887144-97-0

Basic information

• Product Name: 1,3-Dihydro-3,3-dimethyl-1-(trifluoromethyl)-1,2-benziodoxole, Tognis Reagent
• Synonyms: 1,3-Dihydro-3,3-dimethyl-1-(trifluoromethyl)-1,2-benziodoxole, Tognis Reagent;3,3-Dimethyl-1-(trifluoromethyl)-1,2-benziodoxole;1-Trifluoromethyl-3,3-dimethyl-1,2-benziodoxole;Togni's Reagent;1,3-dihydro-3,3-diMethyl-1-(trifluoroMethyl)-1,2-benziodoxole;1,3-Dhydro-3,3-diMethyl-1-(trifluoroMethyl)-1,2-benziodoxole;3,3-DMethyl-1-(trifluoroMethyl)-1,2-benziodoxole;1,3-Dihydro-3,3-diMethyl-1-(trifluoroMethyl)-1,2-b
• CAS NO: 887144-97-0
• Molecular Formula: C₁₀H₁₀F₃IO
• Molecular Weight: 330.08
• Mol File: 887144-97-0.mol
• Article Data: 11

Chemical Properties

• Melting Point: 75-79 °C
• Appearance: /
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Stability: Moisture Sensitive
• CAS DataBase Reference: 1,3-Dihydro-3,3-dimethyl-1-(trifluoromethyl)-1,2-benziodoxole, Tognis Reagent(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dihydro-3,3-dimethyl-1-(trifluoromethyl)-1,2-benziodoxole, Tognis Reagent(887144-97-0)
• EPA Substance Registry System: 1,3-Dihydro-3,3-dimethyl-1-(trifluoromethyl)-1,2-benziodoxole, Tognis Reagent(887144-97-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• RIDADR: 1325
• WGK Germany: 3
• TSCA: No
• HazardClass: 4.1
• PackingGroup: Ⅲ
• Hazardous Substances Data: 887144-97-0(Hazardous Substances Data)

Usage

Description

1,3-dihydro-3,3-dimethyl-1-(trifluoromethyl)-1,2-benziodoxole is in the form of colorless, white solid. It is soluble in all common organic solvents. It is used as effective and very versatile reagent for trifluoromethylation reactions of a variety of compounds including secondary and primary aryland alkylphospines, phenols, peptides containing cysteine residues by SPPS and electrophilic S-trifluoromethylation, arenes and N-heterocycles, and electrophilic N-trifluoromethylation of arozoles.

Reference

J. Charpentier, N. Früh, A. Togni, Electrophilic Trifluoromethylation by use of hypervalent iodine reagents, Chemical Reviews, 2015, vol. 115, pp. 650-682

Chemical Properties

White to light yellow solid

Uses

Different sources of media describe the Uses of 887144-97-0 differently. You can refer to the following data:
1. Mild, electrophilic, hypervalent iodine CF3 reagent effective for the trifluoromethylation of a wide range of substrates.
2. Togni’s Reagent is used in trifluoromethylation reactions.

InChI:InChI=1/C10H10F3IO/c1-9(2)7-5-3-4-6-8(7)14(15-9)10(11,12)13/h3-6H,1-2H3

Synthetic route

1-chloro-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole (69352-04-1) + (trifluoromethyl)trimethylsilane (81290-20-2) → Togni's reagent (887144-97-0)

Conditions	Yield
With fluoride In acetonitrile	93%
With potassium acetate; tetrabutylammonium triphenyldifluorosilicate In acetonitrile at -17 - 20℃; for 22h;	89%
Stage #1: 1-chloro-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole With potassium acetate In acetonitrile at 20℃; for 1h; Schlenk technique; Inert atmosphere; Stage #2: (trifluoromethyl)trimethylsilane With tetrabutylammonium triphenyldifluorosilicate In acetonitrile at -17 - 20℃; for 19h; Schlenk technique; Inert atmosphere;	85%

(trifluoromethyl)trimethylsilane (81290-20-2) + 3,3-dimethyl-1λ3-benzo[d][1,2]iodoxol-1(3H)-yl acetate (175786-58-0) → Togni's reagent (887144-97-0)

Conditions	Yield
With cesium fluoride In acetonitrile at 23℃; for 16h; Inert atmosphere; Darkness;	77%
With cesium fluoride In acetonitrile at 20℃; for 16h;	46%
With fluoride

