mercury bis(trifluoromethanethiolate)
A
Bis(trifluoromethyl)disulfid
C
bis(trifluoromethylthio)tellurium
Conditions | Yield |
---|---|
With tellurium tetrachloride for 1h; Heating; | A n/a B n/a C 83% |
Conditions | Yield |
---|---|
390-420°C, atm. pessure in a continuous flow system; | 80.6% |
390-420°C, atm. pessure in a continuous flow system; | 80.6% |
>200°C, in autoclave; | |
>200°C, in autoclave; |
O,O-diethyl S-trifluoromethyl phosphorothioate
A
thiocarbonyl fluoride
B
diethyl fluorophosphate
C
Bis(trifluoromethyl)disulfid
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 10℃; for 0.166667h; | A n/a B 76% C n/a |
mercury bis(trifluoromethanethiolate)
dimethylamino sulfonyl chloride
A
Bis(trifluoromethyl)disulfid
Conditions | Yield |
---|---|
In acetonitrile | A n/a B 76% |
hydrogen fluoride
chlorothio-trichloro-methane
A
Trifluoromethylsulfenyl chloride
B
Bis(trifluoromethyl)disulfid
C
Trifluoro-methanethiosulfonic acid S-trifluoromethyl ester
Conditions | Yield |
---|---|
180°C; chrom oxide fluoride catalyst; | A 74% B n/a C n/a |
dimethyl(bromo)arsine
Copper(I) trifluoromethanethiolate
A
Bis(trifluoromethyl)disulfid
B
bis(trifluoromethyl)trisulfide
C
bis(trifluoromethyl)tetrasulfide
D
dimethyl(trifluoromethylthio)arsine
Conditions | Yield |
---|---|
at 80 - 90℃; for 6h; Further byproducts given; | A n/a B n/a C n/a D 70% |
Trifluoromethylsulfenyl chloride
toluene
A
Bis(trifluoromethyl)disulfid
B
benzyl trifluoromethyl sulfide
C
benzyl chloride
Conditions | Yield |
---|---|
byproducts: HCl; Irradiation (UV/VIS); | A n/a B 70% C 3% |
byproducts: HCl; Irradiation (UV/VIS); | A n/a B 70% C 3% |
for 0.283333h; Mechanism; Irradiation; effect of bis(heptafluoro-n-propyl) disulfide; |
Conditions | Yield |
---|---|
With hydrogen bromide In further solvent(s) 160-175°C; solvent: tetramethylenesulfone; | 68% |
With HBr In further solvent(s) 160-175°C; solvent: tetramethylenesulfone; | 68% |
Conditions | Yield |
---|---|
In further solvent(s) 150-160°C; solvent: tetramethylenesulfone; | 58% |
In further solvent(s) 150-160°C; solvent: tetramethylenesulfone; | 58% |
2-phenyl-1H-pyrrole
1-phenyl-2-(phenyl-λ3-iodaneylidene)-2-((trifluoromethyl)sulfonyl)ethan-1-one
A
Bis(trifluoromethyl)disulfid
Conditions | Yield |
---|---|
Stage #1: 1-phenyl-2-(phenyl-λ3-iodaneylidene)-2-((trifluoromethyl)sulfonyl)ethan-1-one With copper (II)-fluoride In 1-methyl-pyrrolidin-2-one at 20℃; for 0.333333h; Stage #2: 2-phenyl-1H-pyrrole at 20℃; for 5h; regioselective reaction; | A 28% B 58% |
Trifluoromethylsulfenyl chloride
sodium acetate
A
Bis(trifluoromethyl)disulfid
B
Trifluoro-methanethiosulfonic acid S-trifluoromethyl ester
C
trifluoromethyl-sulfenyl acetate
D
acetic anhydride
Conditions | Yield |
---|---|
at 0℃; for 12h; | A n/a B n/a C 52% D n/a |
tris(trifluoromethylmercapto)amine
A
Bis(trifluoromethyl)disulfid
B
tetrakis (trifluormethylmarcapto)-hydrazine
Conditions | Yield |
---|---|
In trichlorofluoromethane at -73.1℃; for 6h; Irradiation; | A n/a B 50% |
