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CAS No. : | 218632-01-0 | MDL No. : | MFCD04973417 |
Formula : | C7H3FN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OZXCOGPRBUSXLE-UHFFFAOYSA-N |
M.W : | 166.11 | Pubchem ID : | 2783399 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 39.94 |
TPSA : | 69.61 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.26 cm/s |
Log Po/w (iLOGP) : | 1.09 |
Log Po/w (XLOGP3) : | 1.48 |
Log Po/w (WLOGP) : | 2.03 |
Log Po/w (MLOGP) : | 0.69 |
Log Po/w (SILICOS-IT) : | 0.08 |
Consensus Log Po/w : | 1.07 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.11 |
Solubility : | 1.3 mg/ml ; 0.00783 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.55 |
Solubility : | 0.469 mg/ml ; 0.00283 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.14 |
Solubility : | 1.21 mg/ml ; 0.00731 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.87 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
4.5 g | With hydrogenchloride; water; iron In methanol at 22 - 26℃; for 2 h; | To a solution of 3-fluoro-4-nitrobenzonitrile (5.0 g, 0.030 mmol) in MeOH (50 mL) were added iron powder (5 g) and conc.HC1 (20 mL). The reaction mass was stirred at RT for 2 h. The reaction mass was filtered. The filtrate was concentrated and then diluted with water, extracted with EtOAc and basified with 10percent NaHCO3 solution. The organic portion wasdried over Na2504 and concentrated to afford 4.5 g of the title product.’H NMR (300 MHz,DMSO-d6): 7.52-7.48 (d, J= 11.7 Hz, 1H), 7.31-7.29 (d, J= 8.1 Hz, 1H), 6.82.-6.76 (d, J=8.7 Hz, 1H), 6.24 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With lithium tert-butoxide; In tetrahydrofuran; at -10 - 20℃; | c) Ethyl 2-f 5-cvano-2-nitro-phenylV2-hydroxy-2- r5-Cmophiholin-4-ylmethyl)pyridm-2- yl]acetate; A solution of ethyl 2-[5-(mophiholin-4-ylmethyl)pyridin-2-yl]acetate (1.3g, 4.92mmol) and <strong>[218632-01-0]3-fluoro-4-nitrobenzonitrile</strong> (0.9g, 5.41mmol) in tetrahydrofuran (30ml) was cooled down <n="24"/>to -10 C and lithium tert-butoxide solution in tetrahydrofuran (4.92ml, 20w/w%, 10.82mmol) was added dropwise whilst bubbling air through the solution. The resulting dark purple solution was then allowed to stir at room temperature overnight under air. Saturated ammonium chloride solution was then added to the reaction solution followed by5 Celite . The Celite was then filtered off and washed with ethylacetate. The aqueous layer was separated and extracted with ethylacetate and the combined organic layers washed with brine and dried with anhydrous sodium sulphate. After concentration the dark brown oil was dissolved in ethylacetate (15ml) and stand overnight at room temperature. The resulting suspension was filtered and washed with heptane; after drying in an oven at o +500C under vacuum gave ethyl 2-(5-cyano-2-nitro-phenyl)-2-hydroxy-2-[5-(morpholin-4- ylmethyl)pyridin-2-yl]acetate as a solid (1.0 Ig, yield 48%). 1H NMR (400MHz;CDCl3,): delta 8.40 (s, IH), 8.1 (s, IH), 7.85 (d, J=7.96Hz, IH), 7.63 (d, J=8.12Hz, IH), 7.44 (s, IH), 4.2 (m, 2H), 3.57 (br s, 4H), 3.53 (br s, 4H), 2.36 (br s, 4H), 1.15 (t, J=7.09,14.09Hz, 3H); MS (ESI) m/z 427 (M+l)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 - 70℃; for 6h; | A stirred solution of <strong>[218632-01-0]3-fluoro-4-nitrobenzonitrile</strong> (133mg, O.deltaOmmol) in dimethylformamide (4ml) at room temperature under argon was treated with diisopropylethylamine (0.46ml, 2.6mmol) followed by 1-[frans-4-(ethyloxy)cyclohexyl]-4-piperidinamine dihydrochloride (D12, 225mg, 0.75mmol) and heated at 7O0C for 6hrs. The solution was concentrated under vacuum and the residue treated with 10% Na2CO3 solution (10ml) and extracted with dichloromethane (2x15ml). The combined extract was dried (Na2SO4), concentrated under vacuum and the residual solid chromatographed on silica gel (5g) eluting with 0- 10% methanol/dichloromethane to give an orange solid, which was recrystallised from MeOH (8ml) to afford the title compound as an orange solid (175mg, 63%). MH+ 373. 1H NMR delta (CDCI3, 400 MHz): 1-18-1.40 (4H, m), 1.21 (3H, t), 1.60-1.72 (2H, m), 1.90-1.98 (2H, m), 2.03-2.18 (4H, m), 2.32-2.50 (3H, m), 2.88-2.98 (2H, m), 3.13-3.23 (1 H, m), 3.42- 3.58 (3H, q + m), 6.84 (1 H, dd), 7.15 (1 H, d), 8.08 (1 H, d), 8.25 (1 H, d). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 110℃; for 0.333333h;Microwave reactor; | A solution of <strong>[218632-01-0]3-fluoro-4-nitrobenzonitrile</strong> (1 11 mg, 0.67mmol) and 1-[frans-4-(ethyloxy)-1- methylcyclohexyl]-4-piperidinamine dihydrochloride (D58, 200mg, 0.61 mmol) in dimethylformamide (3ml) under argon was treated with diisopropylethylamine (0.3ml, 1.38 mmol) and the reaction mixture heated at 1 1O0C for 20mins in a microwave reactor. The resulting mixture was then concentrated under vacuum, the residue treated using aqueous NaHCO3 solution (30ml) and then extracted using ethyl acetate (2x40ml). The combined extract was dried (MgSO4) and concentrated under vacuum to give crude material as an orange residue. The residue was then chromatographed on silica eluting 0- 10% methanol/dichloromethane to yield the title compound (200mg, 80%) as an orange oil. M+ + H = 387 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.5% | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 5h; | To a solution of <strong>[218632-01-0]3-fluoro-4-nitrobenzonitrile</strong> (6.3 g; 37.93 mmol) and 2-bromophenol (4.4 mL; 37.94 mmol) in DMF (50 mL) was added potassium carbonate (6.29 g; 45.51 mmol). The mixture was stirred for 5 h at rt. Water (100 mL) was added, and a precipitate formed. The solid was separated via filtration, washed with water, and dried to yield 11.20 g (92.5%) of 3-(2-bromo-phenoxy)-4-nitrobenzonitrile, 1a. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(R)-tert-Butyl 5-(5-cyano-2-nitrophenylamino)-2-oxo-3-(l -(pyridm-3-yl)ethyl)- 2,3-dihydroimidazo[4,5-b]pyridine-l-carboxylate (70). A solution of (R)-tert-butyl 5- amino-2-oxo-3-(l-(pyridin-3-yl)ethyl)-2,3-dihydroimidazo[4,5-b]pyridine-l-carboxylate (94 mg) and <strong>[218632-01-0]3-fluoro-4-nitrobenzonitrile</strong> (225 mg) in DMF (6 mL) was cooled to -25 0C and treated with NaH (60% w/w in mineral oil, 75 mg) and slowly allowed to warm to - 15 0C. The mixture was stirred for four hours between -20 0C and -15 0C, then diluted with EtOAc and quenched with saturated ammonium chloride solution. The organic phase was washed three times with brine, separated, dried over sodium sulfate, filtered, and concentrated. Column chromatography (2% MeOH in methylene chloride) provided 100 mg (R)-tert-Butyl 5-(5-cyano-2-nitrophenylamino)-2-oxo-3-(l-(pyridin-3-yl)ethyl)- 2,3-dihydroimidazo[4,5-b]pyridine-l-carboxylate (70). | ||
With sodium hydride; In N,N-dimethyl-formamide; at -25 - -15℃; for 4h; | A solution of (R)-tert-butyl 5-amino-2-oxo-3-(1-(pyridin-3-yl)ethyl)-2,3-dihydroimidazo[4,5-b]pyridine-1-carboxylate (94 mg) and <strong>[218632-01-0]3-fluoro-4-nitrobenzonitrile</strong> (225 mg) in DMF (6 mL) was cooled to -25 C. and treated with NaH (60% w/w in mineral oil, 75 mg) and slowly allowed to warm to -15 C. The mixture was stirred for four hours between -20 C. and -15 C., then diluted with EtOAc and quenched with saturated ammonium chloride solution. The organic phase was washed three times with brine, separated, dried over sodium sulfate, filtered, and concentrated. Column chromatography (2% MeOH in methylene chloride) provided 100 mg (R)-tert-Butyl 5-(5-cyano-2-nitrophenylamino)-2-oxo-3-(1-(pyridin-3-yl)ethyl)-2,3-dihydroimidazo[4,5-b]pyridine-1-carboxylate (70). tert-Butyl 5-(6-cyano-1H-benzo[d]imidazol-1-yl)-2-oxo-3-((R)-1-(pyridin-3-yl)ethyl)-2,3-dihydroimidazo[4,5-b]pyridine-1-carboxylate (72). | |
With sodium hydride; In N,N-dimethyl-formamide; at -25 - -15℃; for 4h; | A solution of (R)-tert- butyl 5-amino-2-oxo-3-(l-(pyridin-3-yl)ethyl)-2,3-dihydroimidazo[4,5-b]pyridine-l- carboxylate (94 mg) and <strong>[218632-01-0]3-fluoro-4-nitrobenzonitrile</strong> (225 mg) in DMF (6 mL) was cooled to -25 0C and treated with NaH (60% w/w in mineral oil, 75 mg) and slowly allowed to warm to -15 0C. The mixture was stirred for four hours between -20 0C and -15 0C, then diluted with EtOAc and quenched with saturated ammonium chloride solution. The organic phase was washed three times with brine, separated, dried over sodium sulfate, filtered, and concentrated. Column chromatography (2% MeOH in methylene chloride) provided 100 mg (R)-tert-Butyl 5-(5-cyano-2-nitrophenylamino)-2-oxo-3-(l-(rhoyridin-3- yl)ethyl)-2,3-dihydroimidazo[4,5-b]pyridine- 1-carboxylate (70). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
te^-Butyl 9-(2,6-difluorobenzyl)-2-(5-cyano-2-nitrophenylamino)-8-oxo-8,9- dihydropurine-7-carboxyIate (58). Sodium hydride (88 mg, 95%) was added, under argon flush, to a solution of tert-bntyl 9-(2,6-difluorobenzyl)-2-amino-8-oxo-8,9- dihydropurine-7-carboxylate (57) (191 mg) and <strong>[218632-01-0]3-fluoro-4-nitrobenzonitrile</strong> (415 mg) in DMF (5 mL) at -40 C. The reaction mixture was allowed to warm to -20 0C over 3 hr then quenched by the addition of sat. aq. NH4Cl, once at RT the mixture was diluted with EtOAc and separated. The organics were washed with brine (3 x), dried, filtered and evaporated, purified via column chromatography, (eluted with DCM and 1 and 2.5 % MeOH/DCM) to yield tert-Butyl 9-(2,6-difluorobenzyl)-2-(5-cyano-2- nitrophenylamino)-8-oxo-8,9-dihydropurine-7-carboxylate (58) (288 mg), MH+ = 524. | ||
