382-31-0

Basic information

• Product Name: 2,2,3,4,4,4-HEXAFLUORO-1-BUTANOL
• Synonyms: 1H,1H,3H-HEXAFLUOROBUTANOL;2,2,3,4,4,4-HEXAFLUORO-1-BUTANOL;2,2,3,4,4,4-HEXAFLUOROBUTAN-1-OL;2,2,3,4,4,4-HEXAFLUOROBUTANOL;2,2,3,4,4,4-HEXAFLUOROBUTANOL-1;1H,1H,3H-PerfluoroButan-1-ol;2,2,3,4,4,4-Hexafluorobutan-1-ol 95%;2,2,3,4,4,4-Hexafluorobutan-1-ol95%
• CAS NO: 382-31-0
• Molecular Formula: C₄H₄F₆O
• Molecular Weight: 182.06
• EINECS: 206-842-7
• Product Categories: Alcohols;C2 to C6;Oxygen Compounds
• Mol File: 382-31-0.mol
• Article Data: 9

Chemical Properties

• Melting Point: 68°C
• Boiling Point: 114 °C740 mm Hg(lit.)
• Flash Point: 125 °F
• Appearance: /
• Density: 1.557 g/mL at 25 °C(lit.)
• Vapor Pressure: 9.94mmHg at 25°C
• Refractive Index: n20/D 1.312(lit.)
• Storage Temp.: 2-8°C
• PKA: 13.10±0.10(Predicted)
• BRN: 1753872
• CAS DataBase Reference: 2,2,3,4,4,4-HEXAFLUORO-1-BUTANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,3,4,4,4-HEXAFLUORO-1-BUTANOL(382-31-0)
• EPA Substance Registry System: 2,2,3,4,4,4-HEXAFLUORO-1-BUTANOL(382-31-0)

Safety Data

• Hazard Codes: Xn,Xi,F
• Statements: 20/22-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: UN 1987 3/PG 3
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 382-31-0(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid

Uses

2,2,3,4,4,4-Hexafluoro-1-butanol may be used in the preparation of fluorinated cationic guar gum (FCGG)., It may be employed as solvent to evaluate the dynamic nuclear polarization (DNP) parameters for the solutions of free radicals Galvinoxyl (GALV) and α,γ-bisdiphenylene-β-phenyl allyl complex with benzene (1:1) (BDPA).

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 910, 1955 DOI: 10.1021/ja01609a033

InChI:InChI=1/C4H4F6O/c5-2(4(8,9)10)3(6,7)1-11/h2,11H,1H2/t2-/m1/s1

Upstream product

• 67-56-1 methanol 
• 116-15-4 perfluoropropylene 
• 94-36-0 dibenzoyl peroxide 
• 58705-93-4 2,2,3,4,4,4-hexafluorobutyl methyl ether 
• 110-63-4 Butane-1,4-diol 
• 107-31-3 Methyl formate 
• 121-43-7 Trimethyl borate 

Downstream Products

• 18820-82-1 Pyridine hydrobromide 
• 379-90-8 2,2,3,4,4,4-Hexafluor-buttersaeure 

Relevant articles and documents

Radical additions to fluoroolefins. Photochemical fluoroalkylation of alkanols and alkane diols with perfluoro vinyl ethers; photo-supported O-alkylation of butane-1,4-diol with hexafluoropropene

Butane-1,4-diol was fluoroalkylated by its photoaddition reactions with hexafluoropropene and perfluoro (propyl vinyl) ether under atmospheric pressure, by which monofluoroalkylated and bis-fluoroalkylated products were obtained. 1,3-Diols were completely unreactive under the conditions. 2,2,2-Trifluoroethanol, tert.butyl alcohol and methyl tert.butyl ether appeared to be inert solvents for the additions while acetonitrile quenched the reactions. The reactivity of perfluoro vinyl ethers was studied ( tested) in their photoaddition reactions with alkanols that were less regioselective (up to 7% rel.of regioisomer) in comparison with hexafluoropropene. Surprisingly, photo-supported base-induced nucleophilic mono-and bis-addition of butane-1,4-diol onto hexafluoropropene was observed in acetonitrile.

Promising prospects for using partially fluorinated alcohols as O-nucleophilic reagents in organofluoric synthesis

Perfluoroolefins react with isopropyl alcohol under the conditions of radical initiation to form partially fluorinated aliphatic alcohols. The reactions of these alcohols with hexafluoropropylene and compounds containing labile halogen atoms (in particular, with allyl bromide and epichlorohydrin) were studied.

METHOD FOR THE PREPARATION OF 2, 2, 3, 4, 4, 4-HEXAFLUORO-1-BUTANOL

The method for preparing 2,2,3,4,4,4-hexafluoro-1-butanol includes reacting methanol and hexafluoropropene in the presence of a free radical initiator such as di-isopropyl peroxydicarbonate at 25-50° C. and a pressure of 100-300 psi in an autoclave. An inert gas such as nitrogen and argon is added to the autoclave when the pressure is lower than 100 psi in the course of the reaction.