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Structure of 1194-02-1
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 1194-02-1 |
Formula : | C7H4FN |
M.W : | 121.11 |
SMILES Code : | C1=C(C=CC(=C1)F)C#N |
MDL No. : | MFCD00001812 |
InChI Key : | AEKVBBNGWBBYLL-UHFFFAOYSA-N |
Pubchem ID : | 14517 |
GHS Pictogram: |
![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H228-H302+H312+H332-H315-H319 |
Precautionary Statements: | P210-P240-P241-P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312+P362+P364-P304+P340+P312-P305+P351+P338+P337+P313-P501 |
Class: | 4.1 |
UN#: | 1325 |
Packing Group: | Ⅱ |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 31.12 |
TPSA ? Topological Polar Surface Area: Calculated from |
23.79 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.63 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.94 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.12 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.88 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.24 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.96 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.31 |
Solubility | 0.598 mg/ml ; 0.00494 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.06 |
Solubility | 1.05 mg/ml ; 0.00863 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.71 |
Solubility | 0.234 mg/ml ; 0.00193 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.66 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
2.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.4 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35.5% | With ammonia; In diethyl ether; ethanol; | EXAMPLE 40 4-Fluorobenzamidine Hydrochloride 4-Fluorobenzonitrile (10 g, 83 mmol) is dissolved in a mixture of anhydrous ethanol (5 mL) and diethyl ether (70 mL). The reaction mixture is cooled to ice-bath temperature and saturated with gaseous hydrogen chloride for 90 minutes. The mixture is allowed to warm to ambient temperature and stirred overnight. The colorless precipitates are filtered off, washed with diethyl ether and dissolved in anhydrous ethanol (20 mL). Diethyl ether (100 mL) saturated with gaseous ammonia is added and the solution is stirred for 3 hours. The resulting suspension is filtered and the solvent of the filtrate is removed in vacuo. The residue is washed with diisopropyl ether. After drying colourless crystals (5.15 g, 35.5percent) of melting point 210° C. are obtained. |
2.9 g (100%) | EXAMPLE 4A 4-Fluorobenzenecarboximidamide Hydrochloride In analogy to the procedure for Example 3A, 2,0 g (16,5 mmol) 4-fluorobenzonitrile and proportionate amounts of the other reagents are used. Yield: 2.9 g (100percent) 1H-NMR (DMSO-d6, 200 MHz): delta=7,5 (m, 2H), 8,0 (m, 2H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39 g | A 1 L four-necked flask was fitted with a constant pressure dropping funnel and mechanical agitation.N2 is replaced three times, and N2 is protected by flow. Turn on mechanical agitation,Add 400 ml of THF and 182 ml of LDA (2 mol/L);40 g of p-fluorobenzonitrile (formula IV, 0.33 mol) was dissolved in 200 ml of THF.Transfer to a constant pressure dropping funnel and start to cool down.Temperature control at -75 ° C ~ -85 ° C dropwise addition of p-fluorobenzonitrile in THF solution; after the end of the addition,The temperature is controlled at -75 ° C ~ -85 ° C for 1 h,At the same time, 26.6 g of DMF was diluted with 30 ml of THF and transferred to a constant pressure dropping funnel. Temperature control at -75 ° C ~ -85 ° C dropwise addition of DMF in THF solution, after the end of the addition,The temperature control was stirred at -75 ° C ~ -85 ° C for 1 h until the reaction with p-fluorobenzonitrile was complete.After the reaction was completed, it was quickly added to 64 ml of acetic acid and quenched, and 400 g of water was added.The layers were separated and the aqueous