684-16-2

Usage

Chemical Properties

generally supplied as liquid under pressure

Uses

Different sources of media describe the Uses of 684-16-2 differently. You can refer to the following data:
1. In the synthesis of polymer, pharmaceutical, and agricultural chemicals; solvent for polyamides, polyesters, and polyacetals; in the synthesis of hexafluoroisopropanol
2. Hexafluoroacetone is a protecting and activatng reagent used in the synthesis of (S)-isoserine from (S)-malic acid. It is also an intermediate used to prepare hexafluorocarbinols as liver X receptor-α agonists.
3. Protecting and activating reagent in peptide chemistry; in synthesis of high performance fluoropolymers, pharmaceutical and agricultural chemicals; in 19F NMR. Solvent for polyamides, polyesters, polyacetals, polyols.

Definition

ChEBI: A ketone that is acetone in which all the methyl hydrogens are replaced by fluoro groups.

Synthesis Reference(s)

Canadian Journal of Chemistry, 33, p. 453, 1955 DOI: 10.1139/v55-055Organic Syntheses, Coll. Vol. 7, p. 251, 1990

General Description

Hexafluoroacetone is a colorless, toxic, and highly reactive gas. At ambient temperatures, Hexafluoroacetone is likely to generate a considerable amount of vapor. Hexafluoroacetone is an irritant to skin, eyes and mucous membranes and is toxic by ingestion, skin absorption, and inhalation. When heated to high temperatures Hexafluoroacetone emits toxic fluoride fumes. Prolonged exposure of the container to fire or intense heat may cause Hexafluoroacetone to violently rupture and rocket. Hexafluoroacetone is used in the production of other chemicals.

Air & Water Reactions

Hygroscopic (i.e., absorbs moisture from the air); reacts with moisture to form a highly acidic sesquihydrate. .

Reactivity Profile

Hexafluoroacetone is incompatible with the following: Water, acids [Note: Hygroscopic (i.e., absorbs moisture from the air); reacts with moisture to form a highly acidic sesquihydrate.] .

Hazard

Toxic by inhalation and skin absorption. Reacts vigorously with water and other substances, releasing considerable heat. Nonflammable.

Health Hazard

TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Vapors are extremely irritating and corrosive. Contact with gas or liquefied gas may cause burns, severe injury and/or frostbite. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control may cause pollution.

Fire Hazard

Some may burn but none ignite readily. Vapors from liquefied gas are initially heavier than air and spread along ground. Some of these materials may react violently with water. Cylinders exposed to fire may vent and release toxic and/or corrosive gas through pressure relief devices. Containers may explode when heated. Ruptured cylinders may rocket.

Purification Methods

Dehydrate hexafluoroacetone by passing the vapours over P2O5. Ethylene is removed by passing the dried vapours through a tube containing Pyrex glass wool moistened with conc H2SO4. Further purification is by low temperature distillation using Warde-Le Roy stills. Store it in the dark at -78o. [Holmes & Kutschke Trans Faraday Soc 58 333 1962, Beilstein 1 IV 3215.]

InChI:InChI=1/C3F6O/c4-2(5,6)1(10)3(7,8)9

Upstream product

• 354-32-5 trifluoracetyl chloride 
• 334-98-5 (trifluoro methyl) magnesiumiodide 
• 353-85-5 trifluoroacetonitrile 
• 382-21-8 perfluoroisobutylene 
• 359-66-0 1,1-Dichloro-2-(trifluoromethyl)-3,3,3-trifluoro-1-propene 
• 67-64-1 acetone 
• 428-59-1 Hexafluoropropene oxide 
• 13994-52-0 cesium heptafluoroisopropoxide 
• 1645-75-6 bis(trifluoromethyl)ketimine 
• 2154-71-4 bis-trifluoromethyl-aminooxyl 
• 791-50-4 2,2,4,4-Tetrakis(trifluoromethyl)-1,3-dithietane 
• 116-15-4 perfluoropropylene 
• 75-63-8 Bromotrifluoromethane 
• 383-63-1 ethyl trifluoroacetate, 