In trichlorofluoromethane at -73.1℃; for 6h; Product distribution; Irradiation; other temperature 298 deg K; | A n/a B 10 % Turnov. |
methyldichloroarsane
mercury bis(trifluoromethanethiolate)
A
methyldifluoroarsine
B
Bis(trifluoromethyl)disulfid
C
bis(trifluoromethyl)trithiocarbonate
Conditions | Yield |
---|---|
at 95 - 100℃; for 4h; | A n/a B n/a C n/a D 48% |
Trifluoromethylsulfenyl chloride
Isobutane
B
tertiary butyl chloride
C
2-methyl-2-[(trifluoromethyl)thio]propane
D
Bis(trifluoromethyl)disulfid
E
isobutyryl chloride
Conditions | Yield |
---|---|
byproducts: HCl; Irradiation (UV/VIS); | A 12% B 33% C 24% D 47% E 1% |
byproducts: HCl; Irradiation (UV/VIS); | A 12% B 33% C 24% D 47% E 1% |
Trifluoromethylsulfenyl chloride
n-butane
A
s-butyl chloride
B
n-Butyl chloride
C
Bis(trifluoromethyl)disulfid
D
Trifluormethyl-sek.-butyl-sulfid
E
1-[(trifluoromethyl)thio]butane
Conditions | Yield |
---|---|
byproducts: HCl; Irradiation (UV/VIS); | A 12% B 1% C 28% D 46% E 13% |
byproducts: HCl; Irradiation (UV/VIS); | A 12% B 1% C 28% D 46% E 13% |
Trifluoromethylsulfenyl chloride
cyclohexane
A
Bis(trifluoromethyl)disulfid
B
cyclohexyl(trifluoromethyl)sulfane
C
cyclohexyl chloride
Conditions | Yield |
---|---|
byproducts: HCl; Irradiation (UV/VIS); | A 35% B 45% C 28% |
byproducts: HCl; Irradiation (UV/VIS); | A 35% B 45% C 28% |
for 0.2h; Mechanism; Irradiation; effect of bis(heptafluoro-n-propyl) disulfide; |
Trifluoromethylsulfenyl chloride
dihydrogen peroxide
A
Bis(trifluoromethyl)disulfid
B
trifluorormethanesulfonic acid
C
trifluoromethane sulfonyl chloride
Conditions | Yield |
---|---|
35% H2O2 soln.; | A 35% B 7% C 40% |
35% H2O2 soln.; | A 35% B 7% C 40% |
Trifluoromethylsulfenyl chloride
A
Bis(trifluoromethyl)disulfid
B
tetrakis(trifluoromethylthiazyl)
Conditions | Yield |
---|---|
With trimethylsilylazide In trichlorofluoromethane at -30℃; for 24h; | A n/a B 37% |
furan
Trifluoromethylsulfenyl chloride
A
2-Trifluormethylmercapto-furan
B
Bis(trifluoromethyl)disulfid
Conditions | Yield |
---|---|
With pyridine at 20℃; for 12h; other sulfenyl chloride; | A 35% B n/a |
With pyridine at 20℃; for 12h; | A 35% B n/a |
Conditions | Yield |
---|---|
-183 to 25°C; | 30% |
-183 to 25°C; | 30% |
bis(fluorosulfuryl) peroxide
trifluoromethylsulfide
A
fluorosulfonyl anhydride
B
Bis(trifluoromethyl)disulfid
C
sulfur dioxide
D
sulfur
Conditions | Yield |
---|---|
CF3SH:S2O6F2 molar ratio 1:1, from -183 to +25°C; | A n/a B 30% C n/a D n/a |
ethylarsenic dichloride
Copper(I) trifluoromethanethiolate
A
Bis(trifluoromethyl)disulfid
B
trifluoromethylmercaptothiocarbonyl fluoride
C
bis(trifluoromethyl)trisulfide
Conditions | Yield |
---|---|
at 85 - 95℃; for 6h; Further byproducts given; | A n/a B n/a C n/a D 25% |
Conditions | Yield |
---|---|
Irradiation (UV/VIS); in Pyrex bulb; | A n/a B 25% |
Irradiation (UV/VIS); in Pyrex bulb; | A n/a B 25% |
Conditions | Yield |
---|---|
With sulfolane; potassium fluoride at 175℃; Inert atmosphere; | 15% |
Trifluoromethylsulfenyl chloride
A
Bis(trifluoromethyl)disulfid
B
