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CAS No. : | 1878-85-9 | MDL No. : | MFCD00014352 |
Formula : | C9H10O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IHONYPFTXGQWAX-UHFFFAOYSA-N |
M.W : | 182.17 | Pubchem ID : | 15882 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319 | 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 |
---|---|---|
With thionyl chloride | ||
With thionyl chloride Heating; | ||
With thionyl chloride In tetrahydrofuran |
With thionyl chloride for 0.5h; Heating; | ||
With thionyl chloride for 2h; Reflux; | ||
With dmap; thionyl chloride In dichloromethane for 2h; Reflux; | ||
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h; Inert atmosphere; | ||
With thionyl chloride; N,N-dimethyl-formamide In tetrahydrofuran at 50℃; for 5h; | General procedure for the synthesis of HY-1a-HY-1f General procedure: A mixture of aryloxyl acid (5a-f) (10 mmol), thionyl chloride(15 mmol), tetrahydrofuran (50 ml) and dimethylformamide(1 ml) was stirred at 50 C for 5 h. Then tetrahydrofuran and thionylchloride were removed in vacuo. Yellow liquid (6a-f) obtainedand pyridine (2.5 ml) were then added to a solution of 10 (10 mmolin 25 ml tetrahydrofuran). The solution was stirred at 50 C for 3 h.When the reaction was completed, the solution was poured intohydrochloric acid (1 mol/L) and extracted with CH2Cl2(20 ml 3). The combined organic phase was washed with brine(20 ml 3), dried over Na2SO4, concentrated to afford yellow solid.Purification by silica gel column chromatography (PE:EA = 15:1) yielded the isoflavone amide derivatives HY-1a-HY-1f | |
With oxalyl dichloride In dichloromethane at 0 - 20℃; for 1h; | General procedure: To a 0 °C stirring solution of substituted aryloxyacetic acid (4a-f, 5.4mmol) in anhydrous dichloromethane (50 mL) was slowly added oxalyl chloride (8 mmol) dropwise. After the reagent addition was complete, the ice bath was removed and the solution was allowed to stand at room temperature for 1 h. The solvent was removed under vacuum to obtain corresponding acyl chloride 5a-f sufficiently pure to be used directly in the next step of the reaction. To a stirred solution of corresponding 1-(substitutedbenzhydryl)piperazine (9a-d, 8mmol), triethylamine (6.8 mL) in dry acetone (30 mL) was slowly added acyl chloride 5a-f, dissolved in anhydrous acetone (30 mL). The mixture was stirred at room temperature for 16h and filtered off. The filtrate was evaporated and purified by column chromatography with AcOEt/petroleum ether (2/1) to give diphenylmethyl-substituted aryloxy acetylpiperazine analogs 10a-s, yield of33-84%. | |
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 12h; | ||
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With sodium hydride In N,N-dimethyl-formamide for 120h; Ambient temperature; | |
man versetzt mit Natronlauge; | ||
With sodium hydroxide |
With sodium hydroxide | ||
With sodium hydroxide | ||
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 12h; | ||
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere; | ||
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With 2,3,4,5,6-pentafluorophenol; dicyclohexyl-carbodiimide In ethyl acetate | |
at 140℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With dicyclohexyl-carbodiimide In ethyl acetate for 14h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With dicyclohexyl-carbodiimide In chloroform for 14h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With toluene-4-sulfonic acid at 20℃; | |
at 30℃; other temperature: 40 deg C; | ||
With sulfuric acid |
With sulfuric acid for 3h; Heating; | ||
With thionyl chloride at 0 - 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With chloroformic acid ethyl ester; triethylamine In chloroform Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; dicyclohexyl-carbodiimide In 1,4-dioxane at 22 - 25℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With sodium hydroxide at 80℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine In dichloromethane at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | Stage #1: (2-methoxyphenoxy)acetic acid With diphenyl-phosphinic acid; triethylamine In N,N-dimethyl-formamide; toluene for 3h; Heating; Stage #2: With water In N,N-dimethyl-formamide; toluene Heating; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With sodium hydroxide In ethanol at 25℃; for 72h; | |
With water; lithium hydroxide In methanol at 20℃; | ||
