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:

1,1,1-trifluoro-2-propanone

hexafluoroacetone hydrate

1,1,1,3,3,3-hexafluoro-2-methoxy-propan-2-ol

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

Refernces

Functionalization of the methylene bridges of the calix[6]arene scaffold

10.1021/jo801187z

The research focuses on the functionalization of the methylene bridges of the calix[6]arene scaffold, aiming to develop a versatile method for the introduction of substituents at all of the methylene groups of the calix[6]arene framework. The study successfully replaced bromine atoms of the hexabromo calixarene derivative with various nucleophiles under SN1 conditions, yielding calix[6]arene derivatives with identical functionalities at all bridges. Key chemicals used in the process include primary and secondary alcohols, hexafluoroisopropanol (HFIP), hexafluoroacetone, sodium azide, aniline, acetic acid, and 2,4-pentanedione. The reactions proceeded with high diastereoselectivity, predominantly yielding the rc5 (all-cis) form, and the resulting calix[6]arene derivatives exhibited a "pinched cone" conformation with 3-fold symmetry. The introduction of substituents at the bridges was found to rigidify the calix[6]arene scaffold, which could be beneficial for preorganization in various applications. The study concluded that a wide array of nucleophiles could be used for this functionalization, and the reactions were generally cleaner compared to those involving tetrabromo derivatives, with fewer side reactions observed.