Trifluoromethylsulfenyl chloride
water
chlorine
trifluoromethane sulfonyl chloride
Conditions | Yield |
---|---|
excess of Cl2 and H2O, 20°C, 7 days; | 98% |
excess of Cl2 and H2O, 20°C, 7 days; | 98% |
Conditions | Yield |
---|---|
260°C, 2 h; | 94% |
260°C, 2 h; | 94% |
Conditions | Yield |
---|---|
With thionyl chloride; N,N-dimethyl-formamide at 40℃; for 12h; Cooling with ice; Green chemistry; | 87.5% |
With phosphorus pentachloride at 100℃; | 85% |
With phosphorus pentachloride |
methanol
trans-chlorotetrafluoro(trifluoromethyl)sulfur(VI)
trifluoromethane sulfonyl chloride
Conditions | Yield |
---|---|
in presence of (CH3)4N, 25°C, 10 h; | 75% |
in presence of (CH3)4N, 25°C, 10 h; | 75% |
chlorine
pentafluoroethanesulfinic acid
trifluoromethane sulfonyl chloride
Conditions | Yield |
---|---|
In acetic acid chlorination; | 74.6% |
In acetic acid chlorination; | 74.6% |
Conditions | Yield |
---|---|
With chlorine In water at 5℃; under 3040 Torr; for 2h; | 70% |
(Dichloroiodo)benzene
pentafluoroethanesulfinic acid
trifluoromethane sulfonyl chloride
Conditions | Yield |
---|---|
chlorination; | 65.7% |
chlorination; | 65.7% |
trifluorormethanesulfonic acid
phosphorus pentachloride
A
trifluoromethane sulfonyl chloride
B
trichlorophosphate
Conditions | Yield |
---|---|
A 63% B n/a | |
A 63% B n/a |
zinc trifluoromethanesulfonate
zinc(II) chloride
trifluoromethane sulfonyl chloride
Conditions | Yield |
---|---|
anhydr. ZnCl2, heating, Fischer burner, 4 h; fractional distn.; | 43% |
anhydr. ZnCl2, heating, Fischer burner, 4 h; fractional distn.; | 43% |
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% |
trans-chlorotetrafluoro(trifluoromethyl)sulfur(VI)
sodium methylate
trifluoromethane sulfonyl chloride
Conditions | Yield |
---|---|
25°C, 10 h; | 30% |
25°C, 10 h; | 30% |
Conditions | Yield |
---|---|
With water; chlorine |
trifluoromethylsulfinyl chloride
trifluoromethane sulfonyl chloride
Conditions | Yield |
---|---|
With water |
trifluoromethanesulfinyl fluoride
A
Trifluoromethylsulfenyl chloride
B
trifluoromethane sulfonyl chloride
C
trifluoromethylsulfinyl chloride
Conditions | Yield |
---|---|
With hydrogenchloride at -183℃; |
zinc trifluoromethanesulfonate
trifluoromethane sulfonyl chloride
Conditions | Yield |
---|---|
With PCl5*2ZnCl2 at 260℃; |
Conditions | Yield |
---|---|
With sulfur tetrafluoride; hydrogen fluoride; water; chlorine 1.) 80 deg C, 16 h, 2.) 20 deg C, 24 h, 40-50 deg C, 24 h; Yield given. Multistep reaction; |
trifluoromethylsulfonic anhydride
A
trifluoromethane sulfonyl chloride
B
seleninyl bis(trifluorometanesulfonate)
Conditions | Yield |
---|---|
With selenium oxychloride at 60℃; |
Conditions | Yield |
---|---|
With chlorine In water at 0 - 10℃; under 2250.2 Torr; for 2h; Yield given; |
trifluoromethanesulfonate
A
phosgene
B
trifluoromethane sulfonyl chloride
Conditions | Yield |
---|---|
distn.; |
trifluoromethylsulfonic anhydride
sodium chloride
trifluoromethane sulfonyl chloride
Conditions | Yield |
---|---|
In further solvent(s) solvent: tetramethylenesulfone, 3 h; |
Conditions | Yield |
