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CAS No. : | 204005-46-9 | MDL No. : | MFCD09763655 |
Formula : | C15H14N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WUWDLXZGHZSWQZ-WQLSENKSSA-N |
M.W : | 238.28 | Pubchem ID : | 5329098 |
Synonyms : |
SU5416;NSC 696819;VEGFR 2 Kinase Inhibitor;Sugen 5416;Semaxanib
|
Num. heavy atoms : | 18 |
Num. arom. heavy atoms : | 11 |
Fraction Csp3 : | 0.13 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 76.42 |
TPSA : | 44.89 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -5.99 cm/s |
Log Po/w (iLOGP) : | 2.37 |
Log Po/w (XLOGP3) : | 2.49 |
Log Po/w (WLOGP) : | 2.44 |
Log Po/w (MLOGP) : | 1.95 |
Log Po/w (SILICOS-IT) : | 3.96 |
Consensus Log Po/w : | 2.64 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.27 |
Solubility : | 0.127 mg/ml ; 0.000534 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.08 |
Solubility : | 0.199 mg/ml ; 0.000836 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -5.43 |
Solubility : | 0.000889 mg/ml ; 0.00000373 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.56 |
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: |
* 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 |
---|---|---|
10.4 g | With piperidine In methanol at 65℃; | To a solution of 2-formyl-3,5-dimethylpyrrole (compound 27, 7.17 g) and indolin-2-one (5.0 g) in methanol (100 mL) was added piperidine (1.0 mL). The mixture was stirred at 65 °C overnight. After cooling down to room temperature, the resulting solid gave desired compound 29 (10.4 g) as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With sodium hydride In DMF (N,N-dimethyl-formamide) at 0 - 20℃; | 52 To a suspension of NaH (60% oil dispersion, 151 mg, 3.8 mmoles) in dry DMF (20 mL) was added under argon at 0°C a solution of 3- (3, 5-dimethyl-lH-pyrrol-2-ylmethylene)- 1, 3-dihydro-indol-2-one (741 mg, 3.1 mmoles) in DMF (28 mL) followed by iodomethane (0.24 mL, 3.8 mmoles). The reaction was stirred and allowed to come to room temperature. The reaction evolution was followed by LC/MS. H2O (25 mL) was added and the mixture was stirred until a thick orange precipitate formed. The solid was filtered. Cristallization from MeOH and H2O afforded the pure title compound as a yellow solid (504 mg, 63% yield). 13C-NMR (DMSO-d6, Z isomer) 8 167.4, 139.2, 135.9, 131.9, 126.5, 125.6, 124.7, 123.3, 121.3, 117.7, 112.5, 111.4, 108.1, 25.9, 13.4, 11.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19% | With caesium carbonate; In acetonitrile; at 40℃; | To a suspension of 3- (3, 5-dimethyl-IH-pyrrol-2-ylmethylene)-1, 3-dihydro-indol-2-one (2. 02 g, 8.5 mmoles) and Cs2C03 (11.05 g, 34 mmoles) in CH3CN (200 mL) was added acetic acid chloromethyl ester (3.3 mL, 34 mmoles). The reaction mixture was heated at 40C and left under stirring overnight. The reaction evolution was followed by LC/MS. The mixture was then concentrated in vacuo together with silica gel. The residue was purified by chromatography using a gradient of petroleum ether/ethyl acetate from 85: 15 to 50: 50, furnishing the title compound (488 mg, 19% yield) as a deep orange solid. 1H-NMR (DMSO-d6, Z isomer) 8 13.01 (s, lH), 7.81 (d, lH), 7.65 (s, lH), 7.26-7. 05 (m, 3H), 6.07 (d, lH), 5.89 (s, 2H), 2.35 (s, 3H), 2.33 (s, 3H), 2.04 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With sodium hydride In DMF (N,N-dimethyl-formamide) at 0 - 20℃; | 51 To a suspension of NaH (60% oil dispersion, 209 mg, 5.25 mmoles) in dry DMF (30 mL) was added under argon at 0°C a solution of 3- (3, 5-dimethyl-lH-pyrrol-2-ylmethylene)- 1, 3-dihydro-indol-2-one (1.2 g, 5 mmoles) in DMF (46 mL) followed by 1-chloromethyl- 4-methoxy-benzene (2.1 mL, 15 mmoles). The reaction was left under stirring and allowed to come to room temperature. The reaction evolution was followed by TLC. After completion of the reaction a saturated aqueous solution of NaHC03 (25 mL) was added followed by H20 (25 mL). The aqueous phase was extracted with EtOAc (3x50 mL). The combined organic phases were washed once with a saturated aqueous solution of NaHC03 (50 mL) and dried over MgS04. After filtration and removal of the solvent, a brown solid was obtained. cristallization from EtOH and H20 afforded the pure title compound as a yellow solid (1. 08 g, 60% yield). 3C-NMR (DMSO-d6, Z isomer) 8 167.4, 158.4, 138.2, 136.3, 132.4, 128.8, 128.6, 126.6, 125.5, 124.8, 123.7, 121.4, 117.9, 113.9, 112.7, 111.1, 108.7, 54.9, 42.1, 13.5, 11.