1-chloro-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole (69352-04-1) → Togni's reagent (887144-97-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / acetonitrile / 15 h / 20 °C 2: 46 percent / CsF / acetonitrile / 16 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: potassium fluoride / acetonitrile / 12 h / 20 °C / Inert atmosphere 2: (trifluoromethyl)trimethylsilane / acetonitrile / 1 h / -10 °C / Inert atmosphere View Scheme

2-(2-iodophenyl)propan-2-ol (69352-05-2) → Togni's reagent (887144-97-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: tBuOCl 2: 100 percent / acetonitrile / 15 h / 20 °C 3: 46 percent / CsF / acetonitrile / 16 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: trichloroisocyanuric acid / acetonitrile / 0.17 h / 75 °C / Inert atmosphere; Reflux 2: potassium fluoride / acetonitrile / 12 h / 20 °C / Inert atmosphere 3: (trifluoromethyl)trimethylsilane / acetonitrile / 1 h / -10 °C / Inert atmosphere View Scheme

2-Iodobenzoic acid (88-67-5) → Togni's reagent (887144-97-0)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 14 h / 23 °C 2.1: diethyl ether / 3 h / 0 - 23 °C / Inert atmosphere 2.2: 1 h / 23 °C / Inert atmosphere 3.1: acetonitrile / 16 h / 23 °C / Inert atmosphere; Darkness 4.1: cesium fluoride / acetonitrile / 16 h / 23 °C / Inert atmosphere; Darkness View Scheme

o-iodo-methyl-benzoic acid (610-97-9) → Togni's reagent (887144-97-0)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: diethyl ether / 3 h / 0 - 23 °C / Inert atmosphere 1.2: 1 h / 23 °C / Inert atmosphere 2.1: acetonitrile / 16 h / 23 °C / Inert atmosphere; Darkness 3.1: cesium fluoride / acetonitrile / 16 h / 23 °C / Inert atmosphere; Darkness View Scheme
Multi-step reaction with 4 steps 1: diethyl ether / -30 °C / Inert atmosphere 2: trichloroisocyanuric acid / acetonitrile / 0.17 h / 75 °C / Inert atmosphere; Reflux 3: potassium fluoride / acetonitrile / 12 h / 20 °C / Inert atmosphere 4: (trifluoromethyl)trimethylsilane / acetonitrile / 1 h / -10 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: magnesium / diethyl ether / 16.67 h / 0 - 20 °C / Inert atmosphere; Reflux 2.1: tert-butylhypochlorite / dichloromethane / 17 h / 0 °C / Darkness; Inert atmosphere 3.1: potassium acetate / acetonitrile / 1 h / 20 °C / Schlenk technique; Inert atmosphere 3.2: 19 h / -17 - 20 °C / Schlenk technique; Inert atmosphere View Scheme

1-fluoro-3,3-dimethyl-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole (1391728-13-4) → Togni's reagent (887144-97-0)

Conditions	Yield
With (trifluoromethyl)trimethylsilane In acetonitrile at -10℃; for 1h; Inert atmosphere;	29.7 g

2-carbomethoxyaniline (134-20-3) → Togni's reagent (887144-97-0)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: sulfuric acid; sodium nitrite / water / 0 - 7 °C / Inert atmosphere 1.2: 1.58 h / -5 - 80 °C / Inert atmosphere 2.1: diethyl ether / -30 °C / Inert atmosphere 3.1: trichloroisocyanuric acid / acetonitrile / 0.17 h / 75 °C / Inert atmosphere; Reflux 4.1: potassium fluoride / acetonitrile / 12 h / 20 °C / Inert atmosphere 5.1: (trifluoromethyl)trimethylsilane / acetonitrile / 1 h / -10 °C / Inert atmosphere View Scheme

1-chloro-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole (69352-04-1) + trifluoromethan (75-46-7) → Togni's reagent (887144-97-0)

Conditions	Yield
Stage #1: trifluoromethan With C12H24KO6(1+)*C13H25B3N3(1-) In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Stage #2: 1-chloro-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere;	78 %Spectr.
Stage #1: trifluoromethan With 18-crown-6 ether; benzyl potassium; hexamethylborazine In tetrahydrofuran at 0℃; for 1.33333h; Sealed tube; Stage #2: 1-chloro-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole In tetrahydrofuran at 0℃;

1-chloro-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole (69352-04-1) + C4H8O*C12H24KO6(1+)*C7H18B3F3N3(1-) → Togni's reagent (887144-97-0)

Conditions	Yield
In tetrahydrofuran at 25℃; for 0.166667h; Inert atmosphere; Glovebox;	78 %Spectr.

