Name: 23978-09-8|4,7,13,16,21,24-Hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane|98%
Brand: Ambeed
SKU: A258790
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1
[ 31364-42-8 ]
[ 23978-09-8 ]

Yield	Reaction Conditions	Operation in experiment
	With Tl(2,2,2)⁺ In water at 25℃;
	With Tl(2,2,2)⁺ In methanol; water at 25℃;

Reference： [1]Cox, B. G.; Garcia-Rosas, J.; Schneider, H. [Journal of the American Chemical Society, 1982, vol. 104, # 9, p. 2434 - 2437]
[2]Cox, B. G.; Garcia-Rosas, J.; Schneider, H. [Journal of the American Chemical Society, 1982, vol. 104, # 9, p. 2434 - 2437]

2
[ 929-59-9 ]
[ 19249-03-7 ]
[ 23978-09-8 ]

Yield	Reaction Conditions	Operation in experiment
61.54%		First, 28.9 mM of triethylene glycol bis(p-toluenesulfonate) and 25 g of Na2C03 were dissolved in 375 mL of acetonitrile and stirred at 40 C for 10 min.Then, 13.5 mmol of 2,2'-(ethylenedioxy)bis(ethylamine) was added, and the mixture was heated to 90 C, refluxed for 16 hours, cooled and filtered to give a filtrate A.[0036] Finally, after the filtrate A was rotary evaporated, it was dissolved by adding 150 mL of ethanol.Add 20mL of 1.8mol/L citric acid solution, heat to 85 C, reflux for 3h,Filtrate B was obtained by filtration. Adjusting the pH of the filtrate B to about 10 with tetramethylammonium hydroxide.Wash three times with chloroform, then dry with 4A molecular sieve, after drying,Pour out the solution and evaporate to give a pale yellow crude product.The crude product was recrystallized from n-hexane.Get a white product 3.3g,That is, amino polyether (2.2.2).. The test results show that the prepared compound is an amino polyether (2.2.2After testing, the purity of amino polyether (2.2.2) is above 98%.The reaction cycle is 27h, and the total yield is 61.54%.Compared with the yield of the comparative example prepared aminopolyether (2.2.2) of 39.1%,It shows that the decomplexation with citric acid can improve the reaction yield.

Reference： [1]Patent: CN108822128,2018,A .Location in patent: Paragraph 0026; 0033-0036; 0038; 0039; 0045-0049; 0050; 0056
[2]Tetrahedron Letters,1993,vol. 34,p. 777 - 778
[3]Tetrahedron Letters,1993,vol. 34,p. 777 - 778

3
[ 99685-96-8 ]
[ 23978-09-8 ]
C₆₀^(4-)*4C₁₈H₃₆N₂O₆*4Na⁽¹⁺⁾ [ No CAS ]

Reference： [1]Chemical Communications,1997,p. 747 - 748

4
[ 375-80-4 ]
[ 23978-09-8 ]
4,7,13,16,21,24-hexaoxa-1,10-diaza-bicyclo[8.8.8]hexacosane; compound with 1,1,2,2,3,3,4,4,5,5,6,6-dodecafluoro-1,6-diiodo-hexane [ No CAS ]

Reference： [1]Tetrahedron,2000,vol. 56,p. 5535 - 5550

5
[ 100-25-4 ]
[ 23978-09-8 ]
C₁₈H₃₆N₂O₆*C₆H₄N₂O₄^(1-)*K⁽¹⁺⁾ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 1797 - 1809

6
[ 3305-83-7 ]
[ 23978-09-8 ]
C₂₄H₄₄P₄^(2-)*2C₁₈H₃₆N₂O₆*2K⁽¹⁺⁾ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2004,vol. 43,p. 4093 - 4097

7
[ 23978-09-8 ]
⁽¹⁸⁾F-fluoride-cryptate complex [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; [18F]fluoride ion, cyclotron produced, NCA; In water;	In a first embodiment, conditions used for the radiolabeling reaction are as follows: No-carrier-added [F-18]fluoride ion was produced by proton bombardment of [O-18]water in a cyclotron target body. No fluorine moieties other than [F-18]ion are produced. The aqueous [F-18]fluoride ion was treated with 1.0 mg of potassium carbonate and 10 mg of Kryptofix 2.2.2. compound to form an aqueous solution. Kryptofix 2.2.2 compound is one example of a family of synthetic bi- and polycyclic multidentate ligands capable of encapsulating a variety of cations, referred to generically as cryptands. Kryptofix 222 is 4,7, 13,16,21,24-Hexaoxa- 1,10- diazabicyclo[8.8.8]-hexacosane (CI 8H36N2O6) with the following chemical structure:The aqueous solution was evaporated at 100 - 120 C and the residue was further dried by azeotropic distillation with acetonitrile.
	With (18F)-fluoride; potassium carbonate; In [18]enriched-H2O; acetonitrile; at 70℃; for 0.166667h;Inert atmosphere;	[18F]Fluoride in [18O]enriched-H2O was transferred to the GE TRACERlab FXF-N synthesizer and passed through an anion exchange resin (Sep-Pak Waters Accell Light QMA cartridge (Waters) in the carbonate form, prepared by washing with 10 mL of 0.5 M K2CO3 and then rinsing with 10 mL of water) under reduced pressure. Trapped [18F]fluoride ions were then eluted from the Sep-Pak cartridge and transferred to the reactor vessel using an eluent solution containing K2CO3 (4 mg in 0.2 mL H2O), acetonitrile (0.8 mL) and Kryptofix-222 (4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane, 13 mg). The mixture was evaporated to dryness at 70 C for 10 minutes followed by addition of dry acetonitrile (1 mL) and evaporation to dryness. The evaporation was carried out at 120 C under nitrogen flow and vacuum in 5 minutes.
	With (18F)-fluoride; potassium carbonate; In water; acetonitrile; at 110℃;Inert atmosphere;	A Sep-Pak light Accell Plus QMA (Waters Corporation) cartridge was activated with 1N NaHCO3 (10 mL), H2O (10 mL), and dried with argon. [18O]-Enriched aqueous solution of fluorine-18 was passed through the activated QMA (light) cartridge. A solution of 1 mL (0.93 mL acetonitrile, 0.07 mL H2O) containing Kryptofix[K222] (11 mg 4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane) and 2 mg K2CO3, was then passed through the QMA cartridge into a reaction vessel to collect the K[222]18F complex to obtain 23.3 mCi. This complex was dried at 110 oC with a flow of argon until most of the solvent was evaporated (10 min). The solution was further azeotroped with the use of acetonitrile (2 x 1 mL) at 110 oC with a stream of argon gas. A solution of tosylate 5 (0.8 mg) in 1 mL of anhydrous acetonitrile was added to the ?dry? K[222]18F complex at 110 oC. After 10 min, the reaction vessel was removed from the oil bath, cooled in an ice/water bath and quenched with 10 mL of H2O. The reaction medium was then passed through an OASIS HLB 3cc cartridge (activated by flushing with 3 mL ethanol followed by 10 mL H2O). The OASIS cartridge was subsequently washed with H2O (3 mL) and the desired radioactive ligand was eluted with acetonitrile (0.60 mL) to provide 11.61 mCi. The acetonitrile solution was diluted with 2 ml of H2O and this solution was purified on a semi-preparative HPLC column (HPLC conditions: Gemini 5mu C18 110A column, 250 x 10.00 mm, 5 micron; Solvent A = ACN; Solvent B = 0.1 % TFA (aq); Gradient 95 % B, 0.0 - 5.0 min; 95 % to 5 % B to A, 5.0 - 45.0 min; at a flow rate of 1.5 mL/ min; collected sample from 37.0 - 39.0 min) to obtain 7.37 mCi. The radioactive sample was then diluted with 18 mL H2O and passed through an activated OASIS HLB 3cc cartridge. The OASIS cartridge was subsequently washed with H2O (3 mL) and the desired radioactive ligand was eluted with 1% TFA/ethanol (0.60 mL) to provide 5.22 mCi (decay correct rcy = 37 %). The eluted ligand was used without any further purification. Radiochemical purity (RCP) of the prosthetic ligand [18F]6 was determined by HPLC (> 99 %). HPLC conditions: Jupiter 10 mu C18 300A column, 250 x 4.60 mm, 10 micron; ACN/0.1 % TFA (aq) 60/40 at a flow rate of 0.5 mL/ min; rt = 8.27 min.