Downstream Products

• 421-50-1 1,1,1-trifluoro-2-propanone 
• 677-71-4 hexafluoroacetone hydrate 
• 662-16-8 1,1,1,3,3,3-hexafluoro-2-methoxy-propan-2-ol 
• 10601-29-3 5,5,7-Tris--8,8,8-trifluor-4,6-dioxa-octyl-benzoat 
• 52786-37-5 2-Benzoylamino-2-hydroxy-1,1,1,3,3,3-hexafluorpropan 
• 150582-53-9 HFA-Tyr 
• 68150-26-5 3-(toluene-4-sulfonyl)-2,2-bis-trifluoromethyl-oxazolidin-5-one 
• 10315-85-2 1,1,1,3,3,3-hexafluoropropan-2-yl benzoate 
• 30184-89-5 1,1,1,3,3,3-Hexafluoro-2-(2-hydroxy-ethylamino)-propan-2-ol 
• 7730-50-9 N-Cyclohexyl-3,3,3-trifluor-2-trifluormethyl-2-acetoxy-propionsaeure-amid 
• 1547-36-0 4,4,4-trifluoro-3-hydroxy-3-trifluoromethyl-butyric acid 
• 15052-92-3 2-(trifluoro methyl) 2-hydroxy (perfluoro buten-⁽³⁾) 
• 25055-33-8 4-Chloro-2-trifluoromethyl-1,1,1,3,4,4-hexafluoro-buten-2 
• 3015-33-6 2-(2-hydroxyhexafluoroisopropyl)-6-methylphenol 

Relevant academic research and scientific papers

Preparation of Hexafluoroacetone by Vapor Phase Oxidation of Hexafluoropropene

Hexafluoroacetone was readily formed by circulating a gaseous mixture of hexafluoropropene and oxygen over platinum group metals supported on carbon.Reaction temperatures, ranging from 130 to 170 deg C, gave both high selectivity and conversion for the hexafluoroacetone formation using a Pd/C catalyst.

Benchtop-Stabssle Hypervalent Bromine(III) Compounds: Versatile Strategy and Platform for Air- And Moisture-Stable λ3-Bromanes

We present the first synthesis of air/moisture-stable λ3-bromanes (9and10) by using a cyclic 1,2-benzbromoxol-3-one (BBX) strategy. X-ray crystallography and NMR and IR spectroscopy ofN-triflylimino-λ3-bromane (12) revealed that the bromine(III) center is effectively stabilized by intramolecular R-Br-O hypervalent bonding. This strategy enables the synthesis of a variety of air-, moisture-, and benchtop-stable Br-hydroxy, -acetoxy, -alkynyl, -aryl, and bis[(trifluoromethyl)sulfonyl]methylide λ3-bromane derivatives.

Equipment for directly producing bis-o-xylylene hexafluoroacetone through HFPO

The utility model provides equipment for directly producing bis-o-xylylene hexafluoroacetone through HFPO, which comprises an isomerization kettle, a gas-liquid separation kettle, a rectification column, a condenser, an HFA storage tank and a condensation kettle, the bottom of the isomerization kettle is connected to the bottom of the gas-liquid separation kettle, and the upper part of the gas-liquid separation kettle is connected with the upper part of the isomerization kettle; wherein the top of the gas-liquid separation kettle is connected to the bottom of the rectification column through apipeline, the upper end of the rectification column is respectively connected to an HFPO feed port and an HFA storage tank of the isomerization kettle, and a condenser is also arranged on a connecting pipeline between the rectification column and the HFA storage tank; and the HFA storage tank is connected to the condensation kettle. According to the device, synchronous HFA production and consumption can be realized, risks caused by HFA transportation and storage are avoided, and meanwhile, the reaction catalyst can be directly recycled through the device, so that the cost is saved, and the harm to the environment is avoided.

Method for preparing hexafluoroacetone by taking perfluoropropylene oxide as raw material

The invention discloses a method for preparing hexafluoroacetone by taking perfluoropropylene oxide as a raw material. The method comprises the following steps: adding the perfluoropropylene oxide, acatalyst and water into a reaction kettle according to a weight ratio of 1: (0.1-0.5): (1-5), carrying out isomerization reaction at 10-80 DEG C for 1-5 hours, and distilling and purifying to obtain the hexafluoroacetone, wherein by condensing substituted phenol and Merrifield resin, and mixing and compounding with a carrier, the catalyst is obtained. According to the method, the Merrifield resinloaded substituted phenol is used as the catalyst for the first time, and is applied to the method for preparing the hexafluoroacetone by taking the perfluoropropylene oxide as the raw material, so that a new preparation thought is provided, and particularly for fluorine chemical enterprises, self-produced intermediate products can be fully utilized. The raw materials of the catalyst are easy to obtain, the cost is low, and the economic benefit is good; the catalyst is simple in preparation process and mild in preparation condition. The yield of the hexafluoroacetone reaches 95% or above, theoperation is safe, and the catalyst can be continuously used.