With sodium hydride; In N,N-dimethyl-formamide; at -40 - -20℃; for 3h; | tert-Butyl 9-(2,6-difluorobenzyl)-2-(5-cyano-2-nitrophenylamino)-8-oxo-8,9-dihydropurine-7-carboxylate (58). Sodium hydride (88 mg, 95%) was added, under argon flush, to a solution of tert-butyl 9-(2,6-difluorobenzyl)-2-amino-8-oxo-8,9-dihydropurine-7-carboxylate (57) (191 mg) and <strong>[218632-01-0]3-fluoro-4-nitrobenzonitrile</strong> (415 mg) in DMF (5 mL) at -40 C. The reaction mixture was allowed to warm to -20 C. over 3 hr then quenched by the addition of sat. aq. NH4Cl, once at RT the mixture was diluted with EtOAc and separated. The organics were washed with brine (3*), dried, filtered and evaporated, purified via column chromatography, (eluted with DCM and 1 and 2.5% MeOH/DCM) to yield tert-Butyl 9-(2,6-difluorobenzyl)-2-(5-cyano-2-nitrophenylamino)-8-oxo-8,9-dihydropurine-7-carboxylate (58) (288 mg), MH+=524. tert-Butyl 9-(2,6-difluorobenzyl)-2-(6-cyano-1H-benzo[d]imidazol-1-yl)-8-oxo-8,9-dihydropurine-7-carboxylate (60). | |
With sodium hydride; In N,N-dimethyl-formamide; at -40 - -20℃; for 3h; | Sodium hydride (88 mg, 95%) was added, under argon flush, to a solution of tert-butyl 9-(2,6-difluorobenzyl)-2-amino-8-oxo-8,9- dihydropurine-7-carboxylate (57) (191 mg) and <strong>[218632-01-0]3-fluoro-4-nitrobenzonitrile</strong> (415 mg) in DMF (5 mL) at -40 0C. The reaction mixture was allowed to warm to -20 0C over 3 hr then quenched by the addition of sat. aq. NH4CI, once at RT the mixture was diluted with EtOAc and separated. The organics were washed with brine (3 x), dried, filtered and evaporated, purified via column chromatography, (eluted with DCM and 1 and 2.5 % MeOH/DCM) to yield ter-Butyl 9-(2,6-drfluorobenzyl)-2-(5-cyano-2-nitrophenylamino)- 8-oxo-8,9-dihydrorhourine-7-carboxylate (58) (288 mg), MH+ = 524. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With urea hydrogen peroxide adduct; potassium carbonate; In water; acetone; at 20℃; for 24h; | Compound 161a: 3-Fluoro-4-nitro-benzamide: The urea/hydrogen peroxide complex (22.65 g, 240.8 mmol, 2.0 eq) was added to a solution of <strong>[218632-01-0]3-fluoro-4-nitro-benzonitrile</strong> (20.0 g, 120.4 mmol, 1.0 eq) and potassium carbonate (33.28 g, 240.8 mmol, 2.0 eq) in 20% water/acetone (500 ml). The reaction was stirred at room temperature for 22 hours when urea/hydrogen peroxide complex (11.33 g, 120.4 mmol, 1.0 eq) and potassium carbonate (16.64 g, 120.4 mmol, 1.0 eq) were added. The reaction was stirred for a further 2 hours at room temperature then diluted with water (300 ml) and DCM (500 ml). The organic layer was removed and the aqueous extracted with DCM (2 x 500 ml). The organics were combined, washed with brine, dried over sodium sulphate, and the solvent removed in vacuo to give the title compound as an orange solid (14.065 g, 76.31 mmol, 63%). 1H NMR shows product in >95% purity. |
60% | With water; urea hydrogen peroxide adduct; potassium carbonate; In acetone; at 20℃; | General Scheme 1; Preparation of 3-fluoro-4-nitro-benzamide; To a stirred solution of <strong>[218632-01-0]3-fluoro-4-nitrobenzonitrile</strong> (15 g, 90.3 mmol) and K2CO3 (25.03 g, 181.1 mmol) in 100 ml_ of acetone / water (4:1 ) was added urea hydrogen peroxide adduct (16.99 g, 180.6 mmol) and the reaction stirred overnight at ambient temperature. DCM (100 ml_) and water (500 ml_) were added to the reaction mixture, the solution partitioned and the organic layer separated. The aqueous layer was extracted with DCM (3 x 100 ml_) and the combined organic portions, washed with brine (100 ml_), filtered through Celite and passed through a PTFE separation frit. The solvent was concentrated in vacuo and the title compound obtained as an orange solid (10 g, 60 % yield) after recrystallisation from EtOAc/ petroleum ether (40-60 0C).1H NMR (400 MHz; d6-DMSO; 25 C): delta 8.35 (br s, 1 H), 8.01 (dd, 1 H), 7.92 (dd, 1 H), 7.89 (br s, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 200℃; for 0.0166667h;Microwave irradiation; | 4-Cyano-2-fluoro-1 -nitrobenzene (300 mg, 0.0018 mol, 1 eq), 1-(tetrahydro-2H-pyran-4- yl)-4~piperidinamine (D9, 330 mg, 0.0018 mol, 1 eq), diisopropylethylamine (350 mg, 0.0027 mol, 1.5 eq), and dimethylformamide (5ml) were combined, heated to 2000C and held for 1 min in a microwave reactor. 