1-TrifluoroMethyl-1,2-benziodoxol-3(1H)-one Chemical Properties

Melting point:

150-158 °C

storage temp. 

2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

powder

color 

white to off-white

Stability:

Light Sensitive

InChI

InChI=1S/C8H4F3IO2/c9-8(10,11)12-6-4-2-1-3-5(6)7(13)14-12/h1-4H

InChIKey

XHEOXSQMBWJOKP-UHFFFAOYSA-N

SMILES

I1(C(F)(F)F)C2=CC=CC=C2C(=O)O1

CAS DataBase Reference

887144-94-7

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-48/20

Safety Statements 

26-24/25

RIDADR 

UN 1325 4.1/PG II

WGK Germany 

3

TSCA 

No

HazardClass 

4.1

PackingGroup 

II

HS Code 

29349990

1-TrifluoroMethyl-1,2-benziodoxol-3(1H)-one Usage And Synthesis

Chemical Properties

White to light yellow solid

Uses

1-TrifluoroMethyl-1,2-benziodoxol-3(1H)-one is used primarily as a reagent in trifluoromethylation reactions.

Uses

Electrophilic trifluoromethylating reagent has shown to be one of the more robust trifluoromethylation reagents on the market. However, a recent report has showed this product to have potential dangerous self-reactivity neat. We now offer a less self-reactive material mixed down in Celatom^?, a silica-based adsorbent, which significantly reduces self-reactivity allowing for safer shipping and storage.

reaction suitability

reaction type: C-C Bond Formation

Synthesis

General procedure for the synthesis of 1-(trifluoromethyl)-1,2-phenyliodonyl-3(1H)-ones from 1-chloro-1,2-phenyliodonyl-3-one and (trifluoromethyl)trimethylsilane: Potassium acetate (10.8 g, 0.110 mol, 2.00 eq.) was dried under vacuum at 150 °C for 30 min and subsequently cooled to room temperature. To this was added 1-chloro-1,2-phenyliodono-3-one (15.6 g, 0.0551 mol, 1.00 eq.) and acetonitrile (155 mL), and the reaction mixture was stirred at 75 °C for 2 hours. After completion of the reaction, the mixture was cooled to room temperature. (Trifluoromethyl)trimethylsilane (8.97 mL, 0.0607 mol, 1.10 eq.) was added all at once and the reaction mixture was stirred at room temperature for 15 hours. Subsequently, acetonitrile (100 mL) was added and the brown reaction mixture was heated to 75 °C. The reaction mixture was filtered through a diatomaceous earth pad, concentrated to a final volume of about 50 mL and cooled to -20 °C. The crystals were filtered out, washed with cold (-20 °C) acetonitrile (50 mL) and dried under vacuum. The mother liquor was reconcentrated to a final volume of about 15 mL and cooled to -20 °C. The crystals were filtered out and washed with cold (-20°C) acetonitrile (10 mL). Both crystallization products were dried under high vacuum to afford 1-(trifluoromethyl)-1,2-phenyliodonyl-3(1H)-one as a white crystalline solid (14.6 g, 0.0463 mol, 84% yield). The NMR data were as follows: 1H NMR (500 MHz, CDCl3, 25 °C, δ): 8.48 (dd, J = 7.2, 1.7 Hz, 1H), 7.85-7.76 (m, 3H). 13C NMR (175 MHz, CDCl3, 25 °C, δ): 165.9, 135.9, 133.9, 132.1, 132.0 , 127.3 (q, J = 2.5 Hz), 114.9, 107.3 (q, J = 378.8 Hz).19F NMR (376 MHz, CDCl3, 25 °C, δ): -34.2 (s). These spectral data are in agreement with literature reports.

References

[1] European Journal of Organic Chemistry, 2017, vol. 2017, # 2, p. 271 - 277
[2] Angewandte Chemie - International Edition, 2014, vol. 53, # 52, p. 14559 - 14563
[3] Angew. Chem., 2014, vol. 126, # 52, p. 14787 - 14791,5
[4] Patent: WO2016/57931, 2016, A1. Location in patent: Page/Page column 55
[5] European Journal of Organic Chemistry, 2018, vol. 2018, # 27, p. 3771 - 3781

1-TrifluoroMethyl-1,2-benziodoxol-3(1H)-one(887144-94-7)Related Product Information

• Silicone oil
• 2-(Trifluoromethyl)benzyl bromide
• 2,2,2-TRIFLUOROETHYLAMINE
• 2-(Trifluoromethyl)benzenesulfonyl chloride
• 2-(Trifluoromethoxy)nitrobenzene
• 2-(Trifluoromethyl)benzyl chloride
• (Difluoromethyl)bis(2,5-dimethylphenyl)sulfonium Tetrafluoroborate
• (PERFLUORO-N-HEXYL)PHENYLIODONIUM TRIFLUOROMETHANESULFONATE
• Diphenyl(trifluoromethyl)sulfonium trifluoromethanesulfonate
• 1,3-Dihydro-3,3-dimethyl-1-(trifluoromethyl)-1,2-benziodoxole, Tognis Reagent
• diphenyl(2,2,2-trifluoroethyl)sulfanium trifluoromethanesulfonate
• (perfluoroethyl)diphenylsulfonium trifluoromethanesulfonate
• Mesityl(2,2,2-trifluoroethyl)iodonium trifluoromethanesulfonate
• (difluoromethyl)(2,4-dimethylphenyl)(phenyl)sulfonium tetrafluoroborate
• Iodonium, (1,1,2,2,3,3,4,4,4-nonafluorobutyl)phenyl-,1,1,1-trifluoromethanesulfonate
• (2,2-difluoroethyl)diphenylsulfonium trifluoromethanesulfonate
• 2,2,2-trifluoroethyl(phenyl)iodonium trifluoromethanesulfonate
• DESICCANT