Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 116230-30-9 | MDL No. : | MFCD00277644 |
Formula : | C10H7BrO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VWSBGGRCEQOTNU-UHFFFAOYSA-N |
M.W : | 223.07 | Pubchem ID : | 613827 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 53.67 |
TPSA : | 20.23 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.57 cm/s |
Log Po/w (iLOGP) : | 2.01 |
Log Po/w (XLOGP3) : | 2.95 |
Log Po/w (WLOGP) : | 3.31 |
Log Po/w (MLOGP) : | 3.24 |
Log Po/w (SILICOS-IT) : | 3.16 |
Consensus Log Po/w : | 2.93 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.7 |
Solubility : | 0.0447 mg/ml ; 0.0002 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.04 |
Solubility : | 0.205 mg/ml ; 0.000918 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.36 |
Solubility : | 0.0098 mg/ml ; 0.000044 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.44 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
84% | With bromine; triphenylphosphine In acetonitrile at 0 - 250℃; for 1.5 h; | A synthetic procedure was based on the literature method [12]. To a vigorously stirred mixture of triphenylphosphine (31.5g, 120mmol) in acetonitrile (50.0mL), bromine (19.2g, 120mmol) was added dropwise at 0°C. The reaction mixture was allowed to reach room temperature, and 2,7-dihydroxynaphthalene 1 (16.0g, 100mmol) was added in one portion. The mixture was heated to 70°C for 30min, after which the solvent was removed by rotary evaporation. The flask was equipped with a gas trap, and the black residue was heated to 250°C for 1h. After cooling to room temperature, the mixture was dissolved in 200mL of dichloromethane and the viscous liquid was obtained after column chromatography (silica gel, petroleum ether/dichloromethane 1:1). The crude product was purified by column chromatography (silica gel, petroleum ether/dichloromethane 3:2) to give the compound 2 (18.8g, 84.3mmol, 84percent) as a beige powder. 1H NMR (400MHz, CDCl3) δ (ppm): 5.09 (s, 1H, –OH), 7.06 (d, 1H, J 2.4Hz, naphthalene-H), 7.10 (dd, 1H, J 8.8, 2.8Hz, naphthalene-H), 7.24 (dd, 1H, J 8.8, 2.0Hz, naphthalene-H), 7.63 (d, 1H, J 8.8Hz, naphthalene-H), 7.72 (d, 1H, J 8.8Hz, naphthalene-H), 7.84 (d, 1H, J 1.2Hz, naphthalene-H). 13C NMR (100MHz, CDCl3) δ (ppm): 108.7, 118.1, 120.8, 127.0, 127.3, 128.3, 129.4, 129.9, 135.7, 154.0. HR-ESI-MS m/z: [M−H]− calcd. for C10H6BrO, 220.9602; found, 220.9601. |
66% | With bromine; triphenylphosphine In acetonitrile at 70℃; for 1 h; Schlenk technique | To a stirring suspension of Triphenyl phosphine (31.5 g) in Acetonitrile (50 mL) in a 250 mL10 Schlenk-flaskwas added carefully Bromine (6.2 mL) at 0 00 with a syringe over 30 mm. The yellow solution was warmed to room temperature and 2,7-Dihydroxynaphthalene (16 g) was added in one portion. The reaction was refluxed at 70 00 for one hour. After cooling to room temperature, the solvent was removed under reduced pressure. The reaction flask was connected to a gas-washing bottle filled with a concentrated sodium hydroxide solution. The flask was heatedto 250 00 for two hours and the black residue dissolved in 100 mL Dichloromethane and purified via column chromatography (DCM:Pentan 1:1 to pure DCM). Product 101 was received as a beige powder (14.7 g, 66percent)DC: Dichloromethane:Pentane, 1:1, R=0,21H-NMR: (300 MHz, ODd3) = 7.76 (d, 1 H), 7.63 (d, 1 H), 7.54 (d, 1 H), 7.32 (dd, 1 H), 7.03 (dd, 1H), 6.98 (d, 1H), 4.98 (b, 1H) |
43% | Stage #1: With bromine; triphenylphosphine In acetonitrile at 10℃; for 0.166667 h; Stage #2: for 3 h; Heating / reflux Stage #3: at 280 - 310℃; for 1.08333 h; Neat (no solvent) |
