684-16-2

Basic information

• Product Name: Hexafluoroacetone
• Synonyms: 1,1,1,3,3,3-hexafluoro-2-propanone;HEXAFLUOROACETONE;HEXAFLUORO-2-PROPANONE;PERFLUOROACETONE;(CF3)2CO;1,1,1,3,3,3-hexafluoro-2-propanon;1,1,1,3,3,3-Hexafluoroacetone;2-Propanone,1,1,1,3,3,3-hexafluoro-
• CAS NO: 684-16-2
• Molecular Formula: C₃F₆O
• Molecular Weight: 166.02
• EINECS: 211-676-3
• Product Categories: Organic Fluorides;organofluorine compounds
• Mol File: 684-16-2.mol
• Article Data: 73

Chemical Properties

• Melting Point: −129 °C(lit.)
• Boiling Point: −26 °C(lit.)
• Appearance: generally supplied as liquid under pressure
• Density: 1,32 g/cm3
• Vapor Density: 1.65 (vs air)
• Vapor Pressure: 4525 mm Hg ( 21.1 °C)
• Refractive Index: 1.247
• Storage Temp.: Refrigerator
• Solubility: Chloroform
• CAS DataBase Reference: Hexafluoroacetone(CAS DataBase Reference)
• NIST Chemistry Reference: Hexafluoroacetone(684-16-2)
• EPA Substance Registry System: Hexafluoroacetone(684-16-2)

Safety Data

• Hazard Codes: T
• Statements: 60-14-23/24/25-34-63
• Safety Statements: 53-26-28-36-45-7/9
• RIDADR: UN 2420 2.3
• WGK Germany: 3
• RTECS: UC2450000
• TSCA: T
• HazardClass: 2.3
• Hazardous Substances Data: 684-16-2(Hazardous Substances Data)

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

• 353-85-5 trifluoroacetonitrile 
• 334-98-5 (trifluoro methyl) magnesiumiodide 
• 67-64-1 acetone 
• 116-15-4 perfluoropropylene 
• 75-63-8 Bromotrifluoromethane 
• 383-63-1 ethyl trifluoroacetate, 
• 51689-98-6 α-(fluorosulfato)pentafluoroacetone 
• 99648-42-7 2-Chlor-1,1,1,3,3,3-hexafluoropropan-2-sulfinylchlorid 
• 334-99-6 trifluoronitrosomethane 
• 51820-85-0 2-<5,5-dimethyl-3,3-bis(trifluoromethyl)-1-pyrazolin-1-ylio>-1,1,1,3,3,3-hexafluoropropan-2-ide 
• 428-59-1 Hexafluoropropene oxide 
• 178984-96-8 C₄BrF₉O 
• 178985-10-9 C₅BrF₁₁O 
• 677-71-4 hexafluoroacetone hydrate 

Downstream Products

• 10482-84-5 <2-Dimethylamino-phenyl>-bis-trifluormethyl-carbinol 
• 730-59-6 N,N-Dimethyl-4-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)aniline 
• 2402-69-9 m-N.N-Dimethylamino-α.α-bis-(trifluormethyl)-benzylalkohol 
• 67565-26-8 4-p-tolyl-2,2,6,6-tetrakis-trifluoromethyl-3,6-dihydro-2H-[1,3,5]oxadiazine 
• 57014-94-5 4-(4-chloro-phenyl)-2,2,6,6-tetrakis-trifluoromethyl-6H-[1,3,5]oxathiazine 
• 42282-14-4 1,1,2,2-tetramethyl-4-phenyl-6,6,8,8-tetrakis-trifluoromethyl-5,7-dioxa-4λ⁵-phospha-spiro[3.4]octane 
• 136264-51-2 5-phenyl-2-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)furan 
• 65797-54-8 5-(2-hydroxyhexafluoroprop-2-yl)indoline 
• 99483-01-9 7-(α-hydroxyhexafluoroisopropyl)indoline 
• 85448-11-9 2-cyclohexanone 
• 116356-56-0 2,6-bis(2-hydroxyperfluoroisopropyl)cyclohexanone 
• 1992-30-9 4-(1-Hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-2-chloroaniline 
• 121953-15-9 4-ethoxycarbonylmethyl-3-phenacyl-2-trifluoroacetylimino-2,3-dihydrothiazole 
• 7594-49-2 1,1,1-trichloro-3,3,3-trifluoro-2-(trifluoromethyl)propan-2-ol 

Relevant articles and documents

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.

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Hexafluoroacetone

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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.

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.

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).