1544-53-2

Basic information

• Product Name: 2,2,2-TRIFLUOROETHANETHIOL
• Synonyms: 2,2,2-TRIFLUOROETHANETHIOL;2,2,2-TRIFLUOROETHANETHIOL 95%;2,2,2-Trifluoroethanthiol
• CAS NO: 1544-53-2
• Molecular Formula: C₂H₃F₃S
• Molecular Weight: 116.11
• Product Categories: Organic Building Blocks;Sulfur Compounds;Thiols/Mercaptans;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfur Compounds
• Mol File: 1544-53-2.mol
• Article Data: 10

Chemical Properties

• Melting Point: 51.3-52.3 °C
• Boiling Point: 34-35 °C(lit.)
• Flash Point: −11 °F
• Appearance: /
• Density: 1.305 g/mL at 25 °C(lit.)
• Vapor Pressure: 7.85 psi ( 20 °C)
• Refractive Index: n20/D 1.352(lit.)
• PKA: 7.60±0.10(Predicted)
• CAS DataBase Reference: 2,2,2-TRIFLUOROETHANETHIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,2-TRIFLUOROETHANETHIOL(1544-53-2)
• EPA Substance Registry System: 2,2,2-TRIFLUOROETHANETHIOL(1544-53-2)

Safety Data

• Hazard Codes: F+,Xn
• Statements: 12-20/21/22-36/37/38
• Safety Statements: 16-33-38
• RIDADR: UN 3336 3/PG 1
• WGK Germany: 3
• HazardClass: 3.1
• PackingGroup: I
• Hazardous Substances Data: 1544-53-2(Hazardous Substances Data)

Usage

General Description

2,2,2-Trifluoroethanethiol is basic in nature and forms charge transfer complexes with molecular iodine.

InChI:InChI=1/C2H3F3S/c3-2(4,5)1-6/h6H,1H2

Synthetic route

2,2,2-trifluoroethylthiomethylbenzene (77745-03-0) → 2,2,2-trifluoroethanethiol (1544-53-2)

Conditions	Yield
With phosphorus pentoxide at 150 - 180℃;	95%
With methanesulfonic acid at 180℃; for 0.75h;

S-(2,2,2-trifluoroethyl) ethanethioate (14897-48-4) → 2,2,2-trifluoroethanethiol (1544-53-2)

Conditions	Yield
With sodium; ethylene glycol for 2h; Inert atmosphere; Reflux;	72%
With benzylamine at 150℃;	58%

2,2,2-Trifluoroacetaldehyde (75-90-1) → 2,2,2-trifluoroethanethiol (1544-53-2)

Conditions	Yield
With hydrogen sulfide at 200℃;

S-(2,2,2-trifluoroethyl) ethanethioate (14897-48-4) → 2,2,2-trifluoroethanethiol (1544-53-2) + acetic acid (64-19-7)

Conditions	Yield
With water at 25℃; Equilibrium constant;

Pyridine 1-oxide; compound with 2,2,2-trifluoro-ethanethiol → pyridine N-oxide (694-59-7) + 2,2,2-trifluoroethanethiol (1544-53-2)

Conditions	Yield
In cyclohexane at 23.3℃; Equilibrium constant;

3,4-Dinitro-phenol; compound with 2,2,2-trifluoro-ethanethiol → 2,2,2-trifluoroethanethiol (1544-53-2) + 3,4-dinitophenol (577-71-9)

Conditions	Yield
In cyclohexane at 23.3℃; Equilibrium constant;

2-(morpholin-4-yl)ethanol (622-40-2) + 2-(6-Methoxy-naphthalen-2-yl)-thiopropionic acid S-(2,2,2-trifluoro-ethyl) ester → 2,2,2-trifluoroethanethiol (1544-53-2) + (2S)-2-(6-methoxy(2-naphthyl))propanoic acid (22204-53-1) + (R)-2-(6-methoxy-2-naphthyl)propionic acid (23979-41-1) + (S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid 2-morpholin-4-yl-ethyl ester + (R)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid 2-morpholin-4-yl-ethyl ester

Conditions	Yield
With Lipase MY In 2,2,4-trimethylpentane at 37℃; for 105h; Product distribution; Mechanism; other naproxen and ibuprofen thioesters; also Candida rugosa lipase as catalyst; var. solvents and time;

2,2,2-Trifluoro-ethanethiol; compound with iodine → 2,2,2-trifluoroethanethiol (1544-53-2) + I2

Conditions	Yield
In cyclohexane at 25℃; Equilibrium constant;

2,2,2-Trifluoroethyl p-toluenesulfonate (433-06-7) → 2,2,2-trifluoroethanethiol (1544-53-2) + bis(2,2,2-trifluoroethyl) disulfide (674-63-5) + Bis-(2,2,2-trifluorethyl)sulfid (674-62-4)

Conditions	Yield
With sodium hydrogen sulfide In 1-methyl-pyrrolidin-2-one at 80℃; under 966.916 Torr; for 3h;
With sodium hydrogen sulfide In 1-methyl-pyrrolidin-2-one at 90℃; for 3h; Reagent/catalyst; Solvent; Temperature; Pressure;

1,1,1-trifluoro-2-chloroethane (75-88-7) → 2,2,2-trifluoroethanethiol (1544-53-2) + bis(2,2,2-trifluoroethyl) disulfide (674-63-5) + Bis-(2,2,2-trifluorethyl)sulfid (674-62-4)

Conditions	Yield
With sodium hydrogen sulfide In 1-methyl-pyrrolidin-2-one at 90℃; under 1328.93 Torr; for 3h;
With sodium hydrogen sulfide In 1-methyl-pyrrolidin-2-one at 90℃; under 1328.93 Torr; for 3h; Solvent; Reagent/catalyst; Temperature;

2,2,2-trifluoroethanethiol (1544-53-2) + heptakis-(6-chloro-6-deoxy)-β-cyclodextrin (155953-27-8) → heptakis-6-deoxy-6-((2,2,2-trifluoroethyl)thio)-β-cyclodextrin (1237753-74-0)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 75℃; for 120h;	100%
Stage #1: 2,2,2-trifluoroethanethiol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: heptakis-(6-chloro-6-deoxy)-β-cyclodextrin In N,N-dimethyl-formamide; mineral oil at 70℃;	88%
Stage #1: 2,2,2-trifluoroethanethiol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: heptakis-(6-chloro-6-deoxy)-β-cyclodextrin In N,N-dimethyl-formamide; mineral oil at 70℃; for 120h;	88%

2-fluoro-5-(methylsulfonyl)benzoic acid (247569-56-8) + 2,2,2-trifluoroethanethiol (1544-53-2) → 5-Methanesulfonyl-2-(2,2,2-trifluoro-ethylsulfanyl)-benzoic acid

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 90℃; for 0.5h;	99%
With caesium carbonate In N,N-dimethyl-formamide at 90℃; for 0.5h;	99%
With caesium carbonate In N,N-dimethyl acetamide at 90℃; for 0.5h;	99%

2,2,2-trifluoroethanethiol (1544-53-2) + 2-Bromo-4'-methoxyacetophenone (2632-13-5) → C11H11F3O2S (948837-90-9)

Conditions	Yield
With potassium carbonate In ethanol at 20℃; for 20h;	99%

2,2,2-trifluoroethanethiol (1544-53-2) + 3-phenyl-5-chloroisoxazole (3356-89-6) → 3-phenyl-5-[(2,2,2-trifluoroethyl)sulfanyl]isoxazole

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 36h;	99%

N-(5-bromopentyl)phthalimide (954-81-4) + 2,2,2-trifluoroethanethiol (1544-53-2) → 5-N-phthalimido-1-pentyl 2’,2’,2’-trifluoroethyl sulfide (1584658-29-6)

Conditions	Yield
Stage #1: 2,2,2-trifluoroethanethiol With sodium methylate In methanol at 20℃; for 15h; Stage #2: N-(5-bromopentyl)phthalimide In methanol at 20℃; for 48h;	98%
Stage #1: 2,2,2-trifluoroethanethiol With sodium methylate In methanol at 0 - 20℃; for 0.25h; Inert atmosphere; Stage #2: N-(5-bromopentyl)phthalimide In 1,2-dimethoxyethane at 0 - 20℃; Inert atmosphere;	89%

4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2,5-difluorobenzonitrile (958031-87-3) + 2,2,2-trifluoroethanethiol (1544-53-2) → 4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-5-fluoro-2-[(2,2,2-trifluoroethyl)thio]benzonitrile (958031-88-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 2h;	97%

2,2,2-trifluoroethanethiol (1544-53-2) + hexakis(2,3,6-tri-O-allyl)-α-cyclodextrin → hexakis{2,3,6-tri-O-[(2,2,2-trifluoroethyl)thio]propyl}-α-cyclodextrin

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In N,N-dimethyl-formamide UV-irradiation;	95%

1,3-dithiane-2-carboxylic acid (20461-89-6) + 2,2,2-trifluoroethanethiol (1544-53-2) → 2,2,2-trifluoroethyl 2-[(1,3-dithian)-2-yl]-ethanthioate

Conditions	Yield
Stage #1: 1,3-dithiane-2-carboxylic acid With benzotriazol-1-ol In dichloromethane at 0℃; for 0.166667h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.5h; Stage #3: 2,2,2-trifluoroethanethiol In dichloromethane at 0 - 20℃;	95%
Stage #1: 1,3-dithiane-2-carboxylic acid With benzotriazol-1-ol In dichloromethane at 0℃; for 0.166667h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.5h; Stage #3: 2,2,2-trifluoroethanethiol In dichloromethane at 0 - 20℃;	95%

para-dinitrobenzene (100-25-4) + 2,2,2-trifluoroethanethiol (1544-53-2) → (4-nitrophenyl)(2,2,2-trifluoroethyl)sulfane

Conditions	Yield
With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 20℃; for 2h;	92%

2,2,2-trifluoroethanethiol (1544-53-2) + 4-tolyl iodide (624-31-7) → (2,2,2-trifluoroethyl) (4-methylphenyl) sulfide (62158-92-3)

Conditions	Yield
With pyridine; (1,2-dimethoxyethane)dichloronickel(II); Ir[dF(CF3)ppy]2(dtbbpy)PF6; 4,4′-di-(tert-butyl)-2,2′-bipyridyl In acetonitrile at 23 - 25℃; for 24h; Irradiation; chemoselective reaction;	92%

(triethylphosphine)chlorogold(I) (15529-90-5) + 2,2,2-trifluoroethanethiol (1544-53-2) → (2,2,2-trifluoroethanethiolato)(triethylphosphine) gold(I)

Conditions	Yield
With sodium methylate In methanol at 20℃;	92%

2,2,2-trifluoroethanethiol (1544-53-2) + bromoacetic acid methyl ester (96-32-2) → methyl 2-(2,2,2-trifluoroethylthio)acetate (675-81-0)

Conditions	Yield
Stage #1: 2,2,2-trifluoroethanethiol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.45h; Inert atmosphere; Stage #2: bromoacetic acid methyl ester In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;	91%

4-trifluoromethyl-nicotinic acid 3-bromopropylamide (750592-58-6) + 2,2,2-trifluoroethanethiol (1544-53-2) → 4-trifluoromethyl-nicotinic acid 3-bromopropylamide

Conditions	Yield
With sodium methylate In methanol at 20 - 50℃; for 6h;	90.1%

2,2,2-trifluoroethanethiol (1544-53-2) + (7-methylimidazo<1,2-a>pyridin-3-yl)methanol (29096-61-5) → 7-methyl-3-(2,2,2-trifluoro-ethylsulfanylmethyl)-imidazo[1,2-a]pyridine

Conditions	Yield
With acetic acid at 80℃; for 2h;	90%

2,2,2-trifluoroethanethiol (1544-53-2) + (tetramethylammonium)2[Fe4S4(methanethiolato)4] → (tetramethylammonium)2[Fe4S4(2,2,2-trifluoroethanethiolato)4]

Conditions	Yield
In tetrahydrofuran for 16h; Schlenk technique; Glovebox; Inert atmosphere; Reflux;	89%

N'-(2,5-dichloro-4-nitrophenyl)-N,N-diethyl-2,2,2-trifluoroethaneimideamide + 2,2,2-trifluoroethanethiol (1544-53-2) → N'-{2-chloro-4-nitro-5-[(2,2,2-trifluoroethyl)thio]phenyl}-N,N-diethyl-2,2,2-trifluoroethaneimideamide

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 15h;	87%

3-chloropivalic acid (13511-38-1) + 2,2,2-trifluoroethanethiol (1544-53-2) → 2,2-dimethyl-3-((2,2,2-trifluoroethyl)thio)propanoic acid

Conditions	Yield
Stage #1: 2,2,2-trifluoroethanethiol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; Stage #2: 3-chloropivalic acid In N,N-dimethyl-formamide; mineral oil at 20 - 24℃;	87%

2-(4-bromobutyl)isoindoline-1,3-dione (5394-18-3) + 2,2,2-trifluoroethanethiol (1544-53-2) → 4-N-phthalimido-1-butyl 2’,2’,2’-trifluoroethyl sulfide (1584658-28-5)

Conditions	Yield
Stage #1: 2,2,2-trifluoroethanethiol With sodium methylate In methanol at 0℃; for 0.25h; Inert atmosphere; Stage #2: 2-(4-bromobutyl)isoindoline-1,3-dione In methanol at 0 - 20℃; Inert atmosphere;	86%
Stage #1: 2,2,2-trifluoroethanethiol With sodium methylate In methanol at 0 - 20℃; for 0.25h; Inert atmosphere; Stage #2: 2-(4-bromobutyl)isoindoline-1,3-dione In 1,2-dimethoxyethane at 0 - 20℃; Inert atmosphere;	86%

2-bromohexanoic acid (616-05-7) + 2,2,2-trifluoroethanethiol (1544-53-2) → S-2,2,2-trifluoroethyl 2-bromohexanethioate (1309379-79-0)

Conditions	Yield
Stage #1: 2-bromohexanoic acid With benzotriazol-1-ol In dichloromethane at 0℃; for 0.166667h; Inert atmosphere; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #3: 2,2,2-trifluoroethanethiol In dichloromethane at 0 - 20℃; Inert atmosphere;	85%

2,2,2-trifluoroethanethiol (1544-53-2) + octakis(6-chloro-6-deoxy)-γ-cyclodextrin (173094-60-5) → octakis[6-deoxy-6-(2,2,2-trifluoroethyl)thio]-γ-cyclodextrin (1237753-77-3)

Conditions	Yield
Stage #1: 2,2,2-trifluoroethanethiol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: octakis(6-chloro-6-deoxy)-γ-cyclodextrin In N,N-dimethyl-formamide; mineral oil at 70℃; for 120h;	84%
Stage #1: 2,2,2-trifluoroethanethiol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: octakis(6-chloro-6-deoxy)-γ-cyclodextrin In N,N-dimethyl-formamide; mineral oil at 70℃;	82%

2,2,2-trifluoroethanethiol (1544-53-2) + 4-Cyanophenacyl bromide (20099-89-2) → 4-(2,2,2-trifluoroethylthiomethylcarbonyl)-benzonitrile (928650-41-3)

Conditions	Yield
Stage #1: 2,2,2-trifluoroethanethiol With sodium hydride In tetrahydrofuran at 0℃; for 0.25h; Stage #2: 4-Cyanophenacyl bromide In tetrahydrofuran at 20℃;	84%