	With [18F]-potassium fluoride; potassium carbonate; In water; acetonitrile;Inert atmosphere;	An aqueous [18F]-Fluoride solution (2.0 ml,33.3 GBq/ 900 mCi) was purchased from P.E.T. Net ^ Pharmaceuticals in West Point PA and directly transferred to a Sep-Pak light QMA [The Sep-Pak light QMA cartridge was pre-conditioned sequentially with 5ml of 0.5 M potassium bicarbonate, 5 ml of deionized water, and 5 ml of MeCN before use.] Upon completion of this transfer, the aqueous [18F] fluoride was released from the QMA Sep-Pak by the sequential addition of potassium carbonate ( 15 mg/ml; 0.1ml) followed by a mixture of potassium carbonate (30 mg/ml, 0.1 ml), 4,7,13,16,21,24-hexaoxa-1,10- diazabicyclo[8.8.8]hexacosane (15 mg, 0.04 mmol) and 1.2 ml of MeCN. The solvent was evaporated under a gentle stream of nitrogen at 90C and vacuum. Azeotropic drying was repeated twice with 1 ml portions of acetonitrile to generate the anhydrous K.2.2.2/K[18F]F complex.
	With potassium carbonate; [18F]fluoride ion, cyclotron produced, NCA; In water; acetonitrile;	Preparation of the [K/K2.2.2]+ 18F (using enriched 95% 18O water)After irradiation, the target content was passed through a column packed with QMA resin. The column was purged with helium for 5 min. The [ FJfluoride adsorbed on the resin was eluted into a reaction vial with 4 ml of a 96 : 4 (by volume) acetonitrile- water mixture containing 19.1 mg of kryptofix 2.2.2 and 2.9 mg of K2CO3; the solution was then evaporated and co-evaporated with anhydrous acetonitrile ( 2 x 1 ml) to dryness in a nitrogen stream at HO0C. After drying procedure the vial was cooled to 40-500C during 3-4 min.
	With potassium carbonate; In water; acetonitrile; at 85 - 90℃;	Example 6: 2 '- [18F] fluoro-folic acid using 2' -nitrofolic acid: The [18F] fluoride which was trapped on an anion exchange cartridge, was directly eluted into a 10 ml sealed reaction vessel using a solution of potassium carbonate (1 mg) and Kryptofix 2.2.2 (5 mg) in 1.5 ml acetonitrile/water (4:1). At 85 - 90 0C the solvents were removed by vacuum and a stream of nitrogen. Subsequently, 1 ml of dry acetonitrile was added three times and evaporated to dryness .
	With potassium carbonate; [18F]fluoride ion, cyclotron produced, NCA; In water; acetonitrile; at 100℃;Inert atmosphere;	An aqueous [18F]fluoride solution (6 - 7 GBq) was added to a 10 mL vial containing anhydrous acetonitrile (1 mL), K2.2.2 (1 equiv) and K2CO3 (1 equiv). The solvent was evaporated under a stream of nitrogen at 100 C under vacuum to produce K[18F]-K2.2.2 complex. This azeotropic drying was repeated twice by further addition of anhydrous acetonitrile (2 x 1 mL).

Reference： [1]Patent: WO2010/8522,2010,A2 .Location in patent: Page/Page column 11-12
[2]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 673 - 677
[3]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 6820 - 6823
[4]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 6992 - 6995
[5]Lab on a chip,2014,vol. 14,p. 902 - 910
[6]Patent: WO2017/210302,2017,A1 .Location in patent: Paragraph 00307
[7]Patent: WO2007/138408,2007,A1 .Location in patent: Page/Page column 24
[8]Patent: WO2008/125617,2008,A2 .Location in patent: Page/Page column 44
[9]Patent: WO2009/129573,2009,A1 .Location in patent: Page/Page column 25

8
[ 534-17-8 ]
[ 23978-09-8 ]
Cs[18F]F/K_2.2.2 complex [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With [18]F-fluoride; In acetonitrile; at 100 - 120℃; for 0.333333 - 0.5h;	First example:18F-fluoride (up to 40 GBq) was azeotropically dried in the presence of Kryptofix 222 (5 mg in 1.5 ml MeCN) and cesium carbonate (2,3 mg in 0.5 ml water) by heating under a stream of nitrogen at 110-1200C for 20-30 minutes. During this time 3 * 1 ml MeCN were added and evaporated. After drying, a solution of the precursor (2 mg) in 150 mul DMSO was added. The reaction vessel was sealed and heated at 50-700C for 5-15 mins to effect labeling. The reaction was cooled to room temperature and dilute with water (2.7 ml). The crude reaction mixture was analyzed using an analytical HPLC. The product was obtained by preparative radio HPLC to give to desired 18F labeled peptide.

Reference： [1]Patent: WO2008/28688,2008,A2 .Location in patent: Page/Page column 62-63

9
[ 31255-13-7 ]
[ 23978-09-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 94 percent / acetone / 20 h / 25 °C / 7500600 Torr 2: 65 percent / triphenylphosphine / dimethylformamide / 5 h / Heating

Reference： [1]Pietraszkiewicz, Marek; Salanski, Piotr; Jurczak, Janusz [Bulletin of the Polish Academy of Sciences: Chemistry, 1985, vol. 33, # 9-10, p. 433 - 436]