---|---|
260°C, 2 h; | 80-85 |
260°C, 2 h; | 80-85 |
Trifluoromethanesulfonyl fluoride
chlorine
hydrazine
trifluoromethane sulfonyl chloride
Conditions | Yield |
---|---|
In further solvent(s) redn. of 95% N2H4 in CFCl2CF2Cl at 0-10°C, after addn. of Cl2; |
trifluoromethylsulfinyl chloride
water
A
Trifluoromethylsulfenyl chloride
B
trifluoromethane sulfonyl chloride
trifluoromethyl hypochlorite
trifluoromethylsulfinyl chloride
A
thionyl chlorofluoride
B
carbon tetrafluoride
C
Carbonyl fluoride
D
chlorotrifluoromethane
E
trifluoromethane sulfonyl chloride
Conditions | Yield |
---|---|
25°C, 2 h; further products; | |
25°C, 2 h; further products; |
trans-chlorotetrafluoro(trifluoromethyl)sulfur(VI)
trifluoromethane sulfonyl chloride
Conditions | Yield |
---|---|
With NaOCH3 25°C, 10 h; | |
With CH3OH in presence of (CH3)3N, 25°C, 10 h; |
trifluoromethane sulfonyl chloride
Conditions | Yield |
---|---|
With water; chlorine at 10 - 30℃; under 73.5572 - 735.572 Torr; |
Conditions | Yield |
---|---|
With rhodium(III) chloride; sulfuryl dichloride; sulfuric acid; dihydrogen peroxide; urea at 65℃; for 12h; |
Conditions | Yield |
---|---|
With copper at 200℃; for 24h; | 100% |
With pyridine; copper dichloride In 1,4-dioxane at 100℃; for 1h; Inert atmosphere; Schlenk technique; | 8 %Spectr. |
3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-adenosine
trifluoromethane sulfonyl chloride
9-[3,5-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-2-trifluoromethylsulfonyloxy-β-D-arabinofuranosyl]-9H-purin-6-amine
Conditions | Yield |
---|---|
With dmap; triethylamine In pyridine at 0 - 20℃; for 3h; Esterification; | 100% |
trifluoromethane sulfonyl chloride
9-[3-O-benzoyl-5-O-(triphenylmethyl)-β-D-ribofuranosyl]-6-chloro-9H-purine
5'-O-trityl-3'-O-benzoyl-2'-O-trifluoromethanesulfonyl-6-chloropurine riboside
Conditions | Yield |
---|---|
With dmap In toluene | 100% |
With dmap In toluene |
(2-hydroxy-6-methoxy-naphthalen-1-yl)-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone
trifluoromethane sulfonyl chloride
trifluoro-methanesulfonic acid 6-methoxy-1-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-naphthalen-2-yl ester
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0℃; for 0.25h; | 100% |
With pyridine In dichloromethane at 0℃; for 0.25h; | 100% |
Stage #1: (2-hydroxy-6-methoxy-naphthalen-1-yl)-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone; trifluoromethane sulfonyl chloride With pyridine In dichloromethane for 0.5h; Stage #2: With water In dichloromethane | 100% |
7-hydroxy-8-nitro-1,2,4,5-tetrahydrobenzo[d]azepine-3-carboxylic acid tert-butyl ester
trifluoromethane sulfonyl chloride
7-nitro-8-trifluoromethanesulfonyloxy-1,2,4,5-tetrahydrobenzo[d]azepine-3-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
With triethylamine In acetone at 20℃; for 1h; | 100% |
With triethylamine In acetone at 0℃; for 0.5h; | 87% |
In acetone at 0 - 20℃; for 2h; Product distribution / selectivity; |
trifluoromethane sulfonyl chloride
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 4 - 15℃; for 17.25h; | 100% |