(3,4-Dimethoxyphenyl)acetic acid (93-40-3) + 2,2,2-trifluoroethanethiol (1544-53-2) → S-2,2,2-trifluoroethyl 3,4-dimethoxyphenylthioacetate (1309379-76-7)

Conditions	Yield
Stage #1: (3,4-Dimethoxyphenyl)acetic acid With benzotriazol-1-ol In dichloromethane at 0℃; for 0.166667h; Inert atmosphere; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #3: 2,2,2-trifluoroethanethiol In dichloromethane at 0 - 20℃; Inert atmosphere;	84%

2,2,2-trifluoroethanethiol (1544-53-2) + 3-chloro-N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethylpropanamide (1374315-14-6) → N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((2,2,2-trifluoroethyl)thio)propanamide (1393662-58-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; sodium iodide In tetrahydrofuran at 50℃;	83%
With N-ethyl-N,N-diisopropylamine; sodium iodide In tetrahydrofuran at 50℃;	83%

1,10-Phenanthroline (66-71-7) + 2,2,2-trifluoroethanethiol (1544-53-2) + copper(l) chloride → [(1,10-phenanthroline)Cu(μ-SCH2CF3)]2

Conditions	Yield
Stage #1: copper(l) chloride With sodium t-butanolate In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: 1,10-Phenanthroline In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere; Stage #3: 2,2,2-trifluoroethanethiol In tetrahydrofuran at 20℃; for 0.333333h; Inert atmosphere;	83%

bis(cyclopentadienyl)tin(II) (26078-96-6) + disulfiram (97-77-8) + 2,2,2-trifluoroethanethiol (1544-53-2) → ((C2H5)2NCS2)2Sn(CF3CH2S)2

Conditions	Yield
In diethyl ether CF3CH2SH was added to (C5H5)2Sn in Et2O, stirred at room temp. for 1 h, ligand was added, refluxed for 5 min, stirred at room temp. for 1 h; solvent was removed in vacuo, recrystd. from THF at -30°C;	82%

tetrakis(dimethylamido)titanium(IV) + 2,2,2-trifluoroethanethiol (1544-53-2) → 2(CH3)2NH2(1+)*Ti(SCH2CF3)6(2-)=((CH3)2NH2)2Ti(SCH2CF3)6

Conditions	Yield
In hexane N2 atm.; thiol was added to a soln. of Ti-compound in hexane, stirred for 3 h; ppt. was filtered, ppt. was washed with hexanes and dried in vac.; elem.anal.;	82%

2,2,2-trifluoroethanethiol (1544-53-2) + 4-bromo-6-fluorobenzonitrile (105942-08-3) → 4-bromo-2-[(2,2,2-trifluoroethyl)sulphanyl]benzonitrile

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;	82%
With sodium hydride In N,N-dimethyl acetamide; mineral oil at 0 - 20℃;	82%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;	82%

2-(2,4-dichloro-5-fluorophenyl)-1H-isoindol-1,3(2H)-dione (958031-89-5) + 2,2,2-trifluoroethanethiol (1544-53-2) → 2-{2,4-dichloro-5-[(2,2,2-trifluoroethyl)thio]phenyl}-1H-isoindol-1,3(2H)-dione (958031-90-8)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 12h;	80%

phenylacetic acid (103-82-2) + 2,2,2-trifluoroethanethiol (1544-53-2) → S-2,2,2-trifluoroethyl phenylthioacetate (1041425-65-3)