100 ml of water was then added and the reaction extracted with 2 x 75 ml dichloromethane. The dichloromethane layers were combined, dried with sodium sulfate, and evaporated to yield the title compound which was used without further purification in the next step. MS (ESI): 331 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With lithium tert-butoxide; In tetrahydrofuran; toluene; at -20℃; for 2.33333h;Product distribution / selectivity; | Example 7; (5-Cvano-2-nitro-phenyl)-(5-morpholin-4-ylmethyl-pyridin-2-yl)-acetic acid ethyl ester using <strong>[218632-01-0]3-fluoro-4-nitrobenzonitrile</strong> in tetrahydrofuran and toluene; To a solution of (5-Morpholin-4-ylmethyl-pyridin-2-yl)-acetic acid ethyl ester (51.03g, 74.5% w/w%, 143.8mmol; Example 5) in toluene (204.1ml) was added a solution of 3- fluoro-4-nitrobenzonitrile (24.5 g, 151mmol) in tetrahydrofuran (357ml) and the solution was degassed three times with nitrogen and then cooled to -200C. Lithium tert-butoxide solution in tetrahydrofuran (137.ml, 20w/w%, 302mmol) was added dropwise over lhr. After stirring for an additional lhr 20min the reaction mixture was then added to a cold aqueous solution of ammonium chloride (188ml, 4.58M, 6862.7mmol) at 00C. The biphasic mixture was warmed to 300C and Celite (76.5g) added, then filtered. The filter cake was washed twice with toluene (153ml) then the combined filtrate was separated and the organic layer washed twice with water (153ml). The organic layer was concentrated by distillation to give (5-Cyano-2-nitro-phenyl)-(5-morpholin-4-ylmethyl-pyridin-2-yl)-acetic <n="31"/>acid ethyl ester as a toluene solution (196ml) (titration, HCIO4, assay 80.47 w/w%) .The crude product mixture is directly used in the next step. | |
With lithium tert-butoxide; In tetrahydrofuran; at -20 - -10℃; for 2.16667h;Product distribution / selectivity; | Example 8; (5-Cvano-2-nitro-phenv?-(5-morpholin-4-ylmethyl-pyridin-2-v?-acetic acid ethyl ester using <strong>[218632-01-0]3-fluoro-4-nitrobenzonitrile</strong> in tetrahydrofuran; To a stirred solution of (5-Morpholin-4-ylmethyl-pyridin-2-yl)-acetic acid ethyl ester (20.7g, 80.7w/w%, 83mmol; Example 6) in tetrahydrofuran (104ml) was added 3-fluoro-4- nitrobenzonitrile (13.2g, 78.3mmol) and nitrogen gas is bubbled through the reaction solution and cooled to -200C. Lithium tert-butoxide solution in tetrahydrofuran (76.8ml, 20w/w%, 186mmol) was added dropwise over lhr 30min. After stirring for an additional 40mins at -100C the reaction mixture is added to a cold aqueous solution of sulphuric acid (208.8ml, 0.45M, 94mmol) at 00C. To the mixture was added tert-butylmethyl ether (62ml) and then warm to 300C with stirring. The aqueous acidic layer was separated and the organic layer extracted with aqueous sulphuric acid solution (34.8m, 0.45M, 15.7mmol). <n="32"/>To the combined acidic layers was added n-butylacetate (104ml) and cooled to 00C. Potassium carbonate solution (72.2ml, 2.17M, 156.5mmol) was added dropwise then the biphasic mixture heated to 300C and the organic layer separated and washed with water (41.4ml). The organic layer was then concentrated by distillation to give (5-Cyano-2-nitro- phenyl)-(5-morpholin-4-ylmethyl-pyridin-2-yl)-acetic acid ethyl ester as an n-butylacetate solution (92ml) (titration, HCIO4, 79.3w/w%) The crude product mixture is directly used in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl acetamide; at 20℃; for 16h; | To a solution of 3-Fluoro-4-nitrobenzonitrile (1.0 g, 6.0 mmol) in DMA (5 inL) were added Beta-Alanine ethyl ester HCl (1.4 g, 9.03 mmol) and DIPEA (1.6 mL, 9.03 mmol). The reaction mixture was stirred at room temperature for 16 h (the recation was completed; the reaction mixture turned to orange from yellow in color). The reaction mixture was then diluted with ethyl acetate and washed with water (x4). The organic phase was then dried over Na2SO4 and concentrated to afford 1.53 g (96%) of the desired product as yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
XIX.1 3-(2-Fluoro-1 -fluoromethyl-ethoxy)-4-nitro-benzonithle1 ,3-Difluoro-propan-2-ol (4.2 g) was dissolved under argon in THF (250 ml) and cooled to 0C. LiHMDS (28 ml) was added to the mixture and stirred at rt for 1 hour. Then the mixture was cooled to 0C and <strong>[218632-01-0]3-fluoro-4-nitrobenzonitrile</strong> (1 .95 ml) was added in portions and stirred for 2 hours. The mixture was poured in water and extracted with DCM. The organic layer was washed with water, dried andconcentrated.Yield: 4.9 g | ||
1,3-Difluoro-propan-2-ol (4.2 g) was dissolved under argon in THF (250 ml) and cooled to 0 C. LiHMDS (28 ml) was added to the mixture and stirred at rt for 1 hour. Then the mixture was cooled to 0 C. and <strong>[218632-01-0]3-fluoro-4-nitrobenzonitrile</strong> (1.95 ml) was added in portions and stirred for 2 hours. The mixture was poured in water and extracted with DCM. The organic layer was washed with water, dried and concentrated. Yield: 4.9 g |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In water; acetone; at 20℃; | VII.1 3-Fluoro-4-nitrobenzamideTo a stirred solution of <strong>[218632-01-0]3-fluoro-4-nitrobenzonitrile</strong> (15.0 g) and K2CO3 (25.0 g) in 100 ml acetone/ water (80:20) was added urea hydrogen peroxide (17.0 g) adduct. The reaction was stirred at room temperature. To the