1493-13-6

Basic information

• Product Name: Trifluoromethanesulfonic acid
• Synonyms: Fluorad FC-24;Methanesulfonic acid, trifluoro-;trifluoromethanesulfonic;trifluoro-methanesulfonicaci;PERFLUOROMETHANESULFONIC ACID;PFC-MS;TRIFLUOROMETHANESULPHONIC ACID;TRIFLUOROMETHANESULFONIC ACID
• CAS NO: 1493-13-6
• Molecular Formula: CHF₃O₃S
• Molecular Weight: 150.0770496
• EINECS: 216-087-5
• Product Categories: straight chain compounds;Organic Fluorides;Organic AcidsVolumetric Solutions;Reference Material Potassium hydrogenphthalateTitration;Acid SolutionsChemical Synthesis;By Reference Material;Solutions for non-aqueous titrations;Synthetic Reagents;Titration;Volumetric Solutions;organofluorine compounds;Pharmaceutical intermediates
• Mol File: 1493-13-6.mol
• Article Data: 61

Chemical Properties

• Melting Point: -40 °C
• Boiling Point: 162 °C(lit.)
• Flash Point: None
• Appearance: slightly brown/Fuming Liquid
• Density: 1.696 g/mL at 25 °C(lit.)
• Vapor Density: 5.2 (vs air)
• Vapor Pressure: 8 mm Hg ( 25 °C)
• Refractive Index: n20/D 1.327(lit.)
• Storage Temp.: −20°C
• Solubility: Miscible in H₂O
• PKA: -14(at 25℃)
• Water Solubility: SOLUBLE
• Sensitive: Hygroscopic
• Stability: Stable. Incompatible with acids, alkalis, metals.
• Merck: 14,9676
• BRN: 1812100
• CAS DataBase Reference: Trifluoromethanesulfonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Trifluoromethanesulfonic acid(1493-13-6)
• EPA Substance Registry System: Trifluoromethanesulfonic acid(1493-13-6)

Safety Data

• Hazard Codes: C
• Statements: 21/22-35-10
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 2
• RTECS: PB2771000
• F: 3-10
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 1493-13-6(Hazardous Substances Data)

Usage

Chemical Description

Trifluoromethanesulfonic acid is an organic compound with the formula CF3SO3H.

InChI:InChI=1/CHF3.H2O3S/c2-1(3)4;1-4(2)3/h1H;4H,(H,1,2,3)

Synthetic route

[η5-C5Me5Ru(μ-SiPr)2Ru(OH2)-η5-C5Me5](OTf)2 + hydrogen (1333-74-0) → trifluorormethanesulfonic acid (1493-13-6) + C26H45Ru2S2(1+)*CF3O3S(1-)

Conditions	Yield
In dichloromethane; water at 20℃; for 1h; Schlenk technique; Inert atmosphere;	A n/a B 98%

Trifluoromethanesulfonyl fluoride (335-05-7) → trifluorormethanesulfonic acid (1493-13-6)

Conditions	Yield
With sulfuric acid Reagent/catalyst;	97.5%
at 100°C for 48 h;	50%
at 20°C for 48 h;	7%

sodium triflate (2926-30-9) → trifluorormethanesulfonic acid (1493-13-6)

Conditions	Yield
With sulfuric acid	97.1%

lithium trifluoromethanesulfonate (33454-82-9) → trifluorormethanesulfonic acid (1493-13-6)

Conditions	Yield
With sulfuric acid	96.8%

ferrocenium trifluoromethanesulfonate → ferrocene (102-54-5) + trifluorormethanesulfonic acid (1493-13-6)

Conditions	Yield
With C26H46ClO3Ru2S2(1+)*CF3O3S(1-); hydrogen In water at 20℃; under 760.051 Torr; for 1.2h; Catalytic behavior; Temperature; Reagent/catalyst; Inert atmosphere; Schlenk technique;	A 95% B n/a
With [(pentamethylcyclopentadienyl)Ru{PhP(C6H4-o-S)2}Ru(pentamethylcyclopentadienyl)](OTf)2; hydrogen In water at 20℃; under 760.051 Torr; for 20h;	A 87% B 86%
With [η5-C5Me5Ru(μ-SiPr)2Ru(OH2)-η5-C5Me5](OTf)2; hydrogen In methanol at 20℃; under 760.051 Torr; for 1.4h; Temperature; Reagent/catalyst; Solvent; Pressure; Schlenk technique;

chloroform (67-66-3) + Chlorine(I) trifluoromethanesulfonate (65597-24-2) → trifluorormethanesulfonic acid (1493-13-6) + trifluoromethylsulfonic anhydride (358-23-6)

