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

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

Uses

Used in Chemical Synthesis:
2-Fluorothiophenol is used as a synthetic intermediate for the production of various organic compounds. Its unique structure allows it to be a versatile building block in the synthesis of complex molecules.
2-Fluorothiophenol is used as a synthetic intermediate for [application reason] in the chemical synthesis industry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Fluorothiophenol may be utilized as a key component in the development of new drugs, particularly those targeting specific biological pathways or receptors. Its unique chemical properties can be exploited to design molecules with enhanced potency and selectivity.
2-Fluorothiophenol is used as a key component in [application reason] for the pharmaceutical industry.
Used in Material Science:
The distinct properties of 2-Fluorothiophenol can also make it a valuable additive or component in the development of new materials with specific characteristics, such as improved stability, reactivity, or conductivity.
2-Fluorothiophenol is used as an additive/component for [application reason] in the material science industry.

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

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

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 
• 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 
• 655-20-9 2-fluorothioanisole 
• 138736-65-9 1-fluoro-2-(isopropylthio)benzene 

Relevant articles and documents

Sulphonamide derivatives

The present invention relates to the potentiation of glutamate receptor function using certain sulphonamide derivatives. It also relates to novel sulphonamide derivatives, to processes for their preparation and to pharmaceutical compositions containing them.

Oxidative cleavage of S-Arylmercaptoacetic acids by pyridinium chlorochromate: Kinetic and correlation analysis

Kinetics of oxidation of 24 S-Arylmercaptoacetic acids (SAMA) by pyridinium chlorochromate (PCC) have been studied in acid medium. The product of oxidation is the corresponding thiophenol. The rate data of meta- and para-substituted acids have been correlated well with σI, σ°R values and the meta-compounds correlate well with F,R values. The reaction constants are negative and of smaller magnitudes. Further, the ortho-substituted acids show a good correlation with triparametric equation involving Taft's σI and σ°R and charton's steric parameter v. There is no considerable steric contribution to the total orthosubstituent effect. Based on these observations, the mechanism involving the formation of protonated arylsulfinylacetic acid intermediate, followed by an intramolecular rearrangement leading to the product thiophenol has been proposed.

Oxidative Cleavage of S-Arylmercaptoacetic Acids by Sodium Perborate: Kinetic and Correlation Study

Kinetics of oxidation of twenty six S-arylmercaptoacetic acids (SAMA) (I) by sodium perborate (PB) have been studied in acid medium.The product of oxidation is the corresponding thiophenol.The rate data of meta- and para-substituted acids have been correlated with DSP equations.While the para-compounds correlate well with ?I and ?0R values, the meta-compounds correlate well with ?I and ?-R values.The reaction constants are negative and of smaller magnitudes.Further, the ortho-substituted acids show a good correlation with a triparametric equation involving Taft's ?I and ?0R and Charton's steric parameter ν.There is a considerable steric contribution to the total ortho-substituent effect.Based on these observations, mechanism involving the formation of protonated arylsulfinylacetic acid intermediate, followed by an intramolecular rearrangement leading to the product thiophenol has been proposed.