With N-ethyl-N,N-diisopropylamine In dichloromethane at 4 - 15℃; for 17.25h; | 100% |
trans-[4-(4-hydroxyphenyl)cyclohexyl]acetic methyl ester
trifluoromethane sulfonyl chloride
(trans)-methyl 2-(4-(4-(((trifluoromethyl)sulfonyl)oxy)phenyl)cyclohexyl)acetate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 4 - 15℃; for 17.25h; | 100% |
With N-ethyl-N,N-diisopropylamine In dichloromethane at 4 - 15℃; for 17.25h; | 100% |
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; |
9-(3,5-O-isopropylidene-β-L-xylofuranosyl)adenine
trifluoromethane sulfonyl chloride
9-(3,5-O-isopropylidene-2-O-triflyl-β-L-xylofuranosyl)adenine
Conditions | Yield |
---|---|
With pyridine at 20℃; | 100% |
trifluoromethane sulfonyl chloride
trifluoro-methanesulfonic acid 6-methoxy-1-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-naphthalen-2-yl ester
Conditions | Yield |
---|---|
Stage #1: (2-hydroxy-6-methoxy-naphthalen-1-yl)-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone With pyridine In dichloromethane at 0℃; Stage #2: trifluoromethane sulfonyl chloride In dichloromethane for 0.5h; Stage #3: With water In dichloromethane | 100% |
9-[2'-O-tert-butyldimethylsilyl-5'-O-(4,4'-dimethoxytrityl)-xylofuranosyl]adenine
trifluoromethane sulfonyl chloride
9-[2'-O-tert-butyldimethylsilyl-5'-O-(4,4'-dimethoxytrityl)-3'-O-trifluoromethanesulfonyl-xylofuranosyl]adenine
Conditions | Yield |
---|---|
With dmap In dichloromethane at 0℃; for 1h; | 100% |
trifluoromethane sulfonyl chloride
triethylamine
acetylacetone
3,3-dichloropentane-2,4-dione
Conditions | Yield |
---|---|
In dichloromethane 1:1 molar mixture of educts per acidic hydrogen, 20-25°C, 1 h; | 100% |
In dichloromethane 1:1 molar mixture of educts per acidic hydrogen, 20-25°C, 1 h; | 100% |
trifluoromethane sulfonyl chloride
triethylamine
malonic acid dimethyl ester
dimethyl 2,2-dichloromalonate
Conditions | Yield |
---|---|
In dichloromethane 1:1 molar mixture of educts per acidic hydrogen, 20-25°C, 1 h; | 100% |
In dichloromethane 1:1 molar mixture of educts per acidic hydrogen, 20-25°C, 1 h; | 100% |
trifluoromethane sulfonyl chloride
ethyl acetoacetate
triethylamine
ethyl 2,2-dichloroacetoacetate
Conditions | Yield |
---|---|
In dichloromethane 1:1 molar mixture of educts per acidic hydrogen, 20-25°C, 1 h; | 100% |
In dichloromethane 1:1 molar mixture of educts per acidic hydrogen, 20-25°C, 1 h; | 100% |
trifluoromethane sulfonyl chloride
triethylamine
methyl 2-cyanoacetate
methyl dichlorocyanoacetate
Conditions | Yield |
---|---|
In dichloromethane 1:1 molar mixture of educts per acidic hydrogen, 20-25°C, 1 h; | 100% |
In dichloromethane 1:1 molar mixture of educts per acidic hydrogen, 20-25°C, 1 h; | 100% |
trifluoromethane sulfonyl chloride
acetylacetone
3,3-dichloropentane-2,4-dione
Conditions | Yield |
---|---|
With 1,5-Diazabicyclo[5.4.0]undec-5-ene In dichloromethane 1:1 molar mixture of educts per acidic hydrogen, 20-25°C, 1 h; | 100% |
With 1,5-diazabicyclo(5.4.0)undec-5-ene In dichloromethane 1:1 molar mixture of educts per acidic hydrogen, 20-25°C, 1 h; | 100% |