10
B₂ H₆ [ No CAS ]
[ 24951-52-8 ]
[ 23978-09-8 ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrogenchloride; diborane; In tetrahydrofuran; water;	EXAMPLE 6 Preparation of 4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8,8,8]hexacosane B2 H6 is prepared according to the process described in "Org. Reactions" 13, 31-32 (1963). A solution of 1 g. of the bicyclic diamide obtained in Example 5 in 20 ml. tetrahydrofurane is slowly added to 15 ml. of the fresh prepared B2 H6 solution under nitrogen atmosphere and at a temperature of 0C. The mixture is agitated at this temperature for 30 minutes and thereafter 1 hour at reflux temperature. The excess reagent is destroyed by adding 5 ml. of water and the solution is evaporated on a rotary evaporator under vacuum. 1 g. of the diborane of the title compound is obtained: SPC15 This compound is hydrolyzed by adding 20 ml. 6N hydrochloric acid under heating and a solution is obtained. The mixture is evaporated to dryness under vacuum on a rotatory evaporator. The residue is dissolved in 10 ml. water and the solution is passed through a column of an anion exchange resin (Dowex 1). The column is washed with water until there is no basic reaction. The water is evaporated. The residue is recrystallized from hexane and dried in vacuum (0.1 mm. Hg). 890 mg. of the desired product is obtained. m.p. = 68C-69C. Yield 95%. PMR (CDCl3): --CH2 --N: 2.65 ppm (triplet); --CH2 --O: 3.65 ppm (singlet + triplet)

Reference： [1]Patent: US3966766,1976,A

11
B₂ H₆ [ No CAS ]
bicyclo diamide [ No CAS ]
[ 24951-52-8 ]
[ 23978-09-8 ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrogenchloride; diborane; In tetrahydrofuran; water;	EXAMPLE 6 Preparation of 4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8,8,8]-hexacosane B2 H6 is prepared according to the process described in "Org. Reactions" 13, 3132 (1963). A solution of 1 g. of the bicyclo diamide obtained in Example 5 in 20 ml. tetrahydrofurane is slowly added to 15 ml. of the fresh prepared B2 H6 solution under nitrogen atmosphere and at a temperature of 0 C. The mixture is agitated at this temperature for 30 minutes and thereafter 1 hour at reflux temperature. The excess reagent is destroyed by adding 5 ml. of water and the solution is evaporated on a rotatory evaporator under vacuum. 1 g. of the diborane of the title compound is obtained: STR37 This compound is hydrolyzed by adding 20 ml. 6N hydrochloric acid under heating and a solution is obtained. The mixture is evaporated to dryness under vacuum on a rotatory evaporator. The residue is dissolved in 10 ml. water and the solution is passed through a column of an anion exchange resin (Dowex 1). The column is washed with water until there is no basic reaction. The water is evaporated. The residue is recrystallized from hexane and dried in vacuum (0.1 mm. Hg.) 890 mg. of the desired product is obtained. m.p. 68 C.-69 C. Yield 95%. PMR (CDCl3): --CH2 N: 2.65 ppm (triplet); --CH2 --O: 3.65 ppm (singlet + triplet)

Reference： [1]Patent: US4156683,1979,A

12
[ 23978-09-8 ]
[ 107371-67-5 ]

Yield	Reaction Conditions	Operation in experiment
	With [18F]-hydrofluoric acid; potassium carbonate; In water; acetonitrile;Product distribution / selectivity;	The radionucleide is produced beforehand, generally by irradiation of 18O enriched water with a proton beam originating from a particle accelerator, as F" (for instance H18F, in an aqueous solution). Then, the 18F is recovered under an activated form through "activating" agents such as KRYPTOFIX (also called K2.2.2), a trademark used in connection with the compound 4, 7, 13, 16, 21, 24-hexaoxo-l, 10-diazabicyclo-[8.8.8]-hexacosane, so as to make it more reactive. In some publications, they are called "phase transfer agents". EPO <DP n="13"/>Practically, the [18O] enriched water containing [18F"] is passed through an anionic resin that can be contained in a Strong Anionic Exchange cartridge such as the one marketed under the trademark QMA SepPak Light Waters.Advantageously, the [ rl8 O] enriched water is removed to the O water collection vial in the module.Collected and activated radioactivity is recovered by washing with K222/K2Ctheta3 CH3CN/H2O mixture solutionAfter this activation, the fluorinating agent, is made totally anhydrous by additions of at least one organic solvent, and by dry evaporations; COMPARATIVE EXAMPLE 1 (according to the synthesis disclosed in the hereinabove cited prior reference Oh et al); EPO <DP n="18"/>Preparation of the kit:Valve 2: QMA + reservoirValve 3 : 7mL of acetonitrile Valve 4: disposable 3OmL syringeValve 5: 40mg of precursor in 3mL of acetonitrileValve 6: connexion to reactor inValve 7: 25OmL of Water For Injection (WFI)Valve 8: NaOH 2M Valve 9: HCl IMValve 10: nothingValve 11: nothingValve 12: HPLC outValve 13: Nothing Valve 14: disposable 3OmL syringeValve 15: reactor outIn that system, there is no pre-purification cartridge between valve 10 and 11.Step fa) al. recovery of the [18O] enriched water using an anionic resin [KRYPTOFIX.(also called K2.2.2)] which is a 18F "activating" agent. a2. recovery, by elution of the anionic resin, of the activity in the form of[K/222].18+, F" in a solution in a mixture CH3CN/H2O. a3. evaporation of the solvent by IR heating (95.0C.) under nitrogen flow (2 min. 30 sec). a4. addition of 0.4 ml CH3CN, evaporation (2 min. 30 sec). a5. addition of 0.4 ml CH3CN, evaporation to siccity.Step fb)Labelling of the precursor. bl . addition of a solution of a labelling precursor (1-50 mg) in CH3CN (3 ml). b2. heating at 160. degree. C. during 6 min.Step (c):Partial evaporation of the fluorination solvent. EPO <DP n="19"/>Step fd):Deprotection (hydrolysis), dl addition of 3mL HCl into the reactor. d2. heating for 300sec at 105 degrees Celcius.Step (e):Neutralization of the hydrolysis mixture. e. addition of NaOH 2M into the reactor.Step (e):HPLC injection.Results :Yield: average is 50% corrected. Total synthesis time: 60 minutes including HPLC purification.In this example, it is emphasized that there is no pre-purification cartridge and that all the process happen in the reactor.; EXAMPLE 2 : Process according to the invention with a HPLC purificationPreparation of the kit:Valve 2: QMA + reservoirValve 3: 7mL of acetonitrile Valve 4: disposable 3OmL syringeValve 5: 1 to 50mg of precursor in 3mL of acetonitrileValve 6: connexion to reactor inValve 7: 25OmL of Water For Injection (WFI)Valve 8: 7mL of ethanol Valve 9: NaOH ethanolic solutionValve 10 TFA 60% (v/v) in water ImLValve 11 : outlet to HPLCValve 12: NothingValve 13: Nothing Valve 14: disposable 3OmL syringeValve 15: reactor out EPO <DP n="20"/>Step (a) al. recovery of the [18O] enriched water using an anionic resin [KRYPTOFIX. (also called K2.2.2)] which is a 18F "activating" agent. a2. recovery, by elution of the anionic resin, of the activity in the form of [K/222].18+, F" in a solution in a mixture CH3CNZH2O. a3. evaporation of the solvent by IR heating (95. C.) under nitrogen flow (2 min. 30 sec). a4. addition of 0.4 ml CH3CN, evaporation (2 min. 30 sec). a5. addition of 0.4 ml CH3CN, evaporation to sicciiy.Step (V)Labelling of the precursor. bl. addition of a solution of a labelling precursor (1-50 mg) in CH3CN (3 ml). b2. heating at 16O° C. during 6 min.Step (c) & (d):Pre-purification with adsorption of the labelled compound on the solid support. between stopcocks 10 & 11. cl. dilution of the resulting solution in 25 ml water. c2dl. transfer of the diluted solution through a Cl 8 cartridge (conditioned beforehand with 5 ml ethanol followed with 10 ml water) to the waste. d2. rinsing of the cartridge with 3 times 10 ml of water which are sent to the waste. d3. drying of the cartridge under nitrogen flow.Step (e): Deprotection (hydrolysis) on solid support in acidic media. el addition of 0.7 ml a 60% (v/v) aqueous solution of trifluoroacetic acid on the Cl 8 cartridge. e2. deprotection (hydrolysis) 2 min. at room temperature.Step (f):Recovery of the labelled compound. f. elution of the bulk solution with 3 ml of an aqueous solution of NaOH into a syringe. fl. rinse of the C- 18 cartridge with 3mL of water which are sent also to the syringe containing the bulk.Step (a):HPLC injection. EP...
		In a typical radiofluorination reaction, [18F]Fluoride in [18O] enriched-H2O is transferred to a GE TRACERIab MXFD0 synthesiser and passed through an anion exchange resin (Sep-Pak Waters Accell Light QMA cartridge in the carbonate form, made by washing with 10 mL 0.5 M K2CO3 and then rinsing with 10 mL of water) under vacuum. Trapped [18F]fluoride ions are then eluted from the Sep-Pak cartridge and transferred to the reactor vessel using an eluent solution containingK2CO3 (7 mg in 300 muL of pure water), 300 muL of acetonitrile and 22 mg of Kryptofix 222 (K222: 4,7, 13,16,2 l,24-hexaoxa-l,10-diazabicyclo [8.8.8] hexacosan). Aliquots of acetonitrile are added and the reaction mixture evaporated to dryness after each addition. (3 times : 80 muL, each time). The evaporation is carried out at 95C under nitrogen flow and vacuum.
	With potassium carbonate; In water; acetonitrile;	Example 2 Preparation of 2-f3-r18F1fluoro-4-(methylamino)phenv?-6-hvdroxy- benzothiazole (11) - see Scheme above (Approach 2) Example 2(0 Preparation of fK/K2.2.2l+ 18F' (using enriched 95% 18O water). After irradiation, the target content was passed through a column packed with QMA resin. The column was purged with helium for 5 minutes. The [18F]fluoride adsorbed on the resin was eluted into a reaction vial with 4 ml of a 96 : 4 (by volume) acetonitrile-water mixture containing 19.1 mg of Kryptofix 2.2.2 and 2.9 mg of K2CO3; the solution was then evaporated and co-evaporated with anhydrous acetonitrile ( 2 x 1 ml) to dryness in a nitrogen stream at 11O0C.

