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[ CAS No. 373-68-2 ] {[proInfo.proName]}

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Chemical Structure| 373-68-2
Chemical Structure| 373-68-2
Structure of 373-68-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 373-68-2 ]

CAS No. :373-68-2 MDL No. :MFCD00011627
Formula : C4H12FN Boiling Point : -
Linear Structure Formula :- InChI Key :GTDKXDWWMOMSFL-UHFFFAOYSA-M
M.W : 93.14 Pubchem ID :67803
Synonyms :

Calculated chemistry of [ 373-68-2 ]

Physicochemical Properties

Num. heavy atoms : 6
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 24.82
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.27 cm/s

Lipophilicity

Log Po/w (iLOGP) : -3.93
Log Po/w (XLOGP3) : 0.84
Log Po/w (WLOGP) : -2.67
Log Po/w (MLOGP) : -2.73
Log Po/w (SILICOS-IT) : -2.93
Consensus Log Po/w : -2.28

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 3.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.95
Solubility : 10.5 mg/ml ; 0.113 mol/l
Class : Very soluble
Log S (Ali) : -0.42
Solubility : 35.2 mg/ml ; 0.378 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.35
Solubility : 4.16 mg/ml ; 0.0447 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 373-68-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H312-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 373-68-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 373-68-2 ]

[ 373-68-2 ] Synthesis Path-Downstream   1~26

  • 1
  • [ 75-57-0 ]
  • [ 373-68-2 ]
YieldReaction ConditionsOperation in experiment
8.40 g With hydrogen fluoride; In water; at 50 - 110℃; for 3h; (1) Take 10g of 99% purity by mass of tetramethylammonium chloride was added 25mL of distilled water, was added 50mL of 40% concentration hydrofluoric acid, stirred and heated to 50oC in the original closed;(2) reaction of starting material at least sufficient 3h, then heated to 110oC, excess hydrogen fluoride was evaporated and the product gas of hydrogen chloride gas, tail gas absorption using calcium oxide, obtained not dehydrated tetramethylammonium fluoride ionic liquids;(3) To a tetramethyl ammonium fluoride ionic liquid was diluted with distilled water, tetramethyl ammonium fluoride volume with distilled water, the ionic liquid is not less than the dehydration 1:50, the diluted solution was added AgNO3 solution, if precipitation production, continue to add 20mL hydrofluoric acid, repeating (1) and (2) step until no precipitate was produced, purified non-dehydrated tetramethyl ammonium fluoride ionic liquids;(4) dewatering the non-purified tetramethyl ammonium fluoride at 120oC ionic liquid was dried under high vacuum at least 48h, in addition to the depth of water, in addition to hydrogen fluoride, to give a viscous liquid, viscous liquid for detection, the viscous liquid was added to distilled water, distilled water and the volume of viscous liquid is less than 1:50, sealed and heated to 60oC, with hydrogen detector dilution residual amount of hydrogen fluoride, if the reading is greater than> 0.1ppm, continue to 120oC and dried under high vacuum In addition to hydrogen fluoride, hydrogen fluoride until the test concentration <0.1ppm; if detected hydrogen fluoride concentration <0.1ppm, the resulting liquid is tetramethyl ammonium ionic liquids, weighing 8.40g.
