421-07-8

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 26, p. 1627, 1961 DOI: 10.1021/jo01064a601

InChI:InChI=1/C3H5F3/c1-2-3(4,5)6/h2H2,1H3

Upstream product

• 74-85-1 ethene 
• 2314-97-8 iodotrifluoromethane 
• 421-02-3 1-chloro-1,1-difluoro-propane 
• 420-89-3 1-bromo-1,1-difluoro-propane 
• 563-58-6 1,1-dichloropropene 
• 460-32-2 3-bromo-1,1,1-trifluoropropane 
• 661-54-1 3,3,3-trifluoroprop-1-yne 
• 677-21-4 1,1,1-trifluoropropylene 
• 2088-35-9 1,1-dichlorocyclopropane 
• 802294-64-0 propionic acid 
• 676-59-5 dimethylphosphane 
• 420-45-1 2,2-difluoropropane 
• 432-04-2 tris(trifluoromethyl)phosphine 
• 201230-82-2 carbon monoxide 

Downstream Products

• 460-35-5 3-chloro-1,1,1-trifluoropropane 
• 421-46-5 1,1,1-trifluoro-2-bromo-propane 
• 460-32-2 3-bromo-1,1,1-trifluoropropane 
• 421-53-4 2,2,2-trifluoro-1,1-ethanediol 
• 461-35-8 1,1,1-trifluoro-3-nitropropane 
• 75-90-1 2,2,2-Trifluoroacetaldehyde 
• 819-07-8 1,1,1-trifluoro-2-nitroethane 
• 1652-89-7 1,1,1,2,2-pentachloro-3,3,3-trifluoropropane 
• 74-84-0 ethane 
• 74-85-1 ethene 
• 430-63-7 1,1-difluoropropene 
• 76-16-4 Hexafluoroethane 
• 7125-94-2 3,3-dibromo-1,1,1-trifluoro-propane 
• 460-69-5 1,1-dichloro-3,3,3-trifluoropropane 

Relevant academic research and scientific papers

Reactivity of 3,3,3-Trifluoropropyne at Rhodium Complexes: Development of Hydroboration Reactions

The rhodium compounds [Rh(C≡CCF3)(PEt3)3] (2), fac-[RhH(C≡CCF3)2(PEt3)3] (3), and fac-[Rh{(E)-CH=CHCF3}(C≡CCF3)2(PEt3)3] (4) were synthesized by reactions of the rhodium(I) complexes [Rh(H)(PEt3)3] (1) and [Rh(Bpin)(PEt3)3] (5, HBpin=pinacolborane) with the alkyne 3,3,3-trifluoropropyne. Reactivity studies of [Rh(C≡CCF3)(PEt3)3] (2) were performed with CO and 13CO to form [Rh(C≡CCF3)(CO)(PEt3)3] (7) and subsequently trans-[Rh(C≡CCF3)(CO)(PEt3)2] (8) as well as the labeled derivatives. Using 1–4 as catalysts, hydroboration reactions selectively afforded borylated building blocks.

The monofluorination of hydrofluorocarbons over cobalt trifluoride

Hydrofluorocarbons (HFCs) have been fluorinated via the high-valency metal fluorides CoF3, MnF3 and KCoF4.The fluorinating powers of these reagents for the monofluorination of 2,2-difluoropropane are in the order CoF3>MnF3>KCoF4.The fluorinations of fluorinated ethanes with CoF3 have been examined in detail.The effects of temperature and the distribution products are described.Furthermore, regioselective monofluorination of gem-difluoro compounds (C3-C5) with CoF3 was achieved at the methylene position adjacent to the gem-difluoro group.The trifluoro compounds were obtained in good yield at low reaction temperatures.

Versatile Reaction Pathways of 1,1,3,3,3-Pentafluoropropene at Rh(I) Complexes [Rh(E)(PEt3)3] (E=H, GePh3, Si(OEt)3, F, Cl): C-F versus C-H Bond Activation Steps

The reaction of the rhodium(I) complexes [Rh(E)(PEt3)3] (E=GePh3 (1), H (6), F (7)) with 1,1,3,3,3-pentafluoropropene afforded the defluorinative germylation products Z/E-2-(triphenylgermyl)-1,3,3,3-tetrafluoropropene and

Activation of pentafluoropropane isomers at a nanoscopic aluminum chlorofluoride: Hydrodefluorination versus dehydrofluorination

The hydrofluorocarbon 245 isomers, 1,1,1,3,3-pentafluoropropane, 1,1,1,2,2- pentafluoropropane, and 1,1,1,2,3-pentafluoro-propane (HFC-245fa, HFC-245cb, and HFC-245eb) were activated through C-F bond activations using aluminium chlorofluoride (ACF) as a catalyst. The addition of the hydrogen source Et3SiH is necessary for the activation of the secondary and tertiary C-F bonds. Multiple C-F bond activations such as hydrodefluorinations and dehydrofluorinations were observed, followed by hydroarylation and Friedel-Crafts-type reactions under mild conditions.