trifluoromethane sulfonyl chloride
phosphonic acid diethyl ester
diethyl chlorophosphate
Conditions | Yield |
---|---|
With 1,5-Diazabicyclo[5.4.0]undec-5-ene In dichloromethane 1:1 molar mixture of educts per acidic hydrogen, 20-25°C, 1 h; | 100% |
With 1,5-diazabicyclo(5.4.0)undec-5-ene In dichloromethane 1:1 molar mixture of educts per acidic hydrogen, 20-25°C, 1 h; | 100% |
trifluoromethane sulfonyl chloride
malonic acid dimethyl ester
dimethyl 2,2-dichloromalonate
Conditions | Yield |
---|---|
With 1,5-Diazabicyclo[5.4.0]undec-5-ene In dichloromethane 1:1 molar mixture of educts per acidic hydrogen, 20-25°C, 1 h; | 100% |
With 1,5-diazabicyclo(5.4.0)undec-5-ene In dichloromethane 1:1 molar mixture of educts per acidic hydrogen, 20-25°C, 1 h; | 100% |
trifluoromethane sulfonyl chloride
ethyl acetoacetate
ethyl 2,2-dichloroacetoacetate
Conditions | Yield |
---|---|
With 1,5-Diazabicyclo[5.4.0]undec-5-ene In dichloromethane 1:1 molar mixture of educts per acidic hydrogen, 20-25°C, 1 h; | 100% |
With 1,5-diazabicyclo(5.4.0)undec-5-ene In dichloromethane 1:1 molar mixture of educts per acidic hydrogen, 20-25°C, 1 h; | 100% |
trifluoromethane sulfonyl chloride
methyl 2-cyanoacetate
methyl dichlorocyanoacetate
Conditions | Yield |
---|---|
With 1,5-Diazabicyclo[5.4.0]undec-5-ene In dichloromethane 1:1 molar mixture of educts per acidic hydrogen, 20-25°C, 1 h; | 100% |
With 1,5-diazabicyclo(5.4.0)undec-5-ene In dichloromethane 1:1 molar mixture of educts per acidic hydrogen, 20-25°C, 1 h; | 100% |
trifluoromethane sulfonyl chloride
diethyl malonate
A
diethyl dichloromalonate
B
trifluoromethanesulfinic acid
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 10 - 50℃; Mechanism; Reagent/catalyst; Solvent; | A 100% B n/a |
trifluoromethane sulfonyl chloride
1,2-diamino-benzene
p-toluenesulfonyl chloride
Conditions | Yield |
---|---|
With trifluoromethylsulfonic anhydride In dichloromethane at -78℃; | 100% |
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; for 0.25h; Inert atmosphere; | 99% |
With triethylamine | 91% |
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere; | 82% |
trifluoromethane sulfonyl chloride
hydroxy(phenyl)-λ3-iodanyl diphenylphosphinate
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 0.25h; | 99% |
trifluoromethane sulfonyl chloride
N-tosyl-(4-pentenyl)amine
N-(4-chloro-6,6,6-trifluorohexyl)-4-methylbenzenesulfonamide
Conditions | Yield |
---|---|
With dipotassium hydrogenphosphate; tris(1,10-phenanthroline)ruthenium(II) dichloride In acetonitrile at 25℃; for 15h; Reagent/catalyst; Solvent; Inert atmosphere; Irradiation; regioselective reaction; | 99% |
With dipotassium hydrogenphosphate; tris(1,10-phenanthroline)ruthenium(II) dichloride In acetonitrile at 25℃; for 15h; Catalytic behavior; Reagent/catalyst; Solvent; Photolysis; Inert atmosphere; regioselective reaction; | 32 mg |
trifluoromethane sulfonyl chloride
N-(but-3-en-1-yl)-4-chlorobenzamide
4-chloro-N-(3-chloro-5,5,5-trifluoropentyl)benzamide
Conditions | Yield |
---|---|