Conditions	Yield
at 22℃; for 1h;	A n/a B 92%

(η5-C5H5)Re(NO)(PPh3)(COCH3) (82582-46-5) + trifluoromethylsulfonic anhydride (358-23-6) + potassium tert-butylate (865-47-4) → {(η5-C5H5)Re(NO)(PPh3)(vinylidene)}(CF3SO3) (82582-34-1) + trifluorormethanesulfonic acid (1493-13-6)

Conditions	Yield
In dichloromethane	A 88% B n/a

2,2,6,6-tetramethyl-piperidine (768-66-1) + (η5-C5H5)Re(NO)(PPh3)(COCH3) (82582-46-5) + trifluoromethylsulfonic anhydride (358-23-6) → {(η5-C5H5)Re(NO)(PPh3)(vinylidene)}(CF3SO3) (82582-34-1) + trifluorormethanesulfonic acid (1493-13-6)

Conditions

Yield

In dichloromethane (CF3SO2)2O added to a stirred soln. of CpRe(NO)(PPh3)(COCH3) in CH2Cl2 at -78°C, after 10 min addn. of TMP, stirring for 1 h at -78°C, (CF3SO2)2O added, after 10 min soln. warmed to room temp., filtration, solvent removed by rotary evapn.;; extn. (CHCl3), extract filtered, solvent removed by rotary evapn.; monitored by (1)H- and (31)P-NMR-spectroscopy (-80°C, CD2Cl2 or CH2Cl2, < 5 min);;

A 88% B n/a

(E)-1-(4-chlorophenyl)-N-(4-methoxyphenyl)methanimine + C26H22O3P(1+)*CF3O3S(1-) → trifluorormethanesulfonic acid (1493-13-6) + Triphenylphosphine oxide (791-28-6) + 4-(4-chlorophenyl)-1-(4-methoxyphenyl)-3-phenoxyazetidin-2-one

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 0.5h; Cyclization; decomposition;	A n/a B n/a C 75%

morpholine (110-91-8) + 1,2:3,4-di-O-isopropylidene-6-O-trifluoromethanesulfonyl-α-D-galactopyranose (71001-09-7) → trifluorormethanesulfonic acid (1493-13-6) + 1,2:3,4-di-O-isopropylidene-6-morpholino-α-D-galactopyranose (98979-39-6)

Conditions	Yield
In N,N-dimethyl-formamide for 24h; Ambient temperature;	A n/a B 74%

4-methylpiperidin (626-58-4) + 1,2:3,4-di-O-isopropylidene-6-O-trifluoromethanesulfonyl-α-D-galactopyranose (71001-09-7) → trifluorormethanesulfonic acid (1493-13-6) + 1,2:3,4-di-O-isopropylidene-6-(4-methylpiperidino)-α-D-galactopyranose

Conditions	Yield
In N,N-dimethyl-formamide for 24h; Ambient temperature;	A n/a B 67%

2,2,6,6-tetramethyl-piperidine (768-66-1) + (η5-C5H5)Re(NO)(PPh3)(COCH2(1-C10H7)) (115365-02-1) + trifluoromethylsulfonic anhydride (358-23-6) → sc-{(η5-C5H5)Re(NO)(PPh3)(CCH(1-C10H7))}(CF3SO3) (115365-04-3) + trifluorormethanesulfonic acid (1493-13-6)

Conditions	Yield
In dichloromethane react. monitored by (1)H- and (31)P-NMR-spectroscopy (-80°C, CD2Cl2 or CH2Cl2, < 5 min); elem. anal.; sc/ac-ratio>99:1;;	A 63% B n/a