extracted with EtOAc EtOAc. The organic phase was combined, washed with 400 ml of diluted HCl (1 mol/L), and the organic layer was washed with 400 ml of brine, and the organic39 g of the compound of formula III are obtained as a bright yellow solid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In N,N-dimethyl-formamide; for 12h;Alkaline conditions; Reflux; Inert atmosphere; | General procedure: To a round bottom flask containing DMF the appropriate phenolanalogue (1.5 equiv.), sodium bicarbonate (5.0 equiv.) and 4-fluorobenzonitrile(1.0 equiv.) were added and refluxed under nitrogen gas for 12h. After, the resulting solution was partitioned between EtOAc and LiBraqueous solution. Using additional EtOAc, the aqueous LiBr solution waswashed three times and the combined organic layers were dried overNa2SO4, filtered, and concentrated via vacuum. The resulting concentratewas purified by silica gel chromatography.4.2.5.1. 4-phenoxybenzonitrile (14a). White solid, yield 80%. 1H NMR(400 MHz, CDCl3) δ: 7.57 (d, J = 9.0 Hz, 2H), 7.40 (dd, J = 8.5, 7.6 Hz,2H), 7.22 (t, J = 7.4 Hz, 1H), 7.06 (dd, J = 8.6, 1.1 Hz, 2H), 6.99 (d, J =9.0 Hz, 2H). 13C NMR (101 MHz, CDCl3) δ: 161.6, 154.7, 134.1, 130.2,125.1, 120.4, 118.8, 117.9, 105.7. HRMS (ESI + ): calcd for C13H10NO[M + H]+ 196.0757, found: 196.0744. |
37% | With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 16h; | To a stirred solution 4-fluorobenzonitrile (1 g, 16.5 mmol, 1.0 eq.) and phenol (1.7 g, 18.18 mmol, 1.1 eq.) in DMF (20 mL) was added K2CO3 (6.8 g, 49.5 mmol, 3 eq.) The resulting mixture heated at 100 C. for 16 h. Following this, reaction was allowed to cool to RT and filtered through celite pad, the celite pad washed with ethyl acetate and water. The aqueous layer was separated extracted using ethyl acetate (3*30 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous Na2SO4, filtered and concentrated under vacuum to get the solid residue. The crude was purified by normal phase silica-gel column provided title compound (1.2 g, 37%). LCMS: 196.1 [M+1]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In dimethyl sulfoxide; at 120℃; for 5h; | Example 3 4- {4- [ (1-CYCLOBUTYL-4-PIPERIDINYL) OXY]-1-PIPERIDINYL} BENZONITRILE HYDROCHLORIDE (E3) Step 1: 4- 4- [ (1-TERT-BUTOXYCARBONYL-4-PIPERIDINYL) OXY]-1-PIPERIDINYL} BENZONITRILE tert-Butyl 4- (4-PIPERIDINYLOXY)-1-PIPERIDINECARBOXYLATE (D4) (0.340g) was reacted with 4- fluorobenzonitrile (0.218g) in DMSO (10ml) containing potassium carbonate (0.331g) for 5h at 120C. The reaction was then evaporated to a minimum volume and the residue redissolved in EtOAc (50ml) and washed with saturated sodium hydrogen carbonate (3No.30ML) and saturated brine (30MOI). Evaporation of the dried (MGS04) organic layer provided the subtitle compound as a pale yellow solid (0.422g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With n-butyllithium; acetic acid; diisopropylamine; In tetrahydrofuran; N-methyl-acetamide; hexane; water; | EXAMPLE 112 2-Fluoro-5-cyano-benzaldehyde To a stirred, cooled solution (0° C.) of diisopropylamine (15.4 mL, 0.11 mol) in anhydrous tetrahydrofuran (200 mL) n-butyllithium (40 mL of 2.5M in hexane, 0.11 mol) was added from a dropping funnel over a period of 30 min. under argon. The mixture was stirred at that temperature for 30 min. and then cooled to -78° C. A solution of 4-fluoro-benzonitrile (12.1g, 0.1 mol) in dry THF (50 mL) was then added dropwise over 15 min. via syringe and stirred for 1 hour at -78° C. Dimethylformamide (8 mL) was added dropwise from a syringe and the stirring was continued for another 20 min. The reaction was quenched by the rapid addition of acetic acid (20 mL) followed by water (500 mL) and the product was extracted with diethyl ether (2*500 mL). The combined organic layers were washed with 1N HCl, water, saturated sodium chloride and then dried over anhydrous magnesium sulfate, and evaporated to give 2-fluoro-5-cyano-benzaldehyde (11.8 g, 79percent yield) as a light yellow solid. 1H NMR (CDCl3): delta10.32 (s, 1H), 8.18 (dd, 1H, J=6.5, 2.5 Hz), 7.88 (m, 1H), 7.33 (t, 1H, J=9.5 Hz). |