Conditions	Yield
Stage #1: phenylacetic acid With benzotriazol-1-ol In dichloromethane at 0℃; for 0.166667h; Inert atmosphere; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #3: 2,2,2-trifluoroethanethiol In dichloromethane at 0 - 20℃; Inert atmosphere;	80%
Stage #1: phenylacetic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.666667h; Stage #2: 2,2,2-trifluoroethanethiol In dichloromethane at 0 - 20℃;
Stage #1: phenylacetic acid With benzotriazol-1-ol In dichloromethane at 0℃; for 0.166667h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.5h; Stage #3: 2,2,2-trifluoroethanethiol In dichloromethane at 0 - 20℃;
Stage #1: phenylacetic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.666667h; Inert atmosphere; Stage #2: 2,2,2-trifluoroethanethiol In dichloromethane at 0 - 20℃; Inert atmosphere;

Upstream product

• 14897-48-4 S-(2,2,2-trifluoroethyl) ethanethioate 
• 75-88-7 1,1,1-trifluoro-2-chloroethane 
• 433-06-7 2,2,2-Trifluoroethyl p-toluenesulfonate 
• 622-40-2 2-(morpholin-4-yl)ethanol 
• 77745-03-0 2,2,2-trifluoroethylthiomethylbenzene 
• 75-90-1 2,2,2-Trifluoroacetaldehyde 

Downstream Products

• 420-46-2 2,2,2-trifluoroethanol 
• 75-38-7 Vinylidene fluoride 
• 3248-58-6 2,2,2-trifluoroethyl 
• 862111-84-0 ethyl 1-(4-methoxybenzyl)-5-[(2,2,2-trifluoroethyl)thio]-1H-1,2,3-triazole-4-carboxylate 
• 885028-67-1 4-(3-nitro-1,2,4-triazolyl)-2-(2,2,2-trifluoroethylthio)benzaldehyde 
• 1132698-40-8 N-[2-chloro-4-[5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]phenyl]methyl-2-(2,2,2-trifluoroethylthio)acetamide 
• 1648-99-3 2,2,2-Trifluoroethanesulfonyl chloride 
• 655-74-3 1-(2,2,2-Trifluorethyl)-2,4-dinitro-phenyl-disulfid 
• 14897-48-4 S-(2,2,2-trifluoroethyl) ethanethioate 
• 1849-36-1 para-nitrobenzenethiol 
• 104315-86-8 1-trifluoromethyl-3-phenylpropane 

Relevant articles and documents

Intrinsic acidity and basicity of 2,2,2-trifluoroethanethiol. The first experimental and theoretical study

The gas phase acidity and basicity of 2,2,2-trifluoroethanethiol (TFET), i.e., the standard Gibbs energy changes for the following two reactions have been determined by means of Fourier transform ion cyclotron resonance spectroscopy: CF3CH2SH(g) → CF3CH2S-(g) + H+(g) and CF3CH2SH2+ (g) → CF3CH2SH(g) + H+(g). Also determined were the equilibrium constants for the 1:1 associations in dilute solution between TFET and pyridine N-oxide, 3,4-dinitrophenol (both in cyclohexane), and molecular iodine (in tetrachloromethane). Quantum-mechanical treatments at the G2(MP2) level were carried out on TFET, 2,2,2-trifluoroethanol, ethanethiol, and ethanol as neutral, protonated, and deprotonated species. Topological analyses of the charge densities and the Laplacians thereof were performed on all of them. This combination of experimental and theoretical information leads to a vastly enlarged view of structural effects on the reactivity of alcohols and thiols as well as to a satisfactory rationalization of the reactivity of TFET.

SYNTHESIS OF 2,2,2-TRIFLUOROETHANETHIOL

A method of making CF3CH2SH, comprising a step of reacting CF3CH2X, wherein X is halide or tosylate, with MSH, where M is an alkali metal such as Na or K, to yield CF3CH2SH. More specifically, a method of making CF3CH2SH, a step of reacting CF3CH2CI with a molar excess of NaSH in a reaction medium of one or more polar organic solvents at a temperature of from about 70C to about 110C for a time of from about 1 to about 5 hours.

Preparation of azacycloalkyloxy-substituted pyrazines, oxadiazoles, and related compounds as muscarinic and nicotinic cholinergic agents.

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