1-fluoro-3,3-dimethyl-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole (1391728-13-4) + (trifluoromethyl)trimethylsilane (81290-20-2) → Togni's reagent (887144-97-0)

Conditions	Yield
With tetrabutylammonium triphenyldifluorosilicate In acetonitrile at -20 - 20℃; for 1.5h;

Togni's reagent (887144-97-0) + 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (2564-83-2, 45842-10-2) + N,N-dibenzylhydroxylamine (621-07-8) → 2,2,6,6-tetramethyl-1-(trifluoromethoxy)piperidine (1335135-19-7)

Conditions	Yield
Concentration; Inert atmosphere;	100%

Togni's reagent (887144-97-0) + L-cysteine ethyl ester hydrochloride (868-59-7) → (R)-ethyl 2-amino-3-((trifluoromethyl)thio)propanoate hydrochloride

Conditions	Yield
In methanol	99%
In methanol at -78 - 20℃; for 1h; Schlenk technique; Inert atmosphere;	97%

Togni's reagent (887144-97-0) + C10H14N4O4S → C11H13F3N4O4S

Conditions	Yield
at -78℃;	99%

Togni's reagent (887144-97-0) + L-cysteine methyl ester hydrochloride (18598-63-5) → methyl S-trifluoromethyl-(L)-cysteinate hydrochloride

Conditions	Yield
at -78℃;	99%

Togni's reagent (887144-97-0) + 5-pentenylbenzoate (29264-40-2) → (E)-6,6,6-trifluorohex-4-en-1-yl benzoate

Conditions	Yield
With 2-iodobenzoic acid potassium salt In N,N-dimethyl-formamide at 80℃; for 12h; Reagent/catalyst; Concentration; Solvent; Schlenk technique;	99%

Togni's reagent (887144-97-0) + trimethylsilyl cyanide (7677-24-9) + 3-bromostyrene (2039-86-3) → C10H7BrF3N

Conditions	Yield
With tetrakis(actonitrile)copper(I) hexafluorophosphate; {3aS-[2(3'aR*,8'aS*),3aα,8aα]}-2,2'-(cyclopropylidene)-bis{3a,8a-dihydro-8H-indeno[1,2-d]-oxazole} In acetonitrile at -20 - 20℃; for 1h; Sealed tube; Inert atmosphere; enantioselective reaction;	99%

Togni's reagent (887144-97-0) + (E)-3-(3-methoxyphenyl)-1-phenylbut-3-en-1-one oxime → (S)-5-(3-methoxyphenyl)-3-phenyl-5-(2,2,2-trifluoroethyl)-4,5-dihydroisoxazole

Conditions	Yield
With C30H39N3O2S; copper diacetate In chloroform at -10℃; for 72h; Inert atmosphere; Schlenk technique; Sealed tube; Molecular sieve; enantioselective reaction;	99%

Togni's reagent (887144-97-0) + (E)-3-(naphthalen-2-yl)-1-phenylbut-3-en-1-one oxime → (S)-5-(naphthalen-2-yl)-3-phenyl-5-(2,2,2-trifluoroethyl)-4,5-dihydroisoxazole

Conditions	Yield
With C30H39N3O2S; copper diacetate In chloroform at -10℃; for 72h; Inert atmosphere; Schlenk technique; Sealed tube; Molecular sieve; enantioselective reaction;	99%

Togni's reagent (887144-97-0) + (E)-1-(3-bromophenyl)-3-phenylbut-3-en-1-one oxime → (S)-3-(3-bromophenyl)-5-phenyl-5-(2,2,2-trifluoroethyl)-4,5-dihydroisoxazole

Conditions	Yield
With C30H39N3O2S; copper diacetate In chloroform at -10℃; for 72h; Inert atmosphere; Schlenk technique; Sealed tube; Molecular sieve; enantioselective reaction;	99%

Togni's reagent (887144-97-0) + (E)-3-phenyl-1-(thiophen-3-yl)but-3-en-1-one oxime → (S)-5-phenyl-3-(thiophen-3-yl)-5-(2,2,2-trifluoroethyl)-4,5-dihydroisoxazole

Conditions	Yield
With C30H39N3O2S; copper diacetate In chloroform at -10℃; for 72h; Inert atmosphere; Schlenk technique; Sealed tube; Molecular sieve; enantioselective reaction;	99%

Togni's reagent (887144-97-0) + benzyl (S)-3-methyl-2-oxo-5-(trifluoromethoxy)indoline-1-carboxylate → benzyl (R)-3-methyl-2-oxo-5-(trifluoromethoxy)-3-(trifluoromethyl)indoline-1-carboxylate

