677-71-4

Usage

Uses

Used in Organic Synthesis:
1,1,1,3,3,3-hexafluoropropane-2,2-diol is used as an intermediate in organic synthesis for various applications. Its unique chemical properties make it a valuable component in the production of various compounds and materials.

Air & Water Reactions

Hygroscopic. Reacts with water to release a large amount of heat.

Reactivity Profile

1,1,1,3,3,3-hexafluoropropane-2,2-diol is incompatible with water, and acids. Reacts with moisture to form a highly acidic sesquihydrate .

Health Hazard

Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Containers may explode when heated. Runoff may pollute waterways.

InChI:InChI=1S/C3H2F6O2/c4-2(5,6)1(10,11)3(7,8)9/h10-11H

Upstream product

• 353-85-5 trifluoroacetonitrile 
• 334-98-5 (trifluoro methyl) magnesiumiodide 
• 684-16-2 Hexafluoroacetone 
• 64-18-6 formic acid 
• 7732-18-5 water 
• 32308-81-9 mercury bis(perfluoro-tert-butanethiolate) 
• 662-23-7 N,N-Difluor-heptafluorisopropylamin 
• 354-32-5 trifluoracetyl chloride 
• 920-66-1 1,1,1,3',3',3'-hexafluoro-propanol 
• 118217-64-4 potassium 3,3,3-trifluoro-2-trifluoromethyl-2-hydroxypropionate 
• 175167-66-5 2-(Di-adamantan-1-yl-phosphinoyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol 
• 78952-21-3 perfluoro-2,6,6-trimethyl-2-heptene 
• 52225-57-7 2,2,2-trifluoro-N-{2,2,2-trifluoro-1-(trifluoromethyl) ethylidene}acetamide 
• 103-69-5 N-ethyl-N-phenylamine 

Downstream Products

• 96943-31-6 N-<4-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)phenyl>anthranilic acid 
• 134538-78-6 N-<4-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)phenyl>-4-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)anthranilic acid 
• 65294-20-4 4,4'-(hexafluoroisopropylidene)-bis-(o-xylene) 
• 684-16-2 Hexafluoroacetone 

Relevant academic research and scientific papers

Conformational equilibria in formic acid and the adduct of formic acid and hexafluoroacetone, HCO2C(CF3)2OH

Low-temperature 1H and 13C NMR spectra of formic acid (1) showed separate signals for the E and Z conformations in solvents containing a hydrogen bond acceptor, dimethyl ether. The population of E-1 (6.2% in 3:1:1 CHClF2/CHCl2F/(CH3)2O) was larger than that for 13C-labeled methyl formate in the same solvent (0.2%), which indicated that the relative populations are not determined by steric effects. The free-energy difference between the E and Z conformations of 1 was 0.9 kcal/mol. In a 1:3 CD2Cl2/ (CH3) 2O solvent mixture, peaks for E and Z conformations were found at low temperatures by 1H and 13C NMR for both formic acid and an adduct with hexafluoroacetone, HCO2C(CF3)2OH (2). The population of E-1 in this solvent mixture was 4.3% by 13C NMR. The carbon spectrum showed two peaks in the carbonyl carbon region of nearly equal intensities at -151.6 °C, with E-2 (48%) absorbing downfield of the major Z-2 (52%). The large population of E-2 confirms that electron-withdrawing groups R′ in RCO2R′ enhance the populations of the E-isomers. The free-energy barriers for 2 of 6.24 (E-to-Z) and 6.26 kcal/·mol (Z-to-E) were determined from rate constants obtained by line shape analysis at -143.2 °C.

Oxidation of fluoroalkyl alcohols using sodium hypochlorite pentahydrate [1]

Fluoroalkyl alcohols are effectivity oxidized to the corresponding fluoroalkyl carbonyl compounds by reaction with sodium hypochlorite pentahydrate in acetonitrile in the presence of acid and nitroxyl radical catalysts. Although the reaction proceeded slower under a nitroxyl radical catalyst- free condition, the desired carbonyl compounds were obtained in high yields. For the reaction with fluoroalkyl allylic alcohols, the corresponding α,β-epoxyketone hydrates were obtained in high yields.

Synthesis of Fluorinated Dialkyl Carbonates from Carbon Dioxide as a Carbonyl Source

Fluorinated dialkyl carbonates (DACs), which serve as environmentally benign phosgene substitutes, were produced successfully from carbon dioxide either directly or indirectly. Nucleophilic addition of 2,2,2-trifluoroethanol to carbon dioxide and subsequent reaction with 2,2,2-trifluoroethyltriflate (3 a) afforded bis(2,2,2-trifluoroethyl) carbonate (1) in up to 79 % yield. Additionally, carbonate 1 was obtained through the stoichiometric reaction of 3 a and cesium carbonate. Although bis(1,1,1,3,3,3-hexafluoro-2-propyl) carbonate (4) was difficult to obtain by either of the above two methods, it could be synthesized through the transesterification of carbonate 1.