hexachloro-3-cyclopentenylidenaminotrifluormethylsulfide
Conditions | Yield |
---|---|
With trimethylsilylazide; hexachlorocyclopentadiene In toluene at 110℃; under 0.01 Torr; for 3h; | A n/a B 6.2% |
Trifluoromethylsulfenyl chloride
trimethylsilylazide
hexachlorocyclopentadiene
A
Bis(trifluoromethyl)disulfid
B
hexachloro-3-cyclopentenylidenaminotrifluormethylsulfide
Conditions | Yield |
---|---|
In toluene at 110℃; under 0.01 Torr; for 3h; | A n/a B 6.2% |
Conditions | Yield |
---|---|
With iodine pentafluoride at 195℃; | |
With mercury(II) fluoride at 500℃; |
Conditions | Yield |
---|---|
With sulfur at 310℃; |
Conditions | Yield |
---|---|
With sulfur tetrafluoride at 250℃; |
Conditions | Yield |
---|---|
iron pentacarbonyl In tetrahydrofuran at -80℃; | |
With perfluoropropylene for 72h; Irradiation; | |
With trifluoro-methoxy-ethene for 0.166667h; Irradiation; Further byproducts given; |
propene
Bis(trifluoromethyl)disulfid
1,2-Bis-trifluoromethylsulfanyl-propane
Conditions | Yield |
---|---|
Irradiation (UV/VIS); 20 h; | 100% |
Irradiation (UV/VIS); 20 h; | 100% |
Irradiation; |
Conditions | Yield |
---|---|
Irradiation (UV/VIS); 44 h; | 100% |
Irradiation (UV/VIS); 44 h; | 100% |
Irradiation; |
Conditions | Yield |
---|---|
In 1,2-dimethoxyethane at -20℃; for 0.166667h; Reduction; | 98.3% |
Bis(trifluoromethyl)disulfid
benzyl tetraethylphosphorodiamidite
A
benzyl trifluoromethyl sulfide
Conditions | Yield |
---|---|
In pentane at -50℃; for 0.0833333h; | A 95% B n/a |
chlorine trifluoride
Bis(trifluoromethyl)disulfid
trifluoro(trifluoromethyl)sulfur(IV)
Conditions | Yield |
---|---|
In dichloromethane -78°C; | 95% |
In dichloromethane -78°C; | 95% |
In Dichlorodifluoromethane excess ClF3, -196 to -78°C; | |
In Dichlorodifluoromethane excess ClF3, -196 to -78°C; |
perfluoropropylene
Bis(trifluoromethyl)disulfid
A
2,5-bis(trifluoromethylmercapto)-4-trifluoromethyl-nonafluoropentane
B
1,2-bis(trifluoromethylsulfanyl)hexafluoropropane
Conditions | Yield |
---|---|
Irradiation (UV/VIS); 184 h; | A 90.5% B 9.5% |
Irradiation (UV/VIS); 184 h; | A 90.5% B 9.5% |
Bis(trifluoromethyl)disulfid
A
Ethyl <(trifluoromethyl)thio>acetate
Conditions | Yield |
---|---|
In pentane at -50℃; for 0.0833333h; | A 90% B n/a |
Bis(trifluoromethyl)disulfid
A
Ethyl 2-<(trifluoromethyl)thio>propanoate
Conditions | Yield |
---|---|
In pentane at -50℃; for 0.0833333h; | A 90% B n/a |
Bis(trifluoromethyl)disulfid
Tetrakis(trifluoromethyl)cyclotetraphosphane
A
Trifluormethyl-(bis-methylmercapto)-phosphin
B
pentakis-trifluoromethyl-cyclopentaphosphane
Conditions | Yield |
---|---|
143°C, 1 h; | A 90% B n/a |
143°C, 1 h; | A 90% B n/a |
20°C, 12 h; | |
20°C, 12 h; |
tetrakis(triphenylphosphine) palladium(0)
Bis(trifluoromethyl)disulfid
Pd(SCF3)2{P(C6H5)3}2
Pd(SCF3)2{P(C6H5)3}2
Conditions | Yield |
---|---|
In pentane Irradiation (UV/VIS); with low-pressure mercury lamp, 25°C, 30 min; | A 10% B 90% |
In pentane Irradiation (UV/VIS); with low-pressure mercury lamp, 25°C, 30 min; | A 10% B 90% |
Bis(trifluoromethyl)disulfid