reaction mixture was added dichloromethane (100 ml) and water (500 ml) and the organic layer was separated. The aqueous layer was extracted with dichloromethane and the combined organic layers were washed with brine, filtered through celite and passed through a phase separator. The residue was concentrated in vacuo to yield an orange solid. The crude product was recrystallised from EtOAc/hexane to give the product.Yield: 2.94 g |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With potassium carbonate; In dichloromethane; at 20℃; for 4h;Inert atmosphere; | To a stirred solution of <strong>[218632-01-0]3-fluoro-4-nitrobenzonitrile</strong> (1 g, 6.02 mmol) in CH2Cl2 (5 mL) under an inert atmosphere was added potassium carbonate (1.66 g, 12.05 mmol) and cyclopropanamine (3.33 mL, 48.19 mmol) drop wise at room temperature. The reaction mixture was stirred at room temperature for 4 h. After consumption of starting material (by TLC), the reaction mixture was diluted with water (30 mL) and extracted with EtOAc (2*40 mL). The combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford 3-(cyclopropylamino)-4-nitrobenzonitrile (900 mg, 4.43 mmol, 74%) as yellow solid. 1H NMR (400 MHz, CDCl3): delta 8.24 (d, J=8.7 Hz, 1H), 8.07 (br s, 1H), 7.64 (d, J=1.7 Hz, 1H), 6.93 (dd, J=8.7, 1.7 Hz, 1H), 2.62-2.57 (m, 1H), 1.03-0.97 (m, 2H), 0.72-0.67 (m, 2H). LC-MS: m/z 201.9 [M-H]+ at 3.25 RT (99.61% purity). |
With potassium carbonate; In dichloromethane; at 20℃; for 3h; | Step A. 3- cvclopropyIamino)-4-nitrobenzonitrile:To a stirred solution of <strong>[218632-01-0]3-fluoro-4-nitrobenzonitrile</strong> (2.0 g, 0.012 mol) in DCM (20 ml), was added 2CO3 (3.3 g, 0.024 mol) and cyclopropyl amine (6.7 ml, 0.096 mol) and the resulting solution was continued to stir at room temperature for 3 h. The reaction was diluted with cold water and extracted with dichloromethane (3 x 100 ml). The combined organic layers were washed with brine, dried over Na2SC>4 and concentrated under vacuum to afford the title compound 3-(cyclopropylamino)-4-nitrobenzonitrile as a yellow solid. 1H NMR (400 MHz, CDCI3), delta: 8.24-8.22 (d, J- 8.8 Hz, 1H), 8.07 (bs, 1H), 7.64 (s, IH), 6.94-6.92 (d, J= 8.8 Hz, IH), 2.59-2.58 (m, IH), 1.25-0.97 (m, 2H), 0.71-0.58 (m, 2H). MS (M+l): 204. | |
With potassium carbonate; In dichloromethane; at 20℃; for 4h;Inert atmosphere; | To a stirred solution of <strong>[218632-01-0]3-fluoro-4-nitrobenzonitrile</strong> (1 g, 6.02 mmol) in CH2C12 (5 mE) under an inert atmosphere was added potassium carbonate (1.66 g, 12.05 mmol) and cyclopropanamine (3.33 mE, 48.19 mmol) drop wise at room temperature. The reaction mixture was stirred at room temperature for 4 h. Afier consumption of starting material (by TEC), the reaction mixture was diluted with water (30 mE) and extracted with EtOAc (2x40 mE). The combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain 3-(cyclopro- pylamino)-4-nitrobenzonitrile (900 mg, crude) as yellow solid used in next step without further purification. ?H NMR (400 MHz, CDC13): oe 8.24 (d, J=8.7 Hz,1H), 8.07 (br s, 1H), 7.64 (d, J=1.7 Hz, 1H), 6.93 (dd, J=8.7,1.7 Hz, 1H), 2.62-2.57 (m, 1H), 1.03-0.97 (m, 2H), 0.72-0.67 (m, 2H). EC-MS: m/z 201.9 [M-H] at 3.25 RT (99.61% purity). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3-Fluoro-4-nitrobenzonitrile (3.50 mmol, 581 mg) in CH2Cl2 (12 mL) was added Et3N (3.85 mmol, 0.54 mL) at -15 C. The reaction solution was stirred at -15 C. for 30 min. To the reaction solution was added 3-methoxypropan-1-amine (3.50 mmole, 0.36 mL) and stirred at -15 C. for 30 min. The cooling bath was removed to let the reaction solution warm to rt and kept stirring at rt for 30 min. The reaction solution containing 3-(3-methoxypropylamino)-4-nitrobenzonitrile (41A) was concentrated in vacuo and carried directly on to the next step without further purification. ESI-MS: m/z 236.3 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | Step 1: 4-Nitro-3-phenylaminobenzonitrile A suspension of <strong>[218632-01-0]3-fluoro-4-nitrobenzonitrile</strong> (1.66 g, 10.0 mmol) in DMSO (5 mL) was purged with a stream of argon prior to addition of phenylamine (1.82 mL, 20.0 mmol) and then the mixture was stirred at 120 C. for 1 h under an argon atmosphere. After cooling to RT, the reaction mixture was partitioned between EtOAc (75 mL) and an aqueous solution of KHSO4 (100 mL). The organic layer was then washed with brine, dried (Na2SO4) and concentrated in vacuo. The resulting residue was triturated with diethyl ether affording 4-Nitro-3-phenylaminobenzonitrile as red crystals (2.35 g, 98%). 