37595-74-7

Basic information

• Product Name: N-Phenyl-bis(trifluoromethanesulfonimide)
• Synonyms: phenyltrifluoromethanesulfonimide;1,1,1-TRIFLUORO-N-PHENYL-N-[(TRIFLUOROMETHYL)SULFONYL]METHANESULFONAMIDE;N-PHENYLBIS(TRIFLUOROMETHANESULFONIMIDE);N-PHENYLBIS(TRIFLUOROMETHANESULPHONIMIDE);N-PHENYLTRIFLUOROMETHANESULFONIMIDE;N-PHENYLTRIFLUOROMETHANESULPHONIMIDE;N,N-BIS(TRIFLUOROMETHYLSULFONYL)ANILINE;PHENYL TRIFLIMIDE
• CAS NO: 37595-74-7
• Molecular Formula: C₈H₅F₆NO₄S₂
• Molecular Weight: 357.25
• EINECS: 1592732-453-0
• Product Categories: API intermediates
• Mol File: 37595-74-7.mol

Chemical Properties

• Melting Point: 100-102 °C(lit.)
• Boiling Point: 305.3 °C at 760 mmHg
• Flash Point: 138.4 °C
• Appearance: White or colorless/Crystals or Crystalline Powder
• Density: 1.766 g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.488
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Soluble in methanol. Slightly soluble in chloroform and ethyl ac
• PKA: -13.12±0.50(Predicted)
• Sensitive: Moisture Sensitive
• Stability: Moisture Sensitive
• BRN: 1269141
• CAS DataBase Reference: N-Phenyl-bis(trifluoromethanesulfonimide)(CAS DataBase Reference)
• NIST Chemistry Reference: N-Phenyl-bis(trifluoromethanesulfonimide)(37595-74-7)
• EPA Substance Registry System: N-Phenyl-bis(trifluoromethanesulfonimide)(37595-74-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 21
• TSCA: No
• HazardClass: IRRITANT
• Hazardous Substances Data: 37595-74-7(Hazardous Substances Data)

Usage

Uses

1. Enantioselective Synthesis:
N-Phenyl-bis(trifluoromethanesulfonimide) is used as a reagent in the enantioselective synthesis of β-amino acids via the Mannich reaction. This application is particularly relevant in the pharmaceutical industry, where the production of chiral molecules with specific configurations is crucial for the development of effective drugs.
2. Pharmaceutical Applications:
In the pharmaceutical industry, N-Phenyl-bis(trifluoromethanesulfonimide) is used as a key intermediate in the synthesis of sphingosine 1-phosphate-1 receptor agonists. These agonists have potential therapeutic applications in treating various diseases and conditions.
3. Carbon Nanotubes:
N-Phenyl-bis(trifluoromethanesulfonimide) acts as a transparent, strong electron-withdrawing p-type dopant in carbon nanotubes. This application is significant in the field of materials science and nanotechnology, where the development of advanced materials with improved properties is a continuous pursuit.
4. Synthesis of Amphoteric Alpha-Boryl Aldehydes:
N-Phenyl-bis(trifluoromethanesulfonimide) is used as a reactant in the synthesis of amphoteric alpha-boryl aldehydes, which are valuable building blocks in organic chemistry and can be used to construct a wide range of complex molecules.
5. Enantioselective Synthesis of Core Ring Skeleton of Leucosceptroids A-D:
N-Phenyl-bis(trifluoromethanesulfonimide) is employed in the enantioselective synthesis of the core ring skeleton of leucosceptroids A-D, which are natural products with potential biological activities.
6. Stereoselective Synthesis of Monoamine Reuptake Inhibitor NS9544 Acetate:
N-Phenyl-bis(trifluoromethanesulfonimide) is used in the stereoselective synthesis of monoamine reuptake inhibitor NS9544 acetate, a molecule with potential applications in the treatment of neurological and psychiatric disorders.
7. Stereoselective Sulfoxidation:
N-Phenyl-bis(trifluoromethanesulfonimide) is also utilized in stereoselective sulfoxidation reactions, which are important for the preparation of chiral sulfoxides and their derivatives, finding applications in various fields, including pharmaceuticals and agrochemicals.