With potassium fluoride; In methanol; at 9 - 20℃; for 5h;Inert atmosphere; Into a 1 L, 3-necked flask equipped with a stirring bar and a thermometer, Me4NC1 (164.4 g, 1.5 mol, technical grade from SACHEM) and MeOH (650 mL, HPLC grade fromFisher) were charged. The mixture was stirred for 15 minutes until all Me4NC1 was dissolved in the MeOH. The temperature dropped from 22 C to 9 C and KF (174.3 g, 3 mol, spray- dried material) was added in portions. The reaction was covered under nitrogen and the mixture was stirred at room temperature for 5 hours. The KC1/KF salt suspension that formed was filtered to provide a filtrate and the filtered solids that were washed with MeOH(3x100 mL). The combined filtrate and washings (750.5 g, TMAF/MeOH solution) were stored in a 1 L amber bottle. The water content was analyzed by using a Karl Fischer Coulometer and the TMAF/MeOH solution was found to contain 2127 ppm of water. After drying at 55 C under a flow of nitrogen for 18 hours, 190 g of the dried, filtered KC1/KF salts were obtained.
  • 2
  • [ 115-86-6 ]
  • [ 373-68-2 ]
  • N(CH3)4(1+)*POF4(1-)=[N(CH3)4]POF4 [ No CAS ]
  • Tetramethylammonium difluorophosphate [ No CAS ]
  • [ 558-32-7 ]
YieldReaction ConditionsOperation in experiment
In 1,2-dimethoxyethane at -40℃;
  • 3
  • [ 13478-20-1 ]
  • [ 373-68-2 ]
  • N(CH3)4(1+)*POF4(1-)=[N(CH3)4]POF4 [ No CAS ]
  • Tetramethylammonium difluorophosphate [ No CAS ]
  • HOF2POPF5 [ No CAS ]
  • [ 558-32-7 ]
YieldReaction ConditionsOperation in experiment
In further solvent(s) -196°C, warming (-140°C), solvent CHF3; not isolated, detected by NMR;
  • 4
  • [ 13478-20-1 ]
  • [ 373-68-2 ]
  • Tetramethylammonium difluorophosphate [ No CAS ]
  • HOF2POPF5 [ No CAS ]
  • N(CH3)4(1+)*OF2POPF5(1-)=[N(CH3)4]OF2POPF5 [ No CAS ]
  • [ 558-32-7 ]
YieldReaction ConditionsOperation in experiment
In further solvent(s) -196°C, warming (-140°C), warming (-90°C), solvent CHF3; not isolated, detected by NMR/IR;
  • 5
  • [ 13478-20-1 ]
  • [ 373-68-2 ]
  • Tetramethylammonium difluorophosphate [ No CAS ]
  • [ 558-32-7 ]
YieldReaction ConditionsOperation in experiment
In sulfur dioxide -78°C; solvent removal (vac.), not isolated, detected by IR;
In neat (no solvent) 25°C; not isolated, detected by IR;
In further solvent(s) -196°C, warming (-140°C), solvent CHF3; solvent removal (vac., -126°C), not isolated, detected by IR;
In further solvent(s) -64°C, solvent POF3; solvent removal (vac.), not isolated, detected by IR;
In acetonitrile -31°C; solvent removal (vac.), not isolated, detected by IR;

