423-46-1

Basic information

• Product Name: 1H,1H-PERFLUOROHEXAN-1-OL
• Synonyms: 2,2,3,3,4,4,5,5,6,6,6-UNDECAFLUORO-1-HEXANOL;1H,1H-PERFLUOROHEXAN-1-OL;1H,1H-PERFLUOROHEXANE-1-OL;5:1 FTOH;2,2,3,3,4,4,5,5,6,6,6-Eicosalfluorohexan-1-ol;1H,1H-Perfluorohexan-1-ol 98%;1H,1H-Perfluorohexan-1-ol98%;2,2,3,3,4,4,5,5,6,6,6-Eicosalfluorohexan-1-ol, 2,2,3,3,4,4,5,5,6,6,6-Undecafluorohexan-1-ol
• CAS NO: 423-46-1
• Molecular Formula: C₆H₃F₁₁O
• Molecular Weight: 300.07
• Mol File: 423-46-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 128°C
• Flash Point: 25 °C
• Appearance: /
• Density: 1.619 g/cm³
• Vapor Pressure: 8.51mmHg at 25°C
• Refractive Index: 1.284
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 12.73±0.10(Predicted)
• CAS DataBase Reference: 1H,1H-PERFLUOROHEXAN-1-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 1H,1H-PERFLUOROHEXAN-1-OL(423-46-1)
• EPA Substance Registry System: 1H,1H-PERFLUOROHEXAN-1-OL(423-46-1)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 23-24/25
• HazardClass: IRRITANT
• Hazardous Substances Data: 423-46-1(Hazardous Substances Data)

Usage

Chemical Properties

Liquid

Uses

1H,1H-Perfluorohexan-1-ol is a reagent in the synthesis of environmentally safer fluoroalkyl ether synthons.

InChI:InChI=1/C6H3F11O/c7-2(8,1-18)3(9,10)4(11,12)5(13,14)6(15,16)17/h18H,1H2

Upstream product

• 424-18-0 perfluorohexanoic acid methyl ester 
• 307-24-4 undecafluorohexanoic acid 

Downstream Products

• 595-00-6 (1H,1H-undecafluoro-hexyl)-vinyl ether 
• 424-24-8 3-methyl-glutaric acid bis-(1H,1H-undecafluoro-hexyl ester) 
• 376-56-7 1H,1H-perfluorohexyl acrylate 
• 1613337-81-7 6,6'-[(2E)-but-2-ene-1,4-diylbis(oxy)]bis-(1,1,1,2,2,3,3,4,4,5,5-undecafluorohexane) 
• 1552323-14-4 6,6'-[(2Z)-but-2-ene-1,4-diylbis(oxy)]bis-(1,1,1,2,2,3,3,4,4,5,5-undecafluorohexane) 
• 1552323-18-8 6,6'-[but-1-ene-1,4-diylbis(oxy)]bis(1,1,1,2,2,3,3,4,4,5,5-undecafluorohexane) 
• 1552323-19-9 6,6'-[but-1-ene-1,4-diylbis(oxy)]bis(1,1,1,2,2,3,3,4,4,5,5-undecafluorohexane) 
• 1552323-16-6 1,1,1,2,2,3,3-heptafluoro-4-[prop-1-en-1-yloxy]butane 
• 1552323-21-3 1,1,1,2,2,3,3-heptafluoro-4-[prop-1-en-1-yloxy]butane 
• 1448858-01-2 5-iodo-1-methyl-2-((2,2,3,3,4,4,5,5,6,6-undecafluorohexyl)oxy)-1H-imidazole 
• 1448857-79-1 5-(2-methoxyphenyl)-1-methyl-2-((2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyl)oxy)-1H-imidazole 
• 1384267-35-9 C₁₈H₁₉F₁₁N₂O 
• 1173199-11-5 2,2,3,3,4,4,5,5,6,6,6-undecafluoro-1-hexaphosphoric acid ester 

Relevant articles and documents

A process for the preparation of the fluoro method

The invention relates to a method of preparing fluoroalcohol of which the structure formula is F3C(CF2)nCH2OH, wherein n is an integer of 2-8. The method includes following steps: (I) mixing fluorocarboxylic acid and isopropyl alcohol and performing a temperature-increasing reflux reaction; (II) when the reaction is finished, distilling the reaction liquid to remove generated water and isopropyl alcohol, and cooling the rest reaction liquid to room temperature; (III) pouring the reaction liquid into distillated water, regulating the pH value to 6.5-7 by an alkali liquid, allowing the reaction liquid to stand to layer the reaction liquid to obtain an organic layer; (IV) removing water from the organic layer to obtain fluorocarboxylic isopropyl ester; (V) adding the fluorocarboxylic isopropyl ester and a solvent into a high-pressure reaction kettle with addition of a hydrogenation catalyst and a co-catalyst, sealing the reaction kettle, increasing the temperature and filling hydrogen to a high pressure for performing a reaction for 20-60 h; (VI) when the reaction is finished, cooling the reaction kettle to room temperature, discharging hydrogen to obtain a reaction mixed liquid; (VII) performing rectification to the reaction mixed liquid to separate the solvent, cooling the rest liquid and pouring the rest liquid into distillated water and regulating the pH value to 6.5-7 by an acid liquid; and (VIII) allowing the mixed liquid to stand to layer the mixed liquid to obtain an organic layer, removing water from the organic layer and distilling the organic layer to obtain the corresponding fluoroalcohol.

Various synthetic approaches to fluoroalkyl p-nitrophenyl ethers

Homologous 1H,1H-perfluoroalkyl p-nitrophenyl ethers (alkyl = C2-C8) were synthesized using different methods. The results are discussed in context with contradictory comments of the literature. The fluoroalkoxylation of p-chloronitrobenzene occurs in only one step, but it is limited to small fluoroalkyl groups. The fluoroalkylation of p-nitrophenol via sulphonic acid esters is a better synthetic route. Differences in reactivity and yield between tosylates, mesylates and inflates are found and discussed. The preferred synthesis includes the use of trifluoromethane sulphonic acid esters.