Conditions	Yield
Stage #1: benzyl (S)-3-methyl-2-oxo-5-(trifluoromethoxy)indoline-1-carboxylate With C25H23N3O4; magnesium bromide ethyl etherate In dichloromethane at 20℃; for 0.0833333h; Schlenk technique; Inert atmosphere; Stage #2: Togni's reagent In dichloromethane at -78 - 20℃; for 19h; Schlenk technique; Inert atmosphere; enantioselective reaction;	99%

Togni's reagent (887144-97-0) + styrene (292638-84-7) + 4-chlorobenzaldehyde (104-88-1) → 1-(4-chlorophenyl)-4,4,4-trifluoro-2-phenylbutan-1-one

Conditions	Yield
With 3-(2,6-diisopropylphenyl)-5,6,7,8-tetrahydro-4H-cyclohepta[d]thiazol-3-ium perchlorate; caesium carbonate In acetonitrile at 60℃; for 12h; Schlenk technique; Inert atmosphere;	99%
With 3-(2,6-diisopropylphenyl)-5,6,7,8-tetrahydro-4H-cyclohepta[d]thiazol-3-ium perchlorate; caesium carbonate In dichloromethane; water at 25℃; for 6h; Catalytic behavior; Reagent/catalyst; Solvent; Schlenk technique; Inert atmosphere; Sealed tube;	84%

Togni's reagent (887144-97-0) + styrene (292638-84-7) + 4-bromo-benzaldehyde (1122-91-4) → 1-(4-bromophenyl)-4,4,4-trifluoro-2-phenylbutan-1-one

Conditions	Yield
With 3-(2,6-diisopropylphenyl)-5,6,7,8-tetrahydro-4H-cyclohepta[d]thiazol-3-ium perchlorate; caesium carbonate In acetonitrile at 60℃; for 12h; Schlenk technique; Inert atmosphere;	99%

Togni's reagent (887144-97-0) + trimethylsilyl cyanide (7677-24-9) + vinyl ester of phenylacetic acid (18120-64-4) → C12H10F3NO2

Conditions	Yield
With carbon tetrabromide; C43H38N2O2; copper (I) acetate In tert-butyl methyl ether at -20℃; for 12h; Inert atmosphere; Sealed tube; enantioselective reaction;	99%

Togni's reagent (887144-97-0) + (4-butylphenyl)acetylene (79887-09-5) → 1-butyl-4-(3,3,3-trifluoroprop-1-ynyl)benzene (1361988-15-9)

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; potassium hydrogencarbonate In dichloromethane at 20℃; for 18h; Inert atmosphere;	98%

Togni's reagent (887144-97-0) + 1-bromo-4-ethenyl-benzene (2039-82-9) + trimethylsilyl cyanide (7677-24-9) → 2-(4-bromophenyl)-4,4,4-trifluorobutanenitrile

Conditions	Yield
With (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline)CuBr In dimethyl sulfoxide at 20℃; for 0.5h; Inert atmosphere;	98%

Togni's reagent (887144-97-0) + 4-n-chlorophenylacetylene (873-73-4) + 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (2564-83-2, 45842-10-2) → 2,2,6,6-tetramethyl-1-(trifluoromethoxy)piperidine (1335135-19-7)

Conditions	Yield
With trimethylsilylazide; copper(I) bromide In methanol at 20℃; for 8h; Sealed tube; Inert atmosphere;	98%

Togni's reagent (887144-97-0) + trimethyl((1-(octyloxy)vinyl)oxy)silane (135066-77-2) → Octyl 3,3,3-trifluoropropanoate (116044-36-1)

Conditions	Yield
With trimethylsilyl bis(trifluoromethanesulfonyl)imide In dichloromethane at -78 - 20℃; for 19h; Inert atmosphere;	98%

Togni's reagent (887144-97-0) + trans-p-methylcinnamic acid (1866-39-3) → (E)-1-methyl-4-(3,3,3-trifluoroprop-1-en-1-yl)benzene (80959-78-0, 78622-56-7)

Conditions	Yield
In N,N-dimethyl-formamide at 120℃; for 24h; Reagent/catalyst; Solvent; Temperature; stereoselective reaction;	98%

Togni's reagent (887144-97-0) + 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (2564-83-2, 45842-10-2) → 2,2,6,6-tetramethyl-1-(trifluoromethoxy)piperidine (1335135-19-7)