  • 6
  • [ 616-42-2 ]
  • [ 373-68-2 ]
  • [ 32149-65-8 ]
YieldReaction ConditionsOperation in experiment
96.3% at 70℃; for 2h; 7 Example 7 Tetramethylammonium Ethylsulfite A mixture of 1.34 g (14.4 mmol) of tetramethylammonium fluoride and 3.17 g (28.8 mmol) of dimethyl sulfite is stirred at 70° C. (temperature of the oil bath) for 2 hours under an inert-gas atmosphere (nitrogen) in a sealed reaction vessel with pressure valves for 1-1.5 bar above atmospheric pressure. The end of the reaction is determined by NMR measurement. The excess dimethyl sulfite is pumped off over the course of 2 hours in vacuo at 13.3 Pa and 100° C. (temperature of the oil bath), giving 2.34 g of solid tetrabutylammonium ethylsulfite. The melting point is 155-157° C. The yield is 96.3%. The product is investigated by means of NMR spectroscopy. 1H NMR (reference: TMS; solvent: D2O), ppm: 3.05 s (4CH3); 3.21 s (CH3O).
  • 8
  • [ 373-68-2 ]
  • [ 174138-46-6 ]
  • [ 328956-88-3 ]
YieldReaction ConditionsOperation in experiment
90.2% In dichloromethane at -40 - 20℃; 9.1.a Example 9 1. Synthesis of the Acid a: Preparation of the Ammonium Salt: (CH3)4N+F-+CF3SO2N(CF3)2→(CH3)4N+N(CF3)2- 0.052 g (0.18 mmol) of CF3SO2N(CF3)2 is added at -40° C. to a solution of 0.017 g (0.18 mmol) of (CH3)4N+F- in 0.5 ml of dry dichloromethane. The reaction solution is warmed to room temperature and diluted with the same amount of dry acetonitrile. Removal of the solvent by distillation in a dry argon atmosphere gives 0.037 g of a colourless, highly hygroscopic material in a yield of 90.2%. 19F NMR (CCl3F): -40.8 s; melting point: 120-125° C. _
In dichloromethane at -40 - 20℃; 5.1.a Example 5; 1. Synthesis of the Acid; a: Preparation of the Ammonium Salt:; (CH3)4N+F-+CF3SO2N(CF3)2→(CH3)4N+N(CF3)2- 0.052 g (0.18 mmol) of CF3SO2N(CF3)2 is added at -40° C. to a solution of 0.017 g (0.18 mmol) of (CH3)4N+F- in 0.5 ml of dry dichloromethane. The reaction solution is warmed to room temperature and diluted with the same amount of dry acetonitrile. Removal of the solvent by distillation in a dry argon atmosphere gives 0.037 g of a colourless, highly hygroscopic material in a yield of 90.2%.19F NMR (CCl3F): -40.8 s; melting point: 120-125° C.
at 20℃; for 1.16667h; Inert atmosphere; Ionic liquid; Ethyl 2-bis(triuoromethyl)aminoacetate; ethyl N,N-bis (triuoromethyl)glycine, (CF3)2NCH2C(O)OEt (4) Anhydrous tetramethylammonium fluoride (5.82 g, 62.5 mmol) was suspended in 30 mL bmpl FAP in a two-neck flask equipped with a dry ice/ethanol reflux-condenser. Under vigorous stirring, N,N-bis(trifluoromethyl)trifluoromethanesulfonamide, CF3SO2N(CF3)2 (7) (18.84 g, 66.1 mmol) was slowly added within 10 min at room temperature, resulting in evolution of trifluoromethylsulfonylfluoride, CF3SO2F. The reaction mixture was stirred for 1 h and then dry-ice/ ethanol reflux-condenser was let to warm up to room temperature to release the rest of the CF3SO2F (b.p. -21.5 °C). Trifluoromethylsulfonyl fluoride, CF3SO2F can be trapped as a side product with dry-ice condenser and converted to CF3SO2N(CH3)2 by reaction with dimethylamine. CF3SO2N(CH3)2 is the starting material for the production of CF3SO2N(CF3)2 by means of electrochemical fluorination process [21]. After removal of the CF3SO2F from the reaction mixture, ethyl-α-bromoacetate, BrCH2C(O)OEt (8.22 g, 49.2 mmol) was added and the mixture was heated for 16 h to 80 °C. The product was isolated by condensation into a trap, cooled with liquid nitrogen, at 0.1 Pa (0.75·10-3 mm Hg) at 80 °C as a clear colourless liquid in 99% yield (11.7 g). The composition of the product is 97 mol% ethyl-2-bis(trifluoromethyl)aminoacetate and 3 mol% ethyl-2-fluoroacetate.
