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.]
Check Digit Verification of cas no
The CAS Registry Mumber 684-16-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,8 and 4 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 684-16:
(5*6)+(4*8)+(3*4)+(2*1)+(1*6)=82
82 % 10 = 2
So 684-16-2 is a valid CAS Registry Number.
InChI:InChI=1/C3F6O/c4-2(5,6)1(10)3(7,8)9
684-16-2Relevant articles and documents
Preparation of Hexafluoroacetone by Vapor Phase Oxidation of Hexafluoropropene
Kurosaki, Akito,Okazaki, Susumu
, p. 17 - 20 (1988)
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.
-
Bell et al.
, p. 722 (1963)
-
Middleton, W. J.
, p. 3731 - 3734 (1966)
Hexafluoroacetone
Van Der Puy, Michael,Anello, Louis G.
, p. 154 - 154 (1985)
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Equipment for directly producing bis-o-xylylene hexafluoroacetone through HFPO
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Paragraph 0047-0048; 0050-0051; 0053-0054; 0056-0057; 0059, (2021/02/13)
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.
Copper-catalyzed synthesis of sulfonamides from nitroarenes: Via the insertion of sulfur dioxide
Wang, Xuefeng,Yang, Min,Kuang, Yunyan,Liu, Jin-Biao,Fan, Xiaona,Wu, Jie
supporting information, p. 3437 - 3440 (2020/03/30)
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).
Novel process for synthesizing hexafluoroacetone
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Paragraph 0021-0022, (2020/07/21)
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%.