Preparation 2 [0100] Preparation of 2-Bromo-7-methoxy-naphthalene. [CHEMMOL-00021] [0101] Preparation of 7-Bromo-2-naphthalenol. [0102] Triphenyl phosphine (89.7 g, 0.342 mol) and acetonitrile (350 mL) were combined in a 1-L flask under N2 atmosphere. The mixture was cooled to 10° C. Bromine (17.6 mL, 0.342 mol) was added dropwise over 10 minutes. The cooling bath was removed and 2,7-dihydroxynaphthalene (50.0 g, 0.312 mol) was added along with 350 mL of CH3CN rinse. The resulting yellow tan mixture was heated at reflux for 3 hours. Acetonitrile was distilled off under a water aspirator pressure over 2 hours, resulting in a grayish white solid. The solid was heated to 280° C. over 30 minutes giving a black liquid. The liquid was heated to 310° C. over 20 minutes and the temperature was maintained at 310° C. for an additional 15 minutes until gas evolution ceased. The black mixture was cooled to room temperature. Chromatography yielded 34.5 g of the intermediate title compound as an off-white solid which was 87percent pure by HPLC (43percent yield). |
43% | Stage #1: With bromine; triphenylphosphine In acetonitrile for 3 h; Heating / reflux Stage #2: at 280 - 310℃; for 1.08333 h; |
Triphenyl phosphine (89.7 g, 0.342 mol) and acetonitrile (350 mL) were combined in a 1-L flask under N2 atmosphere. The mixture was cooled to 10° C. Bromine (17.6 mL, 0.342 mol) was added dropwise over 10 minutes. The cooling bath was removed and 2,7-dihydroxynaphthalene (50.0 g, 0.312 mol) was added along with 350 mL of CH3CN rinse. The resulting yellow tan mixture was heated at reflux for 3 hours. Acetonitrile was distilled off using a water aspirator over 2 hours resulting in a grayish white solid. The solid was heated to 280° C. over 30 minutes giving a black liquid. The liquid was heated to 310° C. over 20 minutes and the temperature was maintained at 310° C. for an additional 15 minutes until gas evolution ceased. The black mixture was cooled to room temperature. Chromatography yielded 34.5 g of the intermediate title compound as an off-white solid which was 87percent pure by HPLC (43percent yield). |
43% | Stage #1: With bromine; triphenylphosphine In acetonitrile at 10 - 20℃; Stage #2: for 3 h; Heating / reflux Stage #3: at 20 - 310℃; for 1.08333 h; Neat (no solvent) |
Triphenyl phosphine (89.7 g, 0.342 mol) and acetonitrile (350 mL) were combined in a 1-L flask under N2 atmosphere. The mixture was cooled to 10 C. Bromine (17.6 mL, 0.342 mol) was added dropwise over 10 minutes. The cooling bath was removed and 2,7-dihydroxynaphthalene (50.0 g, 0.312 mol) was added along with 350 mL of CH3CN rinse. The resulting yellow tan mixture was heated at reflux for 3 hours. Acetonitrile was distilled off using a water aspirator over 2 hours resulting in a grayish white solid. The solid was heated to 280 C. over 30 minutes giving a black liquid. The liquid was heated to 310 C. over 20 minutes and the temperature was maintained at 310 C. for an additional 15 minutes until gas evolution ceased. The black mixture was cooled to room temperature. Chromatography yielded 34.5 g of the intermediate title compound as an off-white solid which was 87percent pure by HPLC (43percent yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19% | Stage #1: With bromine; triphenylphosphine In acetonitrile for 2 h; Reflux Stage #2: at 250℃; Sealed tube |