Conditions	Yield
With tetrakis(actonitrile)copper(I) hexafluorophosphate; trimethylsilyl cyanide; (3aR,3a'R,8aS,8a'S)-2,2'-(cyclopentane-1,1-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole); 2-(pent-4-en-2-yn-1-yl)isoindoline-1,3-dione In acetonitrile at -15 - 20℃; for 2.5h; Reagent/catalyst; Temperature; Sealed tube; Inert atmosphere;	98%
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate In acetone at 25℃; for 24h;	80%
With α-phenylacrylanilide; copper(II) bis(trifluoromethanesulfonate); p-tert-butylphenylboronic acid; (4S,4'S)-2,2'-(1,3-diphenylpropane-2,2-diyl)-bis(4-benzyl-4,5-dihydrooxazole) In methanol at 0℃; for 72h; Inert atmosphere; Sealed tube;	79%

Togni's reagent (887144-97-0) + 6-benzyl-1-methyl-7-((trimethylsilyl)oxy)-2,3,4,5-tetrahydro-1H-azepine → 3-benzyl-1-methyl-3-(trifluoromethyl)azepan-2-one

Conditions	Yield
With trimethylsilyl bis(trifluoromethanesulfonyl)imide In dichloromethane at -78 - 20℃; for 19h; Schlenk technique; Inert atmosphere;	98%

Togni's reagent (887144-97-0) + diphenyl ditelluride (32294-60-3) → 1-iodo-3,3-dimethyl-1-phenyl-1,3-dihydro-2,1λ4-benzoxatellurole

Conditions	Yield
at 80℃; Sealed tube; Inert atmosphere;	98%

Togni's reagent (887144-97-0) + 9-vinyl-9H-carbazole (1484-13-5) + 4-chlorobenzaldehyde (104-88-1) → C22H15ClF3NO

Conditions	Yield
With 3-(2,6-diisopropylphenyl)-5,6,7,8-tetrahydro-4H-cyclohepta[d]thiazol-3-ium perchlorate; caesium carbonate In dichloromethane; water at 25℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube;	98%

Togni's reagent (887144-97-0) + N-vinylphthalimide (3485-84-5) + trimethylsilyl cyanide (7677-24-9) → C12H7F3N2O2

Conditions	Yield
With carbon tetrabromide; C43H38N2O2; copper (I) acetate In tert-butyl methyl ether at -20℃; for 12h; Inert atmosphere; Sealed tube; enantioselective reaction;	98%

Togni's reagent (887144-97-0) + 1-ethenyl-2-pyrrolidinone (88-12-0) + trimethylsilyl cyanide (7677-24-9) → C8H9F3N2O + C8H9F3N2O

Conditions	Yield
With carbon tetrabromide; C43H38N2O2; copper (I) acetate In tert-butyl methyl ether at -20℃; for 12h; Inert atmosphere; Sealed tube; Overall yield = 96 percent; Overall yield = 39.5 mg; enantioselective reaction;	A 98% B n/a

Togni's reagent (887144-97-0) + trimethylsilyl cyanide (7677-24-9) + vinyl benzoate (769-78-8) → C11H8F3NO2

Conditions	Yield
With carbon tetrabromide; C43H38N2O2; copper (I) acetate In tert-butyl methyl ether at -20℃; for 12h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Sealed tube; enantioselective reaction;	98%

Togni's reagent (887144-97-0) + trimethylsilyl cyanide (7677-24-9) + N-benzoylethyleneimine (13313-25-2) → C11H9F3N2O

Conditions	Yield
With carbon tetrabromide; C25H26N2O2; copper (I) acetate In tert-butyl methyl ether at -20℃; for 12h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Inert atmosphere; Sealed tube; enantioselective reaction;	98%

Togni's reagent (887144-97-0) + ethyl (E)-2-(2,2-diphenylhydrazono)acetate → ethyl (E)-2-(2,2-diphenylhydrazono)-3,3,3-trifluoropropanoate

Conditions	Yield
With copper(l) chloride In chloroform at 25℃; for 2h; Inert atmosphere; Sealed tube;	97%

Togni's reagent (887144-97-0) + 5-benzyl-1-methyl-6-((trimethylsilyl)oxy)-1,2,3,4-tetrahydropyridine → 3-benzyl-1-methyl-3-(trifluoromethyl)piperidin-2-one

Conditions	Yield
With trimethylsilyl bis(trifluoromethanesulfonyl)imide In dichloromethane at -78 - 20℃; for 19h; Reagent/catalyst; Schlenk technique; Inert atmosphere;	97%

