33965-65-0

Usage

Chemical structure

A synthetic fluorinated compound containing six fluorine atoms, two phenyl groups, and two hydroxyl (OH) functional groups.

Functional groups

Fluorine atoms, phenyl groups, and hydroxyl groups.

Physical state

Likely a solid at room temperature, due to the presence of multiple fluorine and phenyl groups.

Solubility

Expected to be soluble in organic solvents, such as dichloromethane or acetone, due to its nonpolar nature.

Stability

Relatively stable due to the presence of strong carbon-fluorine and carbon-carbon bonds.

Flammability

Potential use as a flame retardant, likely due to the presence of fluorine atoms which can reduce the compound's reactivity.

Applications

Researched for use in various applications, including as a building block for pharmaceutical compounds and in the field of fluorine chemistry.

Chemical synthesis

HFDPB's unique structure and properties make it a promising candidate for further exploration and development in the field of chemical synthesis and material science.

Safety

As with any chemical compound, appropriate safety precautions should be taken when handling HFDPB, including the use of gloves, eye protection, and a well-ventilated workspace.

Upstream product

• 535-77-3 m-cymene 
• 434-45-7 2,2,2-Trifluoroacetophenone 
• 770-09-2 benzyltrimethylsilane 
• 28493-54-1 benzyltributyltin 
• 98-86-2 acetophenone 
• 340-04-5 1-phenyl-2,2,2-trifluoromethylethanol 
• 99-87-6 4-methylisopropylbenzene 
• 527-84-4 2-methylisopropylbenzene 
• 134-81-6 benzil 

Relevant academic research and scientific papers

GaN nanowires as a reusable photoredox catalyst for radical coupling of carbonyl under blacklight irradiation

Employing photo-energy to drive the desired chemical transformation has been a long pursued subject. The development of homogeneous photoredox catalysts in radical coupling reactions has been truly phenomenal, however, with apparent disadvantages such as the difficulty in separating the catalyst and the frequent requirement of scarce noble metals. We therefore envisioned the use of a hyper-stable III-V photosensitizing semiconductor with a tunable Fermi level and energy band as a readily isolable and recyclable heterogeneous photoredox catalyst for radical coupling reactions. Using the carbonyl coupling reaction as a proof-of-concept, herein, we report a photo-pinacol coupling reaction catalyzed by GaN nanowires under ambient light at room temperature with methanol as a solvent and sacrificial reagent. By simply tuning the dopant, the GaN nanowire shows significantly enhanced electronic properties. The catalyst showed excellent stability, reusability and functional tolerance. All reactions could be accomplished with a single piece of nanowire on Si-wafer. This journal is

Nucleophilic tetrafluoroethylation of carbonyl compounds with fluorinated sulfones

Global interest in the "CF2CF2" building blocks (tetrafluoroethylene, tetrafluoroethyl) is still rather marginal. One of the main reasons is the lack of efficient and selective tetrafluoroethylation reagents. In this context, we pres

19F nuclear magnetic resonance spectroscopy for the quantitative detection and classification of carbonyl groups in lignins

A novel method that permits the quantitative detection and classification of various carbonyl groups in lignins has been developed. The proposed method was optimized with the quantitative trifluoromethylation of a series of carbonyl-containing lignin-like model compounds. This effort was followed by 19F NMR spectral analyses of the resulting fluorine derivatives allowing for a thorough understanding of their structure/19F chemical shift relationships. The various carbonyl groups present in lignins were also investigated by trifluoromethylating them in the presence of catalytic amounts of tetramethylammonium fluoride (TMAF), followed by hydrolysis with TMAF in tetrahydrofuran. By using a variety of selective reactions, it became possible to assign a number of prominent 19F NMR signals to a variety of carbonyl groups present in lignins. These studies demonstrated that the proposed method can be applied to the quantitative determination of carbonyl groups that are present in soluble native and technical lignins.