Triphenylphosphine (500 mg, 2.9 mmol) was dissolved in MeCN (5 mL), and bromine (0.15 mL, 2.9 mmol) was added at 0 °C whilst stirring. The solution was allowed to warm up to rt, and 7-methoxy-naphthalen-2-ol, 44 (490 mg, 2.8 mmol) was added portionwise. The solution was refluxed for 2 h, and the solvent removed in vacuo. The residue was heated to 250 °C in a sealed tube overnight. After cooling to rt, the residue was purified by chromatography using a stepped gradient of 10–20percent EtOAc in heptane to yield 45 as a beige solid. Yield: 120 mg (19percent). 1H NMR (CDCl3), δ: 5.17 (br, 1H, OH), 7.06 (d, J = 2.5, 1H, ArH), 7.11 (dd, J = 8.7, 2.4, 1H, ArH), 7.40 (dd, J = 8.7, 2.0, 1H, ArH), 7.63 (d, J = 8.9, 1H, ArH), 7.72 (d, J = 8.9, 1H, ArH), 7.84 (s, 1H, ArH). LC–MS: Rf = 2.01 min; m/z 221/223 ([M+H]+, 100). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | at 160℃; for 3 h; Inert atmosphere | Weigh 7-bromo-2-naphthol (2.22g, 10mmol), CuCN (1.08g, 12mmol) was dissolved in 3ml of DMF. Under an argon atmosphere and heated to 160 reflux 3h, track after the reaction of the reaction was cooled to room temperature, 20ml of water, extracted with ethyl acetate. Ethanol - water system recrystallization brown powder 1.4g, 83percent yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With bromine; triphenylphosphine; In acetonitrile; at 0 - 250℃; for 1.5h; | A synthetic procedure was based on the literature method [12]. To a vigorously stirred mixture of triphenylphosphine (31.5g, 120mmol) in acetonitrile (50.0mL), bromine (19.2g, 120mmol) was added dropwise at 0C. The reaction mixture was allowed to reach room temperature, and 2,7-dihydroxynaphthalene 1 (16.0g, 100mmol) was added in one portion. The mixture was heated to 70C for 30min, after which the solvent was removed by rotary evaporation. The flask was equipped with a gas trap, and the black residue was heated to 250C for 1h. After cooling to room temperature, the mixture was dissolved in 200mL of dichloromethane and the viscous liquid was obtained after column chromatography (silica gel, petroleum ether/dichloromethane 1:1). The crude product was purified by column chromatography (silica gel, petroleum ether/dichloromethane 3:2) to give the compound 2 (18.8g, 84.3mmol, 84%) as a beige powder. 1H NMR (400MHz, CDCl3) delta (ppm): 5.09 (s, 1H, -OH), 7.06 (d, 1H, J 2.4Hz, naphthalene-H), 7.10 (dd, 1H, J 8.8, 2.8Hz, naphthalene-H), 7.24 (dd, 1H, J 8.8, 2.0Hz, naphthalene-H), 7.63 (d, 1H, J 8.8Hz, naphthalene-H), 7.72 (d, 1H, J 8.8Hz, naphthalene-H), 7.84 (d, 1H, J 1.2Hz, naphthalene-H). 13C NMR (100MHz, CDCl3) delta (ppm): 108.7, 118.1, 120.8, 127.0, 127.3, 128.3, 129.4, 129.9, 135.7, 154.0. HR-ESI-MS m/z: [M-H]- calcd. for C10H6BrO, 220.9602; found, 220.9601. |
66% | With bromine; triphenylphosphine; In acetonitrile; at 70℃; for 1h;Schlenk technique; | To a stirring suspension of Triphenyl phosphine (31.5 g) in Acetonitrile (50 mL) in a 250 mL10 Schlenk-flaskwas added carefully Bromine (6.2 mL) at 0 00 with a syringe over 30 mm. The yellow solution was warmed to room temperature and 2,7-Dihydroxynaphthalene (16 g) was added in one portion. The reaction was refluxed at 70 00 for one hour. After cooling to room temperature, the solvent was removed under reduced pressure. The reaction flask was connected to a gas-washing bottle filled with a concentrated sodium hydroxide solution. The flask was heatedto 250 00 for two hours and the black residue dissolved in 100 mL Dichloromethane and purified via column chromatography (DCM:Pentan 1:1 to pure DCM). Product 101 was received as a beige powder (14.7 g, 66%)DC: Dichloromethane:Pentane, 1:1, R=0,21H-NMR: (300 MHz, ODd3) = 7.76 (d, 1 H), 7.63 (d, 1 H), 7.54 (d, 1 H), 7.32 (dd, 1 H), 7.03 (dd, 1H), 6.98 (d, 1H), 4.98 (b, 1H) |