N-(p-methoxybenzylidene)-p-toluidine (83306-66-5) + C21H20O3P(1+)*CF3O3S(1-) → trifluorormethanesulfonic acid (1493-13-6) + Triphenylphosphine oxide (791-28-6) + (3S,4R)-3-Methoxy-4-(4-methoxy-phenyl)-1-p-tolyl-azetidin-2-one

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 0.5h; Cyclization; decomposition;	A n/a B n/a C 61%

4-methoxy-N-[(1Z)-phenylmethylene]aniline (40339-42-2) + C26H22O3P(1+)*CF3O3S(1-) → trifluorormethanesulfonic acid (1493-13-6) + Triphenylphosphine oxide (791-28-6) + (3S,4R)-1-(4-Methoxy-phenyl)-3-phenoxy-4-phenyl-azetidin-2-one

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 0.5h; Cyclization; decomposition;	A n/a B n/a C 59%

1-indoline (496-15-1) + 1,2:3,4-di-O-isopropylidene-6-O-trifluoromethanesulfonyl-α-D-galactopyranose (71001-09-7) → trifluorormethanesulfonic acid (1493-13-6) + 1,2:3,4-di-O-isopropylidene-6-(indolino)-α-D-galactopyranose

Conditions	Yield
In N,N-dimethyl-formamide for 24h; Ambient temperature;	A n/a B 57%

1,2,3,4-tetrahydroisoquinoline (91-21-4) + 1,2:3,4-di-O-isopropylidene-6-O-trifluoromethanesulfonyl-α-D-galactopyranose (71001-09-7) → trifluorormethanesulfonic acid (1493-13-6) + 1,2:3,4-di-O-isopropylidene-6-(1,2,3,4-tetrahydroisoquinoline)-α-D-galactopyranose

Conditions	Yield
In N,N-dimethyl-formamide for 24h; Ambient temperature;	A n/a B 53%

N-(3-phenyl-2-propenylidene)-4-methoxyaniline (123525-44-0) + C26H22O3P(1+)*CF3O3S(1-) → trifluorormethanesulfonic acid (1493-13-6) + Triphenylphosphine oxide (791-28-6) + (3S,4R)-1-(4-Methoxy-phenyl)-3-phenoxy-4-((E)-styryl)-azetidin-2-one

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 0.5h; Cyclization; decomposition;	A n/a B n/a C 52%

p-methoxyphenylcarboxaldehyde N-(p-methoxyphenyl)imine (83306-67-6) + C26H22O3P(1+)*CF3O3S(1-) → trifluorormethanesulfonic acid (1493-13-6) + Triphenylphosphine oxide (791-28-6) + (3S,4R)-1,4-Bis-(4-methoxy-phenyl)-3-phenoxy-azetidin-2-one

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 0.5h; Cyclization; decomposition;	A n/a B n/a C 46%

N-(2-methyl-3-phenylprop-2-enylidene)-p-anisidine (94612-45-0, 100239-15-4, 106318-92-7, 108908-63-0) + C26H22O3P(1+)*CF3O3S(1-) → trifluorormethanesulfonic acid (1493-13-6) + Triphenylphosphine oxide (791-28-6) + (3S,4R)-1-(4-Methoxy-phenyl)-4-((E)-1-methyl-2-phenyl-vinyl)-3-phenoxy-azetidin-2-one

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 0.5h; Cyclization; decomposition;	A n/a B n/a C 45%

N-(p-methoxybenzylidene)-p-toluidine (83306-66-5) + C26H22O3P(1+)*CF3O3S(1-) → trifluorormethanesulfonic acid (1493-13-6) + Triphenylphosphine oxide (791-28-6) + (3S,4R)-4-(4-Methoxy-phenyl)-3-phenoxy-1-p-tolyl-azetidin-2-one

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 0.5h; Cyclization; decomposition;	A n/a B n/a C 41%

Trifluoromethylsulfenyl chloride (421-17-0) + dihydrogen peroxide (7722-84-1) → Bis(trifluoromethyl)disulfid (372-64-5) + trifluorormethanesulfonic acid (1493-13-6) + trifluoromethane sulfonyl chloride (421-83-0)