C?H and C?F Bond Activation Reactions of Fluorinated Propenes at Rhodium: Distinctive Reactivity of the Refrigerant HFO-1234yf

The reaction of [Rh(H)(PEt3)3] (1) with the refrigerant HFO-1234yf (2,3,3,3-tetrafluoropropene) affords an efficient route to obtain [Rh(F)(PEt3)3] (3) by C?F bond activation. Catalytic hydrodefluorinations were achieved in the presence of the silane HSiPh3. In the presence of a fluorosilane, 3 provides a C?H bond activation followed by a 1,2-fluorine shift to produce [Rh{(E)-C(CF3)=CHF}(PEt3)3] (4). Similar rearrangements of HFO-1234yf were observed at [Rh(E)(PEt3)3] [E=Bpin (6), C7D7 (8), Me (9)]. The ability to favor C?H bond activation using 3 and fluorosilane is also demonstrated with 3,3,3-trifluoropropene. Studies are supported by DFT calculations.

Consecutive Transformations of Tetrafluoropropenes: Hydrogermylation and Catalytic C?F Activation Steps at a Lewis Acidic Aluminum Fluoride

Functionalization reactions of the refrigerants HFO-1234yf (2,3,3,3-tetrafluoropropene) and HFO-1234ze (1,3,3,3-tetrafluoropropene) were developed. The selectivity and reactivity towards CF3 groups of C?F activation reactions can be controlled by employing either a germane or a silane as the hydrogen source. Unique transformations were designed to accomplish consecutive hydrogermylation and C?F activation steps. This allowed for an unprecedented transformation of an olefinic C?F bond into a C?H bond by heterogeneous catalysis. These reactions are catalyzed by nanoscopic aluminum chlorofluoride (ACF) under very mild conditions.

Silver-Catalyzed Decarboxylative Trifluoromethylation of Aliphatic Carboxylic Acids

The silver-catalyzed decarboxylative trifluoromethylation of aliphatic carboxylic acids is described. With AgNO3 as the catalyst and K2S2O8 as the oxidant, the reactions of aliphatic carboxylic acids with (bpy)C

Trifluoromethylation of Alkyl Radicals in Aqueous Solution

The copper-mediated trifluoromethylation of alkyl radicals is described. The combination of Et3SiH and K2S2O8 initiates the radical reactions of alkyl bromides or iodides with BPyCu(CF3)3 (BPy = 2,2′-bipyridine) in aqueous acetone at room temperature to afford the corresponding trifluoromethylation products in good yield. The protocol is applicable to various primary and secondary alkyl halides and exhibits wide functional group compatibility. A mechanism involving trifluoromethyl group transfer from Cu(II)-CF3 intermediates to alkyl radicals is proposed.

Competing reaction pathways of 3,3,3-trifluoropropene at rhodium hydrido, silyl and germyl complexes: C-F bond activation: Versus hydrogermylation

The reaction of the silyl complex [Rh{Si(OEt)3}(PEt3)3] (1) with 3,3,3-trifluoropropene afforded the rhodium complex [Rh(CH2CHCF3){Si(OEt)3}(PEt3)2] (2) which features a bonded fluorinated olefin. In contrast the rhodium hydrido complex [Rh(H)(PEt3)3] (3) yielded on treatment with 3,3,3-trifluoropropene in the presence of a base the fluorido complex [Rh(F)(PEt3)3] (4) together with 1,1-difluoro-1-propene by C-F bond activation. At low temperature the intermediate fac-[Rh(H)(CH2CHCF3)(PEt3)3] (5) was detected by NMR spectroscopy. The germyl complex [Rh(GePh3)(PEt3)3] (6) reacted also with 3,3,3-trifluoropropene by C-F bond activation affording again the fluorido complex [Rh(F)(PEt3)3] (4) as well as the (3,3-difluoroallyl)triphenylgermane 7. The catalytic hydrogermylation of 3,3,3-trifluoropropene in the presence of various germanium hydrides under mild conditions was developed by employing complex 6 as a catalyst. The molecular structures of both germane derivatives (3,3-difluoroallyl)triphenylgermane 7 and 1,1,1-trifluoropropane-3-triphenylgermane 8 were determined by X-ray crystallography.

PROCESS FOR 1-CHLORO-3,3,3-TRIFLUOROPROPENE FROM TRIFLUOROPROPENE

The present invention provides routes for making 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) from commercially available raw materials. More specifically, this invention provides several routes for forming HCFO-1233zd from 3,3,3-trifluoropropene (FC-1234zf).