461-84-7

Basic information

• Product Name: 4-(Trifluoromethylthio)phenol
• Synonyms: 4-(Trifluoromethylth;trifluoromethylthio)phenol;4-[(Trifluoromethyl)sulphanyl]phenol, 4-Hydroxyphenyl trifluoromethyl sulphide;Phenol, 4-[(trifluoromethyl)thio]-;4-TRIFLUOROMETHYLSULFANYL-PHENOL;4-(TRIFLUOROMETHYLTHIO)PHENOL;4-Trifluoromethylmercaptophenol;IFLAB-BB F2108-0151
• CAS NO: 461-84-7
• Molecular Formula: C₇H₅F₃OS
• Molecular Weight: 194.17
• EINECS: 1312995-182-4
• Product Categories: Aromatic Phenols;Organic Building Blocks;Sulfides/Disulfides;Sulfur Compounds
• Mol File: 461-84-7.mol
• Article Data: 17

Chemical Properties

• Melting Point: 57-60 °C(lit.)
• Boiling Point: 77-78 °C7 mm Hg(lit.)
• Flash Point: 57°C
• Appearance: /
• Density: 1.45
• Vapor Pressure: 1.11mmHg at 25°C
• Refractive Index: 1.529
• Storage Temp.: Room temperature.
• Solubility: soluble in Methanol
• PKA: 8.53±0.13(Predicted)
• Sensitive: Stench
• CAS DataBase Reference: 4-(Trifluoromethylthio)phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(Trifluoromethylthio)phenol(461-84-7)
• EPA Substance Registry System: 4-(Trifluoromethylthio)phenol(461-84-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT, STENCH
• Hazardous Substances Data: 461-84-7(Hazardous Substances Data)

Usage

Chemical Properties

Colorless or light yellow crystalline

Uses

4-(Trifluoromethylthio)phenol may be used in the preparation of phenylamino derivative, which is an important intermediate in the synthesis of toltrazuril.

General Description

4-(Trifluoromethylthio)phenol undergoes reaction with NBS (N-Bromosuccinimide), NIS (N-Iodosuccinimide), HNO3, HNO3/H2SO4 and 4-bromobenzyl bromide to afford bromo-, iodo-, nitro- and benzyl substituted products.

InChI:InChI=1/C7H5F3OS/c8-7(9,10)12-6-3-1-5(11)2-4-6/h1-4,11H

Synthetic route

Bromotrifluoromethane (75-63-8) + bis(4-hydroxyphenyl)disulfide (15015-57-3) → (4-trifluoromethylthio)phenol (461-84-7)

Conditions	Yield
With disodium hydrogenphosphate; rongalite In water; N,N-dimethyl-formamide at 20℃; under 9000.9 Torr; for 2.5h;	86%

N,4-dimethyl-N-[(trifluoromethyl)-sulfanyl]benzene-1-sulfonamide + phenol (108-95-2) → (4-trifluoromethylthio)phenol (461-84-7)

Conditions	Yield
Stage #1: N,4-dimethyl-N-[(trifluoromethyl)-sulfanyl]benzene-1-sulfonamide; phenol In 1,2-dichloro-ethane at 20℃; for 0.0166667h; Sealed tube; Stage #2: With trifluorormethanesulfonic acid In 1,2-dichloro-ethane at 80℃; for 18h; Sealed tube;	82%
With trifluorormethanesulfonic acid In 1,2-dichloro-ethane at 80℃; for 18h; Sealed tube;	82%

2-((trifluoromethyl)thio)benzo[d]isothiazol-3(2H)-one 1,1-dioxide + phenol (108-95-2) → (4-trifluoromethylthio)phenol (461-84-7)