43% | Preparation 2 [0100] Preparation of 2-Bromo-7-methoxy-naphthalene. [CHEMMOL-00021] [0101] Preparation of 7-Bromo-2-naphthalenol. [0102] Triphenyl phosphine (89.7 g, 0.342 mol) and acetonitrile (350 mL) were combined in a 1-L flask under N2 atmosphere. The mixture was cooled to 10 C. Bromine (17.6 mL, 0.342 mol) was added dropwise over 10 minutes. The cooling bath was removed and 2,7-dihydroxynaphthalene (50.0 g, 0.312 mol) was added along with 350 mL of CH3CN rinse. The resulting yellow tan mixture was heated at reflux for 3 hours. Acetonitrile was distilled off under a water aspirator pressure over 2 hours, resulting in a grayish white solid. The solid was heated to 280 C. over 30 minutes giving a black liquid. The liquid was heated to 310 C. over 20 minutes and the temperature was maintained at 310 C. for an additional 15 minutes until gas evolution ceased. The black mixture was cooled to room temperature. Chromatography yielded 34.5 g of the intermediate title compound as an off-white solid which was 87% pure by HPLC (43% yield). |
43% | Triphenyl phosphine (89.7 g, 0.342 mol) and acetonitrile (350 mL) were combined in a 1-L flask under N2 atmosphere. The mixture was cooled to 10 C. Bromine (17.6 mL, 0.342 mol) was added dropwise over 10 minutes. The cooling bath was removed and 2,7-dihydroxynaphthalene (50.0 g, 0.312 mol) was added along with 350 mL of CH3CN rinse. The resulting yellow tan mixture was heated at reflux for 3 hours. Acetonitrile was distilled off using a water aspirator over 2 hours resulting in a grayish white solid. The solid was heated to 280 C. over 30 minutes giving a black liquid. The liquid was heated to 310 C. over 20 minutes and the temperature was maintained at 310 C. for an additional 15 minutes until gas evolution ceased. The black mixture was cooled to room temperature. Chromatography yielded 34.5 g of the intermediate title compound as an off-white solid which was 87% pure by HPLC (43% yield). | |
43% | Triphenyl phosphine (89.7 g, 0.342 mol) and acetonitrile (350 mL) were combined in a 1-L flask under N2 atmosphere. The mixture was cooled to 10 C. Bromine (17.6 mL, 0.342 mol) was added dropwise over 10 minutes. The cooling bath was removed and 2,7-dihydroxynaphthalene (50.0 g, 0.312 mol) was added along with 350 mL of CH3CN rinse. The resulting yellow tan mixture was heated at reflux for 3 hours. Acetonitrile was distilled off using a water aspirator over 2 hours resulting in a grayish white solid. The solid was heated to 280 C. over 30 minutes giving a black liquid. The liquid was heated to 310 C. over 20 minutes and the temperature was maintained at 310 C. for an additional 15 minutes until gas evolution ceased. The black mixture was cooled to room temperature. Chromatography yielded 34.5 g of the intermediate title compound as an off-white solid which was 87% pure by HPLC (43% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31 mg | With dipotassium peroxodisulfate; silver(I) acetate; copper diacetate; In water; at 20℃; for 12h; | 1 mmol of 7-bromo-2 naphthol was added to 4 ml of water-soluble (containing 2% Triton-X-100 surfactant), 0.2 mmol of copper acetate was added thereto, 1.0mmol potassium persulfate, 1.0mmol silver acetate, reaction for 12 hours at room temperature, after the reaction was completed, a saturated NaCl aqueous solution was added to the reaction solution, followed by extraction with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated to dryness under reduced pressure to obtain a crude compound. The crude compound was subjected to silica gel column chromatography, and a solution having a volume ratio of ethyl acetate and petroleum ether of 1: 3 was used as a mobile phase. The eluate with an Rf value of 0.3-0.5 was collected by TLC. The resulting eluate was collected, the solvent was removed under reduced pressure, and dried. 31 mg of a pure compound represented by the formula (II-11) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With potassium carbonate; In N,N-dimethyl-formamide; for 72h; | 2-Bromo-7-methoxynaphthalene Methyl iodide (2 mL, 32.1 mmol) was added to a mixture of <strong>[116230-30-9]7-bromonaphthalen-2-ol</strong> (6.26 g, 28.0 mmol) and K2CO3 (4.62 g, 33.4 mmol) in DMF (21 mL). After stirring for 3 days, the mixture was partitioned between ethyl acetate/H2O and the organic solution was further washed with H2O (5*60 mL). The organic solution was then dried (Na2SO4), filtered and evaporated. Purification by flash chromatography (ethyl acetate/hexanes) gave the title compound (6.41 g, 96%). |