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | With sulfuryl dichloride In dichloromethane at 0 - 20℃; for 1.41667h; | 25 To a suspension of 3- (3, 5-dimethyl-lH-pyrrol-2-ylmethylene)-1, 3-dihydro-indol-2-one (2 g, 8.4 mmoles) in dry CH2CI2 (30 mL) was added under argon at 0°C sulfonyl chloride (0.84 mL, 8.4 mmoles). The dark mixture was stirred for 70 minutes at 0°C and then allowed to come to room temperature for 15 minutes. After removal of the solvent and purification by flash chromatography, 770 mg of the title compound were obtained as an orange solid (34% yield). 1H NMR (DMSO-d6) 8 13.72 (s, lH), 10.90 (s, lH), 7.77 (d, lH), 7.61 (s, lH), 7.13 (t, lH), 7. 00 (t, lH), 6.88 (d, lH), 2.32 (s, 3H), 2.28 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10.4 g | With piperidine In methanol at 65℃; | 4.5.14. Preparation of compound 28 To a solution of 2-formyl-3,5-dimethylpyrrole (compound 27, 7.17 g) and indolin-2-one (5.0 g) in methanol (100 mL) was added piperidine (1.0 mL). The mixture was stirred at 65 °C overnight. After cooling down to room temperature, the resulting solid gave desired compound 29 (10.4 g) as a yellow solid. |
92.5 % | With piperidine In ethanol at 90℃; Inert atmosphere; | 1 The preparation of embodiment 1, intermediate 2 Weigh 2-indolinone (0.60g, 4.51mmol) and 3,5-dimethyl-1H-pyrrole-2-carbaldehyde (0.67g, 5.41mmol) into eggplant-shaped bottle (100mL), add 10mL of ethanol are used as solvent, and 3-5 drops of anhydrous piperidine are added dropwise with stirring at room temperature.After dropping, under nitrogen protection, the reaction system was transferred to a 90° C. oil bath for reflux reaction for 3 h.After the reaction solution was naturally cooled to room temperature, a large amount of yellow flocculent solids were precipitated.After suction filtration, the filter cake was washed twice with a small amount of cold absolute ethanol at 0°C, dried, and weighed to obtain 0.99 g of an orange-yellow flocculent solid, with a yield of 92.5%. |
92.5 % | With piperidine In ethanol at 90℃; Inert atmosphere; | 1 The preparation of embodiment 1, intermediate 2 Weigh 2-indolinone (0.60g, 4.51mmol) and 3,5-dimethyl-1H-pyrrole-2-carbaldehyde (0.67g, 5.41mmol) into eggplant-shaped bottle (100mL), add 10mL of ethanol are used as solvent, and 3-5 drops of anhydrous piperidine are added dropwise with stirring at room temperature.After dropping, under nitrogen protection, the reaction system was transferred to a 90° C. oil bath for reflux reaction for 3 h.After the reaction solution was naturally cooled to room temperature, a large amount of yellow flocculent solids were precipitated.After suction filtration, the filter cake was washed twice with a small amount of cold absolute ethanol at 0°C, dried, and weighed to obtain 0.99 g of an orange-yellow flocculent solid, with a yield of 92.5%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.1 g | With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane at 20℃; | 4.5.15. Preparation of compound 29 Compound 28 (1.0 g), NBS (0.785 g) and benzoyl peroxide (25 mg) were mixed with CCl4 (100 mL). The mixture was stirred at room temperature overnight. The resulting solid afforded a crude product. The crude product was recrystallized by methanol to give the product (1.1 g) as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 1 h / 105 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 1 h / 105 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 1 h / 105 °C 3: 10% palladium on activated charcoal; hydrogen / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 1 h / 105 °C 3: 10% palladium on activated charcoal; hydrogen / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 1 h / 105 °C 3: 10% palladium on activated charcoal; hydrogen / tetrahydrofuran / 20 °C 4: triethylamine / isopropyl alcohol / 24 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 1 h / 105 °C 3: 10% palladium on activated charcoal; hydrogen / tetrahydrofuran / 20 °C 4: triethylamine / isopropyl alcohol / 24 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71.2 % | Stage #1: semaxanib With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: m-fluorobenzyl chloride In N,N-dimethyl-formamide at 80℃; | 5 Embodiment 5, the preparation of target compound I-1 to I-13 General procedure: Weigh intermediate 2 (1equiv) and K2CO3powder (2.5equiv) into eggplant-shaped bottle (100mL), use DMF (10mL) as solvent, stir at room temperature for 30min, then slowly drop substituted benzyl chloride (1.2 equiv) or substituted benzyl bromide (1.2equiv) into the reaction solution, and then the reaction system was transferred to an oil bath at 80°C for 3-5h.Cool to room temperature, pour 100mL of cold water (15°C-20°C) into the reaction solution, extract with ethyl acetate (10mL×3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, suction filter, and reduce pressure The solvent was evaporated, and the obtained product was purified by thin layer chromatography (developing system: petroleum ether: ethyl acetate volume ratio 2:1), or recrystallized with methanol to obtain the target compounds I-1 to I-13. |