fluorine
trifluoro(trifluoromethyl)sulfur(IV)
Conditions | Yield |
---|---|
fluorination with F2/He (flow rate 1 mL/min F2 and 60 mL min He) in continuous flow reactor at -120°C (38 h); | 90% |
fluorination with F2/He (flow rate 1 mL/min F2 and 60 mL min He) in continuous flow reactor at -120°C (38 h); | 90% |
with N2 dild. F2 used; | |
with N2 dild. F2 used; |
Conditions | Yield |
---|---|
In pentane Irradiation (UV/VIS); medium-pressure mercury lamp, 25 h; | 90% |
In pentane Irradiation (UV/VIS); medium-pressure mercury lamp, 25 h; | 90% |
dimanganese decacarbonyl
Bis(trifluoromethyl)disulfid
A
Mn2(CO)8(SCF3)2
B
CF3SMn(CO)5
Conditions | Yield |
---|---|
In pentane Irradiation (UV/VIS); medium-pressure mercury lamp, -10°C, 24 h; | A 90% B n/a |
In pentane Irradiation (UV/VIS); medium-pressure mercury lamp, -10°C, 24 h; | A 90% B n/a |
Conditions | Yield |
---|---|
heating at 425-435°C, 3-4 d; | 88% |
Irradiation (UV/VIS); in quartztube, 13 d; | 39% |
Irradiation (UV/VIS); in quartztube, 13 d; | 39% |
Irradiation.UV-Licht; |
Bis(trifluoromethyl)disulfid
(Rp)-t-butyl(phenyl)phosphine oxide
(-)-S-t-butyl(phenyl)-S-trifluoromethyl phosphinothioate
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 6h; | 88% |
hydrido(tricarbonyl)(cyclopentadienyl)molybdenum
Bis(trifluoromethyl)disulfid
Conditions | Yield |
---|---|
In benzene byproducts: HSCF3; (N2 or in vacuum with Schlenk-technique); react. at 25°C for 2 d; chromy. on SiO2-column with benzene/cyclohexane; | 87.3% |
Bis(trifluoromethyl)disulfid
tert-Butylphenylphosphine oxide
Conditions | Yield |
---|---|
In dichloromethane -85 to -80 deg C, 30 min, then 15-20 deg C, 5 h; | 85% |
Bis(trifluoromethyl)disulfid
2-diethylamino-1,3,2-dioxaphosphorinane
Conditions | Yield |
---|---|
In dichloromethane -85 to -80 deg C, 30 min, then 15-20 deg C, 5 h; | 85% |
Bis(trifluoromethyl)disulfid
Conditions | Yield |
---|---|
With cesium fluoride In 1,2-dimethoxyethane at 85℃; for 24h; Inert atmosphere; Sealed tube; | 84% |
Conditions | Yield |
---|---|
In dichloromethane -85 to -80 deg C, 30 min, then 15-20 deg C, 5 h; | 83% |
Conditions | Yield |
---|---|
With cesium fluoride In 1,2-dimethoxyethane at 110℃; for 48h; Inert atmosphere; Sealed tube; | 83% |
Bis(trifluoromethyl)disulfid
Conditions | Yield |
---|---|
With cesium fluoride In 1,2-dimethoxyethane at 110℃; for 37h; Inert atmosphere; Sealed tube; | A n/a B 82% |
Conditions | Yield |
---|---|
In dichloromethane -85 to -80 deg C, 30 min, then 15-20 deg C, 5 h; | 81% |
Bis(trifluoromethyl)disulfid
4-methoxy-N-(8-quinolinyl)benzamide
N-(2,6-di(trifluoromethylthio)-4-methoxybenzoyl)-8-aminoquinoline
Conditions | Yield |
---|---|
With copper diacetate In dimethyl sulfoxide at 100℃; for 5.75h; | 81% |
Bis(trifluoromethyl)disulfid
4-methoxy-aniline
4-methoxyphenyl trifluoromethylsulfide
Conditions | Yield |
---|---|
Stage #1: 4-methoxy-aniline With tetrafluoroboric acid; tert.-butylnitrite In water; acetic acid at 20℃; for 0.0833333h; Green chemistry; Stage #2: Bis(trifluoromethyl)disulfid With sodium acetate In dimethyl sulfoxide at 20℃; for 8h; Inert atmosphere; Green chemistry; | 81% |