Conditions	Yield
35% H2O2 soln.;	A 35% B 7% C 40%
35% H2O2 soln.;	A 35% B 7% C 40%

trifluoromethanesulfonic acid ethyl ester (425-75-2) → trifluorormethanesulfonic acid (1493-13-6)

Conditions	Yield
at 150℃; Pyrolysis;

diethyl ether (60-29-7) + methyl trifluoromethanesulfonate (333-27-7) → ethyl methyl ether (540-67-0) + trifluoromethanesulfonic acid ethyl ester (425-75-2) + trifluorormethanesulfonic acid (1493-13-6)

Conditions	Yield
at 80℃; unter Luftausschluss;

trifluoromethanesulfonic acid ethyl ester (425-75-2) + benzene (71-43-2) → trifluorormethanesulfonic acid (1493-13-6) + ethylbenzene (100-41-4) + ortho-diethylbenzene (253185-02-3) + 9,10-dimethylanthracene (781-43-1)

3-methyl-4-penten-1-ol (51174-44-8) + phenylselenyl triflate (112238-64-9) → trifluorormethanesulfonic acid (1493-13-6) + (2S,3R)-3-Methyl-2-phenylselanylmethyl-tetrahydro-furan (109065-98-7) + (2S,3S)-3-Methyl-2-phenylselanylmethyl-tetrahydro-furan (109065-97-6)

Conditions	Yield
In dichloromethane at 0℃; for 0.25h; Mechanism; Product distribution;

trifluorormethanesulfonic acid (1493-13-6) → trifluoromethyl trifluoromethanesulfonate (3582-05-6)

Conditions	Yield
With pentafluoroethanesulfonic acid anhydride at 60℃; for 4h;	100%
With phosphorus pentoxide In neat (no solvent) at 80 - 180℃; Inert atmosphere;	66%
With phosphorus pentoxide at -78 - 110℃; Inert atmosphere;	56%

bis(diethylamino)dimethylsilane (4669-59-4) + trifluorormethanesulfonic acid (1493-13-6) → (diethylamino)dimethylsilyl-triflat (155166-24-8)

Conditions	Yield
In diethyl ether Ambient temperature;	100%

bis(diethylamino)chloromethylsilane (17891-70-2) + trifluorormethanesulfonic acid (1493-13-6) → C6H13ClF3NO3SSi

Conditions	Yield
In diethyl ether Ambient temperature;	100%

bis(diethylamino)dichlorosilane (18881-64-6) + trifluorormethanesulfonic acid (1493-13-6) → C5H10Cl2F3NO3SSi

Conditions	Yield
In diethyl ether Ambient temperature;	100%

tetrakis(dimethylamino)silane (1624-01-7) + trifluorormethanesulfonic acid (1493-13-6) → tris(dimethylamino)silyl triflate (155166-32-8)

Conditions	Yield
In diethyl ether Ambient temperature;	100%
In toluene for 0.5h; Ambient temperature;

tris(diethylamino)silane (15730-66-2) + trifluorormethanesulfonic acid (1493-13-6) → C9H21F3N2O3SSi

Conditions	Yield
In diethyl ether Ambient temperature;	100%

methyl-tris(diethylamino)silane (18418-65-0) + trifluorormethanesulfonic acid (1493-13-6) → C10H23F3N2O3SSi (154922-03-9)

Conditions	Yield
In diethyl ether Ambient temperature;	100%
In diethyl ether at 0℃; for 0.25h;

SiCl(NEt2)3 (15730-69-5) + trifluorormethanesulfonic acid (1493-13-6) → C9H20ClF3N2O3SSi

Conditions	Yield
In diethyl ether Ambient temperature;	100%

trifluorormethanesulfonic acid (1493-13-6) + tetraphenylsilane (1048-08-4) → Diphenylsilicium-bis(trifluormethansulfonat) (27607-80-3)

Conditions	Yield
In chloroform at 0℃;	100%

trifluorormethanesulfonic acid (1493-13-6) + bis(diethylamino)(methyl)(vinyl)silane (18023-34-2) → C8H16F3NO3SSi

Conditions	Yield
In diethyl ether Ambient temperature;	100%

trifluorormethanesulfonic acid (1493-13-6) + diphenylsilane (775-12-2) → phenylsilanyl trifluoromethanesulfonate (127808-36-0)