19F Nuclear Magnetic Resonance Spectroscopy for the Elucidation of Carbonyl Groups in Lignins. 1. Model Compounds

A new method for the detection of different classes of carbonyl groups in a series of carbonyl-containing lignin-like model compounds has been developed. The method is based on the selective fluoride-induced trifluoromethylation of carbonyl groups with (trifluoromethyl)trimethylsilane (TMS-CF3) in the presence of tetramethylammonium fluoride (TMAF), followed by hydrolysis with aqueous HF or TMAF in the case of quinones. In this study a series of ketones, aldehydes, quinones, and dimeric-lignin model compounds were quantitatively trifluoromethylated followed by 19F NMR spectral analyses of the resulting fluorine-containing derivatives, allowing for a thorough understanding of their structure/19F chemical shift relationships. These studies have shown that the 19F-NMR chemical shifts of the trifluoromethyl groups vary significantly and consistently for various classes of carbonyl groups which may be present in complex lignocellulosic materials. These studies are to form the basis for the development of a novel and sensitive method that can be used to obtain quantitative information on the various carbonyl groups present in such materials.

SET and exciplex pathways in the photochemical reactions between aromatic ketones and benzylsilane and stannane derivatives

The photochemical reaction of α,α,α-trifluoroacetophenone (TFA), benzophenone, and p-cyanoacetophenone with benzyltrimethylsilane in MeCN involves hydrogen transfer from the benzylic position. Desilylation occurs as a minor process only in the case of TFA (but it increases greatly in the presence of MeOH or LiClCO4). The final products result from the statistical recombination of the benzyl and ketyl radicals. Further cases of intramolecular selectivity studied are p-methylbenzyl- and p-methoxybenzyltrimethylsilane (the latter substrate undergoes mainly C-Si bond cleavage in the reaction with TFA) as well as benzyltributylstannane (only destannylation observed with all ketones). Product studies are complemented by the determination of relevant kinetic parameters through steadystate and flash-photolysis experiments. The results are explained in terms of hydrogen transfer proceeding from an exciplex and desilylation from the solvent separated radial ion pair. The latter species predominates when ΔGet -1.

The Competition between Cross-coupling and the Exchange Reaction in the Photoreduction of Aromatic Ketones

Four aromatic ketones K with different reduction potentials and a series of hydrogen atom donors AH2 with different oxidation potentials of AH were irradiated in pairs and the product composition analyzed.Based on the product analysis the rate kex of the exchange reaction K + AH -> KH + A, was characterized as slow, medium fast or fast, respectively, relative to the radical-radical coupling reactions of K and AH.The results clearly point to the value of a knowledge of the oxidation potential of the AH radicals and the reduction potential of the ketones for the prediction of the outcome of the photoreduction of a ketone by an alcohol or another hydrogen atom donor.

Rate Constants for Degenerate Hydrogen Atom Exchange between α-Hydroxy Radicals and Ketones

When a phenyl ketone is irradiated in the presence of 1-phenylethanol, the photoproducts include acetophenone pinacol, the pinacol from the other phenyl ketone, a mixed pinacol, and acetophenone, which is formed by irreversible hydrogen atom exchange between the hemipinacol radical of acetophenone and the other ketone.Rate constants for this hydrogen atom exchange between the hemipinacol radical of acetophenone and three other ketones were determined by measuring how acetophenone yields depend on the concentration of the other ketone.Comparable measurements were made for p-chloroacetophenone formation by irradiating acetophenone in the presence of 1-(p-chlorophenyl)ethanol.As the starting ketone concentration increases, so does the amount of exchange relative to pinacol, while the pinacol content reflects decreasing amounts of the original alcohol.Exchange is measurable at ketone concentrations below 0.01 M and is complete by 0.1 M.Rate constants kex of 3.7, 6.3, 4.2, and 8.6 * 103 M-1 s-1 were deduced for hydrogen transfer to propiophenone, isobutyrophenone, p-methylacetophenone, and p-chloroacetophenone, respectively, based on a competing rate constant for radical coupling of 2 * 109 M-1 s-1.Equilibrium constants for the hydrogen transfer were determined from the product ratios obtained by irradiating a mixture of two ketones with 2-propanol; from these k-ex values of 11.5, 57, 13, and 1.8 * 103 M-1 s-1, respectively, were deduced for hydrogen transfer to acetophenone from the four other ketone hemipinacol radicals.These exchange rate constants depend more on the structure of the radical than on that of the ketone.Actual quantum yields for pinacol formation do not exceed 50 percent ; this maximum quantum efficiency rises to 71 percent for 1-phenylethanol-O-d.From this inverse isotope effect it is concluded that half the reaction of triplet acetophenone with 1-phenylethanol involves abstraction of an OH hydrogen followed by disproportionation of the initial radical pair back to reactants.

