1-Trifluoromethyl-1,2-benziodoxol-3(1H)-one

Base Information

• Chemical Name: 1-Trifluoromethyl-1,2-benziodoxol-3(1H)-one
• CAS No.: 887144-94-7
• Molecular Formula: C8H4F3IO2
• Molecular Weight: 316.018
• Hs Code.: 29349990
• Mol file: 887144-94-7.mol

Synonyms:1-(trifluoromethyl)-1λ³,2-benziodoxol-3-one;;

Chemical Property of 1-Trifluoromethyl-1,2-benziodoxol-3(1H)-one

Chemical Property:

• Appearance/Colour: Off-White Solid
• Melting Point: 106-108°C
• PSA: 26.30000
• LogP: 2.96780
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

98%, ^*data from raw suppliers

TogniReagentII ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-48/20
• Safety Statements: 26-24/25

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 1-Trifluoromethyl-1,2-benziodoxol-3(1H)-one

There total 3 articles about 1-Trifluoromethyl-1,2-benziodoxol-3(1H)-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

1-acetoxy-1,2-benziodoxol-3-one (1829-26-1) + (trifluoromethyl)trimethylsilane (81290-20-2) → Togni's reagent II (887144-94-7)

Guidance literature:

With cesium fluoride; In acetonitrile; at 20 ℃; for 22h; Inert atmosphere;

DOI:10.1021/acs.joc.1c01424

Reference yield: 55.0%

(trifluoromethyl)trimethylsilane (81290-20-2) + 1-methoxy-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one (1829-25-0) → Togni's reagent II (887144-94-7) + Trimethylmethoxysilane (1825-61-2)

Guidance literature:

With cesium fluoride; In acetonitrile; at 20 ℃; for 15h;

DOI:10.1002/chem.200501052

Reference yield:

1-acetoxy-1,2-benziodoxol-3-one (1829-26-1) → Togni's reagent II (887144-94-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 6.78 g / 0.25 h / Heating

2: 55 percent / CsF / acetonitrile / 15 h / 20 °C

With cesium fluoride; In acetonitrile;

DOI:10.1002/chem.200501052

upstream raw materials:

(trifluoromethyl)trimethylsilane

1-methoxy-1λ³-benzo[d][1,2]iodaoxol-3(1H)-one

1-acetoxy-1,2-benziodoxol-3-one

Downstream raw materials:

di-o-tolyl(trifluoromethyl)phosphine

di-p-tolyl(trifluoromethyl)phosphine

bis(4-methoxyphenyl)(trifluoromethyl)phosphine

(trifluoromethyl)-diphenylphosphine

Refernces

• 1、 Choi, Jun-Ho,Park, Cheol-Min. "Three-Component Synthesis of Quinolines Based on Radical Cascade Visible-Light Photoredox Catalysis". supporting information. p. 3553 - 3562. Retrieved 2018/09/22.
• 2、 Matousek, Vaclav,Pietrasiak, Ewa,Schwenk, Rino,Togni, Antonio. "One-pot synthesis of hypervalent iodine reagents for electrophilic trifluoromethylation". . p. 6763 - 6768. Retrieved 2013/07/26.