1810-13-5

Usage

Uses

Used in Pharmaceutical Industry:
3,3,4,4-Tetrafluoropyrrolidine hydrochloride is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to impart unique properties to the final drug molecules, such as enhanced metabolic stability, lipophilicity, and bioavailability.
Used in Agrochemical Industry:
In the agrochemical industry, 3,3,4,4-tetrafluoropyrrolidine hydrochloride is utilized as a building block in the development of novel agrochemicals, including insecticides, herbicides, and fungicides, due to its potential to improve the efficacy and selectivity of these compounds.
Used in Organic Synthesis:
3,3,4,4-Tetrafluoropyrrolidine hydrochloride is employed as a versatile building block in organic synthesis for the preparation of a wide range of fluorinated compounds, which exhibit unique chemical and biological properties, such as increased reactivity, selectivity, and stability.
Used in Material Science:
3,3,4,4-Tetrafluoropyrrolidine hydrochloride is also used in the development of novel materials and chemicals, such as polymers, surfactants, and coatings, where its fluorinated nature can impart specific properties, such as water and oil repellency, thermal stability, and chemical resistance.

InChI:InChI=1/C4H5F4N.ClH/c5-3(6)1-9-2-4(3,7)8;/h9H,1-2H2;1H

Upstream product

• 377-33-3 3,3,4,4-tetrafluorosuccinimide 

Downstream Products

• 845782-52-7 (S)-[5-benzyloxycarbonylamino-1-(3,3,4,4-tetrafluoro-pyrrolidine-1-carbonyl)-pentyl]-carbamic acid tert-butyl ester 
• 1357192-06-3 5-methoxy-1-[2-methoxy-4-(3,3,4,4-tetrafluoropyrrolidin-1-yl)phenyl]-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one 
• 1357191-92-4 1-(3-tert-butoxy-4-nitrophenyl)-3,4-difluoro-1H-pyrrole 
• 1323403-97-9 3-{1-OXO-4-[4-(3,3,4,4-TETRAFLUORO-PYRROLIDIN-1-YL METHYL)-BENZYLOXY]-1,3-DIHYDRO-ISOINDOL-2-YL}-PIPERIDINE-2,6-DIONE 
• 1238698-81-1 1-[2-fluoro-3-(3,3,4,4-tetrafluoropyrrolidin-1-yl)phenyl]-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one 
• 1238696-77-9 1-[2-fluoro-4-(3,3,4,4-tetrafluoropyrrolidin-1-yl)phenyl]-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one 
• 120047-51-0 3,4-difluoro-1H-pyrrole 

Relevant academic research and scientific papers

Synthesis and study of fluorine-functionalized ZnTPPs

Five fluorinated zinc tetraphenyl porphyrins derivatives, fluorinated either on all ortho positions of the meso phenyl rings (Zn(II)-5,10,15,20-tetrakis(2,6-difluorophenyl)porphyrin) or in β-positions with two, four, six or eight fluorine groups (2,3-difluoro-5,10,15,20-tetraphenylporphyrin, 7,8,17,18-tetrafluoro-5,10,15,20-tetraphenylporphyrin, 7,8,12,13,17,18-hexafluoro-5,10,15,20-tetraphenyl-porphyrin and 2,3,7,8,12,13,17,18-octafluoro-5,10,15,20-tetraphenylporphyrin, respectively), were studied to probe the effect of fluorine in on-surface synthesis approaches. Additionally, bulkier substituents have been used in 7,8,17,18-tetrabromo-5,10,15,20-tetraphenylporphyrin and 7,8,17,18-tetramethyl-5,10,15,20-tetraphenylporphyrin, for a direct comparison with the corresponding fluorinated compounds. Reported are the synthesis and electronic structure characterization of the compounds, using UV-vis absorption and fluorescence spectroscopies as well as electronic structure calculations of the ground state molecular properties. Steric and electronic effects of fluorination are explored. For all molecules studied, substitution with fluorine maintains a planar tetrapyrrole macrocycle and shifts in the absorption spectra were consistent with calculated changes in the HOMOs and LUMOs energies of the molecules. In contrast, the bromo and methyl-substituted derivatives exhibit chemical instability and spectral shifts, compared to parent compound ZnTPP, consistent with structural distortions and accounted for calculations. The site-specific effects of fluorination on the electronic structure are discussed in detail.

Synthesis method of 3,3,4,4-tetrafluoropyrrolidine

The invention discloses a synthesis method of 3,3,4,4-tetrafluoropyrrolidine and mainly solves the technical problems of poisonous introduced fluorine, relatively long steps and relatively low yield in the existing synthesis process. The synthesis method disclosed by the invention comprises four steps: firstly, mixing butanedione with chloroform, then, carrying out addition on the mixture and bromine to form 1,4-dibromo-2,3-butanedione; secondly, introducing sulfur tetrafluoride into the obtained 1,4-dibromo-2,3-butanedione, and carrying out a reaction to obtain 1,4-dibromo-2,2,3,3-tetrafluorobutane; thirdly, carrying out a high-temperature reaction on 1,4-dibromo-2,2,3,3-tetrafluorobutane and benzylamine to obtain 1-benzyl-3,3,4,4-tetrafluoropyrrolidine hydrochloride; and fourthly, carrying out catalytic hydrogenation debenzylation on 1-benzyl-3,3,4,4-tetrafluoropyrrolidine hydrochloride to obtain 3,3,4,4-tetrafluoropyrrolidine. The invention provides the synthesis method of 3,3,4,4-tetrafluoropyrrolidine which is relatively low in toxicity, low in raw material price, simple in operation and high in yield.