1H NMR (CDCl3, 400 MHz): delta 9.48 (1H, bs), 8.29 (1H, d, J=8.76 Hz), 7.53-7.40 (3H, m), 7.35 (1H, t, J=7.52 Hz), 7.29-7.22 (2H, m), 6.97 (1H, d, J=8.79 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 80℃; for 16h; | To a well-stirred solution 3- fluoro-4-nitrobenzonitrile (3.5 g, 21.084 mmol) in DMF were added 3-iodoaniline (6.9 g, 31.624 mmol) and DIPEA (54 ml, 42.168 mmol) and the reaction mixture was heated to 80 C for 16 h. The reaction mixture was quenched with water (150 ml), diluted with methanol (50 ml) and stirred for 30 min. The precipitate obtained was filtered to yield 5.8 g of the product; ¾ NMR (300 MHz, DMSO-ife) delta 7.20 (t, J = 7.8 Hz, 1H), 7.29-7.38 (m, 2H), 7.56 (d, J = 5.4 Hz, 2H), 7.70 (s, 1H), 8.22 (d, J = 9.0 Hz, 1H), 9.39 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70.7% | With potassium carbonate; In acetonitrile; at 20 - 40℃; | 3-({r(2R,3RJS)-7-Methyl-2,3-diphenyl-1 ,4-dioxaspiro[4.5]dec-7-yl]methyl)amino)-4- nitrobenzonitrile A solution of acetonitrile (2049 mL) in a 3 L flask was heated to 40C. Next, potassium carbonate (198 g, 1434 mmol), 1-[(2R,3R,7S)-7-methyl-2,3-diphenyl-1 ,4- dioxaspiro[4.5]dec-7- yl]methanamine (242 g, 717 mmol) and <strong>[218632-01-0]3-fluoro-4-nitrobenzonitrile</strong> (1 19 g, 717 mmol) were added slowly. The mixture was allowed to stir at 40C for 2 h, and then cooled to RT. Stirring was continued at RT overnight. The next day, the slurry was filtered and the solids were washed with acetonitrile (500 mL). The filtrate was concentrated to afford the crude product (while keeping the temperature ~60C during concentration). To the thick dark residue was added MeOH. The solution was heated to 60C on the rotovap and concentrated to a minimal volume. To the residue was added -500 mL of MeOH slowly with heating to avoid rapid crystallization, and the solution was heated to reflux. Once at reflux, an additional 250 mL of MeOH was slowly added. The resulting slurry was allowed to stir at reflux for about 60 min, then heating was stopped and the slurry was allowed to cool to RT and stirring was continued for 3 days. The slurry was cooled to ~10C with an ice/water bath. Stirring was continued for ~2 h, and then the slurry was filtered and washed with cold MeOH (100 mL). The solids were dried under reduced pressure to give the desired product as a bright orange solid (245 g, 70.7% yield). |
70.7% | With potassium carbonate; In acetonitrile; at 40℃; for 2h; | 3- r(2R.3RJS)-7-Methyl-2.3-diDhenyl-14-dioxasDiror4.5ldec-7-yllmethyl amino)-4- nitrobenzonitrileA solution of acetonitrile (2049 ml.) in a 3 L flask was heated to 40 C. Next, potassium carbonate (198 g, 1434 mmol), 1-[(2R,3R,7S)-7-methyl-2,3-diphenyl-1 ,4- dioxaspiro[4.5]dec-7- yl]methanamine (242 g, 717 mmol) and <strong>[218632-01-0]3-fluoro-4-nitrobenzonitrile</strong> (1 19 g, 717 mmol) were added slowly. The mixture was allowed to stir at 40 C for 2 h, and then cooled to RT. Stirring was continued at RT overnight. The next day, the slurry was filtered and the solids were washed with acetonitrile (500 ml_). The filtrate was concentrated to afford the crude product (while keeping the temperature -60 C during concentration). To the thick dark residue was added MeOH. The solution was heated to 60 C on the rotovap and concentrated to a minimal volume. To the residue was added -500 ml. of MeOH slowly with heating to avoid rapid crystallization, and the solution was heated to reflux. Once at reflux, an additional 250 ml. MeOH was slowly added. The resulting slurry was allowed to stir at reflux for about 60 min, then heating was stopped and the slurry was allowed to cool to RT and stirring was continued for 3 days. The slurry was cooled to -10 C with an ice/water bath. Stirring was continued for -2 h, and then the slurry was filtered and washed with cold MeOH (100 ml_). The solids were dried under reduced pressure to give the desired product as a bright orange solid (245 g, 70.7% yield). This material was used in the next step. |
70.7% | With potassium carbonate; In acetonitrile; at 40℃; for 2h; | [0080] A solution of acetonitrile (2049 mL) in a 3 L flask was heated to 40 C. Next, potassium carbonate (198 g, 1434mmol), 1-[(2R,3R,7S)-7-methyl-2,3-diphenyl-1,4- dioxaspiro[4.5]dec-7-yl]methanamine (242 g, 717 mmol) and <strong>[218632-01-0]3-fluoro-4-nitrobenzonitrile</strong> (119 g, 717 mmol) were added slowly. The mixture was allowed to stir at 40 C for 2 h, and thencooled to RT. Stirring was continued at RT overnight. The next day, the slurry was filtered and the solids were washedwith acetonitrile (500 mL). The filtrate was concentrated to afford the crude product (while keeping the temperature ?60C during concentration). To the thick dark residue was added MeOH. The solution was heated to 60 C on the rotovapand concentrated to a minimal volume. To the residue was added -500 mL of MeOH slowly with heating to avoid rapidcrystallization, and the solution was heated to reflux. Once at reflux, an