With lithium hydroxide In methanol; water at 50℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 80 percent / Et3N; bis(2-oxo-3-oxazolidinyl)phosphinic chloride / CH2Cl2 / 0 - 20 °C 2: 94 percent / aq. LiOH / tetrahydrofuran; methanol / 45 - 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: N-[2-(1-methyl-pyrrolidin-2-yl)-ethyl]-benzene-1,2-diamine; (2-methoxyphenoxy)acetic acid With 1,1'-carbonyldiimidazole In dichloromethane for 18h; Stage #2: With acetic acid at 80℃; for 4h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: N-[3-(2-methyl-piperidin-1-yl)-propyl]-benzene-1,2-diamine; (2-methoxyphenoxy)acetic acid With 1,1'-carbonyldiimidazole In dichloromethane for 18h; Stage #2: With acetic acid at 80℃; for 4h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 1-[3-(2-amino-phenylamino)-propyl]-pyrrolidin-2-one; (2-methoxyphenoxy)acetic acid With 1,1'-carbonyldiimidazole In dichloromethane for 18h; Stage #2: With acetic acid at 80℃; for 4h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: N-(3-Morpholinopropyl)-1,2-benzenediamine; (2-methoxyphenoxy)acetic acid With 1,1'-carbonyldiimidazole In dichloromethane for 18h; Stage #2: With acetic acid at 80℃; for 4h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: (2-methoxyphenoxy)acetic acid; N-(3-diethylamino-propyl)-benzene-1,2-diamine With 1,1'-carbonyldiimidazole In dichloromethane for 18h; Stage #2: With acetic acid at 80℃; for 4h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: (2-methoxyphenoxy)acetic acid; N-[3-(Dimethylamino)propyl]-1,2-benzenediamine With 1,1'-carbonyldiimidazole In dichloromethane for 18h; Stage #2: With acetic acid at 80℃; for 4h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: (2-methoxyphenoxy)acetic acid; N-[3-(4-methyl-piperazin-1-yl)-propyl]-benzene-1,2-diamine With 1,1'-carbonyldiimidazole In dichloromethane for 18h; Stage #2: With acetic acid at 80℃; for 4h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone; xylene at 50℃; for 2h; | 9 For a 1:2 Co-Crystal by cooling crystallisation. 100 μl of a 27.5% CYP in acetone solution was added to a well in a 96 well plate. lOlμl of a 10% (2-methoxyphenoxy)acetic acid in methanol solution was added to this mixture with a further 75 μl of xylene. The sample was kept at 5O0C for 2 hours, then cooled to 10°C overnight and the remaining liquid was removed. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃; Cooling with ice; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; In ethanol; water; at 20℃; for 1.5h; | General procedure: A mixture of phenols (0.3 mmol), acetone (10 ml), dimethylformamide(10 ml), ethyl chloroacetate (2.5 ml, 0.26 mmol), potassiumcarbonate (2 g) and potassium iodide (0.15 g) was heated at75 C for 12 h. Afterwards, the solid was filtered and the solventof the filtrate was removed in vacuo. The colorless liquid (4a-f)obtained was dissolved in ethanol (20 ml). A solution of potassiumhydroxide (7.2%, 5 ml) was added and stirred at room temperaturefor 1.5 h. The mixture was poured into hydrochloric acid (1 mol/L)and a white precipitate was formed. Purification by recrystallizationfrom methanol afforded the corresponding aryloxyl acid (5a-f) | |
With water; sodium hydroxide; In ethanol; at 20℃; for 4h; | General procedure: A solution of corresponding substituted ethylaryloxyacetate (3a-f, 25 mmol) in ethanol (100 mL) was treated with 10% aqueous sodium hydroxide (9 mmol). After 4 h at room temperature and evaporation under reduced pressure of ethanol, the aqueous phases were acidified at pH 4 with HCl (2 N). Removal of precipitate by filtration yielded the crude acids, which were recrystallized in ethanol to afford substituted aryloxyacetic acid 4a-f, yield 66-90%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With toluene-4-sulfonic acid at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With toluene-4-sulfonic acid at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With toluene-4-sulfonic acid at 60℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sodium hydroxide In water at 20 - 60℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 0.25 h / 20 °C / Inert atmosphere 1.2: 8 h / 0 °C / Inert atmosphere; Reflux 2.1: potassium hydroxide / methanol; water / 20 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1: potassium carbonate / tetrahydrofuran / 20 - 80 °C 2: lithium hydroxide; water / methanol / 20 °C | ||
Multi-step reaction with 2 steps 1: potassium iodide; potassium carbonate / N,N-dimethyl-formamide / 12 h / 75 °C 2: potassium hydroxide / ethanol; water / 1.5 h / 20 °C |
Multi-step reaction with 2 steps 1: sodium hydroxide / water / 8 h / Reflux 2: hydrogenchloride / water / pH 1 | ||
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 5 h / Reflux 2: water; sodium hydroxide / ethanol / 4 h / 20 °C | ||
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 50 °C 1.2: 12 h / 50 °C 2.1: lithium hydroxide / methanol; water / 12 h / 50 °C | ||