71.2 % | Stage #1: semaxanib With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: m-fluorobenzyl chloride In N,N-dimethyl-formamide at 80℃; | 5 Embodiment 5, the preparation of target compound I-1 to I-13 General procedure: Weigh intermediate 2 (1equiv) and K2CO3powder (2.5equiv) into eggplant-shaped bottle (100mL), use DMF (10mL) as solvent, stir at room temperature for 30min, then slowly drop substituted benzyl chloride (1.2 equiv) or substituted benzyl bromide (1.2equiv) into the reaction solution, and then the reaction system was transferred to an oil bath at 80°C for 3-5h.Cool to room temperature, pour 100mL of cold water (15°C-20°C) into the reaction solution, extract with ethyl acetate (10mL×3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, suction filter, and reduce pressure The solvent was evaporated, and the obtained product was purified by thin layer chromatography (developing system: petroleum ether: ethyl acetate volume ratio 2:1), or recrystallized with methanol to obtain the target compounds I-1 to I-13. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70.2 % | Stage #1: semaxanib With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 1-chloromethyl-4-fluorobenzene In N,N-dimethyl-formamide at 80℃; | 5 Embodiment 5, the preparation of target compound I-1 to I-13 General procedure: Weigh intermediate 2 (1equiv) and K2CO3powder (2.5equiv) into eggplant-shaped bottle (100mL), use DMF (10mL) as solvent, stir at room temperature for 30min, then slowly drop substituted benzyl chloride (1.2 equiv) or substituted benzyl bromide (1.2equiv) into the reaction solution, and then the reaction system was transferred to an oil bath at 80°C for 3-5h.Cool to room temperature, pour 100mL of cold water (15°C-20°C) into the reaction solution, extract with ethyl acetate (10mL×3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, suction filter, and reduce pressure The solvent was evaporated, and the obtained product was purified by thin layer chromatography (developing system: petroleum ether: ethyl acetate volume ratio 2:1), or recrystallized with methanol to obtain the target compounds I-1 to I-13. |
70.2 % | Stage #1: semaxanib With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 1-chloromethyl-4-fluorobenzene In N,N-dimethyl-formamide at 80℃; | 5 Embodiment 5, the preparation of target compound I-1 to I-13 General procedure: Weigh intermediate 2 (1equiv) and K2CO3powder (2.5equiv) into eggplant-shaped bottle (100mL), use DMF (10mL) as solvent, stir at room temperature for 30min, then slowly drop substituted benzyl chloride (1.2 equiv) or substituted benzyl bromide (1.2equiv) into the reaction solution, and then the reaction system was transferred to an oil bath at 80°C for 3-5h.Cool to room temperature, pour 100mL of cold water (15°C-20°C) into the reaction solution, extract with ethyl acetate (10mL×3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, suction filter, and reduce pressure The solvent was evaporated, and the obtained product was purified by thin layer chromatography (developing system: petroleum ether: ethyl acetate volume ratio 2:1), or recrystallized with methanol to obtain the target compounds I-1 to I-13. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64.4 % | Stage #1: semaxanib With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 1-Chloro-3-chloromethyl-benzene In N,N-dimethyl-formamide at 80℃; | 5 Embodiment 5, the preparation of target compound I-1 to I-13 General procedure: Weigh intermediate 2 (1equiv) and K2CO3powder (2.5equiv) into eggplant-shaped bottle (100mL), use DMF (10mL) as solvent, stir at room temperature for 30min, then slowly drop substituted benzyl chloride (1.2 equiv) or substituted benzyl bromide (1.2equiv) into the reaction solution, and then the reaction system was transferred to an oil bath at 80°C for 3-5h.Cool to room temperature, pour 100mL of cold water (15°C-20°C) into the reaction solution, extract with ethyl acetate (10mL×3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, suction filter, and reduce pressure The solvent was evaporated, and the obtained product was purified by thin layer chromatography (developing system: petroleum ether: ethyl acetate volume ratio 2:1), or recrystallized with methanol to obtain the target compounds I-1 to I-13. |