Process for Preparation of Hexafluoroacetone Monohydrate

Disclosed is a method for producing hexafluoroacetone monohydrate by (1) allowing, in an organic solvent, hexafluoroacetone to be absorbed into water or a hexafluoroacetone hydrate (water addition method) or by (2) an easy method in which a hexafluoroacetone hydrate is mixed with an organic solvent and then distillation is conducted, thereby removing a mixture of water and the organic solvent as a low-boiling-point composition and obtaining a mixture of hexafluoroacetone monohydrate and the organic solvent as a high-boiling-point composition (dehydration method).

Highly conductive PEDOT:PSS films prepared through a treatment with geminal diols or amphiphilic fluoro compounds

Poly(3,4-ethylene dioxythiophene):poly(styrene sulfonate) (PEDOT:PSS) films with high conductivity can have important application as the transparent electrode of optoelectronic devices. In this paper, we report the significant conductivity enhancement of PEDOT:PSS through a treatment with germinal diols which have two hydroxyl groups connected to one carbon atom or amphiphilic fluoro compounds which have hydrophobic fluorocarbon groups and hydrophilic hydroxyl or carboxylic groups. Several compounds, including hexafluoroacetone, cyclohexanehexone, formaldehyde, acetaldehyde, and perfluorobenzophenone, which could convert into geminal diols, were used to treat PEDOT:PSS films. The conductivity enhancements are generally consistent with the equilibrium constants for the conversion of these compounds into geminal diols. PEDOT:PSS films were also treated with several amphiphilic fluoro compounds. The conductivity was significantly enhanced when PEDOT:PSS films were treated with hexafluoroisopropanol, trifluoroacetic acid and heptafluorobutyric acid, while it hardly changed when they were treated with 2,2,2-trifluoroethanol. Conductivities of more than 1000 S cm-1 were observed on the treated PEDOT:PSS films. The mechanism for the conductivity enhancement of PEDOT:PSS through the treatment with geminal diols or amphiphilic fluoro compounds is attributed to the phase segregation of PSSH from PEDOT:PSS and conformational change of the PEDOT chains as the results of the compounds-induced reduction in the Coulombic attraction between the positively charged PEDOT and negatively charged PSS chains.

METHOD FOR PRODUCING HYDRATE OF FLUOROALKYL KETONE

The present invention relates to a method for producing a compound represented by formula (2): ????????[CF3(CF2)n] [CF3(CF2)m]C(OH)2?????(2) wherein n and m independently represent 0 to 10, the method comprising reacting with a halogen or a halogen-containing oxidizing agent a salt of a compound represented by formula (1): ????????[CF3(CF2)n] [CF3(CF2)m]C(OH)COOH?????(1) wherein n and m independently represent 0 to 10.

The reaction of secondary phosphines and di-1-adamantylphosphine oxide with trifluoroacetic anhydride and hexafluoroacetone

While the secondary phosphines (1-Ad)2PH (1) (1-Ad=adamantyl) and Trt(Ph)PH (2) (Trt=triphenylmethyl) reacted readily with trifluoroacetic anhydride (TFAA) to give the trifluoroacetylphosphines 7 and 8. (1-Ad)2P(:O)H (6) could not be converted into the corresponding trifluoroacetylphosphine oxide 10 by treatment with TFAA. Compound 10 was observed by 19F and 31P NMR spectroscopy in the reaction of (1-Ad)2PC(:O)CF3 (7) with (H2N)2C(:O)·H2O2. Two pathways were observed for the reaction of 1 with excess hexafluoroacetone (HFA), starting from the primary HFA adduct (1-Ad)2PC(CF3)2OH (13). Oxidation of 13 led to the tertiary phosphine oxide 14 which was also available from (1-Ad)2P(:O)H (6) and HFA. Isomerization of 13 gave (1-Ad)2POCH(CF3)2 (15) whose oxidation with excess HFA furnished the phosphorane 16. Hydrolysis of 16 led to the phosphinic ester 17. As is known for Ph2PH (3), Ph(C6F5)PH (4) reacted with HFA to give the α-hydroxyphosphine 19. No reaction was observed when Trt(Ph)PH (2) and (C6F5)2PH (5) were treated with HFA.

FLUOROALIPHATIC ESTERS OF FLUOROSULFONIC ACID. 2. REACTION BIS(FLUOROSULFATO)PERFLUOROALKANES WITH CESIUM FLUORIDE

2,3-Bis(fluorosulfato)perfluoroalkanes split under the action of CsF in the absence of solvents, giving a mixture of α-fluorosulfatoperfluoro ketones, perfluoroalkene sulfates, and perfluoro α-diketones.The occurence of these reactions in solutions results mainly in the formation of oxides of the corresponding fluoroolefins or products of their conversions.The reactions carried out are the first examples of nucleophilic substitution at a secondary carbon atom in a perfluorinated saturated chain.