  • 9
  • [ 1342799-69-2 ]
  • [ 373-68-2 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
80% In 1,2-dimethoxyethane at -30 - 0℃; Inert atmosphere; 19 4.18. 2,4,6-Tris(fluorosulfonyl)fluorobenzene (17) General procedure: To a stirred solution of chlorobenzene 1 (1.2 g, 3.34 mmol) in dry DME (25 mL) at -30 °C in dry argon atmosphere Me4NF [24] (0.44 g, 4.72 mmol) was added in one portion. Reaction mixture was slowly heated to 0 °C. Precipitate was filtered off. Filtrate was concentrated under reduced pressure. Extraction with dry benzene afforded 17 (0.93 g, 81%) as a white powder (insoluble in benzene residue was identified as σ-complex 18).
  • 10
  • [ 1415241-08-5 ]
  • [ 373-68-2 ]
  • [ 1415241-28-9 ]
YieldReaction ConditionsOperation in experiment
82% In acetonitrile at 20℃; for 3h; 7 4.7
Synthetic procedure for tetramethylammonium adamantaneselenothioate (12) In a 20 mL two-necked flask, adamantanecarboselenothioic acid Se-2-(trimethylsilyl)ethyl ester (9d) (0.441 g, 1.23 mmol) was added to a CH3CN (3 mL) suspension of tetramethylammonium fluoride (0.255 g, 2.74 mmol) at 20 °C. After stirring at 20 °C for 3 h, the reaction mixture was filtered through a glass filter (G4) to separate the insoluble parts, and the solvent was removed under reduced pressure. To this was added Et2O (5 mL) and at 20 °C, the mixture was stirred for 5 min. Filtration of the resulting deposits gave 0.334 g (82%) of 12 as a deep green solid; mp: 206-212 °C (decomp.); IR (KBr) 3013, 2902, 2844, 2103, 1524, 1488, 1404, 1256, 1004, 949, 896 cm-1; 1H NMR (DMSO-d6) δ 1.56, 1.93, 2.04 (br s, 15H, Ad), 3.12 (s, 12H, NMe4); 13C NMR (DMSO-d6) δ 29.0, 36.6, 44.8, 54.2, 56.9, 278.5; 77Se NMR (DMSO-d6) δ 1079.1; UV/vis (THF) λmax (log ɛ) 561 (1.34), 349 (3.35), 228 (3.61) nm.
  • 11
  • [ 373-68-2 ]
  • [ 81290-20-2 ]
  • [ 515823-30-0 ]
YieldReaction ConditionsOperation in experiment
89% With sulfur In tetrahydrofuran at -60 - 20℃; for 13h; Inert atmosphere;
87% Stage #1: (trifluoromethyl)trimethylsilane With sulfur In tetrahydrofuran at -60 - 20℃; for 0.5h; Stage #2: tetramethylammonium fluoride In tetrahydrofuran at 20℃; Inert atmosphere;
82% With sulfur In tetrahydrofuran at -60 - 20℃; for 17h; Inert atmosphere; 1-2. Synthesis of Me4N*SCF3. Me4N*SCF3 was synthesized by a following the previously reported method.S2 Elemental sulfur (160 mg, 5.00 mmol) was added to a 100 mL round bottom flask followed by THF (40 mL) at room temperature. TMSCF3 (0.800 mL, 5.41 mmol) was added to the mixture. Then, the reaction mixture was cooled to -60 °C. Me4N*F (0.500 g, 5.37 mmol) was added slowly over 30 min. The reaction mixture was stirred at -60 °C for 30 min and then allowed to warm to room temperature. Additionally, the mixture was stirred for 16 hours. A precipitation was filtered off. Then, the resulting crude material was washed with diethyl ether to give the desired product Me4N*SCF3 as a pale orange solid in 82% yield (718 mg, 4.10 mmol). 1H NMR (CD3CN, 400 MHz): δ = 3.14 (s, 12H). 19F NMR (CD3CN, 376 MHz): δ = -10.8. 13C NMR (CD3CN, 100 MHz): δ = 56.1 (m), 145.4 (q, JCF = 293.1Hz).
80% With sulfur In tetrahydrofuran at -60 - 20℃; for 13h; Inert atmosphere;
Stage #1: (trifluoromethyl)trimethylsilane With sulfur In tetrahydrofuran at -60 - 20℃; Inert atmosphere; Stage #2: tetramethylammonium fluoride In tetrahydrofuran at -60 - 20℃; Inert atmosphere;
With sulfur In tetrahydrofuran at -60 - 20℃; Inert atmosphere;
With sulfur In tetrahydrofuran at -60 - 20℃; for 0.5h; Inert atmosphere;