METHOD FOR PRODUCING TETRAFLUORO COMPOUND

Provided is a method for producing a tetrafluoro nitrogen-containing heterocyclic compound such as tetrafluoropyrrolidine in good yield and at low cost. The method comprises the steps of: (A) reacting a compound represented by the formula (I) with fluorine gas to produce a tetrafluoro compound represented by the formula (II), (B) converting the tetrafluoro derivative represented by the formula (II) to a compound represented by the formula (III), and (C) reacting the compound represented by the formula (III) with an amine compound represented by the formula NH2R9 to produce a tetrafluoro nitrogen-containing heterocyclic compound represented by the formula (IV) or salt thereof.

New fluorinated pyrrolidine and azetidine amides as dipeptidyl peptidase IV inhibitors

Cyclohexylglycine amides of various fluorinated pyrrolidines and azetidines were prepared and tested for activity against dipeptidyl peptidase IV and in vivo in the KK mouse model of type 2 diabetes. The tetrafluoropyrrolidide, cis-3,4-difluoropyrrolidide and the fluorinated azetidides displayed unexpectedly strong activity.

Synthesis of 3,3,4,4-tetrafluoropyrrolidine and novel dipeptidyl peptidase-IV inhibitor compounds

The present invention relates to a method of making novel dipeptidyl peptidase-IV (“DPP-IV’) inhibitor compounds useful for treating, inter alia, diseases that are associated with proteins that are subject to processing by DPP-IV, such as Type 2 diabetes mellitus, metabolic syndrome (Syndrome X or insulin resistance syndrome), hyperglycemia, impaired glucose tolerance, glucosuria, metabolic acidosis, cataracts, diabetic neuropathy, diabetic nephropathy, diabetic retinopathy, diabetic cardiomyopathy, Type 1 diabetes, obesity, hypertension, hyperlipidemia, atherosclerosis, osteoporosis, osteopenia, frailty, bone loss, bone fracture, acute coronary syndrome, infertility due to polycystic ovary syndrome, short bowel syndrome and to prevent disease progression in Type 2 diabetes. The invention also relates to a method of making 3,3,4,4-tetrafluoropyrrolidine, a starting material utilized in the afore-mentioned method for preparing DPP-IV compounds.

FLOURINATED CYCLIC AMIDES AS DIPEPTIDYL PEPTIDASE IV INHIBITORS

The invention relates to new therapeutically active and selective inhibitors of the enzyme dipeptidyl peptidase-IV, pharmaceutical compositions comprising the compounds and the use of such compounds for treating diseases that are associated with proteins that are subject to processing by DPP-IV, such as Type 2 diabetes mellitus, hyperglycemia, impaired glucose tolerance, metabolic syndrome (Syndrome X or insulin resistance syndrome), glucosuria, metabolic acidosis, cataracts, diabetic neuropathy, diabetic nephropathy, diabetic retinopathy, diabetic cardiomyopathy, Type 1 diabetes, obesity, conditions exacerbated by obesity, hypertension, hyperlipidemia, atherosclerosis, osteoporosis, osteopenia, frailty, bone loss, bone fracture, acute coronary syndrome, infertility due to polycystic ovary syndrome, short bowel syndrome, anxiety, depression, insomnia, chronic fatigue, epilepsy, eating disorders, chronic pain, alcohol addiction, diseases associated with intestinal motility, ulcers, irritable bowel syndrome, inflammatory bowel syndrome and to prevent disease progression in Type 2 diabetes. The invention also relates to a method of identifying an insulin secretagogue agent for diabetes.

Superiority of Very Weakly Basic Amines as Catalysts for Alpha-Proton Abstraction via Iminium Ion Formation

Catalysis of the conversions of beta-ketol 6 and beta-acetoxy ketone 7 to enone 3 via amine-carbonyl condensation has been studied by using eight nontertiary amines having a pKa range from 10.61 to 1.22, including the very weakly basic 3,3,4,4-tetrafluoropyrrolidine (pKa = 4.05) and 1,1,1,3,3,3-hexafluoroisopropylamine (pKa = 1.22).Kinetic terms reflecting rate-determining alpha-proton abstraction via iminium ion formation were identified.Primary kinetic isotope effects were observed when appropriately deuterated 6 and 7 were used.Intermediate eniminium and enimmonium ions 17 were detected.Unlike general-base catalysis, catalysis via iminium ion formation becomes more effective as the base strength of the catalyst decreases.With 1 M hexafluoroisopropylamine as catalyst, formation of 3 from 7 occurs > 104 times via the iminium ion pathway for every time it occurs via direct general-base-catalyzed alpha-proton abstraction.