additional 250 mL MeOH was slowly added. Theresulting slurry was allowed to stir at reflux for about 60 min, then heating was stopped and the slurry was allowed tocool to RT and stirring was continued for 3 days. The slurry was cooled to ?10 C with an ice/water bath. Stirring wascontinued for -2 h, and then the slurry was filtered and washed with cold MeOH (100 mL). The solids were dried underreduced pressure to give the desired product as a bright orange solid (245 g, 70.7% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With potassium carbonate; In acetonitrile; at 20℃; for 15h; | 3-((7-((benzyloxy)methyl)-3-(4-methoxybenzyl)-2-oxo-1-oxa-3-azaspiro[4.5]decan-7- yl)methyl)amino)-4-nitrobenzonitrile To a light yellow solution of 7-(aminomethyl)-7-((benzyloxy)methyl)-3-(4-methoxybenzyl)- 1-oxa-3-azaspiro[4.5]decan-2-one (4.27 g, 10.1 mmol) in MeCN (67.1 mL) was added potassium carbonate (2.78 g, 20.1 mmol) and <strong>[218632-01-0]3-fluoro-4-nitrobenzonitrile</strong> (2.51 g, 15.1 mmol). the reaction was stirred at rt. After stirring 15 h, the reaction was filtered through a frit. The collected inorganics were washed with DCM/EtOAc. The filtrate was concentrated onto florisil and purified on a 80 g silica gel column (20 - 55 % EtOAc/hexanes, 30 min gradient; 55 % EtOAc/hexanes, 5 min.; 60 mL/min elution; 254 nm detection) to provide the title compound (5.02 g, 83 % yield) as a reddish-orange oil. MS (m/z) 571.0 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With potassium carbonate; In dichloromethane; acetonitrile; at 20℃; for 120h; | 3-({r(2R,3R,7S)-2,3-Diphenyl-1 ,4-dioxaspiro[4.5]dec-7-yl]methyl)amino)-4-nitrobenzonitrileA mixture of <strong>[218632-01-0]3-fluoro-4-nitrobenzonitrile</strong> (55.5 g, 334 mmol), 1-[(2R,3R,7S)-2,3-diphenyl- 1 ,4dioxaspiro[4.5]dec-7-yl]methanamine (103 g, 318 mmol) and potassium carbonate (88 g, 637 mmol) in acetonitrile (2654 ml.) was stirred at RT for 5 days (-200 ml. DCM was added to help with solubility). The resulting solution was filtered and the solids washed with MeCN. The resulting solution was concentrated to give the crude product that was dissolved in MeOH (500 ml.) and allowed to crystallize with stirring. The slurry was allowed to stir at RT overnight, filtered and the solids dried under reduced pressure to give 3-([(2R,3R,7S)-2,3-diphenyl-1 ,4- dioxaspiro[4.5]dec-7-yl]methyl}amino)-4-nitrobenzonitrile (131.41 g, 88% yield). The product was used without further purification. |
88% | With potassium carbonate; In dichloromethane; acetonitrile; at 20℃; for 120h; | 3-({r(2R,3R,7S)-2,3-Diphenyl-1 ,4-dioxaspiror4.5ldec-7-yllmethyl)amino)-4-nitrobenzonitrile A mixture of <strong>[218632-01-0]3-fluoro-4-nitrobenzonitrile</strong> (55.5 g, 334 mmol), 1-[(2R,3R,7S)-2,3-diphenyl- 1 ,4dioxaspiro[4.5]dec-7-yl]methanamine (103 g, 318 mmol) and potassium carbonate (88 g, 637 mmol) in acetonitrile (2654 ml.) was stirred at RT for 5 days (-200 ml. DCM was added to help with solubility). The resulting solution was filtered and the solids washed with MeCN. The resulting solution was concentrated to give the crude product that was dissolved in MeOH (500 ml.) and allowed to crystallize with stirring. The slurry was allowed to stir at RT overnight, filtered and the solids dried under reduced pressure to give 3-([(2R,3R,7S)-2,3-diphenyl-1 ,4- dioxaspiro[4.5]dec-7-yl]methyl}amino)-4-nitrobenzonitrile (131.41 g, 88% yield). The product was used without further purification. |
88% | With potassium carbonate; In acetonitrile; at 20℃; for 120h; | [0088] A mixture of <strong>[218632-01-0]3-fluoro-4-nitrobenzonitrile</strong> (55.5 g, 334 mmol), 1-[(2R,3R,7S)-2,3-diphenyl-1,4dioxaspiro[4.5]dec-7-yl]methanamine (103 g, 318 mmol) and potassium carbonate (88 g, 637 mmol) in acetonitrile (2654 mL) was stirredat RT for 5 days (?200 mL DCM was added to help with solubility). The resulting solution was filtered and the solidswashed with MeCN. The resulting solution was concentrated to give the crude product that was dissolved in MeOH (500mL) and allowed to crystallize with stirring. The slurry was allowed to stir at RT overnight, filtered and the solids driedunder reduced pressure to give 3-([(2R,3R,7S)-2,3-diphenyl-1,4-dioxaspiro[4.5]dec-7-yl]methyl}amino)-4-nitrobenzonitrile(131.41 g, 88% yield). The product was used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In acetonitrile; at 20℃; for 15h; | 3-{r(3-{r4-(Methyloxy)phenyllmethyl)-2-oxo-7-{r(phenylmethyl)oxylmethyl)-1-oxa-3- azaspiror4.51dec-7-yl)methyllamino)-4-nitrobenzonitrileTo a light yellow solution of 7-(aminomethyl)-7-((benzyloxy)methyl)-3-(4-methoxybenzyl)- 1-oxa-3-azaspiro[4.5]decan-2-one (4.27 g, 10.1 mmol) in acetonitrile (67.1 mL) was added potassium carbonate (2.78 g, 20.1 mmol) and <strong>[218632-01-0]3-fluoro-4-nitrobenzonitrile</strong> (2.51 g, 15.1 mmol) and the reaction was stirred at RT. After stirring 15 h, the reaction was filtered through a frit. The collected inorganics were washed with DCM/EtOAc. The filtrate was concentrated onto florisil and purified on a 80 g silica gel column (20-55% EtOAc/hexanes, 30 min gradient; 55% EtOAc/hexanes, 5 min.; 60 mL/min elution; 254 nm detection) to provide 3-[(3-[4- (methyloxy)phenyl]methyl}-2-oxo-7-[(phenylmethyl)oxy]methyl}-1-oxa-3-azaspiro[4.5]dec-7- yl)methyl]amino}-4-nitrobenzonitrile (5.02 g, 83% yield) as a reddish-orange oil. MS (m/z) 571.0 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.4% | With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; for 3h;Inert atmosphere; | Step 1: To a solution of (S)-3-amino-2-tert-butoxycarbonylamino-propionic acid (Aldrich) (3 g, 14.706 mmol) in DMF (60 mL) was added cesium carbonate (14.34 g, 44.118 mmol) and <strong>[218632-01-0]3-fluoro-4-nitro-benzonitrile</strong> (2.685 mL, 16.176 mmol) at RT and the resulting mixture was stirred for 3 h at RT under nitrogen atmosphere. The reaction mixture was diluted with ethyl acetate, washed with ice cold water, brine, dried and concentrated to give a materialwhich was purified by silica gel chromatography to provide (S)-2-tert-butoxycarbonyl amino-3- (5-cyano-2-nitro-phenylamino)-propionic acid (4.4g, 85.4%) as an orange yellow solid. LC-MS:350.8 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With potassium carbonate; In tetrahydrofuran; for 16h; | 3-[2-(Difluoromethoxy)benzylamino]-4-nitrobenzonitrile 3-Fluoro-4-nitrobenzonitrile (19.19 g, 116 mmol) was added to a mixture of [2-(difluoromethoxy)phenyl]methanamine (20 g, 116 mmol) and K2CO3 (19.16 g, 139 mmol) in THF (200 mL). After 16 h the reaction mixture was diluted with DCM to a total volume of 1 L and then filtered over Kieselguhr. The filtrate was concentrated in vacuo and stripped with isopropyl ether to yield the title compound (36.8 g, 115 mmol, 100%). MS [ESI+] m/z: 320 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With potassium carbonate; In tetrahydrofuran; for 16h; | 3-(2,5-Dichlorobenzylamino)-4-nitrobenzonitrile K2CO3 (9.42 g, 68.2 mmol) was added to a mixture of (2,5-dichlorophenyl)-methanamine (10.00 g, 56.8 mmol) and <strong>[218632-01-0]3-fluoro-4-nitrobenzonitrile</strong> (9.44 g, 56.8 mmol) in THF (200 mL). After 16 h Et2O and water were added. The organic phase was separated and the aqueous phase was extracted twice with Et2O. The combined organic layers were dried over Na2SO4, after which the solvent was removed in vacuo. The aqueous layer was extracted twice with EtOAc and the combined organic extracts were dried over Na2SO4, after which the solvent was added to the residue of the first evaporation. The solvent was then removed in vacuo, yielding the title compound (17.94 g, 52.3 mmol, 92%). deltaH (DMSO-d6, 300 MHz) 4.72 (d, 2H, J 6.6 Hz); 7.09 (dd, 1H, J 1.8, 8.7 Hz); 7.41 (m, 3H); 7.54 (dd, 1H, J 4.2, 5.1 Hz); 8.24 (d, 1H, J 8.7 Hz); 8.64 (t, 1H, J 6.3 Hz). MS [ESI+] m/z: 323 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With potassium carbonate; In tetrahydrofuran; for 17h; | (R)-4-Nitro-3-(1-phenylethylamino)benzonitrile 3-Fluoro-4-nitrobenzonitrile (15.00 g, 90 mmol) was added to a solution of (R)-1-phenylethanamine (10.94 g, 90 mmol) in THF (300 mL). K2CO3 (14.98 g, 108 mmol) was added. After 16 h, (R)-1-phenylethanamine (2.189 g, 18.06 mmol) was added. After 1 h, EtOAc and water were added. The organic phase was separated and the aqueous phase was extracted twice with EtOAc. The combined organic layers were dried over Na2SO4, after which the solvent was removed in vacuo. The residue was triturated with Et2O. The precipitate was filtered off, affording the title compound (14.86 g, 55.6 mmol, 62%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With potassium carbonate; In tetrahydrofuran; for 18h; | (S)-4-Nitro-3-(1-phenylethylamino)benzonitrile 3-Fluoro-4-nitrobenzonitrile (15 g, 90 mmol) was added to a solution of (S)-1-phenylethanamine (11.49 ml, 90 mmol) in THF (150 mL). K2CO3 (18.72 g, 135 mmol) was added. After 2 h, (S)-1-phenylethanamine (3 ml, 23.57 mmol) was added. After 16 h the reaction mixture was diluted with DCM to a total volume of 1 L under stirring. After 15 minutes the precipitated salts were removed by filtration over Kieselguhr. The filtrate was concentrated in vacuo to afford the title compound (24.14 g, 90 mmol, 100%). |
Tags: 218632-01-0 synthesis path| 218632-01-0 SDS| 218632-01-0 COA| 218632-01-0 purity| 218632-01-0 application| 218632-01-0 NMR| 218632-01-0 COA| 218632-01-0 structure
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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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