	With potassium carbonate; [18F]fluoride ion, cyclotron produced, NCA; In methanol; water;	Reactions were completed on an automated Synthra module using 40-100mCi (1.1-2.6GBq). Fluorine-18 labeled potassium cryptand fluoride was eluted from the resin into a glass reactor using a solution consisting of 14mg/mL 4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane (Kyrptofix 222) and 1.35mg/mL K2CO3 in 90% CH3OH/H2O (1mL). Eluted [18F]fluoride was dried by a combination of heating (90C), blowing N2 and vacuum for 5min. After cooling the reactor to 40C, a solution of 3 (7mg, 15mumol) in anhydrous CH3CN (1mL) was added with stirring and heated to 90C for 10min. The mixture was cooled to 40C, the reaction quenched with 3:1 H2O/HPLC mobile phase and then purified by HPLC using a Phenomenex GeminiNX C18 5mum, 250×10mm column with 42.5/57.5 CH3CN/H2O+0.1N ammonium formate as eluent at 7mL/min. The collected fraction containing [18F]1 was added to H2O (23mL) and 1N NaHCO3 (2mL) then trapped onto a pre-conditioned reverse-phase cartridge (Waters Sep-Pak tC18+). Salts and residual CH3CN were removed by washing the cartridge with H2O (5mL). Elution with EtOH (1mL) and isotonic saline (10mL) through a sterile 0.2mum filter placed [18F]1 into a sterile, pyrogen free bottle. Co-injection with the authenticated 1 under several reverse phase HPLC conditions, varying solvents (CH3CN, CH3OH), pH (4 and 7), and several HPLC columns (Phenomenex, Waters, Chiracel) verified the identity of [18F]1. The formulated radiotracer displayed <5% degradation 120min post end of synthesis.
	With potassium carbonate; [18F]fluoride ion, cyclotron produced, NCA; In water;	The n.c.a [ 8F]fluoride (2 - 5 GBq) was trapped on a Sep-Pak Acceli Plus QMA light cartridge (Waters) and eluted with a solution K2C03/Kryptofix 2.2.2. The water was removed using a stream of N2 at 120 C and co-evaporated to dryness with MeCN (3 x 1 mL). Afterwards, a solution of the dissolved precursor was added to the dried K[18F]F-K222 complex. The reaction vial was sealed and heated under conventional heating for 15 min at 130 C. Subsequently, the reaction mixture was quenched with water and the crude product was purified via semi- preparative HPLC. The isolated tracer was diluted with water (35 mL). trapped on a C-18 Plus cartridge (Waters), washed with water (5 mL), eluted with ethanol (1 mL) and formulated in saline.
	With potassium carbonate; [18F]fluoride ion, cyclotron produced, NCA; In water;	The n.c.a [18F]fluoride (2 - 5 GBq) was trapped on a Sep-Pak Accell Plus QMA light cartridge (Waters) and eluted with a solution K2C03/Kryptofix 2.2.2. The water was removed using a stream of N2 at 120 C and co-evaporated to dryness with MeCN (3 x 1 mL). Afterwards, a solution of the dissolved precursor was added to the dried K[18F]F-K222 complex. The reaction vial was sealed and heated under conventional heating for 15 min at 130 C. Subsequently, the reaction mixture was quenched with water and the crude product was purified via semi- preparative HPLC. The isolated tracer was diluted with water (35 mL), trapped on a C-18 Plus cartridge (Waters), washed with water (5 mL), eluted with ethanol (1 mL) and formulated in saline.
	With potassium oxalate; potassium carbonate; [18F]fluoride ion, cyclotron produced, NCA; In acetonitrile;	The Cu-mediated radiolabeling procedure followed our previously optimized method usingseveral structurally dierent drug-like molecules functionalized with a Bpin leaving group [39].The aqueous [18F]F- used in this work was produced by the 18O(p,n)18F nuclear reaction in an IBA(Ottignies-Louvain-la-Neuve, Belgium) Cyclone 18/9 cyclotron and then loaded (approx. 1.5 GBq) into a polystyrene-divinylbenzene in a HCO3- anion exchange cartridge (Chromafix 45-PS-HCO3)without the need of any preconditioning. The cartridge was then washed out to a 5 mL borosilicateglass Wheaton reaction V-vial (containing a stirring bar) with 1 mL of an 80% acetonitrile solution of3.15 mg Krypt-2.2.2, 0.05 mg K2CO3, and 0.5 mg K2C2O4. This solution was submitted to azeotropicdrying with subsequent additions of anhydrous acetonitrile at 105 C to originate moistureless[(Krypt-2.2.2)K+][18F]F-. Then, 0.8 mL of DMA with the boronic pinacol ester derivative labelingprecursor (6, 60 mol) was added to this same vial with the previously dissolved [Cu(OTf)2(py)4]catalyst (20 mol, 0.33 equiv.). This reaction mixture was left under vigorous stirring at 130 C for 20 minto aord 7 after a total synthesis time of under 60 min (Figure S3). The conversion to the 18F-productwas assessed by radio-TLC (TLC-SG developed in hexane:ethyl acetate (1:1 v/v), Rf([18F]F-) = 0.0-0.2and Rf(7) = 0.8-1.0) and radio-High performance liquid chromatography (HPLC) (SymmetryPrepTMC18 7 m 7.8 300 mm; A: sodium acetate 0.05 M pH 4.7, B: acetonitrile; 0±4 min.: 90% A, 4±15 min.:90% A to 20% A, 15-25 min.: 20% A to 5% A, 25-33 min.: 5% A 33-34 min.: 5% A to 90% A, 34-35 min.:90% A; flow: 6 mL.min1.; Rf(8) 16 min Rf(7) 23 min). As a proof-of-concept, 7 was converted to[18F]atorvastatin (8) by a fast (extra 10 min of synthesis time) and nearly quantitative deprotectionof the side chain [45] with HCl followed by NaOH. The final product (8) was then isolated (approx.25 MBq) by HPLC (Figure S4).

