421-17-0

Basic information

• Product Name: TRIFLUOROMETHYLSULPHENYL CHLORIDE
• Synonyms: trifluoro-methanesulfenylchlorid;trifluoromethanesulfenylchloride;trifluoromethane-sulfenylchloride;TRIFLUOROMETHYLSULFENYL CHLORIDE;TRIFLUOROMETHYLSULPHENYL CHLORIDE;trifluoromethanesulphenyl chloride;Trifluoromethylsulphenylchloride97%;Trifluoromethylsulphenyl chloride 97%
• CAS NO: 421-17-0
• Molecular Formula: CClF₃S
• Molecular Weight: 136.52
• EINECS: 207-003-8
• Mol File: 421-17-0.mol
• Article Data: 13

Chemical Properties

• Boiling Point: -3°C
• Flash Point: °C
• Appearance: /
• Density: 1.573g/cm³
• Vapor Pressure: 1850mmHg at 25°C
• Refractive Index: 1.377
• Sensitive: Lachrymatory
• CAS DataBase Reference: TRIFLUOROMETHYLSULPHENYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIFLUOROMETHYLSULPHENYL CHLORIDE(421-17-0)
• EPA Substance Registry System: TRIFLUOROMETHYLSULPHENYL CHLORIDE(421-17-0)

Safety Data

• Hazard Codes: T
• Statements: 26-34
• Safety Statements: 23-24/25-26-36/37/39-45
• RIDADR: 3308
• Hazardous Substances Data: 421-17-0(Hazardous Substances Data)

Usage

General Description

Trifluoromethylsulphenyl Chloride is a specialized chemical compound with the molecular formula CF3SCl. It is predominantly used in the industry as an intermediate in chemical synthesis. Due to the presence of the trifluoromethyl group, this compound is highly effective in introducing fluorine into other chemical combinations. Its reactivity and effectiveness make it an essential ingredient in the preparation of pharmaceuticals, agrochemicals, and in various scientific research projects. Due to the volatile nature of this compound, it should be handled with extreme care, using safety measures to prevent exposure and minimize potential health risks.

InChI:InChI=1/CClF3S/c2-6-1(3,4)5

Synthetic route

hydrogen fluoride (7664-39-3) + chlorothio-trichloro-methane (594-42-3) → Trifluoromethylsulfenyl chloride (421-17-0) + Bis(trifluoromethyl)disulfid (372-64-5) + Trifluoro-methanethiosulfonic acid S-trifluoromethyl ester (358-15-6)

Conditions	Yield
180°C; chrom oxide fluoride catalyst;	A 74% B n/a C n/a

sodium fluoride + chlorothio-trichloro-methane (594-42-3) → Trifluoromethylsulfenyl chloride (421-17-0)

Conditions	Yield
In further solvent(s) in tetramethylsulphone at 170-250°C;	47%
In acetonitrile 170-250°C;	47%
In acetonitrile 170-250°C;	47%
In further solvent(s) in tetramethylsulphone at 170-250°C;	47%
In acetonitrile 170-250°C;	47%

potassium fluoride + chlorodifluoromethansulfenylchloride (993-38-4) → Trifluoromethylsulfenyl chloride (421-17-0) + chlorodifluoromethanesulphenic acid fluoride (17742-03-9)

Conditions	Yield
at 150°C;	A 25% B 5%
at 150°C;	A 25% B 5%

chlorodifluoromethansulfenylchloride (993-38-4) + antimony(III) fluoride (7783-56-4) → Trifluoromethylsulfenyl chloride (421-17-0)

Conditions	Yield
	11%
	11%

chlorodifluoromethansulfenylchloride (993-38-4) → Trifluoromethylsulfenyl chloride (421-17-0)

Conditions	Yield
With antimonypentachloride; antimony(III) fluoride

Bis(trifluoromethyl)disulfid (372-64-5) → Trifluoromethylsulfenyl chloride (421-17-0)

Conditions	Yield
With chlorine Irradiation.bei mehrtaegiger Bestrahlung mit UV-Licht;
With chlorine Irradiation (UV/VIS);
With chlorine Irradiation (UV/VIS);

1,1,1-trifluoromethanesulfenylamine (1512-33-0) → Trifluoromethylsulfenyl chloride (421-17-0) + S2Cl2, Cl3S3N3

Conditions	Yield
With chlorine at -30℃; for 0.5h; Product distribution;

thiocarbonyl fluoride (420-32-6) + chlorine monofluoride (7790-89-8) → Trifluoromethylsulfenyl chloride (421-17-0)

sodium fluoride + chlorothio-trichloro-methane (594-42-3) → chlorodifluoromethansulfenylchloride (993-38-4) + Trifluoromethylsulfenyl chloride (421-17-0)