74.6% | With acetic acid; diisopropylamine;SiO2; In N-methyl-acetamide; ethyl acetate; | A. 4-Fluoro-3-Formylbenzenecarbonitrile Lithium diisopropyi amide (LDA) (22 mL, 49.56 mmol, 2.0 N commercial solution in heptanes) was added to tetrahydrofliran (50 mL), cooled to 78° C. and under nitrogen. 4-Fluorobenzonitrile was weighed out (5.0 g, 41.3 imnol), placed under nitrogen and dissolved in 25 mL of dry tetrahydrofliran. This solution was added dropwise to the solution of LDA. The resulting solution was stirred at -78° C. for one hour before quenching with 4 mL of dimethylformamide. The temperature was maintained for 10 min before adding 8 mL of acetic acid and 20 mL of distilled water. The crude product was extracted with ethyl acetate. Purification by column chromatography (SiO2, 20percent ethyl acetate in hexanes) afforded 4.6 g of pure product as a white solid (74.6percent yield). -A second batch of the title compound (3.5 g, 56.8 percent/yield) was prepared 20 using 5 g of benzonitrile (41.3 mmol): 1H NMR (CDCl3) delta 10.3 (s, 1H), 8.21 (dd, 1H), 7.91 (d of q, 1H), 7.35 (t, 1H); ES-MS M+was not detected. |
With acetic acid; diisopropylamine; lithium diisopropyl amide;SiO2; In tetrahydrofuran; N-methyl-acetamide; ethyl acetate; | A. 4-Fluoro-3-formylbenzenecarbonitrile Lithium diisopropyl amide (LDA) (22 mL, 49.56 mmol, 2.0 N commercial solution in heptanes) was added to tetrahydrofuran (50 mL), cooled to 78° C. and under nitrogen. 4-Fluorobenzonitrile was weighed out (5.0 g, 41.3 mmol), placed under nitrogen and dissolved in 25 mL of dry tetrahydrofuran. This solution was added dropwise to the solution of LDA. The resulting solution was stirred at -78° C. for one hour before quenching with 4 mL of dimethylformamide. The temperature was maintained for 10 min before adding 8 mL of acetic acid and 20 mL of distilled water. The crude product was extracted with ethyl acetate. Purification by column chromatography (SiO2, 20percent ethyl acetate in hexanes) afforded 4.6 g of pure product as a white solid (74.6percent yield). A second batch of the title compound (3.5 g, 56.8percent yield) was prepared 20 using 5 g of benzonitrile (41.3 mmol): 1H NMR (CDCl3) delta 10.3 (s, 1H), 8.21 (dd, 1H), 7.91 (d of q, 1H), 7.35 (t, 1H); ES-MS M+ was not detected. |
With acetic acid; diisopropylamine; lithium diisopropyl amide;SiO2; In tetrahydrofuran; N-methyl-acetamide; ethyl acetate; | A. 4-Fluoro-3-formylbenzenecarbonitrile Lithium diisopropyl amide (LDA) (22 mL, 49.56 mmol, 2.0 N commercial solution in heptanes) was added to tetrahydrofuran (50 mL), cooled to 78° C. and under nitrogen. 4-Fluorobenzonitrile was weighed out (5.0 g, 41.3 mmol), placed under nitrogen and dissolved in 25 mL of dry tetrahydrofuran. This solution was added dropwise to the solution of LDA. The resulting solution was stirred at -78° C. for one hour before quenching with 4 mL of dimethylformamide. The temperature was maintained for 10 min before adding 8 mL of acetic acid and 20 mL of distilled water. The crude product was extracted with ethyl acetate. Purification by column chromatography (SiO2, 20percent ethyl acetate in hexanes) afforded 4.6 g of pure product as a white solid (74.6percent yield). A second batch of the title compound (3.5 g, 56.8percent yield) was prepared 20 using 5 g of benzonitrile (41.3 mmol): 1H NMR (CDCl3) delta 10.3 (s, 1H), 8.21 (dd, 1H), 7.91 (d of q, 1H), 7.35 (t, 1H); ES-MS M+was not detected. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; | B. 4-[(4-Benzyloxyphenyl)ethoxy]benzonitrile To a suspension of sodium hydride (60percent, 2.2 g, 55 mmol) in dry tetrahydrofuran (250 ml) was added a solution of 1-benzyl-oxy-4-(2-hydroxyethyl)benzene (11.4 g, 50 mmol) in tetrahydrofuran (50 ml). The reaction was heated to 40° C. for 1 hour. 4-Fluorobenzonitrile (6.7 g, 55 mmol) was added and the mixture was heated to reflux for 5 hours, cooled and neutralized with concentrated HCl. The precipitate was filtered, the filtrate was concentrated to dryness and the resulting solid was recrystallized from ethanol (12 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | EXAMPLE 7; 8-fluoro-7-methoxydibenzo[b,d]furan-2-carbonitrile; A. 4-(4-fluoro-3-methoxyphenoxy)benzonitrile; This compound was prepared according to the method of Sawyer, et al. (Sawyer, J. Scott; Schmittling, Elisabeth A.; Palkowitz, Jayne A.; Smith, William J., III. Journal of Organic Chemistry (1998), 63(18), 6338-6343) from <strong>[117902-15-5]4-fluoro-3-methoxyphenol</strong> (Belanger, Patrice C.; Lau, C. K.; Williams, Haydn W. R.; Dufresne, C.; Scheigetz, John. Canadian Journal of Chemistry (1988), 66(6), 1479-82) (9.71 g, 68.3 mmol) and 4-fluorobenzonitrile (8.27 g, 68.3 mmol), which provided 4-(4-fluoro-3-methoxyphenoxy)benzonitrile (11.69 g, 70percent) as an orange oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With sodium carbonate; In N,N-dimethyl-formamide; for 24h;Reflux; | General procedure: A suitable phenol or alcohol (1Meq.), 4-fluorobenzonitrile (1Meq.) and Na2CO3 (2Meq.) were suspended in DMF (3.5mL/mmol) and heated. The reaction was followed by TLC, hexane:diethyl ether (9:1), and after completion (approximately 24h), the desired product extracted with CH2Cl2 (3×50mL). The crude product was purified by flash chromatography, using hexane:diethyl ether (100:1) as eluent. |
80% | With caesium carbonate; In N,N-dimethyl-formamide; for 24h;Reflux; | General procedure: A DMF (40 mL) solution containing 4-fluorobenzonitrile (10) (1.0 equiv), m-substituted phenol (11?15) (1.1 equiv), and K2CO3or Cs2CO3(1.0 equiv) was stirred at reflux (24 h). The mixture was cooled, and then H2O (400 mL) was added and the reaction mixture extracted with CH2Cl2(3 x 100 mL). The organic layers were combined, washed with brine (3 x 100 mL), dried (Na2SO4), and evaporated under reduced pressure. The residue was purified by column chromatography using SiO2and 1:30 EtOAc and hexanes as the eluent giving the desired product as a colorless oil. |
With caesium carbonate; In N,N-dimethyl-formamide; at 100℃; for 4h; | 726 mg of 4-fluorobenzonitrile, 890 mg of <strong>[827-99-6]3-trifluoromethoxyphenol</strong>, and 1.95 g of cesium carbonate were added to 6 ml of DMF. The obtained mixture was stirred at 100°C for 4 hours. Thereafter, diluted hydrochloric acid was added to the reaction mixture, and it was then extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, and it was then dried over magnesium sulfate. The resultant was concentrated by centrifugation under reduced pressure. Sodium hydroxide was added to the residue, and the mixture was then extracted with MTBE. The organic layer was washed with water. The resultant was dried over sodium sulfate, and it was then concentrated by centrifugation under reduced pressure, so as to obtain 1.32 g of 4-(3-trifluoromethoxyphenoxy)benzonitrile. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 60℃; for 6h;Inert atmosphere; | To a mixture of 4-fluorobenzonitrile (2.49 g, 20.6 mmol) and 4-formylpyrazole (1.98 g, 20.6 mmo) in 50 mL of DMF at 0 0C was added 95percent sodium hydride (0.54 g, 22.7 mmol) under nitrogen. The mixture was heated to 60 0C for 6 hours and cooled to room temperature, Water was added carefully and the mixture was then extracted with ethyl acetate. The combined extracts were washed with water and brine, and then dried over sodium sulfate, filtered, and concentrated in vacuo to provide crude 4~(4-formyMH-pyrazol-l-yl)benzonitrile. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Under a nitrogen atmosphere, 370 mg (2.42 mmol) of CsF, previously activated with sodium hydroxide, were suspended in 5 ml of DMF and stirred for 30 min. Then, 1.01 g (8.34 mmol) of 4-fluorobenzonitrile were added. After 10 min 1.50 ml (8.34 mmol) of phenoxytrimethylsilane were added, and the mixture was stirred at room temperature for 42 hr. For workup, most of the DMF was removed under vacuum (oil pump), and then 15 ml of water and 25 ml of diethyl ether were added to the reaction mixture. The organic phase was separated, the aqueous phase was extracted with diethyl ether, the organic phases were combined, washed several times with water and dried over magnesium sulfate, and the solvent was removed under vacuum. A red oil is obtained, from which the product crystallizes in form of colorless needles.Yield: 1.27 g (6.51 mmol, 78%), appearance: colorless crystalline solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With sodium hydride; In N,N-dimethyl-formamide; at 20℃; for 10h;Inert atmosphere; | To the flask was added 7,7-dimethyl-5H-indeno [2,1-b] carbazole (15 g, 53 mmol)p-fluorobenzonitrile (6.5 g, 53 mmol) and N, N-dimethylformamide (100 mL), sodium hydride (1.5 g, 64 mmol) was slowly added and reacted at room temperature for 10 hours under nitrogen. Water, extracted with dichloromethane, dried and concentrated. The crude product was purified by column chromatography to give 13 g, 65% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With trimethylsilyl trifluoromethanesulfonate; In toluene; at 0 - 110℃; for 15.1667h; | To a solution of <strong>[2734-70-5]2,6-dimethoxyaniline</strong> (0,5 g, 3 rnrnol) and 4-fluorobenzonitrile (0.5 g, 4 mmol) in toluene (10 ml) at 0 C was added dropwise TMS-OTf (0.65 ml, 3.6 rnmol). The resulting mixture was stirred at 0 C for 10 mm and heated to 110C for 15 hrs. Thereaction mixture was cooled to 0 C, quenched with 1.5 M Na2T-fPO4 (10 mL) solution anddiluted with EtOAc. The organic layer was washed with 1.5 M Na2HPO4 solution and driedover sodium sulfate, concentrated to give a brown oil. The residue was purified by a silica gel (80 g) column and was eluted with 0-100% 0.5% TEA/EtOAc in DCM. Fractions containing compound 37a were combined and the solvent removed to give 37a (0.55 g, 2.0 mrnol, 61 % yield) an off white solid. 1HNMR (500MHz, CDC13) 7.96 (br s, 2H), 7.10 (br s, 2H), 7.02(t, J 8.0 Hz, 1H), 6.64 (d, J 7.7 Hz, 2H), 4.68 (hr s, 2H), 3.80 (s, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In dimethyl sulfoxide; at 80℃; for 4h; | General procedure: To a stirred solution of compound 1 (121.0 mg, 1.0mmol) and2a-e (1.0 mmol) in anhydrous DMSO (10 mL) was added anhydrous K2CO3 (165.6 mg, 1.2 mmol). After stirring 4 h at 80 C, the reactionwas poured into ice, the precipitationwas filtrated to obtain 3a-e ina yield of 45%-75%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate; In N,N-dimethyl-formamide; at 80℃; for 16h; | To a stirred solution of 4-fluorobenzonitrile (474 mg, 3.92 mmol) and 8-oxa-3- azabicyclo[3.2.1 ]octane (443 mg, 3.92 mmol) in DMF (8 ml_) is added cesium carbonate (2.55 g, 7.84 mmol). The resulting mixture is stirred for 16 h at 80 C. The resulting mixture is filtered, the filter cake is washed with methanol and the filtrate is concentrated under reduced pressure. The residue is purified by silica gel column chromatography, eluted with PE/EtOAc (1 :1 ) to afford 4-[8-oxa-3- azabicyclo[3.2.1 ]octan-3-yl]benzonitrile as white solid; HPLC/MS [M+H]+ 215. |
Tags: 1194-02-1 synthesis path| 1194-02-1 SDS| 1194-02-1 COA| 1194-02-1 purity| 1194-02-1 application| 1194-02-1 NMR| 1194-02-1 COA| 1194-02-1 structure
A1537532 [1026413-78-4]
4-Fluorobenzonitrile-cyano-13C
Reason: Stable Isotope
A1537392 []
4-Fluorobenzonitrile-benz-13C6
Reason: Stable Isotope
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 |
Sorry,this product has been discontinued.
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