  • 12
  • [ 661-36-9 ]
  • [ 373-68-2 ]
  • 13
  • [ 373-68-2 ]
  • [ 98-92-0 ]
  • [ 6972-69-6 ]
  • 14
  • [ 50-35-1 ]
  • [ 373-68-2 ]
  • [ 42472-93-5 ]
  • 15
  • [ 915087-33-1 ]
  • [ 373-68-2 ]
  • 4-(3-(4-cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)-2-fluoro-N,N-dimethylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% In toluene at 100℃; for 12h;
  • 16
  • [ 16136-52-0 ]
  • [ 373-68-2 ]
  • [ 628711-58-0 ]
YieldReaction ConditionsOperation in experiment
85% In toluene at 100℃; for 6h;
  • 17
  • [ 17422-33-2 ]
  • [ 373-68-2 ]
  • [ 155868-51-2 ]
  • 18
  • [ 387-44-0 ]
  • [ 373-68-2 ]
  • 7-fluoro-1-methyl-1H-indole [ No CAS ]
  • 19
  • [ 271-63-6 ]
  • [ 373-68-2 ]
  • [ 27257-15-4 ]
  • 20
  • [ 4513-94-4 ]
  • [ 373-68-2 ]
  • [ 34884-10-1 ]
  • 21
  • [ 7697-46-3 ]
  • [ 373-68-2 ]
  • [ 37496-06-3 ]
YieldReaction ConditionsOperation in experiment
96% In toluene at 100℃; for 6h;
  • 22
  • [ 373-68-2 ]
  • [ 104-63-2 ]
  • [ 51353-26-5 ]
YieldReaction ConditionsOperation in experiment
76% In toluene at 100℃; for 8h; chemoselective reaction;
  • 23
  • [ 5192-03-0 ]
  • [ 373-68-2 ]
  • [ 102308-97-4 ]
  • 24
  • [ 373-68-2 ]
  • [ 171199-02-3 ]
YieldReaction ConditionsOperation in experiment
99% With potassium nitrite In tetrahydrofuran at 20℃; for 2h; 9 Example 1 General procedure: A mixture of 1-ethyl-1-methylpyrrolidinium bromide (2.00 g), potassium nitrite (0.91 g), and methanol (24 mL) was stirred at 20° C. for 2 hours. The reaction mixture was filtered under reduced pressure; and the filtrate was evaporated, thereby obtaining 1-ethyl-1-methylpyrrolidinium nitrite (1.45 g) with a yield of 90%. An internal standard substance, trifluoroethanol (0.013 g), was added to the obtained 1-ethyl-1-methylpyrrolidinium nitrite (0.1 g), and the mixture was diluted with heavy water to prepare a sample for NMR measurement. Then, 1H-NMR measurement was performed. The obtained 1-ethyl-1-methylpyrrolidinium nitrite was confirmed to have a purity of 99% or more. Table 1 illustrates the content of impurities other than the main component. The water content of the methanol used in the reaction was measured with a Karl Fischer moisture meter (Table 1).
  • 25
  • [ 373-68-2 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
87% In dichloromethane at 20℃; for 0.5h; General procedure: A solution of trans-[Rh(Cl)(CO)(IMes)2] (1) (0.076 mmol, 50 mg) in CH2Cl2 (2 ml) was added to Me4NF (1.2 mmol, 111 mg) in a PFA tube. After 30 min at room temperature the reaction mixture was filtered, the solvent removed in vacuo from the filtrate, and the residue was dissolved in a minimum amount of CD2Cl2. The solution was filtered through celite and the solvent was removed from the filtrate in vacuo. Yield: 88% (0.068 mmol, 44 mg). Complex trans-[Rh(F)(13CO)(IMes)2] (5’) was prepared in a similar manner by using trans-[Rh(Cl)(13CO)(IMes)2] (1’). Yield: 87% (0.068 mmol, 44 mg).
  • 26
  • [ CAS Unavailable ]
  • [ 373-68-2 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
88% In dichloromethane at 20℃; for 0.5h; Formation of 5: General procedure: A solution of trans-[Rh(Cl)(CO)(IMes)2] (1) (0.076 mmol, 50 mg) in CH2Cl2 (2 ml) was added to Me4NF (1.2 mmol, 111 mg) in a PFA tube. After 30 min at room temperature the reaction mixture was filtered, the solvent removed in vacuo from the filtrate, and the residue was dissolved in a minimum amount of CD2Cl2. The solution was filtered through celite and the solvent was removed from the filtrate in vacuo. Yield: 88% (0.068 mmol, 44 mg). Complex trans-[Rh(F)(13CO)(IMes)2] (5’) was prepared in a similar manner by using trans-[Rh(Cl)(13CO)(IMes)2] (1’). Yield: 87% (0.068 mmol, 44 mg). (0027) Selected Spectroscopic Data for 5: 1H NMR (300.1 MHz, CD2Cl2, 298 K): δ=1.82 - 2.16 (br., 24H, p-CH3), 2.23 - 2.62 (br., 12H, o-CH3), 6.87 - 7.01 (br., 8H, ArH), 7.14 (s, 4H, NCH) ppm. 19F NMR (282.4 MHz, CD2Cl2, 298 K): δ=-264.5 ppm (d, 1JF,Rh=43 Hz, RhF).
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