Reference： [1]Patent: WO2006/133732,2006,A1 .Location in patent: Page/Page column 11-12; 17-21
[2]Journal of labelled compounds and radiopharmaceuticals,2008,vol. 51,p. 435 - 439
[3]Journal of labelled compounds and radiopharmaceuticals,2008,vol. 51,p. 444 - 452
[4]Patent: WO2010/20000,2010,A1 .Location in patent: Page/Page column 28
[5]Journal of labelled compounds and radiopharmaceuticals,2010,vol. 53,p. 24 - 30
[6]Patent: WO2007/20400,2007,A1 .Location in patent: Page/Page column 26
[7]Proceedings of the National Academy of Sciences of the United States of America,2012,vol. 109,p. 690 - 695
[8]RSC Advances,2013,vol. 3,p. 8028 - 8036
[9]Journal of labelled compounds and radiopharmaceuticals,2014,vol. 57,p. 410 - 418
[10]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 288 - 291
[11]Journal of labelled compounds and radiopharmaceuticals,2015,vol. 58,p. 196 - 201
[12]Journal of labelled compounds and radiopharmaceuticals,2015,vol. 58,p. 156 - 162
[13]ChemMedChem,2016,vol. 11,p. 108 - 118
[14]Journal of labelled compounds and radiopharmaceuticals,2016,p. 277 - 283
[15]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 5353 - 5356
[16]Molecular Pharmaceutics,2014,vol. 11,p. 3839 - 3851
[17]Journal of labelled compounds and radiopharmaceuticals,2017,vol. 60,p. 69 - 79
[18]Journal of labelled compounds and radiopharmaceuticals,2017,vol. 60,p. 140 - 146
[19]Patent: WO2018/15546,2018,A1 .Location in patent: Page/Page column 51
[20]Patent: WO2018/15549,2018,A1 .Location in patent: Page/Page column 69
[21]ChemMedChem,2018,vol. 13,p. 241 - 250
[22]Journal of labelled compounds and radiopharmaceuticals,2018,vol. 61,p. 84 - 93
[23]Journal of labelled compounds and radiopharmaceuticals,2019,vol. 62,p. 34 - 42
[24]Molecules,2019,vol. 24

13
[ 584-08-7 ]
[ 23978-09-8 ]
⁽¹⁸⁾F-fluoride-cryptate complex [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With [18F]-hydrofluoric acid; In water; at 130℃;	Example 2. Use Kryptofix 2.2.2 as a catalyst to produce O-(2-[18F]fluoroethyl)-L-Tyrosine [Show Image] (1) Pour [18F]HF solution (0.5-1.3 ml , radioactivity 1-500 mCi) into 5ml pointed-base bottle with potassium carbonate (4.6 mg) and kryptofix 222 (26 mg); heat under 130C, purge with nitrogen gas (200ml/min) and vacuum smoothly until the surface of liquid almost dry. (2) Add slowly 3ml anhydrous acetonitrile in eight minutes while heat under 130C; then purge with nitrogen gas (200ml/min) and vacuum smoothly so that azeotropic dry moisture and acetonitrile. (3) Dissolve 5mg t-BOC-(O-tosyloxyethylhL-Tyr-OBzl in 0.8ml anhydrous acetonitrile, then add into above bottle at 110C for 10mins reaction. (4) After complete the reaction , insert evacuation needle while maintaining at 110C and purge with nitrogen gas (200ml/min) until dry (take about 5 minutes to eliminate acetonitrile). (5) Cold the reaction bottle to room temperature, adds 1.5ml CHCl3 for dissolve reaction mixture and determine its radioactivity. Take a small fraction of solution for thin-layer chromatography (silica gel plate, developing agent CH2Cl2/CHCl3=8/2). Pass above solution through pre-conditioned silica column while increase flow rate by weak hydrogen gas pressure; wash bottle with 1.5ml CHCl3 before pass through the same silica column and the discarded effluent fluid is collected by waste bottle. Again, use 2.5 ml ether for silica column elution and collect effluent ether solution with capped test tube to obtain primary product have protective group. Take a small fraction of collected solution for thin-layer chromatography (silica gel plate, developing agent CH2Cl2/CHCl3=8/2). Determine the radioactivity of collected solution, silica column and reaction bottle. (6) Put capped test tube into 40C water bath, purge with nitrogen (200ml/min) and aspirate slowly until dry. Add 0.3ml 1N hydrochloride after solids dissolve by 0.3ml ethanol and put into heating block (100C) for ten-minute hydrolytic reaction. (7) Take out bottle after complete reaction, neutralize with 0.35ml 1N sodium hydroxide solution and add additional 1.35ml pure water to constitute a total volume of 2ml isotonic solution, then cold to room temperature. (8) Pass product through 0.22 mum bacteria-free filtering film and enter aseptic bottle as to obtain bacteria-free and carrier-free L-[18F]FET solution; determine radioactivity of filtered product (yield 30~40%, decay corrected) and analyze radiochemical purity (>90%) by thin-layer chromatography (reverse C 18 plate, acetonitrile /10 mM ammonium acetate=7/3).
	With [18F]fluoride ion, cyclotron produced, NCA; In H2(18)O; water; acetonitrile; for 0.05h;Heating by microwave irradiation;	10 to 50 mul of aqueous [18F]fluoride solution in [18O]H2O was mixed with 10 mg (26.6 mumol) of Kryptofix 222 (K222). 13 mul of 1 M of aqueous K2CO3 solution and 1 ml of anhydrous MeCN and then transferred into a V-vial (Wheaton) placed into the microwave cavity. A vacuum was applied to the mixed solution and it was exposed to 2OW power for 3 min using a microwave synthesizer (CEM Discover) to remove the water by azeotropic evaporation. After cooling down to room temperature using a strong blowing of cooling air, 1ml of anhydrous MeCN was added into the vial. The azeotropic evaporation was repeated again using the same conditions to produce an anhydrous K222/[18F]F complex.
	With 18F-fluoride; 18O-labeled water; at 118℃;	A Wheaton 5-mL reaction vial containing fluorine-18 (20 mCi) in 0.5 mL of 180 enriched water, Kryptofix 2.2. 2 (10 mg), and potassium carbonate (2 mg) was heated at 118C and solvent was evaporated with the aid of a nitrogen gas flow. The Kl8F/Kryptoflx complex was dried three times by the addition of 1 mL of acetonitrile followed by evaporation of the solvent using a nitrogen flow. A solution of 5 mg of 1- (4- methanesulfonyoxycyclohexyl)-4-phenylpiperazine in 1 ml of acetonitrile was added to the vial and the fluorination reaction was performed at 120C for 10 min. Solvent was removed using a nitrogen flow and replaced with 1 mL of a hexane/ethyl acetate/methanol (50: 45: 5) solution. After mixing, the solution was loaded onto a silica gel SepPak (Waters, Milford, MA) and the activity was eluted with 2 mL of the same solution. The labeled piperazine derivative was purified by HPLC (semi-prep silica gel column, hexane/ethyl acetate/methanol, 50: 45: 5). The solvent was removed and iodomethane (0.1 mL) in acetonitrile (1 mL) was added to a vial containing the activity. The reaction vial was heat at 120C for 2 0 minutes and solvent w as e vaporated t o a fford [F-18]-1- (4-fluorophenyl)-1- methylpiperazinium iodide (7 mCi).