64.4 % | Stage #1: semaxanib With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 1-Chloro-3-chloromethyl-benzene In N,N-dimethyl-formamide at 80℃; | 5 Embodiment 5, the preparation of target compound I-1 to I-13 General procedure: Weigh intermediate 2 (1equiv) and K2CO3powder (2.5equiv) into eggplant-shaped bottle (100mL), use DMF (10mL) as solvent, stir at room temperature for 30min, then slowly drop substituted benzyl chloride (1.2 equiv) or substituted benzyl bromide (1.2equiv) into the reaction solution, and then the reaction system was transferred to an oil bath at 80°C for 3-5h.Cool to room temperature, pour 100mL of cold water (15°C-20°C) into the reaction solution, extract with ethyl acetate (10mL×3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, suction filter, and reduce pressure The solvent was evaporated, and the obtained product was purified by thin layer chromatography (developing system: petroleum ether: ethyl acetate volume ratio 2:1), or recrystallized with methanol to obtain the target compounds I-1 to I-13. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68.3 % | Stage #1: semaxanib With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 1-Chloro-4-(chloromethyl)benzene In N,N-dimethyl-formamide at 80℃; | 5 Embodiment 5, the preparation of target compound I-1 to I-13 General procedure: Weigh intermediate 2 (1equiv) and K2CO3powder (2.5equiv) into eggplant-shaped bottle (100mL), use DMF (10mL) as solvent, stir at room temperature for 30min, then slowly drop substituted benzyl chloride (1.2 equiv) or substituted benzyl bromide (1.2equiv) into the reaction solution, and then the reaction system was transferred to an oil bath at 80°C for 3-5h.Cool to room temperature, pour 100mL of cold water (15°C-20°C) into the reaction solution, extract with ethyl acetate (10mL×3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, suction filter, and reduce pressure The solvent was evaporated, and the obtained product was purified by thin layer chromatography (developing system: petroleum ether: ethyl acetate volume ratio 2:1), or recrystallized with methanol to obtain the target compounds I-1 to I-13. |
68.3 % | Stage #1: semaxanib With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 1-Chloro-4-(chloromethyl)benzene In N,N-dimethyl-formamide at 80℃; | 5 Embodiment 5, the preparation of target compound I-1 to I-13 General procedure: Weigh intermediate 2 (1equiv) and K2CO3powder (2.5equiv) into eggplant-shaped bottle (100mL), use DMF (10mL) as solvent, stir at room temperature for 30min, then slowly drop substituted benzyl chloride (1.2 equiv) or substituted benzyl bromide (1.2equiv) into the reaction solution, and then the reaction system was transferred to an oil bath at 80°C for 3-5h.Cool to room temperature, pour 100mL of cold water (15°C-20°C) into the reaction solution, extract with ethyl acetate (10mL×3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, suction filter, and reduce pressure The solvent was evaporated, and the obtained product was purified by thin layer chromatography (developing system: petroleum ether: ethyl acetate volume ratio 2:1), or recrystallized with methanol to obtain the target compounds I-1 to I-13. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73.7 % | Stage #1: semaxanib With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 3-bromobenzyl chloride In N,N-dimethyl-formamide at 80℃; | 5 Embodiment 5, the preparation of target compound I-1 to I-13 General procedure: Weigh intermediate 2 (1equiv) and K2CO3powder (2.5equiv) into eggplant-shaped bottle (100mL), use DMF (10mL) as solvent, stir at room temperature for 30min, then slowly drop substituted benzyl chloride (1.2 equiv) or substituted benzyl bromide (1.2equiv) into the reaction solution, and then the reaction system was transferred to an oil bath at 80°C for 3-5h.Cool to room temperature, pour 100mL of cold water (15°C-20°C) into the reaction solution, extract with ethyl acetate (10mL×3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, suction filter, and reduce pressure The solvent was evaporated, and the obtained product was purified by thin layer chromatography (developing system: petroleum ether: ethyl acetate volume ratio 2:1), or recrystallized with methanol to obtain the target compounds I-1 to I-13. |