Novel process for synthesizing hexafluoroacetone

The invention discloses a novel process for synthesizing hexafluoroacetone. The novel process comprises the following steps: reacting trifluoroacetic anhydride with a metal fluoride in a solvent to obtain trifluoroacetyl fluoride, adding an alkaline salt and trifluoroacetate, and carrying out a coupling reaction on trifluoroacetate and trifluoroacetyl fluoride to obtain the product hexafluoroacetone. The product yield is 95% or above, and the product purity is higher than 96%.

Copper-catalyzed synthesis of sulfonamides from nitroarenes: Via the insertion of sulfur dioxide

Nitroarenes are used as the coupling partners in the preparation of sulfonamides via the insertion of sulfur dioxide. A three-component reaction of arylboronic acids, nitroarenes, and potassium metabisulfite under copper catalysis proceeds smoothly, giving rise to a range of sulfonamides in good to excellent yields with broad substrate scope. Various functional groups including hydroxyl, cyano, amino, and carbonyl are all tolerated. A plausible mechanism is proposed, showing that arylsulfinate is the intermediate and the copper-assisted interaction of the nitroarene and arylsulfinate is the key step. This approach is also extended to the late-stage modification of a currently marketed drug (flutamide).

From hypochlorites to perfluorinated dialkyl peroxides

The synthesis and characterization of the new perfluorinated hypochlorite, undecafluoro-tert-pentyl hypochlorite, (C2F5)(F3C)2COCl, is reported. Its gas-phase infrared, UV/Vis and NMR spectra have been recorded and its spectroscopic properties are discussed and compared with quantum-chemical predictions and those of other known perfluorinated hypochlorites such as RFOCl [RF = F3C, (F3C)3C, (C2F5)(F3C)2C]. A synthetic route to otherwise difficult to access perfluorinated dialkyl peroxides, RFOORF, is also provided by low-temperature photolysis of the corresponding hypochlorite.

2-Iodoxybenzoic acid ditriflate: The most powerful hypervalent iodine(v) oxidant

A ditriflate derivative of 2-iodoxybenzoic acid (IBX) was prepared by the reaction of IBX with trifluoromethanesulfonic acid and characterized by single crystal X-ray crystallography. IBX-ditriflate is the most powerful oxidant in a series of structurally similar IBX derivatives which is best illustrated by its ability to readily oxidize hydrocarbons and the oxidation resistant polyfluoroalcohols.

Pharmaceutical raw material hexafluoroacetone synthesis method

The invention relates to a pharmaceutical raw material hexafluoroacetone synthesis method, which mainly comprises: adding 3 mol 2,3-dihydroxy-hexafluoroisopentane and 4-6 mol N-methylpropionamide solution to a reaction container, increasing the temperature of the solution to 70-80 DEG C, maintaining for 60-80 min, adding 2-3 mol bismuth molybdate, continuously carrying out the reaction for 50-70 min, reducing the temperature to 40-50 DEG C, carrying out pressure reducing distillation, collecting the distillate at a temperature of 80-89 DEG C, washing with a metacresol solution, washing with am-chloroaniline solution, and re-crystallizing with a methoxytoluene solution to obtain the crystal hexafluoroacetone.

Synthesis of Benzoxazoles Using Electrochemically Generated Hypervalent Iodine

The indirect ("ex-cell") electrochemical synthesis of benzoxazoles from imines using a redox mediator based on the iodine(I)/iodine(III) redox couple is reported. Tethering the redox-active iodophenyl subunit to a tetra-alkylammonium moiety allowed for anodic oxidation to be performed without supporting electrolyte. The mediator salt can be easily recovered and reused. Our "ex-cell" approach toward the electrosynthesis of benzoxazoles is compatible with a range of redox-sensitive functional groups. An unprecedented concerted reductive elimination mechanism for benzoxazole formation is proposed on the basis of control experiments and DFT calculations.