-[2-(2-fluoro-phenylsulfanyl)-ethyl]-2-(4-methoxy-phenyl)-5-methyl-2,4-dihydro-[1,2,4]triazol-3-one (1236442-44-6)

Conditions	Yield
With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 100℃;	96%

2-fluorothiophenol (2557-78-0) + 3-iodoindazole (66607-27-0) → 3-[(2-fluorophenyl)sulphanyl]-1H-indazole (1234572-76-9)

Conditions	Yield
With potassium carbonate; copper(l) iodide In ethylene glycol; isopropyl alcohol at 130℃; for 20h;	96%

2-fluorothiophenol (2557-78-0) + 1,3,5-trimethyl-benzene (108-67-8) → (2-fluorophenyl)(mesityl)sulfane

Conditions	Yield
With [bis(acetoxy)iodo]benzene at 20℃; for 0.5h;	96%

2-chloro-N6-cyclopentyl-9H-(2,3-O-isopropylidene-5-chloro-5-deoxy-β-D-ribofuranosyl)adenine (1141934-35-1) + 2-fluorothiophenol (2557-78-0) → 2-chloro-N6-cyclopentyl-9H-[2,3-O-isopropylidene-5-deoxy-5-(2-fluorophenylthio)-β-D-ribofuranosyl]adenine (1141934-36-2)

Conditions	Yield
Stage #1: 2-fluorothiophenol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; Inert atmosphere; Stage #2: 2-chloro-N6-cyclopentyl-9H-(2,3-O-isopropylidene-5-chloro-5-deoxy-β-D-ribofuranosyl)adenine In N,N-dimethyl-formamide; mineral oil at 20℃; for 5h; Inert atmosphere;	95%

2-fluorothiophenol (2557-78-0) + Bromoacetaldehyde diethyl acetal (2032-35-1) → 2-fluorobenzenethioacetaldehyde diethyl acetal

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	95%

1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4) + 2-fluorothiophenol (2557-78-0) → 2-(2-fluorophenylthio)-5-(methylsulfonyl)nitrobenzene (129846-91-9)

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 4h;	95%

3-Iodoquinoline (79476-07-6) + 2-fluorothiophenol (2557-78-0) → 3-(2-fluorophenylthio)quinoline (1299398-28-9)

Conditions	Yield
With copper(l) iodide; potassium carbonate; ethylene glycol In isopropyl alcohol at 80℃; for 30h; Inert atmosphere;	94%

2-fluorothiophenol (2557-78-0) → 2-fluorobenzenesulfonamide (30058-40-3)

Conditions	Yield
With tert.-butylhydroperoxide; ammonium hydroxide; iodine In water; acetonitrile at 100℃; for 16h;	94%

1-methyl-1-phenylethyl alcohol (617-94-7) + 2-fluorothiophenol (2557-78-0) → 2-fluorophenyl 2-phenylpropan-2-yl sulfide

Conditions	Yield
With indium(III) triflate In nitromethane at 20℃; for 0.5h; Sealed tube; chemoselective reaction;	94%

styrene (100-42-5) + 2-fluorothiophenol (2557-78-0) + acetonitrile (75-05-8) → N-(2-((2-fluorophenyl)sulfanyl)-1-phenylethyl)acetamide

Conditions	Yield
With ammonium peroxydisulfate; sodium iodide In water at 100℃; for 12h;	94%

2-fluorothiophenol (2557-78-0) + 1,3,5-tris(bromomethyl)-2,4,6-trimethylbenzene (21988-87-4) → 1,3,5-Tris-(2-fluoro-phenylsulfanylmethyl)-2,4,6-trimethyl-benzene

Conditions	Yield
Stage #1: 2-fluorothiophenol With sodium ethanolate In ethanol for 0.25h; Stage #2: 1,3,5-tris(bromomethyl)-2,4,6-trimethylbenzene In ethanol for 24h; Heating;	93%

2-fluorothiophenol (2557-78-0) + ethyl 2H-azirine-3-carboxylate (1253040-22-0) → ethyl 2-(2-fluorophenylthio)aziridine-2-carboxylate

Conditions	Yield
With C28H28N4O2S In dichloromethane at -78℃; for 0.5h; Sealed tube; enantioselective reaction;	93%