CF3SCNCFSSCF3 → Trifluoromethylsulfenyl chloride (421-17-0) + trifluoromethylcarbamoyldisulfane (33278-65-8)

Conditions	Yield
With hydrogenchloride; water byproducts: HF;
With HCl; H2O byproducts: HF;

Methanesulfenyl chloride (5813-48-9) + trifluoromethylsulfenyl fluoride (17742-04-0) → Trifluoromethylsulfenyl chloride (421-17-0) + trifluoromethyl disulphide (14410-21-0) + Methylsulfur trifluoride (65082-47-5)

Conditions	Yield
-50°C;
-50°C;

1,1,1-trifluoromethanesulfenylamine (1512-33-0) → Trifluoromethylsulfenyl chloride (421-17-0) + ammonium chloride

Conditions	Yield
With hydrogenchloride
With HCl

trifluoromethylmercaptoisocyanate (691-03-2) + bis(trifluoromethylthio) amine (763-24-6) + dichlorofluoromethanesulphenyl chloride (2712-93-8) → Trifluoromethylsulfenyl chloride (421-17-0) + trifluoromethylmercapto-bis(dichlorofluoromethylmercapto)amine (34153-27-0) + trimethylamine hydrochloride (593-81-7)

chlorodifluoromethanesulphenic acid fluoride (17742-03-9) → Trifluoromethylsulfenyl chloride (421-17-0)

Conditions	Yield
room temp.;

chlorodifluoromethansulfenylchloride (993-38-4) + trifluoromethylmercaptoisocyanate (691-03-2) + bis(trifluoromethylthio) amine (763-24-6) → Trifluoromethylsulfenyl chloride (421-17-0) + trifluoromethylmercapto-bis(chlorodifluoromethylmercapto)amine (34153-25-8) + trimethylamine hydrochloride (593-81-7)

chlorothio-trichloro-methane (594-42-3) → Trifluoromethylsulfenyl chloride (421-17-0) + Bis(trifluoromethyl)disulfid (372-64-5) + trifluoromethanesulfinyl fluoride (812-12-4)

Conditions	Yield
fluorination;
fluorination;

trifluoromethylmercapto carbamic acid chloride (6080-81-5) → Trifluoromethylsulfenyl chloride (421-17-0) + 14,14,14-Trifluor-13-thia-2,4,6,8,10,12-hexaaza-tetradecan-pentaon-(3,5,7,9,11)-saeurechlorid (6417-75-0)

Conditions	Yield
20°C;
20°C;

N-Chlor-bis(fluorcarbonyl)-amin (42016-33-1) + mercury bis(trifluoromethanethiolate) (21259-75-6) → Trifluoromethylsulfenyl chloride (421-17-0) + Hg(2+)*(FCO)2N(1-)*SCF3(1-)=(FCO)2NHgSCF3

mercury bis(trifluoromethanethiolate) (21259-75-6) + chlorine (7782-50-5) → Trifluoromethylsulfenyl chloride (421-17-0) + Bis(trifluoromethyl)disulfid (372-64-5) + trifluoromethylthio-mercury(II) chloride

Conditions	Yield
-22°C;

N,N'-bis(trifluoromethylmercapto)-chloroformamidine (36668-60-7) + N,N,N'-tris(trifluoromethylmercapto)-chloroformamidine (36668-61-8) → Trifluoromethylsulfenyl chloride (421-17-0) + (CF3S)2NCN + hexakis(trifluoromethylmercapto)melamine (36757-19-4)

Conditions	Yield
With trimethylamine	A n/a B 0% C n/a
With (CH3)3N	A n/a B 0% C n/a

Trifluoromethylsulfenyl chloride (421-17-0) + hypofluorous acid trifluoromethyl ester (373-91-1) → trifluoro(trifluoromethyl)sulfur(IV) (374-10-7)

Conditions	Yield
at -78°C, 0.5 h;	100%
at -78°C, 0.5 h;	100%

Trifluoromethylsulfenyl chloride (421-17-0) + N-chlorobistrifluoromethylketimine (10181-78-9) → trifuloromethylsulfur perfluoroisopropylideneamide (31340-34-8)

Conditions	Yield
With mercury in Carius tube;	100%

Trifluoromethylsulfenyl chloride (421-17-0) + water (7732-18-5) + chlorine (7782-50-5) → trifluoromethane sulfonyl chloride (421-83-0)