95.4% | Step 1: 2-bromo-7-methoxynaphthalene[00434j To a suspention of 60 % NaH (888 mg, 22.20 mmol) in 30 mL of DMF was added <strong>[116230-30-9]7-bromonaphthalen-2-ol</strong> (4.50 g, 20.20 mmol) dropwies under N2 at ice bath. After the addition, the mixture was stirred at rt for 30 minutes. Then the mixture was cooled at ice bath again, and to the mixture was added iodomethane (4.30 g, 30.30 mmol) dropwies. After the addition, the mixture was stirred at rt overnight, quenched with water (100 mL), and extracted with EtOAc (50 mL x 2). The combined organic phases were washed with water (50 mL x 2) and saturated brine (100 mL), dried over anhydrous Na2SO4 (10 g), filtered and concentrated in vacuo. The crude was purified by silica column chromatography (PE/EtOAc (v/v) = 100/1) to give the title compound as a white solid (4.57 g, 95.4 %). | |
84.4% | With potassium carbonate; In acetone; for 2h;Inert atmosphere; Reflux; | Example 1 Production of Compound (1) Under the argon atmosphere, 500 mL of dry acetone was added to 80.0 g (359 mmol) of <strong>[116230-30-9]2-bromo-7-hydroxynaphthalene</strong> and 149 g (1.08 mol) of potassium carbonate, and the mixture was stirred at room temperature. After 44.9 mL (720 mmol) of iodomethane was added dropwise to the mixture, and then refluxed for two hours. The reaction mixture was cooled to room temperature, and 250 mL of water was added thereto. Acetone was distilled off under the reduced pressure, 750 mL of water was further added thereto, and the mixture was stirred for 10 minutes. The generated white precipitate was filtered and the filtrate was washed with 1.5 L of water. The obtained white solid is dried to thereby obtain 71.8 g of 2-bromo-7-methoxynaphthalene (yield, 84.4%).?H NMR (300 MHz, CDC13): oe7.89 (d, J=Hz, 1H), oe7.69 (d, J=9.3 Hz, 1H), oe7.62 (s, J=9.0 Hz, 6H), oe7.40 (dd, J=1.8Hz, 8.4 Hz, 1H), oe7.14 (dd, J=2.4 Hz, 9.0 Hz, 1H), oe7.02 (s,J=2.4 Hz, 1H) |
With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 20℃; for 3.75h; | Preparation of Final Title Compound. [0104] 2-Bromo-7-hydroxynaphthalene (34.1 g, 0.134 mol), DMF (290 mL) and powdered potassium carbonate (31.8 g, 0.230 mol) were combined in a 500-mL flask under N2 atmosphere. Methyl iodide (14.3 mL, 0.230 mol) was added at once and the dark yellow mixture was stirred vigorously at room temperature for 3 ¾ hours. Water (290 mL) was added dropwise over 15 minutes to induce crystallization. The mixture was stirred at room temperature for 1 hour. The product was filtered off and washed with 200 mL of a 1:1 mixture of DMF and water. The solid was dried in vacuo at 50 C. to yield 32.6 g of pale yellow solid (HPLC: 89%). The solid was dissolved in 300 mL of boiling MeOH. The hot solution was filtered, then placed in a freezer overnight. The resulting crystals were filtered and washed with 100 mL of cold MeOH. The solid was dried in vacuo at 50 C. to give 27.0 g of pale yellow solid (HPLC: 95%). The solid was dissolved in 100 mL of boiling i-PrOH then allowed to cool to room temperature. The resulting solid was filtered and washed with 100 mL of i-PrOH. The solid was dried in vacuo at 50 C. to yield 22.8 g of final title compound as pale yellow crystals. | |
With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 20℃; for 3.75h; | 2-Bromo-7-hydroxynaphthalene (34.1 g, 0.134 mol), DMF (290 mL) and powdered potassium carbonate (31.8 g, 0.230 mol) were combined in a 500-mL flask under N2 atmosphere. Methyl iodide (14.3 mL, 0.230 mol) was added at once and the dark yellow mixture was stirred vigorously at room temperature for 3¾ hours. Water (290 mL) was added dropwise over 15 minutes to induce crystallization. The mixture was stirred at room temperature for 1 hour. The product was filtered off and washed with 200 mL of a 1:1 mixture of DMF and water. The solid was dried in vacuo at 50 C. to yield 32.6 g of pale yellow solid (HPLC: 89%). The solid was dissolved in 300 mL of boiling MeOH. The hot solution was filtered, then placed in the freezer overnight. The resulting crystals were filtered and washed with 100 mL of cold MeOH. The solid was dried in vacuo at 50 C. to give 27.0 g of pale yellow solid (HPLC: 95%). The solid was dissolved in 100 mL of boiling i-PrOH then allowed to cool to room temperature. The resulting solid was filtered and washed with 100 mL of i-PrOH. The solid was dried in vacuo at 50 C. to yield 22.8 g of final title compound as pale yellow crystals | |
With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 20℃; for 3.75h; | 2-Bromo-7-hydroxynaphthalene (34.1 g, 0.134 mol), DMF (290 mL) and powdered potassium carbonate (31.8 g, 0.230 mol) were combined in a 500-mL flask under N2 atmosphere. Methyl iodide (14.3 mL, 0.230 mol) was added at once and the dark yellow mixture was stirred vigorously at room temperature for 3 hours. Water (290 mL) was added dropwise over 15 minutes to induce crystallization. The mixture was stirred at room temperature for 1 hour. The product was filtered off and washed with 200 mL of a 1:1 mixture of DMF and water. The solid was dried in vacuo at 50 C. to yield 32.6 g of pale yellow solid (HPLC: 89%). The solid was dissolved in 300 mL of boiling MeOH. The hot solution was filtered, then placed in the freezer overnight. The resulting crystals were filtered and washed with 100 mL of cold MeOH. The solid was dried in vacuo at 50 C. to give 27.0 g of pale yellow solid (HPLC: 95%). The solid was dissolved in 100 mL of boiling i-PrOH then allowed to cool to room temperature. The resulting solid was filtered and washed with 100 mL of i-PrOH. The solid was dried in vacuo at 50 C. to yield 22.8 g of the title compound as pale yellow crystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium hydrogen sulfite; ammonia; In water; at 150℃; for 27h; | Example 13 Synthesis of 2-amino-7-bromonaphthalene (Intermediate 26) According to the procedure described in the aforementioned reference [L. C. Anderson et al., Journal of the American Chemical Society (J. Am. Chem. Soc.), vol. 65, p.241, 1943], <strong>[116230-30-9]2-bromo-7-hydroxynaphthalene</strong> (2.23 g, MAYB) was added with 30% aqueous ammonia (30 ml) and ammonium sulfite monohydrate (2.69 g, WAKO) and stirred in a shield tube at 150 C. for 27 hours.The reaction mixture was added with ethyl acetate (90 ml) for extraction and then added with 1 N aqueous hydrochloric acid (1.5 l).The aqueous layer was separated, washed with ethyl acetate, then neutralized by adding 5 N aqueous sodium hydroxide (300 ml) under ice cooling and extracted with ethyl acetate again.The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure to obtain the title compound (Intermediate 26, 1.00 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With tetrabutylammomium bromide; potassium carbonate; In acetonitrile; for 1h;Heating / reflux; | To a solution of 7-bromo-naphth-2-ol (1.0 g, 4.5 mmol, prepared according to patent WO 0146187 A1) in acetonitrile (10 ml) was added diethyl sulfate (1.04 g, 6.7 mmol), K2CO3 (0.92 g) and tetrabutylammonium bromide (10 mg). The reaction mixture was refluxed for 1 hour, poured on water and extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered and the solvent was removed under reduced pressure to provide 2-bromo-7-ethoxynaphthalene (89%), MS: m/e=252 (M+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 1 Preparation of 2-[(7-bromo-2-naphthalenyl)oxy]-N-(2-methoxy-l, 1- dimethylethyl)butanamide (Compound 7)Step A: Preparation of methyl 2-[(7-bromo-2-naphthalenyl)oxy]butanoate To a solution of 7-bromo-2-naphthol (4.5 g, 20 mmol) in acetone (200 mL) was added cesium carbonate (16.4 g, 50 mmol) at room temperature under nitrogen atmosphere with stirring. After the addition, the mixture was stirred at the room temperature for 3 minutes and then methyl-2-bromobutyrate (5.4 g, 30 mmol) was added. The mixture was stirred under nitrogen atmosphere at reflux overnight. The reaction mixture was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the resultant residue was purified by column chromatography (ethyl acetate in hexanes in volume ratios from 10 to 40 % as eluents) to give the title compound (6.08 g) as a solid. .H NMR (CDCI3) delta 1.11 (t, 3H), 2.05 (m, 2H), 3.75 (s, 3H), 4.71 (t, 1H), 6.95 (s, 1H), 7.2 (d, 1H), 7.39 (d, 1H), 7.59 (d, 1H), 7.7 (d, 1H), 7.84 (s, 1H). | ||
To a solution of 7-bromo-2-naphthol (4.5 g, 20 mmol) in acetone (200 mL) was added cesium carbonate (16.4 g, 50 mmol) at room temperature under nitrogen atmosphere with stirring. After the addition, the mixture was stirred at the room temperature for 3 minutes and then methyl-2-bromobutyrate (5.4 g, 30 mmol) was added. The mixture was stirred under nitrogen atmosphere at reflux overnight. The reaction mixture was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the resultant residue was purified by column chromatography (ethyl acetate in hexanes in volume ratios from 10 to 40 % as eluents) to give the title compound (6.08 g) as a solid. 1H MR (CDC13) delta 1.1 1 (t, 3H), 2.05 (m, 2H), 3.75 (s, 3H), 4.71 (t, 1H), 6.95 (s, 1H), 7.2 (d, 1H), 7.39 (d, 1H), 7.59 (d, 1H), 7.7 (d, 1H), 7.84 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1H-imidazole; In dichloromethane; at 0 - 20℃; | EXAMPLE 18 Preparation of 2-[(7-iodo-2-naphthalenylyl)oxy]-2-methoxy-N-(2-methoxy-l,l- dimethylethyl)acetamide (Compound 103)Step A: Preparation of 2-bromo-7-[[(l,l-dimethylethyl)dimethylsilyl]oxy]naphthalene To a solution of 7-bromo-2-naphthol (2.23 g, 10 mmol) in dichloromethane (21 mL) at 0 C was added imidazole (1.5 g, 22 mmole) and t-butyldimethylsilylchloride (1.66 g, 11 mmole). The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane (70 mL) and the resulting mixture was washed with saturated aqueous NaHCC^ solution twice (100 mL each). The organic phase was separated, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (over silica gel with ethyl acetate and hexanes in volume ratios from 10 to 40 % as eluents) to give the title compound (3.3 g) as an oil. in NMR (CDCI3) delta 0.25 (s, 6H), 1.02 (s, 9H), 7.08 (m, 2H), 7.4 (d, 1H), 7.6 (d, 1H), 7.7 (d, 1H), 7.85 (s, 1H). | |
With 1H-imidazole; In dichloromethane; at 0 - 20℃; | To a solution of 7-bromo-2-naphthol (2.23 g, 10 mmol) in dichloromethane (21 mL) at 0 C was added imidazole (1.5 g, 22 mmole) and ?