73.7 % | Stage #1: semaxanib With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 3-bromobenzyl chloride In N,N-dimethyl-formamide at 80℃; | 5 Embodiment 5, the preparation of target compound I-1 to I-13 General procedure: Weigh intermediate 2 (1equiv) and K2CO3powder (2.5equiv) into eggplant-shaped bottle (100mL), use DMF (10mL) as solvent, stir at room temperature for 30min, then slowly drop substituted benzyl chloride (1.2 equiv) or substituted benzyl bromide (1.2equiv) into the reaction solution, and then the reaction system was transferred to an oil bath at 80°C for 3-5h.Cool to room temperature, pour 100mL of cold water (15°C-20°C) into the reaction solution, extract with ethyl acetate (10mL×3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, suction filter, and reduce pressure The solvent was evaporated, and the obtained product was purified by thin layer chromatography (developing system: petroleum ether: ethyl acetate volume ratio 2:1), or recrystallized with methanol to obtain the target compounds I-1 to I-13. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69.1 % | Stage #1: semaxanib With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: p-bromobenzyl chloride In N,N-dimethyl-formamide at 80℃; | 5 Embodiment 5, the preparation of target compound I-1 to I-13 General procedure: Weigh intermediate 2 (1equiv) and K2CO3powder (2.5equiv) into eggplant-shaped bottle (100mL), use DMF (10mL) as solvent, stir at room temperature for 30min, then slowly drop substituted benzyl chloride (1.2 equiv) or substituted benzyl bromide (1.2equiv) into the reaction solution, and then the reaction system was transferred to an oil bath at 80°C for 3-5h.Cool to room temperature, pour 100mL of cold water (15°C-20°C) into the reaction solution, extract with ethyl acetate (10mL×3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, suction filter, and reduce pressure The solvent was evaporated, and the obtained product was purified by thin layer chromatography (developing system: petroleum ether: ethyl acetate volume ratio 2:1), or recrystallized with methanol to obtain the target compounds I-1 to I-13. |
69.1 % | Stage #1: semaxanib With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: p-bromobenzyl chloride In N,N-dimethyl-formamide at 80℃; | 5 Embodiment 5, the preparation of target compound I-1 to I-13 General procedure: Weigh intermediate 2 (1equiv) and K2CO3powder (2.5equiv) into eggplant-shaped bottle (100mL), use DMF (10mL) as solvent, stir at room temperature for 30min, then slowly drop substituted benzyl chloride (1.2 equiv) or substituted benzyl bromide (1.2equiv) into the reaction solution, and then the reaction system was transferred to an oil bath at 80°C for 3-5h.Cool to room temperature, pour 100mL of cold water (15°C-20°C) into the reaction solution, extract with ethyl acetate (10mL×3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, suction filter, and reduce pressure The solvent was evaporated, and the obtained product was purified by thin layer chromatography (developing system: petroleum ether: ethyl acetate volume ratio 2:1), or recrystallized with methanol to obtain the target compounds I-1 to I-13. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82.3 % | Stage #1: semaxanib With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 3-(chloromethyl)benzonitrile In N,N-dimethyl-formamide at 80℃; | 5 Embodiment 5, the preparation of target compound I-1 to I-13 General procedure: Weigh intermediate 2 (1equiv) and K2CO3powder (2.5equiv) into eggplant-shaped bottle (100mL), use DMF (10mL) as solvent, stir at room temperature for 30min, then slowly drop substituted benzyl chloride (1.2 equiv) or substituted benzyl bromide (1.2equiv) into the reaction solution, and then the reaction system was transferred to an oil bath at 80°C for 3-5h.Cool to room temperature, pour 100mL of cold water (15°C-20°C) into the reaction solution, extract with ethyl acetate (10mL×3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, suction filter, and reduce pressure The solvent was evaporated, and the obtained product was purified by thin layer chromatography (developing system: petroleum ether: ethyl acetate volume ratio 2:1), or recrystallized with methanol to obtain the target compounds I-1 to I-13. |