Reference： [1]Patent: EP1760056,2007,A1 .Location in patent: Page/Page column 6-7
[2]Patent: WO2010/33196,2010,A2 .Location in patent: Page/Page column 9-10
[3]Patent: WO2005/82425,2005,A1 .Location in patent: Page/Page column 75-76

14
[ 23978-09-8 ]
4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosan/[18F]fluoride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; 18O-labeled water; In water; at 100℃;Proton beam of 19 MeV;	[18F]Fluorobenzaldehyde is prepared following the method by S. M. Haka et a./ [J. Labelled Cpd. and Radiopharm. 27 (1989) 823]. Briefly, 18F-fluorine is obtained from a cyclotron using the 18O(p,n)18F nuclear reaction with a proton beam of 19 MeV and enriched [18O]H2O (30 %) as target material. To the irradiated target water (370 MBq, 10 mCi, 1 ml) is added a mixture of Kryptofix(10 mg), potassium carbonate (1 mg), and acetonitrile (0.8 ml). The mixture is heated to 1000C under a stream of nitrogen. After the removal of solvent, acetonitrile (0.5 ml) is added and again evaporated. This step is repeated twice. The vial containing anhydrous [18F]KF-kryptate is cooled to room temperature and a solution of 4-trimethylammoniurn benzaldehyde trifluoromethylsulfonate (1 mg) in anhydrous DMSO (0.2 ml) is added. The mixture is heated at 900C for 15 min and cooled to room temperature.
	With potassium carbonate; In water; acetonitrile;	After irradiation, the target content was passed through a pre-conditioned QMA cartridge. The column was purged with helium for five minutes. The [18F] fluoride adsorbed on the resin was eluted into a reaction vial with 3 ml of a 96:4 (by volume) acetonitrile-water mixture containing 13.8 mg of kryptofix 2.2.2 and 3.2 mg Of K2CO3; the solution was then evaporated and co-evaporated with anhydrous acetonitrile (2 x 1 ml) to dryness in a nitrogen stream at 11O0C as shown below.
	With [18F]-potassium fluoride; potassium carbonate; In water; acetonitrile;	Cyclotron-produced [18F]fluoride ion in [18O]water was passed through an exchange resin (QMA light, Waters, ABX) eluted with aqueous K2CO3 (300 muL, 2 mg mL-1) and acetonitrile (300 muL). The aqueous [18F]fluoride solution was collected into a conical Reactivial containing Kryptofix 2.2.2. (22 mg) and K2CO3 (7 mg) dissolved in a water:acetonitrile mixture (600 muL, 1:1, v:v). The water was removed azeotropically with acetonitrile (3 × 1 mL) under a stream of nitrogen at 105 C. A solution of the labeling precursor 17 (5 mg, 12.7 mumol) dissolved in DMSO (500 muL) was added to the dried [K/K222]+ 18F- complex and the sealed reaction vial was heated at 140 C for 15 min. The reaction mixture was diluted with water (6 mL) and passed through a SPE C18 cartridge (Waters). The cartridge was washed with water (6 mL) and eluted by acetonitrile or dichloromethane (2 mL) in a conical Reactivial yielding 24 +/- 5% (n = 15) of the labeled compound [18F]18 with a radiochemical purity greater than 90%. After evaporation of the solvent followed by azeotropic distillation of residual water with acetonitrile (2 × 1 mL), triflic acid (300 muL) was added to the reaction vessel. Then triethylsilane (800 muL) was added dropwise to the solution and the mixture was vigorously stirred at 105 C for 5 min affording [18F]7a. The reactants were evaporated under nitrogen flow at 105 C for 5 min. HBr (500 muL, 48%) was added and heated at 160 C for 15 min leading to [18F]2a. NaOH solution (6 mL, 6 N) was added and the solution was passed through a SPE C18 cartridge (Waters). The cartridge was washed with water (6 mL) and the product was eluted with methanol (2 mL). The purification occurred on a HPLC column (XTerra C18, Waters, 250 × 10 mm) at 6 mL min-1 with H2O/acetonitrile/TEA (74:26:0.01) as eluent and the collected fraction containing [18F]2a (tR = 28 min) was diluted with water. The solution was passed through two SPE C18 cartridges (Chromafix Shorty 20 mg, Macherey-Nagel). [18F]2a was eluted with EtOH (200 muL) and diluted with saline (>2 mL). Specific radioactivity and radiochemical purity were assayed by analytical HPLC using a Luna C18 column (Phenomenex, 4.6 × 250 mm, 1 mL min-1) with acetonitrile/H2O/TEA as eluent (50:50:0.01) and radio thin layer chromatography (TLC) on silica gel (Merck; CH2Cl2/MeOH/NH4OH (90:10:0.1)). The radiochemical purities of [18F]2a (tR = 6.6 min) were greater than 99%.