Conditions	Yield
at 20℃;	100%
In toluene at 0℃; for 0.25h;	78%
In chloroform at 0℃; for 0.166667h; Yield given;
In dichloromethane at 0 - 20℃; for 0.5h;

trifluorormethanesulfonic acid (1493-13-6) + bis(diethylamino)(methyl)(phenyl)silane (1023-81-0) → CH3C6H5Si(C2H5)2NCF3SO3 (154922-06-2)

Conditions	Yield
In diethyl ether Ambient temperature;	100%
In diethyl ether at 0℃; for 0.25h;

trifluorormethanesulfonic acid (1493-13-6) + N-benzoyl-N-(α-benzoylbenzyl)aniline (81640-85-9) → 2,3,4,5-tetraphenyloxazolium trifluoromethanesulphonate (81640-37-1)

Conditions	Yield
	100%

trifluorormethanesulfonic acid (1493-13-6) + vinyl-tris(diethylamino)silane (61423-53-8) → C11H23F3N2O3SSi

Conditions	Yield
In diethyl ether Ambient temperature;	100%

trifluorormethanesulfonic acid (1493-13-6) + benzenetellurinic acid anhydride (94971-86-5) → benzenetellurinyl trifluoromethanesulfonate (122745-21-5)

Conditions	Yield
In dichloromethane for 0.5h; Ambient temperature;	100%

trifluorormethanesulfonic acid (1493-13-6) + (E)-2-(3-oxo-1,3-diphenylpropylidene)-3,4-dihydronaphthalen-1(2H)-one (35339-16-3) → 2,4-diphenyl-5,6-dihydro-7,8-benzochromenylium trifluoromethanesulphonate (76017-15-7)

Conditions	Yield
In ethanol 1.) 60 deg C, 4 h, 2.) 25 deg C, 12 h;	100%
In ethanol Heating;

trifluorormethanesulfonic acid (1493-13-6) + 1,1,2,2-tetraphenyl-1,2-di-tert-butyl-1,2-disilane (122131-73-1) → 1,2-di-tert-butyl-1,2-diphenyldisilane-1,2-bis(triflate) (155166-11-3)

Conditions	Yield
In toluene Ambient temperature;	100%

trifluorormethanesulfonic acid (1493-13-6) + C10H23F3N2O3SSi (154922-03-9) → C7H13F6NO6S2Si (155166-33-9)

Conditions	Yield
In diethyl ether Ambient temperature;	100%

trifluorormethanesulfonic acid (1493-13-6) + (Allyl-bis-diethylamino-silanyl)-diethyl-amine → C12H25F3N2O3SSi

Conditions	Yield
In diethyl ether Ambient temperature;	100%

trifluorormethanesulfonic acid (1493-13-6) + C9H21F3N2O3SSi → C6H11F6NO6S2Si

Conditions	Yield
In diethyl ether Ambient temperature;	100%

trifluorormethanesulfonic acid (1493-13-6) + tris(dimethylamino)silyl triflate (155166-32-8) → C6H12F6N2O6S2Si

Conditions	Yield
In diethyl ether Ambient temperature;	100%

trifluorormethanesulfonic acid (1493-13-6) + C9H20ClF3N2O3SSi → C6H10ClF6NO6S2Si

Conditions	Yield
In diethyl ether Ambient temperature;	100%

trifluorormethanesulfonic acid (1493-13-6) + C12H25F3N2O3SSi → C9H15F6NO6S2Si

Conditions	Yield
In diethyl ether Ambient temperature;	100%

trifluorormethanesulfonic acid (1493-13-6) + C11H23F3N2O3SSi → C8H13F6NO6S2Si

Conditions	Yield
In diethyl ether Ambient temperature;	100%

trifluorormethanesulfonic acid (1493-13-6) + 2,3-dihydro-2-(p-methoxybenzylthio)-1H-indolizinium chloride → 2,3-dihydro-2-metcapto-1H-indolizinium trifluoromethanesulfonate

Conditions	Yield
With trifluoroacetic acid In various solvent(s) for 1h; Ambient temperature;	100%

trifluorormethanesulfonic acid (1493-13-6) + 2,3-dihydro-1-(p-methoxybenzylthio)-1H-indolizinium p-toluenesulfonate → 2,3-dihydro-1-metcapto-1H-indolizinium trifluoromethanesulfonate

Conditions	Yield
With trifluoroacetic acid In various solvent(s) for 1h; Ambient temperature;	100%

trifluorormethanesulfonic acid (1493-13-6) + 1H-2,4,6-tri-isopropyl-1,3,5-triazinium triflate (86774-69-8) + 1,3-Dimethoxybenzene (151-10-0) → 2-(2,4-dimethoxyphenyl)-2,4,6-tri-isopropyl-1,2-dihydro-1,3,5-triazinium triflate (86774-78-9)

Conditions	Yield
In benzene for 1.5h; Ambient temperature;	100%

trifluorormethanesulfonic acid (1493-13-6) + 1,1,2,2,3,3-hexaphenyltrisilane (18816-18-7) → 1,2,3-triphenyl-1,2,3-tris(trifluoromethansulfonyloxy)trisilan

Conditions	Yield
In toluene at 0℃; for 2h;	100%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + trifluorormethanesulfonic acid (1493-13-6) → N,N'-difluoro-1,4-diazoniabicyclo<2.2.2>octane bis(triflate)

Conditions	Yield
With fluorine In various solvent(s)	100%

trifluorormethanesulfonic acid (1493-13-6) + 1,3-Dibromo-1,3-di-p-tolyl-[1,3]disiletane → Trifluoro-methanesulfonic acid 1,3-dibromo-3-trifluoromethanesulfonyloxy-[1,3]disiletan-1-yl ester

Conditions	Yield
In diethyl ether; toluene for 1h; Ambient temperature;	100%

Upstream product

• 335-05-7 Trifluoromethanesulfonyl fluoride 
• 110-89-4 piperidine 
• 71001-09-7 1,2:3,4-di-O-isopropylidene-6-O-trifluoromethanesulfonyl-α-D-galactopyranose 
• 496-15-1 1-indoline 
• 67-66-3 chloroform 
• 65597-24-2 Chlorine(I) trifluoromethanesulfonate 
• 354-88-1 perfluoroethanesulfonic acid 
• 3582-05-6 trifluoromethyl trifluoromethanesulfonate 
• 74501-94-3 trifluoromethanesulfonate de pentafluoroethyle 
• 81324-89-2 methoxytriphenylphosphonium trifluoromethanesulfonate 
• 83306-67-6 p-methoxyphenylcarboxaldehyde N-(p-methoxyphenyl)imine 
• 72450-51-2 bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate salt 
• 625-45-6 2-methoxyacetic acid 
• 122-59-8 2-phenoxyacetic acid 

Downstream Products

• 421-83-0 trifluoromethane sulfonyl chloride 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 61836-02-0 ethoxycarbonylmethyl trifluoromethanesulfonate 
• 425-75-2 trifluoromethanesulfonic acid ethyl ester 
• 63780-71-2 trifluoromethanesulfonic acid 2,2,2-trifluoro-1-phenyl-1-trifluoromethyl-ethyl ester 
• 62861-51-2 phenacyl trifluoromethanesulfonate 
• 41029-44-1 isopropyl triflate 
• 60669-69-4 di-n-butylboryl trifluoromethanesulfonate 
• 72251-50-4 dicyclopentylboron trifluoromethanesulfonate 
• 27607-81-4 Phenylsilicium-tris(trifluormethansulfonat) 
• 27607-88-1 Tetrakis(trifluormethan-sulfonyloxy)-diphenyl-disiloxan 
• 335-05-7 Trifluoromethanesulfonyl fluoride 
• 3582-05-6 trifluoromethyl trifluoromethanesulfonate 
• 1885-46-7 trifluoromethanesulfonic acid difluoromethyl ether 

Relevant articles and documents

The vibrational spectrum of trifluoromethanesulphonic acid, CF3SO3H, and the determination of its degrees of discociation in aqueous solution by Raman spectroscopy

The Raman and i.r. spectra of trifluoromethanesulphonic acid, CF3SO3H, have been obtained, and vibrational assignments made which are consistent with Cs molecular symmetry.The degrees of dissociation of CF3SO3H in aqueous solution in the concentration range 1.8-11.1 M were determined from Raman intensity measurements on the Δν = 1034 cm-1 band characteristic of the CF3SO3- ion.The results confirm that CF3SO3H is more dissociated into CF3SO3- ions than CH3SO3H is into CH3SO3- at similar concentrations.A limiting value of Kc = 280 mol dm-3 is calculated for low acid concentrations of CF3SO3H.