InChI:InChI=1/C8H5F6NO4S2/c9-7(10,11)20(16,17)15(6-4-2-1-3-5-6)21(18,19)8(12,13)14/h1-5H

Synthetic route

trifluoromethylsulfonic anhydride (358-23-6) + aniline (62-53-3) → N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7)

Conditions	Yield
Stage #1: trifluoromethylsulfonic anhydride; aniline With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 40℃; under 600.06 - 1725.17 Torr; for 8h; Sealed tube; Large scale; Stage #2: With dmap In dichloromethane; acetonitrile under 450.045 - 1575.16 Torr; for 15h; Sealed tube; Large scale;	94%
With triethylamine In dichloromethane at 25℃; for 16h; Inert atmosphere; Industry scale; Cooling with ice;	86%
With triethylamine In dichloromethane at 20℃; Cooling with ice;	86%

C10F17IN2O8S4 + bis(trifluoromethanesulfonyl)amide (82113-65-3) + benzene (71-43-2) → N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + C14H5F11INO4S2

Conditions	Yield
at 120℃; Glovebox;	A 7%Spectr. B 93%

Trifluoromethanesulfonyl fluoride (335-05-7) + aniline (62-53-3) → N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7)

Conditions	Yield
Stage #1: Trifluoromethanesulfonyl fluoride; aniline With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 60℃; under 675.068 Torr; for 8h; Sealed tube; Large scale; Stage #2: With dmap In toluene at 60℃; under 750.075 - 1950.2 Torr; for 10h; Pressure; Solvent; Sealed tube; Large scale;	92.1%
With dmap; potassium carbonate In dichloromethane at -40 - 0℃; under 150.015 - 750.075 Torr; for 12h; Reagent/catalyst;	90.7%

Li(1+)*C6H5N(SO2CF3)(1-)=C6H5NLi(SO2CF3) + trifluoromethane sulfonyl chloride (421-83-0) → N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7)

Conditions	Yield
In tetrahydrofuran	60%
In tetrahydrofuran	60%

Na(1+)*CF3SO2NC6H5(1-)=NaCF3SO2NC6H5 + trifluoromethylsulfonic anhydride (358-23-6) → N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7)

Conditions	Yield
In freon 113=1,1,2-trichloro-trifluoroethane at 95°C;	34%
In 1,1,2-Trichloro-1,2,2-trifluoroethane

benzenediazonium tetrafluoroborate (369-57-3) + 1-butyl-3-methylimidazolium trifluoromethanesulfonimide (174899-83-3) → C8H5F6NO4S2 + N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7)

Conditions	Yield
With [Bmim][Br] at 24.84℃; for 24h; Kinetics;
at 24.84℃; for 24h; Kinetics;

benzenediazonium tetrafluoroborate (369-57-3) + 1-butyl-3-methylimidazolium trifluoromethanesulfonimide (174899-83-3) → C8H5F6NO4S2 + fluorobenzene (462-06-6) + N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7)

Conditions	Yield
at 90℃; for 0.216667h;

trifluoromethanesulfonic acid anhydride (1025373-45-8) + aniline (62-53-3) → N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7)

Conditions	Yield
With triethylamine In dichloromethane at -78 - 20℃; Inert atmosphere;

trifluoromethane sulfonyl chloride (421-83-0) + aniline (62-53-3) → N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + methyl 2,2-dimethyl-3-oxobutanoate (38923-57-8) → methyl 2,2-dimethyl-3-0-(trifluoromethanesulfonate)-but-3-enoate (143225-17-6)

Conditions	Yield
Stage #1: methyl 2,2-dimethyl-3-oxobutanoate With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.25h; Inert atmosphere; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran; hexane at -78℃; for 1.25h; Inert atmosphere;	100%
Stage #1: methyl 2,2-dimethyl-3-oxobutanoate With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -20℃; for 0.166667h; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide at -10℃; for 2h;	87%
With lithium diisopropyl amide In tetrahydrofuran -78 deg C to RT;
Stage #1: methyl 2,2-dimethyl-3-oxobutanoate With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.258333h; Inert atmosphere; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran; hexane Inert atmosphere;