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 60 °C 2: sodium hydroxide / ethanol; water / Reflux | ||
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / Reflux 2: sodium hydroxide; ethanol / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: (2-methoxyphenoxy)acetic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: (+/-)-[4-chloro-2-(1,2,3,4-tetrahydroisoquinolin-1-yl)phenoxy]acetic acid ethyl ester In dichloromethane; N,N-dimethyl-formamide at 20℃; for 18h; | 406 Amide coupling and subsequent saponification Method A: To a solution of (2-methoxyphenoxy)acetic acid (22 mg, 0.12 mmol, 1.2 eq.) in DMF (0.3 mL), TBTU (39 mg, 0.12 mmol, 1.2 eq.) and Si-DEA (400 mg, 0.50 mmol, 5.0 eq.) were added. The resulting mixture was stirred at r.t. for 30 min. A solution of (+)-[4- chloro-2-(1 ,2,3,4-tetrahydro-isoquinolin-1 -yl)-phenoxy]-acetic acid ethyl ester hydrochloride (38 mg, 0.10 mmol, 1 .0 eq.) in DCM/DMF 5:1 (0.6 mL) was added. The mixture was stirred at r.t. for 18 hours. The resulting suspension was filtered, the solids were rinsed with DCM (5 mL), and the filtrate was concentrated in vacuo. The residue was dissolved in THF (1 mL) and 1 M aq. NaOH (1 mL) was added. The mixture was stirred at r.t. for 30 min. The mixture was acidified with 2M aq. HCI soln. and concentrated in vacuo. The residue was purified by prep. HPLC (column : Waters X-Bridge, 30x75 mm, 10 urn, UV/MS, acidic conditions) and evaporated to give the desired acid as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: (2-methoxyphenoxy)acetic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: (+/-)-[4-chloro-2-(2,3-dihydro-1H-isoindol-1-yl)phenoxy]acetic acid ethyl ester hydrochloride In N,N-dimethyl-formamide at 20℃; for 1h; | 502 Amide coupling and subsequent saponification; To a solution of (2-methoxyphenoxy)acetic acid (22 mg, 0.12 mmol, 1 .2 eq.) in DMF (1 mL), TBTU (39 mg, 0.12 mmol, 1.2 eq.) and DIPEA (51 μΙ_, 0.30 mmol, 3.0 eq.) were added. The resulting mixture was stirred at r.t. for 30 min. A solution of (+/-)-[4-chloro-2-(2,3-dihydro- 1 H-isoindol-1 -yl)-phenoxy]-acetic acid ethyl ester hydrochloride (37 mg, 0.10 mmol, 1 .0 eq.) in DMF (0.5 mL) was added. The mixture was stirred at r.t. for 1 hour. 1 M aq. NaOH (1 mL) was added and the mixture was stirred at r.t. for 30 min, then concentrated in vacuo. The residue was purified by prep. HPLC (column : Waters X-Bridge, 30x75 mm, 10 urn, UV/MS, acidic conditions) and evaporated to give the desired acid as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | 2-(2-Methoxyphenoxy) acetic acid (76, 5.0 mmol) was dissolved in thionyl chloride (15 mL) at rt. After refluxing for 4 h, the reaction mixture was cooled to rt and concentrated under vacuum. The residue was dissolved in dichloromethane (50 mL) and aluminum chloride (10.0 mmol) was added slowly at 0 C. After stirring for 0.5 h at 0 C and 1 h at rt, the reaction mixture was then poured intoice water (60 mL) and extracted with ethyl acetate (3 x 30 mL). The combined organic phases were washed with brine, dried over anhydrous Na2SO4, and evaporated under vacuum. The residue was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate = 30/1) to afford the title compound. Bright yellowsolid, yield 27%; 1H NMR (400 MHz, CDCl3) delta 7.22-7.17 (m, 1H), 7.05 (d, J = 7.9 Hz, 1H), 7.00-6.93 (m, 1H), 4.61 (s, 2H), 3.89 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; diisopropyl-carbodiimide | 6.2. General solid-phase synthetic procedure for the preparation of the dipeptides (9) General procedure: The resulting intermediate 7 was then treated with 20% piperidine in DMF for 20 min to remove the Fmoc-group and subsequently reacted with the corresponding carboxylic acid (3 equiv) by the DIC-HOBt method or acid chloride (3 equiv) in the presence of Et3N to produce 8. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: (2-methoxyphenoxy)acetic acid With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane In tetrahydrofuran at -75 - 50℃; Inert atmosphere; Stage #2: 3,5-dimethoxy-4-(tetrahydro-2H-pyran-2-yloxy)benzaldehyde In tetrahydrofuran at -75℃; for 1h; Inert atmosphere; | Z-2-(2-methoxyphenoxy)-3-(3,4,5-trimethoxyphenyl)-2-propenoic acid (2) General procedure: A 250ml three-necked flask was used in the experiments. The flask was equipped with an inlet and an outlet for nitrogen, a septum for injection of reagents. A slow stream of nitrogen was allowed to pass through the reaction vessel (the flow rate was registered by means of a silicone oil seal). Using a syringe, n-Butyl lithium in THF (42mmol, 24ml 1.6M solution) was injected in to the solution of hexamethyldisilazane (8.28ml, 40mmol) in THF (50ml). To