Fluorinating Reagents & Building Blocks
for Fluorinated Biochemical Compounds

Introduction of fluorine into a certain position of bioactive compound such as a pharmaceutical and an agricultural chemical may remarkably reduce the toxicity of the compound, or improve the efficiency of medicine. This is due to the mimic and blocking effect characterized by fluorine. Many compounds, such as 5-fluorouracil, have been reported as success case.
Attempts to efficiently synthesize fluorine-containing compounds are performed in many fields. Methods to introduce fluorine into a certain position through the use of fluorinating agents or the use of fluorine-containing building blocks have been reported.

Recently, triethyl 2-fluoro-2-phosphonoacetate has increasingly been utilized as a useful bifunctional fluorine-containing intermediate. This compound is very useful in the generation of physiologically active compounds because it can generate α-fluoro-α,β-unsaturated ester from the reaction with carbonyl compounds in the presence of a base. A subsequent reduction of the above ester leads to the corresponding aldehyde or alcohol. As examples, vitamin A derivatives1), pheromone of insect origin, synthesis of Pyrethroide having insecticidal efficacy, etc., can be given.

Building Blocks

Electrophilic Fluorinating Reagents

Nucleophilic Fluorinating Reagents

Fits Reagents

Building Blocks

F0518 F0518 D2525 D2525 D2524 D2524
T1570 T1570 T0435 T0435 M1193 M1193
T1604 T1604 T1512 T1512 B1801 B1801
F0340 F0340 B1673 B1673 C0990 C0990
C1503 C1503 F0283 F0283 D2523 D2523
D1423 D1423 E0663 E0663 D2782 D2782
E0547 E0547 T0810 T0810 B1463 B1463
C1458 C1458 C1467 C1467 D2530 D2530
D2498 D2498 F0030 F0030 T0432 T0432
F0341 F0341 H0598 H0598 T1245 T1245
C1586 C1586 F0311 F0311 T1516 T1516
C0991 C0991 T0791 T0791 T0433 T0433
F0518 (1-Fluorovinyl)methyldiphenylsilane
D2525 (R)-N-(2,2-Difluoroethylidene)-1-phenylethylamine
D2524 (S)-N-(2,2-Difluoroethylidene)-1-phenylethylamine
T1570 (Trifluoromethyl)trimethylsilane [Trifluoromethylating Reagent]
T0435 2,2,2-Trifluoroethanol
M1193 2,2,2-Trifluoroethyl Methanesulfonate
T1604 2,2,2-Trifluoroethyl Trifluoromethanesulfonate
T1512 2-(Trifluoromethyl)acrylic Acid
B1801 2-Bromo-3,3,3-trifluoro-1-propene (stabilized with Copper chip)
F0340 2-Fluoro-2-phosphonoacetic Acid Triethyl Ester
B1673 Bromofluoroacetic Acid Ethyl Ester
C0990 Chlorodifluoroacetic Acid
C1503 Chlorodifluoroacetic Anhydride
F0283 Diethyl Fluoromalonate
D2523 Difluoroacetaldehyde Ethyl Hemiacetal
D1423 Difluoroacetic Acid
E0663 Ethyl 2-Fluoropropionate
D2782 Ethyl 3-(Dimethylamino)-3-ethoxy-2,2-difluoropropionate
E0547 Ethyl 3-Ethoxy-2,2-difluoro-3-hydroxypropionate
T0810 Ethyl 4,4,4-Trifluoroacetoacetate
B1463 Ethyl Bromodifluoroacetate
C1458 Ethyl Chlorodifluoroacetate
C1467 Ethyl Chlorofluoroacetate
D2530 Ethyl Dibromofluoroacetate
D2498 Ethyl Difluoroacetate
F0030 Ethyl Fluoroacetate
T0432 Ethyl Trifluoroacetate
F0341 Fluoromethyl Phenyl Sulfone
H0598 Hexafluoropropene Diethylamine [Fluorinating Reagent]
T1245 Methyl 4,4,4-Trifluoroacetoacetate
C1586 Methyl Chlorodifluoroacetate
F0311 Methyl Fluorosulfonyldifluoroacetate
T1516 p-Toluenesulfonic Acid 2,2,2-Trifluoroethyl Ester
C0991 Sodium Chlorodifluoroacetate
T0791 Trifluoroacetaldehyde Ethyl Hemiacetal (contains 10% Ethanol at maximum)
T0433 Trifluoroacetic Anhydride