Thermodynamics of methanesulfonic acid revisited

Recently we reported a study of the thermodynamics of methanesulfonic acid and some of its derivatives. The foundation of these results was a measurement of the heat of reaction of S-methyl thioacetate with aq sodium hypochlorite, leading to methanesulfonic acid. We have reinvestigated this reaction and discovered that contrary to the initial stoichiometry experiments, the stoichiometry under the reaction conditions is not as was believed and that the heat of reaction observed was spuriously high. We have found a new reaction, that of sulfite ion with methyl methanesulfonate, which does allow a clean determination of the heat of formation of methanesulfonic acid. Revised thermodynamic quantities for methanesulfonic acid, methanesulfonyl chloride, and methyl methanesulfonate are reported here.

SYNTHESIS OF TRIFLUOROMETHANESULFONATE ESTERS BY REATION OF ALKYL CHLORIDES WITH CHLORINE (I) AND BROMINE (I) TRIFLUOROMETHANESULFONATE

The synthesis of the first trifluoromethanesulfonate esters of the type CF3SO3(CH2)nO3SCF3(n=1,2,3) are reported.The new compounds are prepared from Cl(CH2)nCl by substitutive electrophilic dehalogenation reactions with CF3SO2OX (x=Cl,Br).The extension of this reaction to HCCl3 results in HC(O3SCF3)3 but the compound is unstable at 22 deg.

Remarkable Acid Catalysis in Proton-Coupled Electron-Transfer Reactions of a Chromium(III)-Superoxo Complex

Much enhanced acid catalysis was observed in oxygen atom transfer (OAT) reactions by a mononuclear nonheme Cr(III)-superoxo complex, [(Cl)(TMC)CrIII(O2)]+ (1), in the presence of triflic acid. In the acid-catalyzed reactions, the reactivity of 1 in OAT of thioanisole was enhanced significantly, showing more than 104-fold acceleration in rate. Electron transfer (ET) from electron donors to 1 also occurred only in the presence of HOTf. The enhanced reactivity of 1 by HOTf was explained by proton-coupled electron transfer from electron donors, such as ferrocene, to 1 in light of the Marcus theory of ET. The present study reports for the first time the dramatic proton effect on the chemical properties of metal-superoxo species.

Synthesis of trifluoromethanesulfonic acid from CHF3

Trifluoromethane is transformed to trifluoromethanesulfonic acid (TFMSA) at low temperature in a liquid-phase reaction in a strong acid such as fuming sulfuric acid as well as in a strong basic solution such as t-BuOK/DMF.

PROCESS FOR THE PREPARATION OF HALOALKANESULFONIC ACIDS FROM SULFUR TRIOXIDE AND A HALOALKANE

The present invention relates to a process for preparing haloalkanesulfonic acids from sulfur trioxide and a haloalkane, particularly to a process for preparing trifluoromethane sulfonic acid from sulfur trioxide and trifluoromethane.

Water determines the products: An unexpected Br?nsted acid-catalyzed PO-R cleavage of P(iii) esters selectively producing P(O)-H and P(O)-R compounds

Water is found able to determine the selectivity of Br?nsted acid-catalyzed C-O cleavage reactions of trialkyl phosphites: with water, the reaction quickly takes place at room temperature to afford quantitative yields of H-phosphonates; without water, the reaction selectively affords alkylphosphonates in high yields, providing a novel halide-free alternative to the famous Michaelis-Arbuzov reaction. This method is general as it can be readily extended to phosphonites and phosphinites and a large scale reaction with much lower loading of the catalyst, enabling a simple, efficient, and practical preparation of the corresponding organophosphorus compounds. Experimental findings in control reactions and substrate extension as well as preliminary theoretical calculation of the possible transition states all suggest that the monomolecular mechanism is preferred.