achieve α-lithiation of the carboxylic acid, the mixture was stirred magnetically for about 0.5h. A solution of (2-methoxyphenoxy) acetic acid (3.65g, 20mmol) in THF (25ml) was slowly injected into the flask. The mixture was kept at -75°C for 0.5h (magnetic stirring). The stirring was continued for 1.5-2h at 45-50°C and after cooling to -75°C, a solution of the methylated syringaldehyde (20mmol, 3.92g) in THF (15ml) was slowly added to the reaction mixture. Stirring was continued for 1h at -75°C, after which the mixture was stirred at room temperature overnight, it was cooled to 0°C and acidified to pH=2 with 3M HCI. The organic layer was separated and the aqueous layer was extracted with diethyl ether (100+3×50ml). The combined organic layers were extracted with 0.2M NaOH (3×75ml). The extract was acidified with 3M hydrochloric acid (21ml) and extracted with ether (250ml+3×100ml). The extract was dried (Na2SO4) and solvents were removed by film evaporation that gave an oily residual. The crude product was chromatographed on a silica gel, eluents dichloromethane/ethyl acetate (9:1) and (5:1)] which gave an essentially pure Z isomer (yield, 50%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | Stage #1: (2-methoxyphenoxy)acetic acid With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane In tetrahydrofuran at -75 - 50℃; Inert atmosphere; Stage #2: 3,4,5-trimethoxy-benzaldehyde In tetrahydrofuran at -75℃; for 1h; Inert atmosphere; | Z-2-(2-methoxyphenoxy)-3-(3,4,5-trimethoxyphenyl)-2-propenoic acid (2) General procedure: A 250ml three-necked flask was used in the experiments. The flask was equipped with an inlet and an outlet for nitrogen, a septum for injection of reagents. A slow stream of nitrogen was allowed to pass through the reaction vessel (the flow rate was registered by means of a silicone oil seal). Using a syringe, n-Butyl lithium in THF (42mmol, 24ml 1.6M solution) was injected in to the solution of hexamethyldisilazane (8.28ml, 40mmol) in THF (50ml). To achieve α-lithiation of the carboxylic acid, the mixture was stirred magnetically for about 0.5h. A solution of (2-methoxyphenoxy) acetic acid (3.65g, 20mmol) in THF (25ml) was slowly injected into the flask. The mixture was kept at -75°C for 0.5h (magnetic stirring). The stirring was continued for 1.5-2h at 45-50°C and after cooling to -75°C, a solution of the methylated syringaldehyde (20mmol, 3.92g) in THF (15ml) was slowly added to the reaction mixture. Stirring was continued for 1h at -75°C, after which the mixture was stirred at room temperature overnight, it was cooled to 0°C and acidified to pH=2 with 3M HCI. The organic layer was separated and the aqueous layer was extracted with diethyl ether (100+3×50ml). The combined organic layers were extracted with 0.2M NaOH (3×75ml). The extract was acidified with 3M hydrochloric acid (21ml) and extracted with ether (250ml+3×100ml). The extract was dried (Na2SO4) and solvents were removed by film evaporation that gave an oily residual. The crude product was chromatographed on a silica gel, eluents dichloromethane/ethyl acetate (9:1) and (5:1)] which gave an essentially pure Z isomer (yield, 50%). 1HNMR (CDCl3): δ 3.929 (3H, s, OCH3), 3.948 (3H, s, OCH3), 3.961 (3H, s, OCH3), 3.969 (3H, OCH3), 6.93-7.39 (7H, m, vinyl, H-Ar), 9.89 (1H, s, COOH). 13CNMR(CDCl3): δ 56.66 (OCH3), 56.69 (OCH3), 61.35 (OCH3), 67.75 (OCH3), 107-154 (Ar), 171.75 (C=C), 173.50 (C=C), 191.70 (COOH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With ammonium peroxydisulfate; silver nitrate In water; acetonitrile at 80℃; for 0.0833333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With trichlorophosphate at 90℃; for 8h; | 1.1 5.2 General procedure for the syntheses of 3-tert-butyl-7-(aryloxymethyl)-4H-[1,3,4]thiadiazolo[2,3-c][1,2,4]triazin-4-ones (5a-5n) General procedure: An equimolar mixtures of 4-amino-6-tert-butyl-3-mercapto-1,2,4-triazine-5(H)-one (0.01mol) (3) and substituted aryloxyacetic acids (0.01mol) (4) were condensed in presence of POCl3 at 90°C, for 8h. The reactions were carried out in dry condition. The reaction mixtures were cooled and poured into crushed ice drop wise with vigorous shaking, yielded solid product, filtered and recrystallized from ethanol to afford analytical samples (5a-5n) (Scheme 2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With dipotassium peroxodisulfate; silver nitrate In water; acetonitrile at 60℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride; N,N-dimethyl-formamide In tetrahydrofuran at 50℃; for 5h; | General procedure for the synthesis of HY-1a-HY-1f General procedure: A mixture of aryloxyl acid (5a-f) (10 mmol), thionyl chloride(15 mmol), tetrahydrofuran (50 ml) and dimethylformamide(1 ml) was stirred at 50 C for 5 h. Then tetrahydrofuran and thionylchloride were removed in vacuo. Yellow liquid (6a-f) obtainedand pyridine (2.5 ml) were then added to a solution of 10 (10 mmolin 25 ml tetrahydrofuran). The solution was stirred at 50 C for 3 h.When the reaction was completed, the solution was poured intohydrochloric acid (1 mol/L) and extracted with CH2Cl2(20 ml 3). The combined organic phase was washed with brine(20 ml 3), dried over Na2SO4, concentrated to afford yellow solid.Purification by silica gel column chromatography (PE:EA = 15:1) yielded the isoflavone amide derivatives HY-1a-HY-1f |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In water | 2.1 Synthesis of phenoxyacetic acid and ring-substituted phenoxyacetic acids General procedure: General procedure: To a solution of phenol or ring-substituted phenol (20 mmol) in water (20 mL) was added sodium chloroacetate (22 mmol) at rt. The mixture was heated and stirred at reflux for 8 h. The reaction mixture was cooled and the pH was adjusted to a value of 1.0 with 5 N HCl. The solution was filtered and the obtained solid was recrystallized from dehydrated ethanol to afford the pure product. 2-Methoxyphenoxyacetic acid (1d) Following the general procedure the compound 1d was obtained in 82 % yield as a white solid. m.p. 119-120 °C. 1H NMR (400 MHz, CDCl3) δ9.83 (s, 1H), 7.09-6.95 (m,1H), 6.95-6.82 (m, 3H), 4.70 (s, 2H), 3.90 (s, 3H). MS (ESI) m/z: 181 [M-H]-.(S3) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine; pivaloyl chloride / toluene / 80 °C / Reflux 2: magnesium chloride / chloroform-d1 / 24.5 h / 0 - 5 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine; pivaloyl chloride / toluene / 80 °C / Reflux 2: triethylamine; magnesium chloride / dichloromethane / 24.5 h / 0 - 5 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: triethylamine; pivaloyl chloride / toluene / 80 °C / Reflux 2: triethylamine; magnesium chloride / dichloromethane / 24.5 h / 0 - 5 °C / Inert atmosphere 3: trifluoroacetic acid / 0.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: triethylamine; pivaloyl chloride / toluene / 80 °C / Reflux 2: triethylamine; magnesium chloride / dichloromethane / 24.5 h / 0 - 5 °C / Inert atmosphere 3: trifluoroacetic acid / 0.5 h 4: sodium tetrahydroborate; hydrogen / tetrahydrofuran / 1 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: triethylamine; pivaloyl chloride / toluene / 80 °C / Reflux 2.1: N-ethyl-N,N-diisopropylamine; di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 0.5 h / 0 - 5 °C / Inert atmosphere 2.2: 4 h / -78 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: triethylamine; pivaloyl chloride / toluene / 80 °C / Reflux 2.1: N-ethyl-N,N-diisopropylamine; di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 0.5 h / 0 - 5 °C / Inert atmosphere 2.2: 4 h / -78 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: triethylamine; pivaloyl chloride / toluene / 80 °C / Reflux 2.1: N-ethyl-N,N-diisopropylamine; di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 0.5 h / 0 - 5 °C / Inert atmosphere 2.2: 4 h / -78 - 20 °C / Inert atmosphere 3.1: sodium tetrahydroborate; hydrogen |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: triethylamine; pivaloyl chloride / toluene / 80 °C / Reflux 2.1: N-ethyl-N,N-diisopropylamine; di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 0.5 h / 0 - 5 °C / Inert atmosphere 2.2: 4 h / -78 - 20 °C / Inert atmosphere 3.1: sodium tetrahydroborate; hydrogen |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: triethylamine; pivaloyl chloride / toluene / 80 °C / Reflux 2.1: N-ethyl-N,N-diisopropylamine; di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 0.5 h / 0 - 5 °C / Inert atmosphere 2.2: 4 h / -78 - 20 °C / Inert atmosphere 3.1: sodium tetrahydroborate; hydrogen 4.1: hydrogen; palladium 10% on activated carbon / methanol / 12 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: triethylamine; pivaloyl chloride / toluene / 80 °C / Reflux 2.1: N-ethyl-N,N-diisopropylamine; di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 0.5 h / 0 - 5 °C / Inert atmosphere 2.2: 4 h / -78 - 20 °C / Inert atmosphere 3.1: sodium tetrahydroborate; hydrogen 4.1: hydrogen; palladium 10% on activated carbon / methanol / 12 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine; pivaloyl chloride / toluene / 80 °C / Reflux 2: triethylamine; magnesium chloride / dichloromethane / 24.5 h / 0 - 5 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: triethylamine; pivaloyl chloride / toluene / 80 °C / Reflux 2.1: N-ethyl-N,N-diisopropylamine; di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 0.5 