Photochemical Hydrogen Abstraction from Cymenes

The three isomeric cymenes are examined in photochemical reactions involving hydrogen transfer with 1,4-naphthalenedicarbonitrile (NDN), α,α,α-trifluoroacetophenone (TFA), and benzophenone (BP).Selectivity for attack at primary vs tertiary position (P/T) and quantum yield are determined.The reactions are rationalized as involving loose perpendicular complexes yielding a low P/T ratio in the products (with BP n? triplet), a face-to-face charge transfer complex yielding a high P/T (with TFA ??* triplet and also NDN singlet, but only as far as the benzylnaphthalenes 1 and 2 are concerned), and a tighter charge transfer complex yielding again a low P/T in the formation of dibenzomethanocyclooctenes 3, the main products from NDN.The energetic limit of such a directing effect of the conformation of the intermediate complex onto photochemical reactivity is evidenced by the different results obtained with o-cymene.

Extent of Charge Transfer in the Photoreduction of Phenyl Ketones by Alkylbenzenes

Rate constants for triplet-state reaction of various ring-substituted benzophenones (BPs), acetophenones (APs), and α,α,α-trifluoroacetophenones (TFAs) with toluene and p-xylene have been determined by a combination of flash kinetics, steady-state quenching, and quantum yield measurements.The relative amounts of primary and tertiary radicals formed by reaction of the same ketons with p-cymene have also been measured.For all three types of ketones, rate constants correlate well with triplet ketone reduction potentials.The magnitude of the kinetic isotope effects observed with toluene-d8 and p-xylene-d10 diminishes as the ketones become easier to reduce.All of the ketone triplets react with alkylbenzenes primarily by a charge-transfer mechanism, with the rate-determining step changing from complexation to hydrogen transfer as the ketones become harder to reduce.The least reactive AP triplets probably react significantly via simple hydrogen atom abstraction as well.Those ketones with n,?* lowest triplets (all BPs and some APs) react with p-cymene to give primary/tertiary radical ratios that vary no more than a factor of 2 from the 0.40 value displayed by tert-butoxy radicals; those with ?,?* lowest triplets (TFAs and some APs) give ratios that favor primary radicals and that vary by an order of magnitude with the triplet ketone reduction potential.The variation in cymene product ratios reflect different orientations for attack on cymene by n,?* and ?,?* triplets and differing degrees of partial electron transfer within the exciplexes, which are not tight radical ion pairs.The variation seen for ?,?* triplets represents a stereoelectronic effect within face-to-face exciples, as evidenced by the excerptional behavior of p-diacylbenzenes, which give the highest ratio of tertiary radicals from cymene.There is no set intrinsic ratio of reactivity for ?,?* triplets vs. n,?* triplets in these CT reactions.The two types of triplets show similar reactivity for the more easily reduced triplets, with the harder to reduce ?,?* triplets being only one-tenth as reactive as n,?* triplets of comparable triplet reduction potential.When the extent of electron transfer in the exciplex is small, hydogen transfer is rate determining and ?,?* reactivity drops.A study of two radical reactions which generate benzyl and α-hydroxy-α-methylbenzyl radicals indicates that radical disproportionation cannot explain the low quantum yields (0.10) of most ketone-toluene photoreductions, which apparently involve substantial radiation less decay by the exciplex intermediates.

ORGANOZINNVERBINDUNGEN XXXII. ZUR PHOTOCHEMISCHEN REAKTION VON KETONEN MIT TETRAMETHYL-1,2-BIS(PHENYLTHIO)DISTANNAN

The photolytic reductive dimerization of a number of diaryl and aryl alkyl ketones by means of the distannane Me2(PhS)Sn-Sn(SPh)Me2 gives the corresponding 1,3,2-dioxastannolanes which are easily hydrolyzed yielding pinakols.Several diketones react in the same way with C-C coupling.Depending on the type of carbonyl compound, the different mechanism either exclude or compete with one another.One reaction proceeds via a ketyl radical ArRC.-OSn(SPh)Me2 and the bismetalated pinakol giving ultimately the five-membered ring and Me2Sn(SPh)2.However, with fluorinated acetones, a stannylenoid mechanism may be considered, and an organometallic 1,3-dipol RR'C--O-Sn+Me2 is proposed as a shortlived intermediate.