3,5,8-trioxabicyclo[5.1.0]octane (286-48-6) + 2-fluorothiophenol (2557-78-0) → 6-((2-fluorophenyl)thio)-1,3-dioxepan-5-ol

Conditions	Yield
In methanol for 3h; Alkaline conditions;	93%

2-fluorothiophenol (2557-78-0) + diphenylphosphane (829-85-6) → ((2-fluorophenyl)thio)diphenylphosphane

Conditions	Yield
With tris[2-phenylpyridinato-C2,N]iridium(III); benzaldehyde In acetonitrile under 760.051 Torr; for 12h; Inert atmosphere; Irradiation;	93%
With tris[2-phenylpyridinato-C2,N]iridium(III); benzaldehyde In acetonitrile at 25℃; Inert atmosphere; Sealed tube; Irradiation;	93%

2-fluorothiophenol (2557-78-0) + (4S,5S)-2,2-dimethyl-4,5-bis(trifluoromethylsulfonyloxymethyl)-1,3-dioxolane (123136-05-0) → (4R,5R)-4,5-Bis-(2-fluoro-phenylsulfanylmethyl)-2,2-dimethyl-[1,3]dioxolane

Conditions	Yield
Stage #1: 2-fluorothiophenol With sodium hydride In tetrahydrofuran at 25℃; for 1h; Stage #2: (4S,5S)-2,2-dimethyl-4,5-bis(trifluoromethylsulfonyloxymethyl)-1,3-dioxolane In tetrahydrofuran at 0℃; for 3.5h;	92%

2-fluorothiophenol (2557-78-0) + (2-methylallyl)triethylgermane (4531-38-8) → triethyl[(o-fluorophenyl)thio]germane

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) In acetonitrile at 20℃; for 0.25h;	92%

2-fluorothiophenol (2557-78-0) + (3αS,5αS,9βS)-5α,9-dimethyl-3-methylene-3α,5,5α,9β-tetrahydronaphtho[1,2-β]furan-2,8(3H,4H)-dione (66726-11-2) → 3-((2-fluorophenylthio)methyl)-3a,4,5,5a-tetrahydro-5a,9-dimethylnaphtho[1,2-b]furan-2,8(3H,9bH)-dione

Conditions	Yield
With triethylamine In methanol at 0 - 20℃; for 3.25h; Michael Addition; stereospecific reaction;	92%

N-(2-pyrimidyl)indole (221044-05-9) + 2-fluorothiophenol (2557-78-0) → 2-((2-fluorophenyl)thio)-1-(pyrimidin-2-yl)-1H-indole

Conditions	Yield
With indium(III) triflate; carbonyl(pentamethylcyclopentadienyl)cobalt diiodide; copper diacetate; p-benzoquinone In 1,4-dioxane at 60℃; for 5h; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction;	92%

Upstream product

• 705-02-2 o-Fluorophenylthioglycolic acid 
• 348-54-9 2-Fluoroaniline 

Downstream Products

• 83986-05-4 5-Chloro-2-(2-fluorophenylthio)benzaldehyde 
• 129846-93-1 4-(ethylthio)-3-nitrophenyl methyl sulfone 
• 129846-91-9 2-(2-fluorophenylthio)-5-(methylsulfonyl)nitrobenzene 
• 129846-92-0 3,4-bis(2-fluorophenylthio)phenyl methyl sulfone 
• 87033-71-4 2-((2-fluorophenyl)thio)benzoic acid 
• 129846-82-8 2-(2-fluorophenylthio)-5-(methylthio)nitrobenzene 
• 104967-31-9 3-(2-Fluorophenylthiomethyl)-4-methoxybenzaldehyde 
• 126799-50-6 2-Fluoro-4'-(trifluoromethyl)diphenyl Sulfide 
• 83986-21-4 2-(2-Fluorophenylthio)-5-trifluoromethylbenzaldehyde 
• 83986-17-8 2-(2-Flurophenylthio)-5-methoxybenzaldehyde 
• 14135-38-7 bis(2-fluorophenyl) disulfide 
• 83193-43-5 2-(2-Fluorophenylthio)benzaldehyde 
• 98796-23-7 2-fluorophenyl 2-nitrophenyl thioether 
• 126799-49-3 2-Fluoro-2'-(trifluoromethyl)diphenyl Sulfide 

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