Electrophilic Fluorinating Reagents

F0346 F0346 F0328 F0328 F0344 F0344
F0334 F0334 F0343 F0343 F0327 F0327
F0342 F0342 F0358 F0358 F0335 F0335
F0346 1-Fluoro-2,4,6-trimethylpyridinium Tetrafluoroborate [Fluorinating Reagent]
F0328 1-Fluoro-2,4,6-trimethylpyridinium Trifluoromethanesulfonate [Fluorinating Reagent]
F0344 1-Fluoro-2,6-dichloropyridinium Tetrafluoroborate [Fluorinating Reagent]
F0334 1-Fluoropyridinium Pyridine Heptafluorodiborate [Fluorinating Reagent]
F0343 1-Fluoropyridinium Tetrafluoroborate [Fluorinating Reagent]
F0327 1-Fluoropyridinium Trifluoromethanesulfonate [Fluorinating Reagent]
F0342 2,6-Dichloro-1-fluoropyridinium Trifluoromethanesulfonate [Fluorinating Reagent]
F0358 N-Fluoro-N'-(chloromethyl)triethylenediamine Bis(tetrafluoroborate)
F0335 N-Fluorobenzenesulfonimide [Fluorinating Reagent]

Nucleophilic Fluorinating Reagents

D1868 D1868 D2831 D2831 B2440 B2440
T1295 T1295 T1909 T1909 T1592 T1592
T1635 T1635 T1338 T1338 T1339 T1339
T2027 T2027 T2026 T2026 T2023 T2023
T2022 T2022
D1868 (Diethylamino)sulfur Trifluoride [Fluorinating Reagent]
D2831 2,2-Difluoro-1,3-dimethylimidazolidine
B2440 Bis(2-methoxyethyl)aminosulfur Trifluoride
T1295 Tetrabutylammonium Bifluoride
T1909 Tetrabutylammonium Difluorotriphenylsilicate
T1592 Tetrabutylammonium Difluorotriphenylstannate
T1635 Tetrabutylammonium Dihydrogen Trifluoride
T1338 Tetrabutylammonium Fluoride (1mol/L in Tetrahydrofuran)
T1339 Tetrabutylammonium Fluoride (70-75% in Water)
T2027 Tetraethylammonium Fluoride Tetrahydrofluoride
T2026 Tetraethylammonium Fluoride Trihydrofluoride
T2023 Triethylamine Pentahydrofluoride
T2022 Triethylamine Trihydrofluoride

Fits Reagents

P1081 P1081 P1080 P1080 P1659 P1659
P1082 P1082
P1081 (Perfluoro-n-octyl)phenyliodonium Trifluoromethanesulfonate
P1080 (Perfluorohexyl)phenyliodonium Trifluoromethanesulfonate
P1659 (Perfluoroisopropyl)phenyliodonium Trifluoromethanesulfonate
P1082 (Perfluoropropyl)phenyliodonium Trifluoromethanesulfonate

Literature

1)Synthesis of fluorinated retinoic acids and their analogs
R. S. H. Liu, H. Matsumoto, A. E. Asato, M. Denny, Y. Shichida, T. Yoshizawa, F. W. Dahlquist, J. Am. Chem. Soc., 1981, 103, 7195; A. J. Lovey, B. A. Pawson, J. Med. Chem., 1982, 25, 71.
2)Triethyl 2-Fluoro-2-phosphonoacetate
M. Kikuchi, T. Onozawa, Yuki Gosei Kagaku Kyokaishi (J. Synth. Org. Chem., Jpn.), 1997, 55, 88.


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