13171-18-1

Basic information

• Product Name: Hexafluoroisopropyl methyl ether
• Synonyms: ether,methyl2,2,2-trifluoro-1-(trifluoromethyl)ethyl;hexafluoropropylmethylether;isoindoklon;1,1,1,3,3,3-Hexafluoroisopropyl methyl ether 97%;1,1,1,3,3,3-Hexafluoroisopropylmethylether97%;HFMOP;Isoflurothyl;Methyl 1-(trifluoromethyl)-2,2,2-trifluoroethyl ether
• CAS NO: 13171-18-1
• Molecular Formula: C₄H₄F₆O
• Molecular Weight: 182.06
• Product Categories: Fluoro series
• Mol File: 13171-18-1.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 50 °C
• Flash Point: >93℃
• Appearance: /
• Density: 1.39
• Vapor Pressure: 329.604mmHg at 25°C
• Refractive Index: 1.284
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: Hexafluoroisopropyl methyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: Hexafluoroisopropyl methyl ether(13171-18-1)
• EPA Substance Registry System: Hexafluoroisopropyl methyl ether(13171-18-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 3334
• RTECS: KO2282000
• HazardClass: IRRITANT, GAS
• PackingGroup: II
• Hazardous Substances Data: 13171-18-1(Hazardous Substances Data)

Usage

General Description

Hexafluoroisopropyl methyl ether, also known as Perfluoro-2-methoxypropane is a fluoroether compound that is primarily used as the several powerful solvents. Its chemical formula is C4F8O. This colorless gas is characterized by high thermal stability, thus it is commonly used in industry for heat transfer applications. Moreover, it is utilized in the production of semiconductors, as it can generate highly reactive atoms when exposed to high temperatures. However, due to such properties, it is considered as a strong greenhouse gas when released to the atmosphere. On the safety perspective, although it is low in toxicity, chronic inhalation exposure may cause harm.

InChI:InChI=1/C4H4F6O/c1-11-3(7,2(5)6)4(8,9)10/h2H,1H3

Upstream product

• 920-66-1 1,1,1,3',3',3'-hexafluoro-propanol 
• 28523-86-6 sevoflurane 
• 124-41-4 sodium methylate 
• 67674-48-0 toluene-4-sulfonic acid 2,2,2-trifluoro-1-trifluoromethyl-ethyl ester 
• 616-38-6 carbonic acid dimethyl ester 
• 67-56-1 methanol 
• 149-73-5 trimethyl orthoformate 
• 421-20-5 Methyl fluorosulfonate 
• 74-87-3 methylene chloride 
• 85762-91-0 potassium 1,1,1,3,3,3-hexafluoropropoxide 
• 7594-51-6 methyl 3,3,3-trifluoro-2-hydroxy-2-(trifluoromethyl)propionate 
• 1000699-24-0 C₆H₅F₇O₃ 
• 13859-30-8 Methyl 3,3,3-trifluoro-2-trifluoromethyl-2-methoxypropionate 
• 37021-26-4 1,1,3,3,3-pentafluoro-2-methoxy-propene 

Downstream Products

• 353-50-4 Carbonyl fluoride 
• 431-47-0 trifluoroacetic acid-methyl ester 
• 684-16-2 Hexafluoroacetone 
• 26103-07-1 1,1,1,3,3,3-hexafluoroisopropyl chloromethyl ether 

Relevant articles and documents

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Sensory irritation mechanisms investigated from model compounds: Trifluoroethanol, hexafluoroisopropanol and methyl hexafluoroisopropyl ether

Quantitative structure-activity relationships (QSAR) have suggested the importance of hydrogen bonding in relation to activation of the sensory irritant receptor by nonreactive volatile organic chemicals. To investigate this possibility further, three model compounds with different hydrogen bond acidity, trifluoroethanol, hexafluoroisopropanol and methyl hexafluoroisopropyl ether, were selected for study. The potency of each chemical is obtained from the concentration necessary to reduce respiratory rate in mice by 50% (RD50). The RD50 values obtained were: methyl hexafluoroisopropyl ether (≥ 160,000 ppm), trifluoroethanol (11,400-23,300 ppm), and hexafluoroisopropanol (165 ppm). QSAR showed that trifluoroethanol and methyl hexafluoroisopropyl ether behaved as predicted as nonreactive sensory irritants, whereas hexafluoroisopropanol was much more potent than predicted. The higher than predicted potency of hexafluoroisopropanol could be due to a coupled reaction, involving both strong hydrogen bonding and weak Bronsted acidity. A concerted reaction could thus be more efficient in activation of the receptor. Hydrogen bonding properties and concerted reactions may be important in the activation of the sensory irritant receptor by nonreactive volatile organic chemicals.

A novel vapor-phase catalytic synthetic approach for industrial production of 1,1,1,3,3,3-hexafluoroisopropyl methylether

1,1,1,3,3,3-Hexafluoroisopropylmethyl ether (HFE-356mmz) is an important substitute for chlorofluorocarbons and hydrochlorofluorocarbons due to its zero ozone depletion potential and low global warming potential. However, mass production of HFE-356mmz remains a long-standing challenge. Herein, we applied metal fluorides as catalysts in the methylation of 1,1,1,3,3,3-hexafluoroisopropanol to produce HFE-356mmz for the first time. The catalyst not only improves the synthetic efficiency, but also makes the reaction solvent-free. The pollution-free, recyclable, and continuous synthetic process enables industrial production of HFE-356mmz. To optimize the synthetic efficiency, a series of metal fluorides (AlF3, MgF2, CaF2, SrF2, and BaF2) was used, among which MgF2 exhibited the highest activity. Through careful examination of each metal fluoride, it was found that the activity of the catalyst was determined by co-operative action of the surface acid–base properties and the total amount of surface acid sites. Based on these results, a rational mechanism for the vapor-phase methylation was proposed.

Preparation method of hexafluoroisopropyl methyl ether

The invention discloses a preparation method of 1,1,1,3,3,3-hexafluoroisopropyl methyl ether. The preparation method includes reacting trifluoroacetate with formate to obtain 1,1,1,3,3,3-hexafluoroisopropanol, and applying a methylation reagent to the 1,1,1,3,3,3-hexafluoroisopropanol to obtain the 1,1,1,3,3,3-hexafluoroisopropyl methyl ether. The preparation method has the advantages that raw materials are cheap and easy to obtain, the preparation process is mild and the method is simple to operate.