82.3 % | Stage #1: semaxanib With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 3-(chloromethyl)benzonitrile In N,N-dimethyl-formamide at 80℃; | 5 Embodiment 5, the preparation of target compound I-1 to I-13 General procedure: Weigh intermediate 2 (1equiv) and K2CO3powder (2.5equiv) into eggplant-shaped bottle (100mL), use DMF (10mL) as solvent, stir at room temperature for 30min, then slowly drop substituted benzyl chloride (1.2 equiv) or substituted benzyl bromide (1.2equiv) into the reaction solution, and then the reaction system was transferred to an oil bath at 80°C for 3-5h.Cool to room temperature, pour 100mL of cold water (15°C-20°C) into the reaction solution, extract with ethyl acetate (10mL×3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, suction filter, and reduce pressure The solvent was evaporated, and the obtained product was purified by thin layer chromatography (developing system: petroleum ether: ethyl acetate volume ratio 2:1), or recrystallized with methanol to obtain the target compounds I-1 to I-13. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79.6 % | Stage #1: semaxanib With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 4-cyanobenzyl chloride In N,N-dimethyl-formamide at 80℃; | 5 Embodiment 5, the preparation of target compound I-1 to I-13 General procedure: Weigh intermediate 2 (1equiv) and K2CO3powder (2.5equiv) into eggplant-shaped bottle (100mL), use DMF (10mL) as solvent, stir at room temperature for 30min, then slowly drop substituted benzyl chloride (1.2 equiv) or substituted benzyl bromide (1.2equiv) into the reaction solution, and then the reaction system was transferred to an oil bath at 80°C for 3-5h.Cool to room temperature, pour 100mL of cold water (15°C-20°C) into the reaction solution, extract with ethyl acetate (10mL×3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, suction filter, and reduce pressure The solvent was evaporated, and the obtained product was purified by thin layer chromatography (developing system: petroleum ether: ethyl acetate volume ratio 2:1), or recrystallized with methanol to obtain the target compounds I-1 to I-13. |
79.6 % | Stage #1: semaxanib With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 4-cyanobenzyl chloride In N,N-dimethyl-formamide at 80℃; | 5 Embodiment 5, the preparation of target compound I-1 to I-13 General procedure: Weigh intermediate 2 (1equiv) and K2CO3powder (2.5equiv) into eggplant-shaped bottle (100mL), use DMF (10mL) as solvent, stir at room temperature for 30min, then slowly drop substituted benzyl chloride (1.2 equiv) or substituted benzyl bromide (1.2equiv) into the reaction solution, and then the reaction system was transferred to an oil bath at 80°C for 3-5h.Cool to room temperature, pour 100mL of cold water (15°C-20°C) into the reaction solution, extract with ethyl acetate (10mL×3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, suction filter, and reduce pressure The solvent was evaporated, and the obtained product was purified by thin layer chromatography (developing system: petroleum ether: ethyl acetate volume ratio 2:1), or recrystallized with methanol to obtain the target compounds I-1 to I-13. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80.5 % | Stage #1: semaxanib With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 3-Trifluoromethylbenzyl chloride In N,N-dimethyl-formamide at 80℃; | 5 Embodiment 5, the preparation of target compound I-1 to I-13 General procedure: Weigh intermediate 2 (1equiv) and K2CO3powder (2.5equiv) into eggplant-shaped bottle (100mL), use DMF (10mL) as solvent, stir at room temperature for 30min, then slowly drop substituted benzyl chloride (1.2 equiv) or substituted benzyl bromide (1.2equiv) into the reaction solution, and then the reaction system was transferred to an oil bath at 80°C for 3-5h.Cool to room temperature, pour 100mL of cold water (15°C-20°C) into the reaction solution, extract with ethyl acetate (10mL×3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, suction filter, and reduce pressure The solvent was evaporated, and the obtained product was purified by thin layer chromatography (developing system: petroleum ether: ethyl acetate volume ratio 2:1), or recrystallized with methanol to obtain the target compounds I-1 to I-13. |
