Hexafluoroacetone

Base Information

• Chemical Name: Hexafluoroacetone
• CAS No.: 684-16-2
• Molecular Formula: C3F6 O
• Molecular Weight: 166.023
• Hs Code.: 2914700090
• European Community (EC) Number: 211-676-3
• ICSC Number: 1057
• NSC Number: 202438
• UN Number: 2420
• UNII: AKU9463N1Y
• DSSTox Substance ID: DTXSID9043778
• Nikkaji Number: J1.724H
• Wikipedia: Hexafluoroacetone
• Wikidata: Q416322
• Metabolomics Workbench ID: 56306
• Mol file: 684-16-2.mol

Synonyms:hexafluoroacetone;hexafluoroacetone dihydrate;hexafluoroacetone hydrate;hexafluoroacetone monohydrate;hexafluoroacetone sesquihydrate;hexafluoroacetone trihydrate

Chemical Property of Hexafluoroacetone

Chemical Property:

• Appearance/Colour: generally supplied as liquid under pressure
• Vapor Pressure: 4525 mm Hg ( 21.1 °C)
• Melting Point: -129 ºC
• Boiling Point: -26 ºC
• PSA: 17.07000
• Density: 1,32 g/cm3
• LogP: 1.68010
• Storage Temp.: Refrigerator
• Solubility.: Chloroform
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 0
• Exact Mass: 165.98533359
• Heavy Atom Count: 10
• Complexity: 124
• Transport DOT Label: Poison Gas Corrosive

Purity/Quality:

97% ^*data from raw suppliers

Hexafluoroacetone ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 60-14-23/24/25-34-63
• Safety Statements: 53-26-28-36-45-7/9

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Corrosive Gases
• Canonical SMILES: C(=O)(C(F)(F)F)C(F)(F)F
• Inhalation Risk: A harmful concentration of this gas in the air will be reached very quickly on loss of containment.
• Effects of Short Term Exposure: The substance is severely irritating to the eyes, skin and respiratory tract. Inhalation of this gas may cause lung oedema. Rapid evaporation of the liquid may cause frostbite. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: Animal tests show that this substance possibly causes malformations in human babies. Animal tests show that this substance possibly causes toxic effects upon human reproduction.
• Uses: In the synthesis of polymer, pharmaceutical, and agricultural chemicals; solvent for polyamides, polyesters, and polyacetals; in the synthesis of hexafluoroisopropanol 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. 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.

Technology Process of Hexafluoroacetone

There total 102 articles about Hexafluoroacetone 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: 98.5%

2,3-dihydroxyhexafluoroisopentane → Hexafluoroacetone (684-16-2)

Guidance literature:

2,3-dihydroxyhexafluoroisopentane; With N-methylpropanamide; at 80 ℃; for 1.33333h;

With bismuth molybdate; at 50 ℃; for 1.16667h; Temperature;

Reference yield: 97.0%

C12F24O4 + C12HF23O4 (395058-38-5) → perfluoro-2,5-dimethyl-3,6-dioxanonanoyl fluoride (2641-34-1) + Hexafluoroacetone (684-16-2)

Guidance literature:

With potassium fluoride; at 200 ℃; for 2h; Autoclave;

DOI:10.1246/bcsj.80.1611

Reference yield: 97.0%

Hexafluoropropene oxide (428-59-1,25038-02-2) → Hexafluoroacetone (684-16-2)

Guidance literature:

In water; at 50 ℃; for 3h; Temperature; Reagent/catalyst; Large scale;

upstream raw materials:

trifluoracetyl chloride

(trifluoro methyl) magnesiumiodide

trifluoroacetonitrile

perfluoroisobutylene

Downstream raw materials:

5,5,7-Tris--8,8,8-trifluor-4,6-dioxa-octyl-benzoat

HFA-Tyr

2-(trifluoro methyl) 2-hydroxy (perfluoro buten-⁽³⁾)

4-Chloro-2-trifluoromethyl-1,1,1,3,4,4-hexafluoro-buten-2

Refernces

• 1、 Nicholson,Ogden. "-". . p. 2617,2624. Retrieved 1968.
• 2、 Ohno, Fumihiko,Kawashima, Takayuki,Okazaki, Renji. "Synthesis, crystal structure, and thermolysis of a pentacoordinate 1,2λ6-oxathietane: An intermediate of the Corey-Chaykovsky reaction of oxosulfonium ylides?". . p. 697 - 698. Retrieved 1996.
• 3、 Knunyants,I.L. et al.. "-". . . Retrieved 1973.
• 4、 Anello, Louis G.,Puy, Michael Van Der. "A Convenient Synthesis of Hexafluoroacetone". . p. 377 - 378. Retrieved 1982.
• 5、 Miyamoto, Kazunori,Saito, Motomichi,Tsuji, Shunsuke,Takagi, Taisei,Shiro, Motoo,Uchiyama, Masanobu,Ochiai, Masahito. "Benchtop-Stabssle Hypervalent Bromine(III) Compounds: Versatile Strategy and Platform for Air- And Moisture-Stable λ3-Bromanes". supporting information. p. 9327 - 9331. Retrieved 2021/07/01.
• 6、 Nissen, Jan H.,Wickemeyer, Lucas,Stüker, Tony,Steinhauer, Simon,Beckers, Helmut,Riedel, Sebastian. "From hypochlorites to perfluorinated dialkyl peroxides". . . Retrieved 2019/12/26.