With dipotassium hydrogenphosphate; tris(1,10-phenanthroline)ruthenium(II) dichloride In acetonitrile at 25℃; for 15h; Inert atmosphere; Irradiation; Sealed tube; regioselective reaction; | 99% |
6-chloroindole
trifluoromethane sulfonyl chloride
Conditions | Yield |
---|---|
With 1,2,2,3,4,4-hexamethylphosphetane 1-oxide; phenylsilane In 1,4-dioxane at 40℃; Schlenk technique; Sealed tube; Inert atmosphere; | 99% |
With triphenylphosphine; sodium iodide In acetonitrile at 60℃; for 4h; Schlenk technique; Inert atmosphere; | 91% |
With phosphonic acid diethyl ester In acetonitrile at 90℃; for 10h; | 80% |
trifluoromethane sulfonyl chloride
5-methoxycarbonylindole
3-trifluoromethylsulfanyl-5,1H-indolecarboxylc acid methyl ester
Conditions | Yield |
---|---|
With 1,2,2,3,4,4-hexamethylphosphetane 1-oxide; phenylsilane In 1,4-dioxane at 40℃; Schlenk technique; Sealed tube; Inert atmosphere; | 99% |
With triphenylphosphine; sodium iodide In acetonitrile at 60℃; for 22h; Schlenk technique; Inert atmosphere; | 90% |
Conditions | Yield |
---|---|
With [5,10,15,20-tetraphenylporphyrin]cobalt(III) chloride; Langlois reagent In acetonitrile at 100℃; for 12h; Inert atmosphere; Sealed tube; | 99% |
trifluoromethane sulfonyl chloride
bis(trifluoromethane)sulfonimide lithium
Conditions | Yield |
---|---|
With lithium carbonate In acetonitrile Reagent/catalyst; | 98.8% |
The Trifluoromethanesulfonyl chloride, with the CAS registry number 421-83-0 and EINECS registry number 207-009-0, is a kind of lachrymatory chemical with the apperance of clear colorless to faintly colored liquid. And the molecular formula of this chemical is CClF3O2S.
The physical properties of Trifluoromethanesulfonyl chloride are as following: (1)ACD/LogP: 1.76; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.76; (4)ACD/LogD (pH 7.4): 1.76; (5)ACD/BCF (pH 5.5): 12.77; (6)ACD/BCF (pH 7.4): 12.77; (7)ACD/KOC (pH 5.5): 215.51; (8)ACD/KOC (pH 7.4): 215.51; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 42.52 Å2; (13)Index of Refraction: 1.359; (14)Molar Refractivity: 20.68 cm3; (15)Molar Volume: 93.8 cm3; (16)Polarizability: 8.2×10-24cm3; (17)Surface Tension: 28.6 dyne/cm; (18)Density: 1.795 g/cm3; (19)Enthalpy of Vaporization: 26.46 kJ/mol; (20)Boiling Point: 30.5 °C at 760 mmHg; (21)Vapour Pressure: 624 mmHg at 25°C.
Uses of Trifluoromethanesulfonyl chloride: It can react with 2-aziridin-1-yl-ethanol to produce 2-(1-aziridinyl)ethyl trifluoromethanesulfonate. This reaction will need reagent sodium hydride, and the solvent tetrahydrofuran. The reaction time is 4 hours with temperature of -80°C, and the yield is about 65%.
You should be cautious while dealing with this chemical. It reacts violently with water, and may also cause burns. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice; In case of accident or if you feel unwell, seek medical advice immediately (show label where possible).
You can still convert the following datas into molecular structure:
(1)SMILES: FC(F)(F)S(Cl)(=O)=O
(2)InChI: InChI=1/CClF3O2S/c2-8(6,7)1(3,4)5
(3)InChIKey: GRGCWBWNLSTIEN-UHFFFAOYAL
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