80.5 % | Stage #1: semaxanib With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 3-Trifluoromethylbenzyl chloride In N,N-dimethyl-formamide at 80℃; | 5 Embodiment 5, the preparation of target compound I-1 to I-13 General procedure: Weigh intermediate 2 (1equiv) and K2CO3powder (2.5equiv) into eggplant-shaped bottle (100mL), use DMF (10mL) as solvent, stir at room temperature for 30min, then slowly drop substituted benzyl chloride (1.2 equiv) or substituted benzyl bromide (1.2equiv) into the reaction solution, and then the reaction system was transferred to an oil bath at 80°C for 3-5h.Cool to room temperature, pour 100mL of cold water (15°C-20°C) into the reaction solution, extract with ethyl acetate (10mL×3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, suction filter, and reduce pressure The solvent was evaporated, and the obtained product was purified by thin layer chromatography (developing system: petroleum ether: ethyl acetate volume ratio 2:1), or recrystallized with methanol to obtain the target compounds I-1 to I-13. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75.7 % | Stage #1: semaxanib With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 4-trifluoromethylbenzyl chloride In N,N-dimethyl-formamide at 80℃; | 5 Embodiment 5, the preparation of target compound I-1 to I-13 General procedure: Weigh intermediate 2 (1equiv) and K2CO3powder (2.5equiv) into eggplant-shaped bottle (100mL), use DMF (10mL) as solvent, stir at room temperature for 30min, then slowly drop substituted benzyl chloride (1.2 equiv) or substituted benzyl bromide (1.2equiv) into the reaction solution, and then the reaction system was transferred to an oil bath at 80°C for 3-5h.Cool to room temperature, pour 100mL of cold water (15°C-20°C) into the reaction solution, extract with ethyl acetate (10mL×3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, suction filter, and reduce pressure The solvent was evaporated, and the obtained product was purified by thin layer chromatography (developing system: petroleum ether: ethyl acetate volume ratio 2:1), or recrystallized with methanol to obtain the target compounds I-1 to I-13. |
75.7 % | Stage #1: semaxanib With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 4-trifluoromethylbenzyl chloride In N,N-dimethyl-formamide at 80℃; | 5 Embodiment 5, the preparation of target compound I-1 to I-13 General procedure: Weigh intermediate 2 (1equiv) and K2CO3powder (2.5equiv) into eggplant-shaped bottle (100mL), use DMF (10mL) as solvent, stir at room temperature for 30min, then slowly drop substituted benzyl chloride (1.2 equiv) or substituted benzyl bromide (1.2equiv) into the reaction solution, and then the reaction system was transferred to an oil bath at 80°C for 3-5h.Cool to room temperature, pour 100mL of cold water (15°C-20°C) into the reaction solution, extract with ethyl acetate (10mL×3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, suction filter, and reduce pressure The solvent was evaporated, and the obtained product was purified by thin layer chromatography (developing system: petroleum ether: ethyl acetate volume ratio 2:1), or recrystallized with methanol to obtain the target compounds I-1 to I-13. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67.8 % | Stage #1: semaxanib With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 3,4-difluorobenzyl chloride In N,N-dimethyl-formamide at 80℃; | 5 Embodiment 5, the preparation of target compound I-1 to I-13 General procedure: Weigh intermediate 2 (1equiv) and K2CO3powder (2.5equiv) into eggplant-shaped bottle (100mL), use DMF (10mL) as solvent, stir at room temperature for 30min, then slowly drop substituted benzyl chloride (1.2 equiv) or substituted benzyl bromide (1.2equiv) into the reaction solution, and then the reaction system was transferred to an oil bath at 80°C for 3-5h.Cool to room temperature, pour 100mL of cold water (15°C-20°C) into the reaction solution, extract with ethyl acetate (10mL×3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, suction filter, and reduce pressure The solvent was evaporated, and the obtained product was purified by thin layer chromatography (developing system: petroleum ether: ethyl acetate volume ratio 2:1), or recrystallized with methanol to obtain the target compounds I-1 to I-13. |
67.8 % | Stage #1: semaxanib With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 3,4-difluorobenzyl chloride In N,N-dimethyl-formamide at 80℃; | 5 Embodiment 5, the preparation of target compound I-1 to I-13 General procedure: Weigh intermediate 2 (1equiv) and K2CO3powder (2.5equiv) into eggplant-shaped bottle (100mL), use DMF (10mL) as solvent, stir at room temperature for 30min, then slowly drop substituted benzyl chloride (1.2 equiv) or substituted benzyl bromide (1.2equiv) into the reaction solution, and then the reaction system was transferred to an oil bath at 80°C for 3-5h.Cool to room temperature, pour 100mL of cold water (15°C-20°C) into the reaction solution, extract with ethyl acetate (10mL×3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, suction filter, and reduce pressure The solvent was evaporated, and the obtained product was purified by thin layer chromatography (developing system: petroleum ether: ethyl acetate volume ratio 2:1), or recrystallized with methanol to obtain the target compounds I-1 to I-13. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72.7 % | Stage #1: semaxanib With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 3,4-Dichlorobenzyl chloride In N,N-dimethyl-formamide at 80℃; | 5 Embodiment 5, the preparation of target compound I-1 to I-13 General procedure: Weigh intermediate 2 (1equiv) and K2CO3powder (2.5equiv) into eggplant-shaped bottle (100mL), use DMF (10mL) as solvent, stir at room temperature for 30min, then slowly drop substituted benzyl chloride (1.2 equiv) or substituted benzyl bromide (1.2equiv) into the reaction solution, and then the reaction system was transferred to an oil bath at 80°C for 3-5h.Cool to room temperature, pour 100mL of cold water (15°C-20°C) into the reaction solution, extract with ethyl acetate (10mL×3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, suction filter, and reduce pressure The solvent was evaporated, and the obtained product was purified by thin layer chromatography (developing system: petroleum ether: ethyl acetate volume ratio 2:1), or recrystallized with methanol to obtain the target compounds I-1 to I-13. |
72.7 % | Stage #1: semaxanib With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 3,4-Dichlorobenzyl chloride In N,N-dimethyl-formamide at 80℃; | 5 Embodiment 5, the preparation of target compound I-1 to I-13 General procedure: Weigh intermediate 2 (1equiv) and K2CO3powder (2.5equiv) into eggplant-shaped bottle (100mL), use DMF (10mL) as solvent, stir at room temperature for 30min, then slowly drop substituted benzyl chloride (1.2 equiv) or substituted benzyl bromide (1.2equiv) into the reaction solution, and then the reaction system was transferred to an oil bath at 80°C for 3-5h.Cool to room temperature, pour 100mL of cold water (15°C-20°C) into the reaction solution, extract with ethyl acetate (10mL×3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, suction filter, and reduce pressure The solvent was evaporated, and the obtained product was purified by thin layer chromatography (developing system: petroleum ether: ethyl acetate volume ratio 2:1), or recrystallized with methanol to obtain the target compounds I-1 to I-13. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65.1 % | Stage #1: semaxanib With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 4-chloromethyl-1,2-dimethoxy-benzene In N,N-dimethyl-formamide at 80℃; | 5 Embodiment 5, the preparation of target compound I-1 to I-13 General procedure: Weigh intermediate 2 (1equiv) and K2CO3powder (2.5equiv) into eggplant-shaped bottle (100mL), use DMF (10mL) as solvent, stir at room temperature for 30min, then slowly drop substituted benzyl chloride (1.2 equiv) or substituted benzyl bromide (1.2equiv) into the reaction solution, and then the reaction system was transferred to an oil bath at 80°C for 3-5h.Cool to room temperature, pour 100mL of cold water (15°C-20°C) into the reaction solution, extract with ethyl acetate (10mL×3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, suction filter, and reduce pressure The solvent was evaporated, and the obtained product was purified by thin layer chromatography (developing system: petroleum ether: ethyl acetate volume ratio 2:1), or recrystallized with methanol to obtain the target compounds I-1 to I-13. |
65.1 % | Stage #1: semaxanib With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 4-chloromethyl-1,2-dimethoxy-benzene In N,N-dimethyl-formamide at 80℃; | 5 Embodiment 5, the preparation of target compound I-1 to I-13 General procedure: Weigh intermediate 2 (1equiv) and K2CO3powder (2.5equiv) into eggplant-shaped bottle (100mL), use DMF (10mL) as solvent, stir at room temperature for 30min, then slowly drop substituted benzyl chloride (1.2 equiv) or substituted benzyl bromide (1.2equiv) into the reaction solution, and then the reaction system was transferred to an oil bath at 80°C for 3-5h.Cool to room temperature, pour 100mL of cold water (15°C-20°C) into the reaction solution, extract with ethyl acetate (10mL×3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, suction filter, and reduce pressure The solvent was evaporated, and the obtained product was purified by thin layer chromatography (developing system: petroleum ether: ethyl acetate volume ratio 2:1), or recrystallized with methanol to obtain the target compounds I-1 to I-13. |
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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