Conditions	Yield
excess of Cl2 and H2O, 20°C, 7 days;	98%
excess of Cl2 and H2O, 20°C, 7 days;	98%

Trifluoromethylsulfenyl chloride (421-17-0) + bis(sulfinylamido)tellurane (124824-09-5) → bis(sulfinylamido) tellurium(IV) chloride (160785-74-0)

Conditions	Yield
In dichloromethane byproducts: CF3SSCF3; 2 equiv. of CF3SCl was condensed to Te-compd., stirred for 12 h at -60 ° C; volatiles were removed in vac., solid was dried in vac. for 12 h at 20 °C.;	97%

Trifluoromethylsulfenyl chloride (421-17-0) + ethyl acetate (141-78-6) → ethyl esetrs of α-(trifluoromethylthio)acetic acid (42105-37-3)

Conditions	Yield
-20 to +24°C;	96%
-20 to +24°C;	96%

Trifluoromethylsulfenyl chloride (421-17-0) + bis(sulfinylamido) tellurium(IV) chloride (160785-74-0) → Te2Cl5N

Conditions	Yield
In dichloromethane byproducts: SO2, CF3SSCF3; Te-compd. and CF3SCl in 1:2 molar ratio were stirred for 12 h at 22 ° C; volatiles were detected by IR;	96%
In dichloromethane byproducts: SO2, CF3SNSO; 1 equiv. of CF3SCl was condensed to Te-compd., stirred for 3 d at -15 ° C; volatiles were identified by GC-MS and (19)F NMR;	95%

Trifluoromethylsulfenyl chloride (421-17-0) + cyclohexene (110-83-8) → rac-(1R,2R)-1-chloro-2-[(trifluoromethyl)sulfanyl]cyclohexane

Conditions	Yield
trifluoroacetic acid at -20℃;	95%

Trifluoromethylsulfenyl chloride (421-17-0) → bis(trifluoromethylthio)tellurium (83665-28-5)

Conditions	Yield
With bis(triphenylstannyl)tellurium In various solvent(s) at 20℃; for 4h;	95%

Trifluoromethylsulfenyl chloride (421-17-0) + chlorine trifluoride (7790-91-2) → trifluoro(trifluoromethyl)sulfur(IV) (374-10-7)

Conditions	Yield
In dichloromethane -78°C;	95%
In dichloromethane -78°C;	95%
In further solvent(s) in CF2Cl2 at -196 to -78°C;
In further solvent(s) in CF2Cl2 at -196 to -78°C;

Trifluoromethylsulfenyl chloride (421-17-0) → trifluoromethylsulfinyl chloride (20621-29-8)

Conditions	Yield
With m-chloroperbenzoic acid oxidn., from -20 to +25°C, 12 h;	95%

Trifluoromethylsulfenyl chloride (421-17-0) + Trifluormethylselenosilber (75264-94-7) → trifluoromethyl trifluoromethanesulfenoselenoate (73076-98-9)

Conditions	Yield
at -60℃;	93%
-60°C;	93-94

Trifluoromethylsulfenyl chloride (421-17-0) + β-aminocinnamic amide (23787-16-8) → β-amino-α-trifluoromethylthio-cinnamic acid amide

Conditions	Yield
In chloroform Heating; 0 deg C, 30 min, room temperature, 20 h;	90%

Trifluoromethylsulfenyl chloride (421-17-0) + β-imino-β-phenylpropionitrile (16187-90-9) → β-amino-α-trifluoromethylthio-cinnamic acid nitrile

Conditions	Yield
In chloroform Heating; 0 deg C, 30 min, room temperature, 20 h;	90%

Trifluoromethylsulfenyl chloride (421-17-0) + 1,2-Dichloroethylene (540-59-0) → Trifluormethyl-1,2,2-trichlorethyl-sulfid (40302-61-2)

Conditions	Yield
Irradiation (UV/VIS); 3:2 cis-trans isomer 1,2-dichloroethylene; distn.;	90%
Irradiation (UV/VIS); 3:2 cis-trans isomer 1,2-dichloroethylene; distn.;	90%
	80%
	80%

Trifluoromethylsulfenyl chloride (421-17-0) + silver fluoride → trifluoromethylsulfenyl fluoride (17742-04-0) + difluoro(trifluoromethyl)trifluormethylsulfanylsulfur(IV) (26391-89-9)

Conditions	Yield
at 100°C;	A 10% B 90%
at 100°C;	A 10% B 90%

Trifluoromethylsulfenyl chloride (421-17-0) + Hg(2+)*Cl(1-)*OC(CF3)3(1-)=HgCl{OC(CF3)3} → Perfluor-tert.-butyl-trifluormethansulfenat (66700-53-6)

Conditions	Yield
with Hg(Cl)OC(CF3)3 excess at 0°C (24 h);	90%
excess of (CF3)3COHgCl, 24 h, 0°C;	90%
with Hg(Cl)OC(CF3)3 excess at 0°C (24 h);	90%

Trifluoromethylsulfenyl chloride (421-17-0) + acrylic acid methyl ester (292638-85-8) → CF3SCH2CHClCO2CH3 + α-(Trifluormethylthio)-β-chlorpropionat (34033-72-2) + 2-Chloromethyl-4-trifluoromethylsulfanyl-pentanedioic acid dimethyl ester (34033-73-3)

Conditions	Yield
CF3SCl excess; gas chromy. and (19)F-NMR detection;	A 10% B 90% C n/a
CF3SCl excess; gas chromy. and (19)F-NMR detection;	A 10% B 90% C n/a

Trifluoromethylsulfenyl chloride (421-17-0) → N-Sulfinyl-trifluormethansulfenamid (22089-64-1)

Conditions	Yield
With N-sulfinyl trimethylsilanamine at 0℃; for 4h; ultrasound;	89%

Trifluoromethylsulfenyl chloride (421-17-0) + Se,Se-bis(trifluoromethyl) carbonodiselenothioate (54393-47-4) → Bis(trifluormethylselenyl)chlormethyl-trifluormethyldisulfan

Conditions	Yield
for 2h; Irradiation;	88%

Trifluoromethylsulfenyl chloride (421-17-0) + 3-oxo-3-phenylpropanamide (3446-58-0) → α,α-bis(trifluoromethylthio)benzoylacetic acid amide + α-trifluoromethylthio-benzoylacetic acid amide (116073-28-0)

Conditions	Yield
In chloroform Heating; 0 deg C, 30 min, room temperature, 20 h;	A 4% B 88%

Trifluoromethylsulfenyl chloride (421-17-0) + adenine (66224-66-6, 66224-67-7, 66224-68-8, 66224-69-9, 134434-48-3, 134434-49-4, 134454-76-5, 134461-75-9) → C5N4H3NHSCF3 (55055-52-2)

Conditions	Yield
In tetrahydrofuran 20°C for 1.5 h, Carius tube;	88%
In tetrahydrofuran 20°C for 1.5 h, Carius tube;	88%

Trifluoromethylsulfenyl chloride (421-17-0) + Bis<2,2,4,4-tetrakis(trifluormethyl)-4H-1,3,5-dioxazin-6-ylthio>quecksilber (93383-98-3) → <2,2,4,4-Tetrakis(trifluormethyl)-4H-1,3,5-dioxazin-6-yl>(trifluormethyl)disulfan (103191-46-4)

Conditions	Yield
In dichloromethane at -196℃; for 12h;	87%

Trifluoromethylsulfenyl chloride (421-17-0) + acetone (67-64-1) → 1-trifluoromethylthio-2-propanone (42105-30-6)

Conditions	Yield
bomb tube (-80 to +20°C);	86%
bomb tube (-80 to +20°C);	86%
	71%

Trifluoromethylsulfenyl chloride (421-17-0) + dimedone (126-81-8) → 2-(trifluoromethylthio)-5,5-dimethyl-1,3-cyclohexanedione (128402-12-0)

Conditions	Yield
With pyridine In chloroform Ambient temperature;	86%

Trifluoromethylsulfenyl chloride (421-17-0) → bis(trifluoromethylthio)selenide

Conditions	Yield
With dmap; hydrogen selenide In dichloromethane at -78℃; for 3h;	86%

Trifluoromethylsulfenyl chloride (421-17-0) + 5-amino-1-(2-chloro-6-fluoro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile (1000815-86-0) → 5-amino-3-cyano-1-(2-chloro-6-fluoro-4-trifluoromethylphenyl)-4-trifluoro-methylthiopyrazole (1000815-85-9)

Conditions	Yield
Stage #1: Trifluoromethylsulfenyl chloride; 5-amino-1-(2-chloro-6-fluoro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile In dichloromethane at 0 - 25℃; Stage #2: With sodium hydrogencarbonate In dichloromethane; water	86%

2,5-DIMETHYLTHIOPHENE (638-02-8) + Trifluoromethylsulfenyl chloride (421-17-0) → 2,5-dimethyl-3-trifluoromethylsulfanyl-thiophene (60830-50-4)

Conditions	Yield
tin(IV) chloride	86%
tin(IV) chloride	86%

Trifluoromethylsulfenyl chloride (421-17-0) + silver-2,3,4,5-tetrakis(trifluoromethylsulfanyl)-1H-pyrrolide (71940-96-0) → 1,2,3,4,5-Pentakis(trifluoromethylthio)pyrrole (87840-93-5)

Conditions	Yield
at 20℃; for 24h;	85%

Trifluoromethylsulfenyl chloride (421-17-0) + N-silver(I) succinimide (55047-82-0) → 1-((trifluoromethyl)thio)pyrrolidine-2,5-dione

Conditions	Yield
In diethyl ether 1) -78 deg C to 20 deg C, 16 h, 2) 20 deg C, 24 h;	85%

Trifluoromethylsulfenyl chloride (421-17-0) + 1,1,1-trifluoro-N-(3-methoxyphenyl)methanesulfonamide (23384-33-0) → N-(Trifluormethyl-sulfonyl)-4,6-bis-(trifluormethylthio)-3-methoxy-anilin (66476-52-6)

Conditions	Yield
In pyridine; chloroform -40°C;	85%
In pyridine; chloroform -40°C;	85%

Upstream product

• 993-38-4 chlorodifluoromethansulfenylchloride 
• 372-64-5 Bis(trifluoromethyl)disulfid 
• 6080-81-5 trifluoromethylmercapto carbamic acid chloride 
• 42016-33-1 N-Chlor-bis(fluorcarbonyl)-amin 
• 21259-75-6 mercury bis(trifluoromethanethiolate) 
• 7782-50-5 chlorine 
• 763-24-6 bis(trifluoromethylthio) amine 
• 10545-99-0 sulfur dichloride 
• 7647-01-0 hydrogenchloride 
• 60646-40-4 bis(trifluoromethyl)sulfimine 
• 185315-59-7 4-[(trifluoromethyl)thio]methyl-1-chlorobenzene 
• 1242101-33-2 anthracene bis-9,10-methyl trifluoromethyl sulfide 
• 1242101-30-9 (naphthalen-1-ylmethyl)(trifluoromethyl)sulfane 
• 13780-57-9 pentafluorosulfanyl chloride 

Downstream Products

• 75-46-7 trifluoromethan 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 372-64-5 Bis(trifluoromethyl)disulfid 
• 374-10-7 trifluoro(trifluoromethyl)sulfur(IV) 
• 461-84-7 (4-trifluoromethylthio)phenol 
• 75-36-5 acetyl chloride 
• 80413-22-5 2-Methyl-1,3-bis-trifluoromethylsulfanyl-indolizine 
• 1643-70-5 [(trifluoromethyl)disulfanyl]benzene 
• 709-96-6 2-methyl-4-(trifluoromethylthio)phenol 
• 183267-04-1 1-((trifluoromethyl)thio)pyrrolidine-2,5-dione 
• 75-72-9 chlorotrifluoromethane 
• 106285-01-2 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-dichlorofluoromethylsulphenyl-3-methyl-pyrazole 
• 825-83-2 4-trifluoromethylbenzenethiol 
• 71601-84-8 2,4,6-tris(trifluoromethylthio)phenol 

Relevant articles and documents

Bis(trifluormethylsulfanyl)carben (CF3S)2C:; Generierung und Nachweis

Irradiation of bis(trifluoromethylsulfanyl)ketene (2) with UV light in an Ar matrix at 10 K produces CO, CS2 and C2F6, which have been identified by infrared spectroscopy and interpreted as the decomposition products of bis(trifluoromethylsulfanyl)carbene (1).Irradiation of 2 in n-hexane at 283 K provides the bis(trifluoromethylsulfanyl)methyl radical (3) as an unstable intermediate by ESR spectroscopy.If 2 is irradiated neat or in C6F6 solution, small yields of (CF3S)2C=C(SCF3)2 (5) are obtained.The formation of 3 from 1 is discussed.

METHOD FOR PREPARATION OF PERFLUOROALKYL SULFENYL CHLORIDE

The present disclosure provides a process for the preparation of perfluoroalkyl sulfenyl chloride by reacting a compound of formula [I] with at least one fluoride compound and thiophosgene.

PROCESS FOR SYNTHESIS OF FIPRONIL

A process for preparation of a trifluoromethylsulfinyl pyrazole compound of formula (I) from a compound of formula (III) is provided, wherein R, R1 and R2 represent a group containing halogen respectively and R3 represents a perhaloalkyl.