h / 0 - 5 °C / Inert atmosphere 2.2: 4 h / -78 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: triethylamine; pivaloyl chloride / toluene / 80 °C / Reflux 2.1: N-ethyl-N,N-diisopropylamine; di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 0.5 h / 0 - 5 °C / Inert atmosphere 2.2: 4 h / -78 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine; pivaloyl chloride / toluene / 80 °C / Reflux 2: triethylamine; magnesium chloride / dichloromethane / 24 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine; pivaloyl chloride / toluene / 80 °C / Reflux 2: triethylamine; magnesium chloride / dichloromethane / 24 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With pivaloyl chloride; triethylamine In toluene at 80℃; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pivaloyl chloride; triethylamine In toluene at 80℃; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With pivaloyl chloride; triethylamine In toluene at 80℃; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pivaloyl chloride; triethylamine In toluene at 80℃; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With pivaloyl chloride; triethylamine In toluene at 80℃; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With pivaloyl chloride; triethylamine In toluene at 80℃; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With potassium carbonate In acetone Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; | (General Method 2): General procedure: To a round bottom flaskwas added 1 (1.41 g, 4.5 mmol), (3-methyl-phenoxy)acetic acid (3.0 g,18.1 mmol), and DMAP (550 mg, 4.5 mmol) in DCM (30 ml) at ambienttemperature. Once a homogenous solution was observed, DIC wasadded (2.8 ml, 18.1 mmol). The mixture was allowed to stir overnight.The next morning the mixture was filtered, and the filtrate was rotovapedonto silica gel and subjected to flash chromatography. The resultantfoam was then crystallized from methanol and DCM yielding1.08 g of white crystal (73%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 12h; | 3.1 Step 1: Synthesis of A3 To a mixture of A2 (501 mg, 2.75 mmol), HOBT (507 mg, 3.75 mmol) and EDCI (719 mg, 3.75 mmol) in DMF (5.00 mL) were added DIEA (1.29 g, 10.0 mmol) and A1 (500 mg, 2.50 mmol) at 20° C. The mixture was stirred at 20° C. for 12 h until LCMS showed that the reaction was completed. The mixture was dissolved in EtOAc (30 mL) and washed with water (30 mL*2) and brine (20 mL*2). The organic phase was dried over Na2SO4, filtered and the filtrate was concentrated under vacuum to provide a residue, which was purified by silica gel chromatography (petroleum ether/ethyl acetate=30/1 to 1/1) to give A3 (800 mg, yield: 88%) as yellow oil. 1H NMR: (CDCl3 400 MHz) δ: 7.08-7.16 (m, 1H), 7.00-7.06 (m, 1H), 6.91-6.95 (m, 3H), 5.30-5.32 (m, 1H), 4.52-4.55 (m, 2H), 3.97-4.06 (m, 1H), 3.88-3.91 (m, 3H), 3.66-3.76 (m, 1H), 3.46-3.55 (m, 1H), 3.22-3.33 (m, 1H), 1.86-1.95 (m, 1H), 1.56 (d, J=7.0 Hz, 1H), 1.43 (s, 9H), 1.24-1.29 (m, 1H), 1.18-1.23 (m, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98 % ee | With glucose dehydrogenase; D-glucose; YGL039w from saccharomyces cerevisiae; nicotinamide adenine dinucleotide phosphate In aq. acetate buffer at 30℃; for 1h; Enzymatic reaction; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With riboflavin tetraacetate In acetonitrile at 25℃; for 22h; Inert atmosphere; Irradiation; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With riboflavin tetraacetate In acetonitrile at 25℃; Sealed tube; Inert atmosphere; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With riboflavin 2',3',4',5'-tetra-acetate In acetonitrile at 30℃; for 15h; Inert atmosphere; Sealed tube; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | Stage #1: (2-methoxyphenoxy)acetic acid; C14H12ClFN2O2 With 2,6-dimethylpyridine In dichloromethane at 25 - 30℃; for 0.5h; Stage #2: With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In dichloromethane at 0 - 5℃; | General procedure for the synthesisof di-phenoxyacetamide benzene analogs DPA (7a-t) General procedure: Compounds (4a-g, 0.002 mol) were added to Compounds(6a-g, 0.002 mol) in dry DCM (10 ml) at 25-30 C followedby the addition of lutidine (0.001 mol). The mixture wasstirred at 25-30 C for 30 min and then cooled to 0-5 C inan ice bath and TBTU (0.003 mol) was added for a periodof 20 min while maintaining the temperature below 4 C.The reaction was stirred for 14-16 h and monitored by TLCusing a hexane and ethyl acetate (3:1) system. When thereaction is over, the mixture was diluted with 20 ml of DCMand then washed with a solution of 10% sodium bicarbonate(3 × 25 ml) followed by distilled water (3 × 25 ml). Afterthat, the organic layer was dried over anhydrous sodiumsulphate and concentrated to yield crude title CompoundsDPA (7a-t). Finally, these title Compounds DPA(7a-t) wererecrystallized with ethanol to achieve pure samples. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | Stage #1: N-(2-aminophenyl)-2-(2-isopropylphenoxy)acetamide; (2-methoxyphenoxy)acetic acid With 2,6-dimethylpyridine In dichloromethane at 25 - 30℃; for 0.5h; Stage #2: With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In dichloromethane at 0 - 5℃; | General procedure for the synthesisof di-phenoxyacetamide benzene analogs DPA (7a-t) General procedure: Compounds (4a-g, 0.002 mol) were added to Compounds(6a-g, 0.002 mol) in dry DCM (10 ml) at 25-30 C followedby the addition of lutidine (0.001 mol). The mixture wasstirred at 25-30 C for 30 min and then cooled to 0-5 C inan ice bath and TBTU (0.003 mol) was added for a periodof 20 min while maintaining the temperature below 4 C.The reaction was stirred for 14-16 h and monitored by TLCusing a hexane and ethyl acetate (3:1) system. When thereaction is over, the mixture was diluted with 20 ml of DCMand then washed with a solution of 10% sodium bicarbonate(3 × 25 ml) followed by distilled water (3 × 25 ml). Afterthat, the organic layer was dried over anhydrous sodiumsulphate and concentrated to yield crude title CompoundsDPA (7a-t). Finally, these title Compounds DPA(7a-t) wererecrystallized with ethanol to achieve pure samples. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | Stage #1: (2-methoxyphenoxy)acetic acid; N-(2-aminophenyl)-2-(4-bromophenoxy) acetamide With 2,6-dimethylpyridine In dichloromethane at 25 - 30℃; for 0.5h; Stage #2: With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In dichloromethane at 0 - 5℃; | General procedure for the synthesisof di-phenoxyacetamide benzene analogs DPA (7a-t) General procedure: Compounds (4a-g, 0.002 mol) were added to Compounds(6a-g, 0.002 mol) in dry DCM (10 ml) at 25-30 C followedby the addition of lutidine (0.001 mol). The mixture wasstirred at 25-30 C for 30 min and then cooled to 0-5 C inan ice bath and TBTU (0.003 mol) was added for a periodof 20 min while maintaining the temperature below 4 C.The reaction was stirred for 14-16 h and monitored by TLCusing a hexane and ethyl acetate (3:1) system. When thereaction is over, the mixture was diluted with 20 ml of DCMand then washed with a solution of 10% sodium bicarbonate(3 × 25 ml) followed by distilled water (3 × 25 ml). Afterthat, the organic layer was dried over anhydrous sodiumsulphate and concentrated to yield crude title CompoundsDPA (7a-t). Finally, these title Compounds DPA(7a-t) wererecrystallized with ethanol to achieve pure samples. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | Stage #1: (2-methoxyphenoxy)acetic acid; C15H15ClN2O2 With 2,6-dimethylpyridine In dichloromethane at 25 - 30℃; for 0.5h; Stage #2: With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In dichloromethane at 0 - 5℃; | General procedure for the synthesisof di-phenoxyacetamide benzene analogs DPA (7a-t) General procedure: Compounds (4a-g, 0.002 mol) were added to Compounds(6a-g, 0.002 mol) in dry DCM (10 ml) at 25-30 C followedby the addition of lutidine (0.001 mol). The mixture wasstirred at 25-30 C for 30 min and then cooled to 0-5 C inan ice bath and TBTU (0.003 mol) was added for a periodof 20 min while maintaining the temperature below 4 C.The reaction was stirred for 14-16 h and monitored by TLCusing a hexane and ethyl acetate (3:1) system. When thereaction is over, the mixture was diluted with 20 ml of DCMand then washed with a solution of 10% sodium bicarbonate(3 × 25 ml) followed by distilled water (3 × 25 ml). Afterthat, the organic layer was dried over anhydrous sodiumsulphate and concentrated to yield crude title CompoundsDPA (7a-t). Finally, these title Compounds DPA(7a-t) wererecrystallized with ethanol to achieve pure samples. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | Stage #1: (2-methoxyphenoxy)acetic acid; C15H16N2O3 With 2,6-dimethylpyridine In dichloromethane at 25 - 30℃; for 0.5h; Stage #2: With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In dichloromethane at 0 - 5℃; | General procedure for the synthesisof di-phenoxyacetamide benzene analogs DPA (7a-t) General procedure: Compounds (4a-g, 0.002 mol) were added to Compounds(6a-g, 0.002 mol) in dry DCM (10 ml) at 25-30 C followedby the addition of lutidine (0.001 mol). The mixture wasstirred at 25-30 C for 30 min and then cooled to 0-5 C inan ice bath and TBTU (0.003 mol) was added for a periodof 20 min while maintaining the temperature below 4 C.The reaction was stirred for 14-16 h and monitored by TLCusing a hexane and ethyl acetate (3:1) system. When thereaction is over, the mixture was diluted with 20 ml of DCMand then washed with a solution of 10% sodium bicarbonate(3 × 25 ml) followed by distilled water (3 × 25 ml). Afterthat, the organic layer was dried over anhydrous sodiumsulphate and concentrated to yield crude title CompoundsDPA (7a-t). Finally, these title Compounds DPA(7a-t) wererecrystallized with ethanol to achieve pure samples. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | Stage #1: (2-methoxyphenoxy)acetic acid; C14H13FN2O2 With 2,6-dimethylpyridine In dichloromethane at 25 - 30℃; for 0.5h; Stage #2: With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In dichloromethane at 0 - 5℃; | General procedure for the synthesisof di-phenoxyacetamide benzene analogs DPA (7a-t) General procedure: Compounds (4a-g, 0.002 mol) were added to Compounds(6a-g, 0.002 mol) in dry DCM (10 ml) at 25-30 C followedby the addition of lutidine (0.001 mol). The mixture wasstirred at 25-30 C for 30 min and then cooled to 0-5 C inan ice bath and TBTU (0.003 mol) was added for a periodof 20 min while maintaining the temperature below 4 C.The reaction was stirred for 14-16 h and monitored by TLCusing a hexane and ethyl acetate (3:1) system. When thereaction is over, the mixture was diluted with 20 ml of DCMand then washed with a solution of 10% sodium bicarbonate(3 × 25 ml) followed by distilled water (3 × 25 ml). Afterthat, the organic layer was dried over anhydrous sodiumsulphate and concentrated to yield crude title CompoundsDPA (7a-t). Finally, these title Compounds DPA(7a-t) wererecrystallized with ethanol to achieve pure samples. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: (2-methoxyphenoxy)acetic acid; 1,2-diamino-benzene With 2,6-dimethylpyridine In dichloromethane at 20℃; for 0.5h; Stage #2: With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In dichloromethane at 0 - 4℃; | General procedure for the synthesis of phenoxyacetamideanalogs (6a-g) General procedure: Compounds (6a-g) were synthesized as per the earlierreported method from our group [20].To a solution of Compounds(4a-g, 0.009 mol), in 10 ml dry dichloromethane (DCM), lutidine (1.3 vol.) was added at room temperaturefollowed by 1, 2-diaminobenzene (5, 0.009 mol). Then,the reaction mixture was stirred for 30 min, then cooled to0-4 °C and 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethylammoniumtetrafluoroborate (TBTU, 0.02 mol) wasadded for a period of 30 min maintaining the temperaturebelow 4 °C. The reaction mixture was stirred for 14-16 hand monitored using TLC with the mobile phase system[hexane:ethyl acetate (4:1)]. After the reaction, the reactionmixture was diluted with 25 ml of DCM and then treatedwith 2N hydrochloric acid solution (30 ml) to remove unreacted1,2-diaminobenzene. The organic layer was washedwith distilled water (3 × 25 ml) and then with a brine solution(3 × 25 ml). Finally, the organic layer was dried overanhydrous sodium sulphate and concentrated to afford crudeCompounds (6a-g) which were purified by recrystallizationwith ethanol. | |
Stage #1: (2-methoxyphenoxy)acetic acid; 1,2-diamino-benzene With 2,6-dimethylpyridine In dichloromethane at 20℃; for 0.5h; Stage #2: With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In dichloromethane at 0 - 5℃; | General procedure for the synthesis of N-(2-Amino-phenyl)-2-phenoxy-acetamide analogs (6a-h) General procedure: The syntheses of compounds of N-(2-aminophenyl)-2-phenoxyacetamide analogs (6a-h), were accomplished using the condensation procedure. To a solution of (4a-h, 0.009 mol), in dry dichloromethane (DCM) (10 ml), lutidine (1.3 vol.) was added, followed by the addition of o-phenylenediamine (5, 0.009 mol), the mixture was stirred at room temperature for 30 min. The reaction mixture was cooled to 0-5 °C, TBTU(0.02 mol) was added, over a period for 30 min while maintaining the temperature below 5 °C. The reaction was allowed to stir overnight. After completion of the reaction which was monitored by TLC using a mobile-phase system [hexane: ethyl acetate (3:1)], the mixture was diluted with 20 ml of DCM and treated with 2 N hydrochloric acid solution (20 ml). The organic layer was washed with water (3 × 25 ml) and brine (3 × 25 ml). Finally, the organic layer was dried over anhydrous sodium sulfate and concentrated to afford compounds (6a-h). |
Tags: 1878-85-9 synthesis path| 1878-85-9 SDS| 1878-85-9 COA| 1878-85-9 purity| 1878-85-9 application| 1878-85-9 NMR| 1878-85-9 COA| 1878-85-9 structure
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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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