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + (1RS,2RS,6SR,7RS,8SR)-7-bromo-3-oxo-1-vinyl-9-azatricyclo[4.4.0.02,8]decane-9-carboxylic acid methyl ester (120566-50-9) → (1RS,2RS,6SR,7RS,8SR)-7-bromo-3-trifluoromethanesulfonyloxy-1-vinyl-9-azatricyclo[4.4.0.02,8]dec-3-ene-9-carboxylic acid methyl ester (120566-52-1)

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at -78 - 0℃;	100%
Stage #1: (1RS,2RS,6SR,7RS,8SR)-7-bromo-3-oxo-1-vinyl-9-azatricyclo[4.4.0.02,8]decane-9-carboxylic acid methyl ester With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran; hexane at -78 - 0℃;

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + 6-methoxy-3,4-dihydro-1(2H)-naphthalenone (1078-19-9) → 6-methoxy-3,4-dihydronaphthalene-1-yl triflate (115375-59-2)

Conditions	Yield
Stage #1: 6-methoxy-3,4-dihydro-1(2H)-naphthalenone With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.75h; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78 - 0℃; for 3h;	100%
With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; for 16h; Inert atmosphere;	89%
Stage #1: 6-methoxy-3,4-dihydro-1(2H)-naphthalenone With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78 - 20℃; Inert atmosphere;	80%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + 3-hydroxy-benzeneacetic acid, methyl ester (42058-59-3) → methyl [3-[[(trifluoromethyl)sulfonyl]oxy]phenyl]-acetate (147283-87-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane Ambient temperature;	100%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + 2,2-dimethyl-cyclohexanone (1193-47-1) → 6,6-dimethylcyclohex-1-en-1-yl trifluoromethanesulfonate (32363-23-8)

Conditions	Yield
Stage #1: 2,2-dimethyl-cyclohexanone With lithium diisopropyl amide In tetrahydrofuran at -78℃; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78℃;	100%
Stage #1: 2,2-dimethyl-cyclohexanone With lithium diisopropyl amide In tetrahydrofuran at -78℃; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78 - 23℃;	100%
Stage #1: 2,2-dimethyl-cyclohexanone With n-butyllithium; diisopropylamine In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78 - 20℃; for 2.5h; Inert atmosphere;	55%
With lithium diisopropyl amide 1.) THF, -78 deg C, 2 h, 2.) THF, 0 deg C, 12 h; Yield given. Multistep reaction;

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + raloxifene (188823-98-5) → Trifluoro-methanesulfonic acid 6-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-3-trifluoromethanesulfonyloxy-6H-5-oxa-11-thia-benzo[a]fluoren-9-yl ester (188824-03-5)

Conditions	Yield
With triethylamine; N,N-dimethyl-formamide In tetrahydrofuran for 12h;	100%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + (4aS,5R,6R,8aS)-5,6,8a-Trimethyl-5-(2-triisopropylsilanyloxy-ethyl)-octahydro-naphthalen-1-one (214413-28-2) → Trifluoro-methanesulfonic acid (4aS,5R,6R,8aS)-5,6,8a-trimethyl-5-(2-triisopropylsilanyloxy-ethyl)-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl ester (218453-51-1)

Conditions	Yield
With sodium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1h; Esterification;	100%
With lithium diisopropyl amide Yield given. Multistep reaction;

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + dimethyl 2-hydroxy-5-iodoisophthalate → dimethyl 5-iodo-2-{[(trifluoromethyl)sulphonyl]oxy}isophthalate (263160-77-6)

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 16h; sulphonylation;	100%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + 2,6-dimethyl-4-nitro phenol (2423-71-4) → 2,6-dimethyl-4-nitrophenyl trifluoromethanesulphonate (156740-78-2)

Conditions	Yield
With sodium hydride In DMF (N,N-dimethyl-formamide) at 0℃; for 2h;	100%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 8h; Acylation;	89%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + 5-dodecanolide (713-95-1) → trifluoro-methanesulfonic acid 6-heptyl-5,6-dihydro-4H-pyran-2-yl ester (445462-86-2)

Conditions	Yield
With potassium hexamethylsilazane In tetrahydrofuran; toluene at -78℃; for 0.25h;	100%
With potassium hexamethylsilazane In tetrahydrofuran; toluene at -78℃; for 0.25h;