	With potassium carbonate; In water; at 110℃; for 0.166667h;Inert atmosphere;	The activated K[18F]F-K222-complex was obtained by a conventional method. Briefly, the aqueous [18F]fluoride from target was flushed through an anion exchange resin (SepPak Light Accell Plus QMA cartridge, Waters). The radioactivity was eluted to the reactor with 1.0 mL of a carbonate potassium (3 mg) and Kryptofix (15 mg) solution (AcN/H2O 30/70). Solvents were evaporated under reduced pressure and under a gentle stream of helium at 110C for 10 min. A second azeotropic drying was repeated by addition of 1 mL of anhydrous acetonitrile.
	With potassium carbonate; In water; at 110℃; for 0.166667h;Inert atmosphere;	The activated K[18F]F-K222-complex was obtained by a conventional method. Briefly, the aqueous [18F] fluoride from target was flushed through an anion exchange resin (SepPak Light Accell Plus QMA cartridge, Waters). The radioactivity was eluted to the reactor with 1.0 mL of a carbonate potassium (3 mg) and Kryptofix (15 mg) solution (AcN/H20 30/70). Solvents were evaporated under reduced pressure and under a gentle stream of helium at 110 C for 10 min. A second azeotropic drying was repeated by addition of 1 mL of anhydrous acetonitrile.
	With potassium carbonate; [18F]fluoride ion, cyclotron produced, NCA;	The n.c.a [18F]fluoride (2 - 5 GBq) was trapped on a Sep-Pak Accell Plus QMA light cartridge (Waters) and eluted with a solution I^CCVKryptofix 2.2.2. The water was removed using a stream of N2 at 120 C and co-evaporated to dryness with MeCN (3 x 1 mL). Afterwards, a solution of the dissolved precursor was added to the dried K[18F]F-K222 complex. The reaction vial was sealed and heated under conventional heating for 15 min at 130 C. Subsequently, the reaction mixture was quenched with water and the crude product was purified via semi- preparative HPLC. The isolated tracer was diluted with water (35 mL), trapped on a C-18 Plus cartridge (Waters), washed with water (5 mL), eluted with ethanol (1 mL).
	With (18F)-fluoride; In acetonitrile; at 90℃;Inert atmosphere;	[00330] An aqueous [?8F]-Fluoride solution (2.0 ml,33.3 GBq/ 900 mCi) was purchased from P.E.T. Net Pharmaceuticals in West Point PA and directly transfeffed to a Sep-Pak light QMA [The Sep-Pak light QMA cartridge was pre-conditioned sequentially with 5m1 of 0.5 M potassium bicarbonate, 5 ml of deionized water, and 5 ml of MeCN before use.] Upon completion of this transfer, the aqueous [?8F] fluoride was released from the QMA Sep-Pak by the sequential addition of potassium carbonate (15 mg/ml; 0. lml) followed by a mixture of potassium carbonate (30 mg/ml, 0.1 ml), 4,7,13,16,21 ,24-hexaoxa- 1,10- diazabicyclo[8.8.8]hexacosane (15 mg, 0.04 mmol) and 1.2 ml of MeCN. The solvent was evaporated under a gentle stream of nitrogen at 90C and vacuum. Azeotropic drying was repeated twice with 1 ml portions of acetonitrile to generate the anhydrous K.2.2.2/K[?8F]F complex.
	With potassium carbonate; 18O-labeled water; In water; acetonitrile; at 130℃;Inert atmosphere;	The fluorine-18 radionuclide (the half-life is T1/2 = 110 min) in the form of [18F]fluoride was prepared by the 18O(p,n)18F nuclear reaction carried out by proton irradiation of [18O]H2O in an aqueous niobium target of the cyclotron with a volume of 2.3 mL. The irradiated water containing [18F]fluoride was transferred by helium flow on a Sep-Pak Light Waters Ac- cellTM Plus QMA anion-exchange cartridge activated by passing 0.5 M potassium carbonate (10 mL) and water (15 mL); the cartridge was flushed with helium for 5-10 min to remove residual water. The 18F radionuclide was eluted with complex-com- position solutions (2 mL) into a 5-mL conical reaction vessel placed to a heating unit. The eluent had the following composi- tion: K2.2.2. (9.8 mg), K2CO3 (2.1 mg), H2O (0.09 mL), and MeCN (2 mL). The solvents were removed in the stream of nitrogen for 4-6 min at 130 C, MeCN (1 mL) was added, and residual water was removed by azeotropic distillation. The re- sulting activated complex [K/K2.2.2.]+[18F]- was used in radiofluorination.
	With [18F]-potassium fluoride; potassium carbonate; In water;	A 12 MeV proton beam accelerated by the cyclotron Cypris HM12 (produced by Sumitomo Heavy Industries, Ltd.) was irradiated to [18O]H2O with an isotropic purity of 97% or higher (produced by Taiyo Nippon Sanso Corporation) for 40 minutes, thereby effecting an 18O(p,n)18F nuclear reaction to synthesize 18F-. Then, the solution was passed through a cation exchange resin (AG1-X8) to trap 18F- on the resin. The trapped 18F- was eluted with a 33 mM solution of K2CO3 to give an aqueous solution of [18F]KF/K2CO3. An appropriate amount of radioactivity (55-65 mCi) of the aqueous solution was taken in a volume of about 150-250 muL, and added to a reaction vial containing 800 muL of a Kryptfix 2.2.2. MeCN solution (20 mg/mL), and the contents were azeotropically dried under stream of helium in an oil bath at 100 C.

Reference： [1]Patent: WO2006/30197,2006,A2 .Location in patent: Page/Page column 10
[2]Patent: WO2007/144725,2007,A2 .Location in patent: Page/Page column 17
[3]European Journal of Medicinal Chemistry,2011,vol. 46,p. 2295 - 2309
[4]Journal of labelled compounds and radiopharmaceuticals,2011,vol. 54,p. 260 - 266
[5]Patent: EP2657213,2013,A1 .Location in patent: Paragraph 0121
[6]Patent: WO2013/160808,2013,A1 .Location in patent: Page/Page column 36
[7]Patent: WO2015/110263,2015,A1 .Location in patent: Page/Page column 301
[8]Organic and Biomolecular Chemistry,2016,vol. 14,p. 1915 - 1920
[9]Journal of labelled compounds and radiopharmaceuticals,2016,vol. 59,p. 54 - 62
[10]Journal of labelled compounds and radiopharmaceuticals,2015,vol. 58,p. 473 - 478
[11]Patent: WO2016/86021,2016,A1 .Location in patent: Paragraph 00330
[12]Russian Chemical Bulletin,2016,vol. 65,p. 507 - 512
Izv. Akad. Nauk, Ser. Khim.,2016,p. 507 - 512,6
[13]Journal of labelled compounds and radiopharmaceuticals,2017,vol. 60,p. 586 - 591
[14]Patent: US2018/30074,2018,A1 .Location in patent: Paragraph 0230-0231