Conditions	Yield
With trifluorormethanesulfonic acid; bis(4-methoxyphenyl)selenide In chloroform at 20℃; for 0.5h; Reagent/catalyst;	81%
With trifluorormethanesulfonic acid In dichloromethane at 60℃; for 8h; Schlenk technique;	75%
With methanesulfonic acid In dichloromethane at 60℃; for 8h; Reagent/catalyst; Solvent; Temperature; Green chemistry;	75%

N-[(trifluoromethyl)sulfanyl]aniline (1045821-71-3) + phenol (108-95-2) → (4-trifluoromethylthio)phenol (461-84-7)

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane at 20℃; Reagent/catalyst; regioselective reaction;	77%

thioorthocarbonotrifluoridic acid 4-amino-phenyl ester (372-16-7) → (4-trifluoromethylthio)phenol (461-84-7)

Conditions	Yield
With uranyl acetate monohydrate; water; trifluoroacetic acid for 60h; Irradiation; Inert atmosphere;	73%

4-sulfanylphenol (637-89-8) + Langlois reagent (2926-29-6) → (4-trifluoromethylthio)phenol (461-84-7)

Conditions	Yield
With dipotassium peroxodisulfate; silver nitrate In water; acetonitrile at 80℃; for 24h; Inert atmosphere;	72%
With tetrabutylammonium tetrafluoroborate; sodium bromide In acetonitrile at 20℃; for 10h; Electrolysis; Inert atmosphere;	16%

1-methyl-4-{[(trifluoromethyl)sulfanyl]sulfonyl}benzene (15223-20-8) + 4-amino-phenol (123-30-8) → (4-trifluoromethylthio)phenol (461-84-7)

Conditions	Yield
Stage #1: 4-amino-phenol With tetrafluoroboric acid In water Stage #2: With sodium nitrite In water at 0 - 25℃; for 0.5h; Stage #3: 1-methyl-4-{[(trifluoromethyl)sulfanyl]sulfonyl}benzene With dichlorotris( 1,10-phenanthroline)ruthenium(II) hydrate In dimethyl sulfoxide at 25℃; for 16h; Irradiation; Inert atmosphere;	53%

(4-(allyloxy)phenyl)(trifluoromethyl)sulfane (653578-27-9) → (4-trifluoromethylthio)phenol (461-84-7)

Conditions	Yield
Stage #1: (4-(allyloxy)phenyl)(trifluoromethyl)sulfane With C12H37NiP4(1+)*C2F6NO4S2(1-) In tetrahydrofuran at 20℃; for 0.5h; Glovebox; Schlenk technique; Inert atmosphere; Stage #2: With toluene-4-sulfonic acid In tetrahydrofuran for 15h; Glovebox; Schlenk technique; Reflux; Inert atmosphere;	34%

4-thiocyanato-phenol (3774-52-5) + potassium trifluoroacetate (2923-16-2) → (4-trifluoromethylthio)phenol (461-84-7)

Conditions	Yield
With iron(II) chloride In N,N-dimethyl-formamide at 140℃; for 16h; Inert atmosphere;	29%

iodotrifluoromethane (2314-97-8) + 4-sulfanylphenol (637-89-8) → (4-trifluoromethylthio)phenol (461-84-7)

Conditions	Yield
In ammonia Irradiation;
With tris(2,2'-bipyridyl)ruthenium dichloride; triethylamine In acetonitrile at 20℃; for 1h; Time; Irradiation;

Trifluoromethylsulfenyl chloride (421-17-0) + phenol (108-95-2) → (4-trifluoromethylthio)phenol (461-84-7)

Conditions	Yield
With pyridine
With pyridine In chloroform
With pyridine

diazotized 4-trifluoromethylsulfanyl-aniline → (4-trifluoromethylthio)phenol (461-84-7)

Conditions	Yield
With water

phenol (108-95-2) → (4-trifluoromethylthio)phenol (461-84-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride / acetonitrile / 12 h / 25 °C / Inert atmosphere 2: caesium carbonate / acetonitrile / 12 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: aluminum (III) chloride / acetonitrile / 60 °C / Inert atmosphere 2: iron(II) chloride / N,N-dimethyl-formamide / 16 h / 140 °C / Inert atmosphere View Scheme

4-thiocyanato-phenol (3774-52-5) + (trifluoromethyl)trimethylsilane (81290-20-2) → (4-trifluoromethylthio)phenol (461-84-7)

Conditions	Yield
With caesium carbonate In acetonitrile at 20℃; for 12h; Inert atmosphere;	163 mg

(2,2'-bipyride-kN1,kN1')(1,1,1-trifluoromethanethiolato-kS)-copper (1413732-47-4) + (p-hydroxyphenyl)boronic acid (71597-85-8) → (4-trifluoromethylthio)phenol (461-84-7)

Conditions	Yield
With oxygen In 1-methyl-pyrrolidin-2-one at 20℃; for 1h;	92 %Spectr.

C11H12F3O3S(1+) → (4-trifluoromethylthio)phenol (461-84-7)

Conditions	Yield
With diethylamine In acetonitrile Inert atmosphere;	14.8 mg

(4-trifluoromethylthio)phenol (461-84-7) + 1-(tert-butoxycarbonyl)piperidin-4-yl methanesulfonate (141699-59-4) → 4-(4-trifluoromethylsulfanyl-phenoxy)-piperidine-1-carboxylic Acid tert-butyl Ester (474711-20-1)

Conditions	Yield
With sodium hydroxide In diethyl ether; diethylene glycol dimethyl ether; ethyl acetate	100%

(4-trifluoromethylthio)phenol (461-84-7) + 1-chloro-2-methyl-4-nitrobenzene (13290-74-9) → 3-methyl-4-(4-((trifluoromethyl)thio)phenyl)oxy-1-nitrobenzene

Conditions	Yield
With potassium carbonate; dimethyl sulfoxide In toluene at 125 - 135℃; for 4h; Temperature; Large scale;	98.1%
With potassium carbonate In dimethyl sulfoxide; toluene at 125 - 135℃; for 4h; Temperature; Large scale;	97.1%
Stage #1: (4-trifluoromethylthio)phenol With potassium carbonate In dimethyl sulfoxide at 70℃; for 20h; Inert atmosphere; Stage #2: 1-chloro-2-methyl-4-nitrobenzene In dimethyl sulfoxide at 70℃; for 18h; Inert atmosphere;	60%
With potassium carbonate In dimethyl sulfoxide at 90 - 130℃; for 5h;	155.9 g

(4-trifluoromethylthio)phenol (461-84-7) + methyl iodide (74-88-4) → 4-methoxyphenyl trifluoromethylsulfide (78914-94-0)

Conditions	Yield
With [bmim]BF4; potassium carbonate In water at 20℃; for 0.166667h;	98%

(4-trifluoromethylthio)phenol (461-84-7) → 2,6-dichloro-5-hydroxyphenyl trifluoromethylsulfide

Conditions	Yield
With [bmim]BF4; trichloroisocyanuric acid; water at 20℃; for 0.0833333h;	96%

(4-trifluoromethylthio)phenol (461-84-7) → 2-chloro-4-(trifluoromethylsulfanyl)phenol (70783-74-3)

Conditions	Yield
With diisobutylamine; sulfuryl dichloride In toluene at 25℃; for 2h;	95%
With diisobutylamine; sulfuryl dichloride In toluene at 20℃; for 1h;	78%

(4-trifluoromethylthio)phenol (461-84-7) + 1-bromomethyl-4-bromobenzene (589-15-1) → (4-(4-bromobenzyloxy)phenyl)(trifluoromethyl)sulfane

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃;	95%

(4-trifluoromethylthio)phenol (461-84-7) → 2,6-dibromo-4-(trifluoromethylthio)phenol (457-25-0)

Conditions	Yield
With N-Bromosuccinimide; 1-butyl-3-methylimidazolium Tetrafluoroborate at 20℃; for 0.333333h;	94%
With bromine; acetic acid

(4-trifluoromethylthio)phenol (461-84-7) + 1-(6-bromopyridin-3-yl)propan-1-one (1194020-10-4) → 1-(6-(4-((trifluoromethyl)thio)phenoxy)pyridin-3yl)propan-1-one

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 130℃; for 5h; Inert atmosphere;	92%
With potassium carbonate In N,N-dimethyl-formamide at 130℃; for 5h; Inert atmosphere;	92%

(4-trifluoromethylthio)phenol (461-84-7) → 2,6-diiodo-4-(trifluoromethylthio)phenol

Conditions	Yield
With N-iodo-succinimide; 1-butyl-3-methylimidazolium Tetrafluoroborate at 20℃; for 0.333333h;	90%

(4-trifluoromethylthio)phenol (461-84-7) + 1-(4-(bromomethyl)phenyl)propan-1-one (95889-09-1) → 1-(4-((4-((trifluoromethyl)thio)phenoxy)methyl)phenyl)propan-1-one

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 3h; Inert atmosphere;	90%
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 10h;

(4-trifluoromethylthio)phenol (461-84-7) + 4-chlorobenzonitrile (100-00-5) → 4-(4-nitrophenoxy)-(trifluoromethylthio)benzene (1244974-58-0)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 195℃; for 0.166667h; Microwave irradiation;	87%

(4-trifluoromethylthio)phenol (461-84-7) → 4-Hydroxyphenyltrifluoromethylsulphone (432-84-8)

Conditions	Yield
With ruthenium trichloride; sodium periodate In water; 1,2-dichloro-ethane; acetonitrile at 20℃; for 22h; Cooling with ice;	85%
With sodium tungstate (VI) dihydrate; dihydrogen peroxide at 70 - 80℃; for 7.5h;	10.81 g
With 2-Ethylhexanoic acid; sulfuric acid; dihydrogen peroxide at 10 - 70℃; for 8.5h; Reagent/catalyst; Temperature;	19.1 g
With sodium tungstate (VI) dihydrate; dihydrogen peroxide In water at 75℃; for 37h; Reagent/catalyst;	45.1 g
Stage #1: (4-trifluoromethylthio)phenol With sodium tungstate (VI) dihydrate; dihydrogen peroxide; acetic acid at 65℃; Stage #2: With sodium disulfite; water; sodium hydroxide pH=8;

(4-trifluoromethylthio)phenol (461-84-7) + 3-nitrobenzene-1,2-dicarbonitrile (51762-67-5) → 3-(4-(trifluoromethylthio)phenoxy)phthalonitrile

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 72h; Inert atmosphere;	85%
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 72h; Inert atmosphere;

1-oxyl-4-carboxyl-2,2,6,6-tetramethylpiperidine (37149-18-1) + (4-trifluoromethylthio)phenol (461-84-7) → C17H21F3NO3S

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 2-methyltetrahydrofuran at 0 - 20℃; Steglich Esterification; Inert atmosphere;	84%

N-methoxyethylpiperidine-4-fluorophenylsulfone ethyl ester (226396-34-5) + (4-trifluoromethylthio)phenol (461-84-7) → C24H28F3NO6S2 (226400-93-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 24h;	81%

(4-trifluoromethylthio)phenol (461-84-7) + 1-(4-iodo-3-methylphenyl)-3-methyl-1,3,5-triazine-2,4,6-trione → toltrazuril (69004-03-1)

Conditions	Yield
With potassium phosphate; copper(l) iodide; N-(2-phenylphenyl)-N′-benzyl oxalamide In acetonitrile at 90℃; for 24h; Inert atmosphere;	80.6%

(4-trifluoromethylthio)phenol (461-84-7) + tert-butyl 4-(4-((methylsulfonyloxy)methyl)cyclohexyl)piperazine-1-carboxylate (1403676-88-9) → tert-butyl 4-((1r,4r)-4-((4-(trifluoromethylthio)phenoxy)methyl)cyclohexyl)piperazine-1-carboxylate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃;	79%

(4-trifluoromethylthio)phenol (461-84-7) + benzoyl chloride (98-88-4) → 4-((trifluoromethyl)thio)phenyl benzoate

Conditions	Yield
With triethylamine In dichloromethane at 0 - 23℃; for 16h; Inert atmosphere;	73%

(4-trifluoromethylthio)phenol (461-84-7) + allyl bromide (106-95-6) → (4-(allyloxy)phenyl)(trifluoromethyl)sulfane (653578-27-9)

Conditions	Yield
With potassium carbonate In acetone Reflux;	70%
With caesium carbonate In N,N-dimethyl-formamide at 50℃; for 2h;

4'-Bromopropiophenone (10342-83-3) + (4-trifluoromethylthio)phenol (461-84-7) → 1-(4-(4-((trifluoromethyl)thio)phenoxy)phenyl)propan-1-one

Conditions	Yield
With 2-Picolinic acid; potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 110℃; for 10h; Inert atmosphere;	67%

(4-trifluoromethylthio)phenol (461-84-7) + Diphenyliodonium triflate (66003-76-7) → 1-phenoxy-4-[(trifluoromethyl)sulfanyl]benzene (1333415-80-7)

Conditions	Yield
Stage #1: (4-trifluoromethylthio)phenol With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.25h; Inert atmosphere; Stage #2: Diphenyliodonium triflate In tetrahydrofuran at 40℃; for 3h; Inert atmosphere;	64%

(4-trifluoromethylthio)phenol (461-84-7) + para-bromoacetophenone (99-90-1) → 1-(4-(4-((trifluoromethyl)thio)phenoxy)phenyl)ethanone

Conditions	Yield
With 2-Picolinic acid; potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 110℃; for 10h; Inert atmosphere;	64%

(4-trifluoromethylthio)phenol (461-84-7) + 2,5-bis-methanesulfonyl-pyridine (85330-63-8) → 5-(methylsulfonyl)-2-(4-((trifluoromethyl)thio)phenoxy)pyridine

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran; water; dimethyl sulfoxide	60%
With potassium tert-butylate In tetrahydrofuran; water; dimethyl sulfoxide	60%

(4-trifluoromethylthio)phenol (461-84-7) + acetic anhydride (108-24-7) → 4-((trifluoromethyl)thio)phenyl acetate

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;	60%

Upstream product

• 1413732-47-4 (2,2'-bipyride-kN₁,kN₁')(1,1,1-trifluoromethanethiolato-kS)-copper 
• 71597-85-8 (p-hydroxyphenyl)boronic acid 
• 372-16-7 thioorthocarbonotrifluoridic acid 4-amino-phenyl ester 
• 653578-27-9 (4-(allyloxy)phenyl)(trifluoromethyl)sulfane 
• 15223-20-8 1-methyl-4-{[(trifluoromethyl)sulfanyl]sulfonyl}benzene 
• 123-30-8 4-amino-phenol 
• 637-89-8 4-sulfanylphenol 
• 2926-29-6 Langlois reagent 
• 3774-52-5 4-thiocyanato-phenol 
• 2923-16-2 potassium trifluoroacetate 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 108-95-2 phenol 
• 1045821-71-3 N-[(trifluoromethyl)sulfanyl]aniline 
• 75-63-8 Bromotrifluoromethane 

Downstream Products

• 102794-04-7 2,6-dichloro-5-hydroxyphenyl trifluoromethylsulfide 
• 78914-94-0 4-methoxyphenyl trifluoromethylsulfide 
• 1333415-80-7 1-phenoxy-4-[(trifluoromethyl)sulfanyl]benzene 
• 69004-03-1 toltrazuril 

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