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + 4-(benzo[d]oxazol-2ʹ-yl)-2-methoxyphenol (3164-07-6) → 4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl trifluoromethanesulfonate (540497-27-6)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h;	100%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + 1-(3-methoxy-4-hydroxyphenyl)ethanone (498-02-2) → 4-acetyl-2-methoxyphenyl trifluoromethanesulfonate (149105-13-5)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide; acetonitrile at 20℃; for 12h;	100%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + 7-Methoxy-1-tetralone (6836-19-7) → trifluoromethanesulfonic acid 7-methoxy-3,4-dihydronaphthalen-1-yl ester (724707-85-1)

Conditions	Yield
Stage #1: 7-Methoxy-1-tetralone With lithium hexamethyldisilazane In tetrahydrofuran at -79℃; for 0.75h; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78 - 0℃; for 3h;	100%
With potassium hexamethylsilazane In tetrahydrofuran at -78℃; for 1h;	96%
With potassium hexamethylsilazane In tetrahydrofuran at -78℃; for 1.5h;	96%

cyclohexanedione monoethylene ketal (4746-97-8) + N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) → 1,4-dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonate (170011-47-9)

Conditions	Yield
With potassium hexamethylsilazane In tetrahydrofuran; toluene at -78℃; for 4h;	100%
With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; for 0.5h; Inert atmosphere;	100%
With lithium hexamethyldisilazane at -78 - 20℃; Inert atmosphere;	100%

Norbornan-2-on (497-38-1) + N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) → 2-trifluoromethanesulfonyloxybicyclo[2.2.1]hept-2-ene (82361-91-9)

Conditions	Yield
Stage #1: Norbornan-2-on With lithium diisopropyl amide In tetrahydrofuran at -78 - 20℃; for 0.5h; Inert atmosphere; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78 - 20℃; for 3h; Inert atmosphere;	100%
With n-butyllithium; diisopropylamine In tetrahydrofuran	59%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + 5-(4-hydroxy-phenyl)-pyrrolidin-2-one (207989-87-5) → γ-4-trifluoromethylsulphonyloxyphenyl-γ-butyrolactam (207989-88-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	100%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	96%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + 3-[6-amino-8-(3-bromophenyl)-2,3,4,8-tetrahydroimidazo[1,5-a]pyrimidin-8-yl]phenol → 3-[6-amino-8-(3-bromophenyl)-2,3,4,8-tetrahydroimidazo[1,5-a]pyrimidin-8-yl]phenyl trifluoromethanesulfonate

Conditions	Yield
With triethylamine In dichloromethane at 25℃; for 12h;	100%
With triethylamine In dichlorometane at 0 - 25℃; for 12h;	100%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + 1-[7-(5-cyanopyridin-2-yl)-5-hydroxybenzothiazol-2-yl]-3-ethylurea (1000289-72-4) → trifluoromethanesulfonic acid 7-(5-cyanopyridin-2-yl)-2-(3-ethylureido)benzothiazol-5-yl ester (1000289-73-5)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 2h;	100%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + 3-hydroxy-6-methyl-2-(O-tert-butyldimethylsilyl)hydroxymethylpyran-4(1H)-one (958457-26-6) → 6-methyl-2-(O-tert-butyldimethylsilyl)hydroxymethyl-3-trifluoromethanesulfonyloxy-pyran-4(1H)-one (958457-27-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1.5h; Inert atmosphere;	100%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;
With potassium carbonate In N,N-dimethyl-formamide for 1.66667h;

C27H32O10SSiN2 + N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) → C28H31F3O12S2SiN2

Conditions	Yield
With 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine In tetrahydrofuran at 20℃;	100%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + 2-fluoro-5-(8-fluoro-7-trifluoromethylquinolin-4-yl)phenol (693818-37-0) → trifluoromethanesulphonic acid 2-fluoro-5-(8-fluoro-7-trifluoromethyl-quinolin-4-yl)phenyl ester (693818-38-1)

Conditions	Yield
With triethylamine at 20℃; for 16h;	100%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + methyl 1-hydroxy-5,6,7,8-tetrahydronaphthalene-2-carboxylate (54815-88-2) → methyl 1-{[(trifluoromethyl)sulphonyl]oxy}-5,6,7,8-tetrahydronaphthalene-2-carboxylate (812690-21-4)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; dmap In dichloromethane at 20℃; for 18.5h;	100%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + C29H40N2O4 (762300-05-0) → C30H39F3N2O6S (762300-07-2)

Conditions	Yield
Stage #1: N,N-phenylbistrifluoromethane-sulfonimide; C29H40N2O4 With triethylamine In dichloromethane at 20℃; Stage #2: With sodium hydroxide In dichloromethane; water at 20℃; for 0.5h;	100%

2-methoxy-8-hydroxyquinoline (74668-72-7) + N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) → 1,1,1-trifluoromethanesulfonic acid 2-methoxyquinolin-8-yl ester (642477-88-1)

Conditions	Yield
With triethylamine In DMF (N,N-dimethyl-formamide) at 40℃; for 8h;	100%

C24H31NO + N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) → C25H30F3NO3S

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	100%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) → tert-butyl 5-(methoxymethoxy)-4-(trifluoromethylsulfonyloxy)spiro[chromene-2,4'-piperidine]-1'-carboxylate (911227-82-2)

Conditions	Yield
Stage #1: tert-butyl 5-(methoxymethoxy)-4-oxospiro[chroman-2,4'-piperidine]-1'-carboxylate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1h; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78 - 20℃; for 12h;	100%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) → C23H22F3NO5S (911228-44-9)

Conditions	Yield
Stage #1: benzyl 4-oxo-3,4-dihydro-1H-spiro[naphthalene-2,4'-piperidine]-1'-carboxylate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.75h; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78 - 20℃; for 2.5h;	100%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + (3R,4S)-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-4-(3'-hydroxybiphenyl-4-yl)-1-phenylazetidin-2-one (852204-40-1) → 4'-{(2S,3R)-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-4-oxo-1-phenylazetidin-2-yl}biphenyl-3-yl trifluoromethanesulfonate (852204-41-2)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 2h;	100%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + 2-({4-[(4-fluorophenyl)amino]-1-piperidinyl}carbonyl)-3-pyridinol (920511-31-5) → 2-({4-[(4-fluorophenyl)amino]-1-piperidinyl}carbonyl)-3-pyridinyl trifluoromethanesulfonate (920511-33-7)

Conditions	Yield
With triethylamine In dichloromethane	100%
With triethylamine In dichloromethane at 20℃;
With triethylamine In dichloromethane at 20℃;

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + tert-butyl [6-hydroxy-2-isobutyl-4-(4-methylphenyl)-1-oxo-1,2-dihydro-3-isoquinolinyl]methylcarbamate → tert-butyl [2-isobutyl-4-(4-methylphenyl)-1-oxo-6-trifluoromethanesulfonyloxy-1,2-dihydro-3-isoquinolinyl]methylcarbamate

Conditions	Yield
In N,N-dimethyl-formamide	100%

Upstream product

• 369-57-3 benzenediazonium tetrafluoroborate 
• 174899-83-3 1-butyl-3-methylimidazolium trifluoromethanesulfonimide 
• 82113-65-3 bis(trifluoromethanesulfonyl)amide 
• 71-43-2 benzene 
• 1025373-45-8 trifluoromethanesulfonic acid anhydride 
• 62-53-3 aniline 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 1493-13-6 trifluorormethanesulfonic acid 
• 335-05-7 Trifluoromethanesulfonyl fluoride 

Downstream Products

• 143564-87-8 ethyl (Z)-4-phenyl-3-<<(trifluoromethyl)sulfonyl>oxy>-2-butenoate 
• 134405-85-9 ethyl (E)-4-phenyl-3-<<(trifluoromethyl)sulfonyl>oxy>-2-butenoate 
• 154084-93-2 2-(2-(2,6,6-trimethyl-2-cyclohexenyl)ethyl)-3-(trifluoromethansulfonyl)oxy-cyclohexenone 
• 153868-73-6 tert-Butyl <(1S,4R,5R)-4-ethyl-5-phenyl-2-(trifluoromethanesulfoxy)cyclopent-2-en-1-yl>acetate 
• 154085-01-5 2-<(2-benzyloxymethyl)-1-(tert-butyldimethylsiloxy-2-cyclohexen-1-yl)ethyl>phenyl trifluoromethanesulfonate 
• 155725-35-2 Trifluoro-methanesulfonic acid (E)-2-chloro-1-naphthalen-2-yl-2-(toluene-4-sulfinyl)-vinyl ester 
• 154569-08-1 (2S,4aS,5R,8aR)-5-Methyl-2-propyl-4-trifluoromethanesulfonyloxy-4a,5,6,7,8,8a-hexahydro-2H-quinoline-1-carboxylic acid phenyl ester 
• 156564-13-5 Trifluoro-methanesulfonic acid 5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-cyclopent-1-enyl ester 
• 170951-66-3 Trifluoro-methanesulfonic acid (Z)-1-[1-chloro-1-(toluene-4-sulfinyl)-meth-(E)-ylidene]-octadec-9-enyl ester 
• 109459-28-1 3-(trifluoromethanesulfonyloxy)-2-cyclohexen-1-one 
• 122539-74-6 2-trifluoromethanesulfonyloxy-cyclopent-1-enecarboxylic acid ethyl ester 
• 123753-47-9 Trifluoro-methanesulfonic acid 2-(4-methylene-non-8-enyl)-3-oxo-cyclohex-1-enyl ester 
• 123753-35-5 Trifluoro-methanesulfonic acid 3-oxo-2-pent-4-enyl-cyclohex-1-enyl ester 
• 32363-21-6 2-methyl-1-cyclohexenyl triflate 

Relevant articles and documents

Preparation method of N-phenyl bis (trifluoromethanesulfonyl) imine

The invention relates to a preparation method of N-phenyl bis (trifluoromethanesulfonyl) imine, and belongs to the technical field of chemical engineering. The method comprises the following steps: dissolving trifluoromethanesulfonic acid and organic alkali in an organic solvent, and adding HATU for reaction; the reaction temperature is greater than or equal to 15 DEG C, and the organic solvent is not boiled; after the reaction is finished, a reaction solution containing trifluoromethanesulfonic acid active ester is obtained; adding aniline into the reaction liquid, and reacting at 25 +/-5 DEG C for 6-12 hours; and after the reaction is finished, removing the organic solvent to obtain a crude product containing the N-phenyl bis (trifluoromethanesulfonyl) imine, washing, and recrystallizing and purifying by using an alcohol solvent with 1-3 carbon atoms to obtain the N-phenyl bis (trifluoromethanesulfonyl) imine. The N-phenyl bis (trifluoromethanesulfonyl) imine with high purity and high yield can be prepared by the method, the reaction condition is mild, the utilization rate of raw materials is high, and the method is green and environment-friendly.

Preparation method of N-phenyl-bis(trifluoromethanesulfonyl)imide

The invention provides a preparation method of N-phenyl-bis(trifluoromethanesulfonyl)imide. The preparation method comprises the following steps: subjecting trifluoromethanesulfonic acid to reacting with thionyl chloride to produce trifluoromethanesulfonyl chloride; and dissolving aniline in a solvent, adding organic alkali such as triethylamine as an acid-binding agent, and dropwise adding trifluoromethanesulfonyl chloride to prepare N-phenyl-bis(trifluoromethanesulfonyl)imide. According to the invention, raw materials are cheap and easily available; trifluoromethanesulfonyl chloride participates in reaction, the utilization rate of groups is high, and the reaction is efficient; special devices such as low-temperature or under-pressure devices are not needed, and operation is easy; and basically no solid three wastes are generated.

Meta Selective C-H Borylation of Sterically Biased and Unbiased Substrates Directed by Electrostatic Interaction

An electrostatically directed meta borylation of sterically biased and unbiased substrates is described. The borylation follows an electrostatic interaction between the partially positive and negative charges between the ligand and substrate. With this strategy, it has been demonstrated that a wide number of challenging substrates, especially 4-substituted substrates, can selectively be borylated at the meta position. Moreover, unsubstituted substrates also displayed excellent meta selectivity. The reaction employs a bench-stable ligand and proceeds at a milder temperature, precluding the need to synthesize a bulky and sophisticated ligand/template.

Preparation method of N-phenyl bis (trifluoromethanesulfonyl) imide

The invention discloses a preparation method of N-phenyl bis (trifluoromethanesulfonyl) imide. According to the method, trifluoromethanesulfonyl fluoride is adopted as a raw material, in a strong polar solvent, organic alkali is adopted as an acid-binding agent to react with aniline to generate N-phenyl trifluoromethanesulfonamide, most of the solvent is removed through distillation, a weak polarsolvent and a catalyst are added, trifluoromethanesulfonyl fluoride continues to be introduced for the reaction, and N-phenyl bis (trifluoromethanesulfonyl) imide is prepared. According to the scheme,the cost is low, the reaction is mild, excessive trifluoromethanesulfonyl fluoride cannot be discharged to generate pollution without using shielding gas, the prepared product is high in purity and yield, and industrial popularization can be achieved.

Method for preparing N-phenyl-bis (perfluoroalkyl sulfonyl) imide

The invention relates to a method for preparing N-phenyl-bis (perfluoroalkyl sulfonyl) imide, and belongs to the technical field of preparation of perfluoroalkyl sulfonylation reagents. According to the method, perfluoroalkyl sulfonyl fluoride and aniline are used as raw materials, and N-phenyl-bis (perfluoroalkyl sulfonyl) imide is prepared under the action of a catalyst. The method disclosed bythe invention is simple in process flow, mild in reaction, good in safety, low in cost, high in yield and high in purity.

DIRECT OXIDATIVE AMINATION OF HYDROCARBONS

Provided is a process for converting a hydrocarbon comprising at least one C-H bond to a nitrogen-functionalized product. The process comprises contacting a hydrocarbon and (i) an oxidizing electrophile comprising (a) a main group element or transition metal in oxidized form and (b) at least one nitrogen-containing ligand, or (ii) an oxidant and a reduced form of an oxidizing electrophile comprising (a) a main group element or transition metal and (b) at least one nitrogen-containing ligand, in a solvent to provide the nitrogen-functionalized product and an electrophile reduction product. Further provided is an oxidizing composition comprising the oxidizing electrophile with at least one nitrogen-containing ligand and a non?oxidizable liquid.

Synthesis method of trimethoxystilbene

The invention discloses a synthesis method of trimethoxystilbene. The method comprises the following steps of (1) at room temperature, adding trifluoromethanesulfonic acid into dichloromethane; stirring the mixture; slowly dripping sulfoxide chloride; after the dripping is completed, performing stirring reaction for 12 hours at room temperature; concentrating a reaction system to obtain a coarse product of trifluoromethanesulfonyl chloride; (2) adding aniline and triethylamine into dichloromethane; lowering the temperature to 0 DEG C; dripping the obtained coarse product of trifluoromethanesulfonyl chloride through a dropping funnel; after the dripping is completed, raising the temperature to room temperature for reaction for 2 hours; performing water washing, drying and concentration on the reaction system; then, performing recrystallization by petroleum ether to obtain trimethoxystilbene. The synthesis method has the beneficial effects that the raw materials of trifluoromethanesulfonic acid used by the synthesis method of trimethoxystilbene provided by the invention are common chemical raw materials; the price is low; the acquisition is easy; the cost is greatly reduced; special equipment such as low-temperature kettles is not needed in the production process; the operation is easy; the method is suitable for industrial production.

PIPERIDINE UREAS AS CATHEPSIN CYSTEINE PROTEASE INHIBITORS

The present invention relates to substituted piperidine urea derivatives that are inhibitors of cathepsin K proteases and which are therefore useful in the treatment of certain disorders that can be prevented or treated by inhibition of these enzymes. In addition, the invention relates to the compounds, methods for their preparation, pharmaceutical compositions containing the compounds and the uses of these compounds in the treatment of certain disorders. It is expected that the compounds of the invention will find application in the treatment of bone diseases such as osteoporosis and osteoarthritis as well as other diseases and conditions. The compounds have the general formula: [Formula should be inserted here]

METALLO-BETA-LACTAMASE INHIBITORS

The present invention relates to compounds of formula (I) that are metallo-β-lactamase inhibitors, the synthesis of such compounds, and the use of such compounds for use with β-lactam antibiotics for overcoming resistance.

COMPOSITIONS AND METHODS FOR MODULATING DNA METHYLATION

Disclosed herein are compositions and methods for modulating DNA methylation of one or more gene promoters, treating a subject diagnosed with or suspected of having a disease or disorder characterized by DNA hypermethylation, decreasing c-myc expression, increasing desmoplakin expression, and inhibiting metastases. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.