15
potassium fluoride [ No CAS ]
[ 23978-09-8 ]
[ 12569-51-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In water; acetonitrile;	n-(3-fluoropropyl)-N-(2-PMB-thioethyl)-dansylamide (5): 1 mmol of KF, 1 mmol of Kryptofix [2,2,2] and 0.5 mmol of K2CO3 were dissolved in 10% water in acetonitrile. The solution was evaporated until dryness, residue dissolved in dry acetonitrile and solvent removed again. This process was repeated three more times opening the evaporator into a nitrogen atmosphere. A solution containing 0.2 mmol of product 3 dissolved in dry acetonitrile was added to the dry residue and mixture refluxed for 15 min. Solvent was then removed and residue dissolved in minimal volume of 25% petroleum ether in DCM. Solution was directly applied to a silica gel column and eluted with the above solvents mixture. First yellow fluorescent substance eluted was collected. ESI-MS and 1H-NMR was in accordance with desired substance 5. 19F-NMR (CDCl3, =ppm): -44.50, m. 1H-NMR (CDCl3, =ppm): 8.55 (1H, d); 8.25 (1H, d); 8.15 (1H, dd); 7.50 (2H, m); 7.15 (3H,m); 6.80 (2H, d); 4.40 (1H, t); 4.25 (1H, t); 3.75 (3H, s); 3.60 (2H, m); 3.35 (4H, m); 2.95 (3H, s), 2.85 (6H, s); 2.50 (2H, m), 1.80 (2H, m). ESI-MS: m/z+H+=491.72. 0.5 mmol of product 5 were dissolved in 5 ml TFA. 200 mul of anisole were added followed by 1 mmol of mercuric acetate. Solution was kept 15 min. at room temperature and protected from light. Then, TFA was removed by flash evaporation and residue washed with ether. Solid was filtered out, washed with fresh ether and dissolved in methanol. A stream of H2S was bubbled through the solution for 3 min. Solution was stirred for another 5 min. and black precipitate was filtered out through a pad of celite. Sodium acetate was added until neutral pH and solvent removed. Crude was purified by LC eluted with DCM. First yellow fluorescent substance eluted was analyzed to confirm product 6 structure. NST 839 [n-(3-fluoropropyl)-N-(2-thioethyl)-dansylamide (6)] was isolated and characterized as follows: 19F-NMR (CDCl3, =ppm): -44.70, m. 1H-NMR (CDCl3, =ppm): 8.55 (1H, d); 8.30 (1H, d); 8.20 (1H, d); 7.55 (2H, m); 7.20 (1H,m); 6.80 (2H, d); 4.40 (1H, t); 4.30 (1H, t); 3.45 (4H, m); 2.85 (6H, s); 2.65 (2H, q), 1.90 (2H, m); 1.30 (1H, t). ESI-MS: m/z+H+=371.14.

Reference： [1]Patent: US2007/232702,2007,A1 .Location in patent: Page/Page column 10-11

16
[ 1019996-49-6 ]
[ 23978-09-8 ]
potassium [2.2.2]cryptand [2-(fluorodimethylsilyl)phenyl]fluorodimesitylborate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 4222 - 4223

17
[ 1019996-52-1 ]
[ 23978-09-8 ]
potassium [2.2.2]cryptand [2-(fluorodiphenylsilyl)phenyl]fluorodimesitylborate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 4222 - 4223

18
[ 91-20-3 ]
[ 111379-11-4 ]
[ 7440-09-7 ]
[ 23978-09-8 ]
2{K(4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo{8.8.8}hexacosane)}⁽¹⁺⁾*{Ti(CO)6}^(2-) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1990,vol. 112,p. 6022 - 6025

19
[ 23978-09-8 ]
[ 54761-04-5 ]
[⁽²²⁾Yb(2-cryptand)](OTf)₃ [ No CAS ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1989,p. 367 - 370
[2]Inorganic Chemistry,2019,vol. 58,p. 9602 - 9612

20
[ 91-20-3 ]
[ 113035-23-7 ]
[ 7440-09-7 ]
[ 23978-09-8 ]
{K(cryptand 2.2.2)}2{hafnium hexacarbonyl} [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1990,vol. 112,p. 6022 - 6025

21
[ 91-20-3 ]
[ 113035-22-6 ]
[ 7440-09-7 ]
[ 23978-09-8 ]
{K(cryptand 2.2.2)}2{zirconium hexacarbonyl} [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1990,vol. 112,p. 6022 - 6025

22
[ 34557-72-7 ]
[ 23978-09-8 ]
[ 106335-75-5 ]

Reference： [1]Journal of the American Chemical Society,1987,vol. 109,p. 1425 - 1434

23
3K⁽¹⁺⁾*Sb₇^(3-)=K₃Sb₇ [ No CAS ]
[ 13007-90-4 ]
[ 107-15-3 ]
[ 23978-09-8 ]
3(K(N₂(C₂H₄OC₂H₄OC₂H₄)3))⁽¹⁺⁾*Sb₇Ni₃(CO)3^(3-)*H₂NC₂H₄NH₂=(K(N₂(C₂H₄OC₂H₄OC₂H₄)3))3(Sb₇Ni₃(CO)3)*H₂NC₂H₄NH₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1993,vol. 115,p. 5837 - 5838

24
[ 12129-67-8 ]
3K⁽¹⁺⁾*P₇^(3-) = K₃P₇ [ No CAS ]
[ 23978-09-8 ]
[K(4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane)]3[P₇Cr(CO)3]*ethylendiamine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1994,vol. 116,p. 8077 - 8086

25
[ 12129-69-0 ]
3K⁽¹⁺⁾*P₇^(3-) = K₃P₇ [ No CAS ]
[ 23978-09-8 ]
[K(4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane)]3[P₇W(CO)3]*ethylendiamine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1994,vol. 116,p. 8077 - 8086

26
4Rb⁽¹⁺⁾*Ge₉^(4-)=Rb₄[Ge₉] [ No CAS ]
[ 107-15-3 ]
[ 23978-09-8 ]
(Rb(4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]-hexacosane)6)[Ge₉=Ge₉=Ge₉]*3ethylenediamine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 10990 - 10991
[2]Journal of the American Chemical Society,2002,vol. 124,p. 10990 - 10991

27
[ 12129-69-0 ]
3K⁽¹⁺⁾*P₇^(3-) = K₃P₇ [ No CAS ]
[ 5197-95-5 ]
[ 23978-09-8 ]
2((CH₂)18(6O)(2N))*2K⁽¹⁺⁾*(CH₂C₆H₅)P₇W(CO)3^(2-)=[2((CH₂)18(6O)(2N))*2K][(CH₂C₆H₅)P₇W(CO)3] [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1995,vol. 117,p. 5303 - 5311

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CAS No. :	23978-09-8	MDL No. :	MFCD00005111
Formula :	C₁₈H₃₆N₂O₆	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AUFVJZSDSXXFOI-UHFFFAOYSA-N
M.W :	376.49	Pubchem ID :	72801
Synonyms :		Chemical Name :	4,7,13,16,21,24-Hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane

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

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 23978-09-8 ] {[proInfo.proName]}

Quality Control of [ 23978-09-8 ]

Related Doc. of [ 23978-09-8 ]

Product Details of [ 23978-09-8 ]

Safety of [ 23978-09-8 ]

Application In Synthesis of [ 23978-09-8 ]

[ 23978-09-8 ] Synthesis Path-Downstream 1~27

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry