75-90-1

Usage

Uses

Used in Pharmaceutical Industry:
TRIFLUOROACETALDEHYDE is used as a key intermediate for the synthesis of GABAB agonists, which are potential therapeutic agents for the treatment of pain. These agonists modulate the GABAB receptor, a G-protein coupled receptor involved in various physiological processes, including pain transmission. The presence of the trifluoromethyl group in TRIFLUOROACETALDEHYDE enhances the lipophilicity and metabolic stability of the resulting GABAB agonists, improving their overall efficacy.
Used in Enzyme Inhibition:
TRIFLUOROACETALDEHYDE is also used as a reagent in the synthesis of ketone-based inhibitors of human renin, an enzyme that plays a crucial role in the regulation of blood pressure. These inhibitors can potentially be used in the development of antihypertensive drugs, as they help to reduce the production of angiotensin II, a potent vasoconstrictor. The trifluoromethyl group in TRIFLUOROACETALDEHYDE contributes to the increased binding affinity and selectivity of the resulting inhibitors towards the target enzyme.

InChI:InChI=1/C2HF3O/c3-2(4,5)1-6/h1H

Upstream product

• 354-32-5 trifluoracetyl chloride 
• 421-07-8 1,1,1-trifluoropropane 
• 353-85-5 trifluoroacetonitrile 
• 76-05-1 trifluoroacetic acid 
• 407-25-0 trifluoroacetic anhydride 
• 420-46-2 2,2,2-trifluoroethanol 
• 75-89-8 2,2,2-trifluoroethanol 
• 87191-88-6 2-oxo-ethen-1-id-1-yl 
• 431-46-9 2,2,2-trifluoro-1-methoxy-ethanol 
• 102967-52-2 (5Z)-7-(<2RS,4RS,5SR>-4-o-hydroxyphenyl-2-trifluoromethyl-1,3-dioxan-5-yl)hept-5-enoic acid 
• 433-27-2 ethyl trifluoroacetaldehyde hemiacetal 
• 383-63-1 ethyl trifluoroacetate, 
• 420-45-1 2,2-difluoropropane 
• 460-73-1 1,1,1,3,3-Pentafluoropropane 

Downstream Products

• 431-46-9 2,2,2-trifluoro-1-methoxy-ethanol 
• 374-01-6 1,1,1-trifluoroisopropanol 
• 108535-39-3 α-trifluoromethyl-β-phenylethanol 
• 6776-45-0 N-(2,2,2-trifluoro-1-hydroxyethyl)-acetamide 
• 31185-58-7 4-methyl-5-phenyl-2-trifluoromethyl-oxazolidine 
• 31185-59-8 2-pentafluoroethyl-oxazolidine 
• 31185-61-2 2-trifluoromethyl-[1,3]oxazocane 
• 50905-87-8 anti-2-(1'-hydroxy-2',2',2'-trifluoroethyl)cyclohexanone 
• 50905-87-8 syn-2-(1'-hydroxy-2',2',2'-trifluoroethyl)cyclohexanone 
• 31185-54-3 2-trifluoromethyl-oxazolidine 
• 31185-57-6 4,4-dimethyl-2-trifluoromethyl-oxazolidine 
• 1524-15-8 4,4,4-trifluoro-3-hydroxy-1-phenylbutan-1-one 
• 31185-56-5 5-methyl-2-trifluoromethyl-oxazolidine 
• 66681-54-7 Acetic acid 1-(3,4-dichloro-phenyl)-2,2,2-trifluoro-ethyl ester 

Relevant academic research and scientific papers

A study of the IR and UV-Vis absorption cross-sections, photolysis and OH-initiated oxidation of CF3CHO and CF3CH2CHO

Infrared and ultraviolet-visible absorption cross-sections, effective quantum yields of photolysis and OH reaction rate coefficients for CF 3CHO and CF3CH2CHO are reported. Relative rate measurements at 298(2) K and 1013(10) hPa, give k(OH + CF3CHO)/k(OH + CH3CH3) = 2.00(13), k(OH + CF3CH 2CHO)/ k(OH + CH3CH2OH) = 1.21(5) and k(OH + CF3CH2CHO)/k(OH + HC(O)OC2H5) = 3.51(9) (2σ). The effective quantum yield of photolysis was measured under pseudo-natural conditions in the European simulation chamber, Valencia, Spain (EUPHORE). Over the wavelength range 290-400 nm, the effective quantum yields of photolysis for CF3CHO and CF3CH2CHO are less than 2 × 10-2 and 4 × 10-2, respectively. The tropospheric lifetimes are estimated to be: τOH(CF3CHO) ～ 26 days; τ photol(CF3CHO) > 27 days; τOH(CF 3CH2CHO) ～ 4 days; τphotol(CF 3CH2CHO) > 15 days.

An efficient enantioselective total synthesis of a trifluoromethyl analog of blastmycinolactol

A novel synthetic strategy for the total synthesis of fluorinated analog of blastmycinolactol has been developed using α-pinene based alkoxyallylboration, chelation controlled diastereoselective reduction, and a single step lactonization of the 1,4-diol to the γ-lactone as key steps.

Breslow Intermediates from a Thiazolin-2-ylidene and Fluorinated Aldehydes: XRD and Solution-Phase NMR Spectroscopic Characterization

The first generation and X-ray diffraction (XRD) analysis of a crystalline Breslow intermediate (BI) derived from a thiazolin-2-ylidene, that is, the aromatic heterocycle present in vitamin B1, is reported. Key to success was the combined use of pentafluorobenzaldehyde and a thiazolin-2-ylidene carrying an enol-stabilizing dispersion energy donor as N-substituent. A so-called primary intermediate (PI) could be isolated in protonated form (pPI) as well and analyzed by XRD. Furthermore, the first stable BI derived from an aromatic thiazolin-2-ylidene and an aliphatic aldehyde (trifluoroacetaldehyde) was prepared and characterized by NMR spectroscopy in solution. When switching to a saturated thiazolidin-2-ylidene, reaction with pentafluorobenzaldehyde afforded a new BI in solution (NMR spectroscopy). Attempts to crystallize the latter BI resulted in the isolation of a novel thiazolidin-2-ylidene dimer that had undergone rearrangement to a hexahydro[1,4]-thiazino[3,2-b]-1,4-thiazine.

Catalytic gas phase oxidation of methanol to formaldehyde

Two gas-phase catalytic cycles for the two-electron oxidation of primary and secondary alcohols were detected by multistage mass spectrometry experiments. A binuclear dimolybdate center [Mo2O6(OCHR2)]- acts as the catalyst in both these cycles. The first cycle proceeds via three steps: (1) reaction of [Mo2O6(OH)]- with alcohol R2HCOH and elimination of water to form [Mo2O6(OCHR2)]-; (2) oxidation of the alkoxo ligand and its elimination as aldehyde or ketone in the rate-determining step; and (3) regeneration of the catalyst via oxidation by nitromethane. Step 2 does not occur at room temperature and requires the use of collisional activation to proceed. The second cycle is similar but differs in the order of reaction with alcohol and nitromethane. The nature of each of these reactions was probed by kinetic measurements and by variation of the substrate alcohols (structure and isotope labeling). The role of the binuclear molybdenum center was assessed by examination of the relative reactivities of the mononuclear [MO3(OH)]- and binuclear [M2O6(OH)]- ions (M = Cr, Mo, W). The molybdenum and tungsten binuclear centers [M2O6(OH)]- (M = Mo, W) were reactive toward alcohol but the chromium center [Cr2O6(OH)]- was not. This is consistent with the expected order of basicity of the hydroxo ligand in these species. The chromium and molybdenum centers [M2O6(OCHR2)]- (M = Cr, Mo) oxidized the alkoxo ligand to aldehyde, while the tungsten center [W2O6(OCHR2)]- did not, instead preferring the non-redox elimination of alkene. This is consistent with the expected order of oxidizing power of the anions. Each of the mononuclear anions [MO3(OH)]- (M = Cr, Mo, W) was inert to reaction with methanol, highlighting the importance of the second MoO3 unit in these catalytic cycles. Only the dimolybdate center has the mix of properties that allow it to participate in each of the three steps of the two catalytic cycles. The three reactions of these cycles are equivalent to the three essential steps proposed to occur in the industrial oxidation of gaseous methanol to formaldehyde at 300-400°C over solid-state catalysts based upon molybdenum(VI)-trioxide. The new gas-phase catalytic data is compared with those for the heterogeneous process.

Reaction of trifluoroacetaldehyde with some bromoesters

Reformatsky reactions of trifluoroacetaldehyde with lower bromoesters gave their corresponding adducts.The reaction of trifluoroacetaldehyde with methyl 2-(bromomethyl)acrylate gave γ-trifluoromethyl-α-methylene-γ-butyrolactone.

Kinetic study of the reaction of chlorine and fluorine atoms with CF3CHO at 295 ± 2 K

Using a relative rate technique the reactions of chlorine and fluorine atoms with CF3CHO have been determined to proceed with rate constants of (1.8 ± 0.4) × 10-12 and (2.7 ± 0.1) × 10-11 cm3 molecule-1 s-1, respectively. Experiments were performed as 295 ± 2 K and 700 torr total pressure of nitrogen. The results are discussed with respect to the design and interpretation of laboratory studies of the atmospheric chemistry of CFC replacements.

PRODUCTION METHOD OF FLUORINE-CONTAINING UNSATURATED CARBOXYLIC ACID

PROBLEM TO BE SOLVED: To provide a production method of a compound of formula (4), that is, a fluorine-containing unsaturated carboxylic acid, which is industrially preferable, economical, and environmentally friendly. SOLUTION: A production method of a compound of formula (4) includes subjecting a compound of formula (3) to a reaction in the presence of a base (here Rf is a 1-4C perfluoroalkyl). SELECTED DRAWING: None COPYRIGHT: (C)2021,JPO&INPIT

Method for oxidative cracking of compound containing unsaturated double bonds

The invention relates to a method for oxidative cracking of a compound containing unsaturated double bonds. The method comprises the following steps: (A) providing a compound (I) containing unsaturated double bonds, a trifluoromethyl-containing reagent and a catalyst, wherein the catalyst is shown as a formula (II): M(O)mL1yL2z (II), M, L1, L2, m, y, z, R1, R2 and R3 being defined in the specification; and (B) mixing the compound containing the unsaturated double bonds and the trifluoromethyl-containing reagent, and performing an oxidative cracking reaction on the compound containing the unsaturated double bonds in the presence of air or oxygen by using the catalyst to obtain a compound represented by formula (III),.

METHOD FOR OXIDATIVE CLEAVAGE OF COMPOUNDS WITH UNSATURATED DOUBLE BOND

A method for oxidative cleavage of a compound with an unsaturated double bond is provided. The method includes the steps of: (A) providing a compound (I) with an unsaturated double bond, a trifluoromethyl-containing reagent, and a catalyst; wherein, the catalyst is represented by Formula (II): M(O)mL1yL2z??(II);wherein, M, L1, L2, m, y, z, R1, R2 and R3 are defined in the specification; and(B) mixing the compound with an unsaturated double bond and the trifluoromethyl-containing reagent to perform an oxidative cleavage of the compound with the unsaturated double bond by using the catalyst in air or under oxygen atmosphere condition to obtain a compound represented by Formula (III):

METHOD FOR OXIDATIVE CLEAVAGE OF COMPOUNDS WITH UNSATURATED DOUBLE BOND

A method for oxidative cleavage of a compound with an unsaturated double bond is provided. The method comprises the following step: (A) providing a compound (I) with an unsaturated double bond, a reagent with trifluoromethyl, and a catalyst; wherein the catalyst is represented by the following formula (II): M(O)mL1yL2z (II); wherein, M, L1, L2, m, y, z, R1, R2 and R3 are defined in the specification; and (B) mixing the compound with an unsaturated double bond and the reagent with a trifluoromethyl to perform an oxidation of the compound with the unsaturated double bond by using the catalyst at air or an oxygen condition to get a compound presented as formula (III):