Stage #1: 4-methoxy-aniline With tetrafluoroboric acid; sodium nitrite In water at 0℃; for 0.666667h; Stage #2: Bis(trifluoromethyl)disulfid With tris(bipyridine)ruthenium(II) dichloride hexahydrate In dimethyl sulfoxide at 20℃; for 1h; Reagent/catalyst; Inert atmosphere; Irradiation; | 131.2 mg |
Bis(trifluoromethyl)disulfid
Conditions | Yield |
---|---|
With cesium fluoride In 1,2-dimethoxyethane at 110℃; for 46h; Inert atmosphere; Sealed tube; | 81% |
Bis(trifluoromethyl)disulfid
phosphorous acid trimethyl ester
A
methyl trifluoromethyl sulphide
B
O,O-dimethyl-S-trifluoromethyl phosphorthioate
Conditions | Yield |
---|---|
In dichloromethane 1) -75 deg C, 2) 20 deg C, 50 min; | A n/a B 80% |
In dichloromethane -75 to 20°C; | A n/a B 80% |
In dichloromethane -75 to 20°C; | A n/a B 80% |
Bis(trifluoromethyl)disulfid
Conditions | Yield |
---|---|
In dichloromethane a soln. of Mo-complex and CF3SSCF3 was stirred under N2 at room temp. for 2 h (IR monitoring); solvent was removed by evapn. under a stream of N2, product purified by chromy. on Al2O3 and crystn.; | 80% |
Bis(trifluoromethyl)disulfide ,its CAS register number is 372-64-5,it's also named as Bis(trifluoromethyl)-disulfid ; Di(methyl) disulfide, perfluoro- ; Di(Trifluoromethyl)disulfide ; Disulfide, bis(trifluoromethyl) ; Hexafluorodimethyldisulfide ; Perfluorodimethyl disulfide;perfluorodimethyldisulfide ; Trifluoromethyl disulfide ; CID67795 ; ZINC04329251 ; LS-63073 ,and so on.
IUPAC Name: Trifluoro(trifluoromethyldisulfanyl)methane
CAS: 372-64-5
Molecular Formula: C2F6S2
Molecular Weight: 202.14
Molecular structure:
ACD/LogD (pH 5.5): 5.75
ACD/LogD (pH 7.4): 5.75
ACD/BCF (pH 5.5): 13799.75
ACD/BCF (pH 7.4): 13799.75
ACD/KOC (pH 5.5): 31982.18
ACD/KOC (pH 7.4): 31982.18
H bond acceptors: 0
H bond donors: 0
Freely Rotating Bonds: 1
Index of Refraction: 1.378
Molar Refractivity: 28.22 cm3
Molar Volume: 122.2 cm3
Polarizability: 11.18 10-24cm3
Surface Tension: 20.5 dyne/cm
Density: 1.653 g/cm3
Enthalpy of Vaporization: 26.81 kJ/mol
Boiling Point: 34.6 °C at 760 mmHg
Vapour Pressure: 538 mmHg at 25°C
Bis(trifluoromethyl)disulfide (CAS No.372-64-5) is commonly used as chemical reagent.
Mixtures of the solid with chlorine mono- or tri- fluorides are explosive. Dilute with halogenated solvents. When heated to decomposition it emits toxic fumes of F− and SOx.
Hazard Codes: T
Risk Statements: 23/24/25 (R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.)
Safety Statements: 23-36/37/39-45 (S23:Do not breathe vapour. S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.))
RIDADR: 2810
Hazard Note: Highly Toxic
Removal in wastewater treatment of Bis(trifluoromethyl)disulfide (CAS No.372-64-5) can be stated as follows:
Total removal:96.99 percent
Total biodegradation:0.06 percent
Total sludge adsorption:12.51 percent
Total to Air:84.42 percent
(using 10000 hr Bio P,A,S)
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