Togni's reagent (887144-97-0) → tert-butyl (R)-3-(4-fluorobenzyl)-2-oxo-3-(trifluoromethyl)indoline-1-carboxylate

Conditions

Yield

Stage #1: tert-butyl 3-(4-fluorobenzyl)-2-oxoindoline-1-carboxylate With magnesium bromide ethyl etherate; {3aS-[2(3'aR*,9'bS*),3aα,9bα]}-2,2'-(2,6-pyridinediyl)bis[3a,4,5,9b-tetrahydronaphth[1,2-d]oxazole] In dichloromethane at 20℃; for 0.0833333h; Schlenk technique; Inert atmosphere; Stage #2: Togni's reagent In dichloromethane at -78 - 20℃; for 19h; Catalytic behavior; Reagent/catalyst; Schlenk technique; Inert atmosphere; enantioselective reaction;

97%

Upstream product

• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 175786-58-0 3,3-dimethyl-1λ³-benzo[d][1,2]iodoxol-1(3H)-yl acetate 
• 69352-04-1 1-chloro-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole 
• 1391728-13-4 1-fluoro-3,3-dimethyl-1,3-dihydro-1λ³-benzo[d][1,2]iodaoxole 
• 75-46-7 trifluoromethan 
• 134-20-3 2-carbomethoxyaniline 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 88-67-5 2-Iodobenzoic acid 
• 69352-05-2 2-(2-iodophenyl)propan-2-ol 

Downstream Products

• 403-66-7 p-nitrophenyl trifluoromethyl sulfide 
• 351-81-5 4-trifluoromethylthioacetanilide 
• 69352-05-2 2-(2-iodophenyl)propan-2-ol 
• 1023971-97-2 rac-(2-methoxyphenyl)(phenyl)(trifluoromethyl)phosphine 
• 1023971-92-7 di-o-tolyl(trifluoromethyl)phosphine 
• 1023971-93-8 di-p-tolyl(trifluoromethyl)phosphine 
• 1023971-96-1 bis(4-methoxyphenyl)(trifluoromethyl)phosphine 
• 1605-56-7 (trifluoromethyl)-diphenylphosphine 
• 1023971-91-6 dicyclohexyl(trifluoromethyl)phosphine sulfide 
• 3796-24-5 4-trifluoromethylpyridine 
• 3796-23-4 3-(trifluoromethyl)pyridine 
• 368-48-9 2-(trifluoromethyl)pyridine 
• 213019-67-1 3-trifluoromethyl-2-aminopyrazine 
• 1214346-70-9 4-methoxy-3-(trifluoromethyl)pyridine 

Relevant articles and documents

Borazine-CF3? Adducts for Rapid, Room Temperature, and Broad Scope Trifluoromethylation

A fluoroform-derived borazine CF3? transfer reagent is used to effect rapid nucleophilic reactions in the absence of additives, within minutes at 25 °C. Inorganic electrophiles spanning seven groups of the periodic table can be trifluoromethylated in high yield, including transition metals used for catalytic trifluoromethylation. Organic electrophiles included (hetero)arenes, enabling C?H and C?X trifluoromethylation reactions. Mechanistic analysis supports a dissociative mechanism for CF3? transfer, and cation modification afforded a reagent with enhanced stability.

Recyclable Trifluoromethylation Reagents from Fluoroform

We present a strategy to rationally prepare CF3- transfer reagents at ambient temperature from HCF3. We demonstrate that a highly reactive CF3- adduct can be synthesized from alkali metal hydride, HCF3, and borazine Lewis acids in quantitative yield at room temperature. These nucleophilic reagents transfer CF3- to substrates without additional chemical activation, and after CF3 transfer, the free borazine is quantitatively regenerated. These features enable syntheses of popular nucleophilic, radical, and electrophilic trifluoromethylation reagents with complete recycling of the borazine Lewis acid.

One-pot synthesis of hypervalent iodine reagents for electrophilic trifluoromethylation

Simplified syntheses suited for large scale preparations of the two hypervalent iodine reagents 1 and 2 for electrophilic trifluoromethylation are reported. In both cases, the stoichiometric oxidants sodium metaperiodate and tert-butyl hypochlorite have been replaced by trichloroisocyanuric acid. Reagent 1 is accessible in a one-pot procedure from 2-iodobenzoic acid in 72% yield. Reagent 2 was prepared via fluoroiodane 11 in a considerably shorter reaction time and with no need of an accurate temperature control.