-butyldimethylsilylchloride (1.66 g, 1 1 mmole). The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane (70 mL) and the resulting mixture was washed with saturated aqueous NaHCC^ solution twice (100 mL each). The organic phase was separated, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (over silica gel with ethyl acetate and hexanes in volume ratios from 10 to 40 % as eluents) to give the title compound (3.3 g) as an oil. .H MR (CDCI3) delta 0.25 (s, 6H), 1.02 (s, 9H), 7.08 (m, 2H), 7.4 (d, 1H), 7.6 (d, 1H), 7.7 (d, 1H), 7.85 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With potassium phosphate; 1-(3,5-bis(trifluoromethyl)phenyl)-3-((1S)-(6-methoxyquinolin-4-yl)(5-vinylquinuclidin-2-yl)methyl)thiourea; In toluene; at 30℃; for 24h; | General procedure: Arenesulfonylalkylindoles 1 (0.1 mmol), 2-naphthols 2 (0.1 mmol), Catalyst 3b (0.01 mmol), K3PO4(0.3 mmol) were put into anordinary test tube equipped with a magnetic stirring bar and then sealed in theair. Then, toluene (1 mL) was added, and the resulting mixture was stirred at 30 C for 24 h. The products 4 were isolated by flash chromatography on silica gel(DCM/petroleum ether = 1:2-1:20). All the products wereconfirmed by 1H NMR and 13CNMR spectroscopic analysis. The enantiomeric excess was determined bychiral-phase HPLC analysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With potassium phosphate; 1-(3,5-bis(trifluoromethyl)phenyl)-3-((1S)-(6-methoxyquinolin-4-yl)(5-vinylquinuclidin-2-yl)methyl)thiourea; In toluene; at 30℃; for 24h; | General procedure: Arenesulfonylalkylindoles 1 (0.1 mmol), 2-naphthols 2 (0.1 mmol), Catalyst 3b (0.01 mmol), K3PO4(0.3 mmol) were put into anordinary test tube equipped with a magnetic stirring bar and then sealed in theair. Then, toluene (1 mL) was added, and the resulting mixture was stirred at 30 C for 24 h. The products 4 were isolated by flash chromatography on silica gel(DCM/petroleum ether = 1:2-1:20). All the products wereconfirmed by 1H NMR and 13CNMR spectroscopic analysis. The enantiomeric excess was determined bychiral-phase HPLC analysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With caesium carbonate; In N,N-dimethyl-formamide; at 80℃; for 16h; | Ste 1 : 2-bromo-7-((cis-4-(trifluoromethyl)cyclohexyl)oxy)naphthalene A mixture of <strong>[116230-30-9]7-bromonaphthalen-2-ol</strong> (6.6 g, 30.0 mmol, 1.0 eq), CS2CO3 (19.5 g, 60.0 mmol, 2.0 eq) and cis-4-(trifluoromethyl)cyclohexyl methanesulfonate (11.2 g, 45.0 mmol, 1.5 eq ) in DMF (80 mL) was stirred at 80 C for 16 h and cooled down. The mixture was diluted with EtOAc (200 mL) and washed with water (200 mLx2). The organic layer was dried over Na2S04 and concentrated to yield a crude product, which was purified by column chromatography on silica gel (petroleum ether as eluent) to give 2-bromo-7-((cis-4-(trifluoromethyl)cyclohexyl)oxy)naphthalene (6.5 g, Y: 55%) as yellow solid. 1H NMR (400 MHz, CDC13) delta: 7.86 (d, = 1.6 Hz, 1H), 7.71 (d, = 8.8 Hz, 1H), 7.62 (d, = 8.4 Hz, 1H), 7.39 (dd, / = 1.6 Hz, 8.4 Hz, 1H), 7.17 (dd, / = 2.4 Hz, 8.8 Hz, 1H), 7.04 (d, = 2.4 Hz, 1H), 4.71 (s, 1H), 2.26-2.22 (m, 2H), 2.17-2.07 (m, 1H), 1.87-1.77 (m, 4H), 1.64-1.59 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 1h; | 2-bromo-7-((cis-4-ethylcyclohexyl)oxy)naphthalene Into a mixture of <strong>[116230-30-9]7-bromonaphthalen-2-ol</strong> (10 g, 45 mmol, 1.0 eq) and trans-4-ethylcyclohexanol (6.92 g, 54 mmol, 1.2 eq ) in THF (100 mL) was added PPh3 (23.6 g, 90 mmol, 2.0 eq), followed by DIAD (18.1 g, 90 mmol, 2.0 eq) at rt. The mixture was stirred at rt for 1 h and diluted with petroleum ether (1000 mL). The precipitate was filtered off and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (petroleum ether as eluent) to give 2-bromo-7-((cis-4-ethylcyclohexyl)oxy)naphthalene as white solid (7.5 g, Y: 50%). ESI-MS (M+H) +: 333.1. XH NMR (400 MHz, CDC13) delta: 7.85 (s, 1H), 7.69 (d, = 9.2 Hz , 1H), 7.60 (d, = 8.4 Hz, 1H), 7.37 (dd, / = 2.0 Hz, 8.8 Hz, 1H), 7.16 (dd, / = 2.4 Hz, 9.2 Hz, 1H), 7.04 (d, = 2.4 Hz, 1H), 4.65 (s, 1H), 2.08-2.04 (m, 2H), 1.66- 1.55 (m, 4H), 1.16-1.30 (m, 5H), 0.90 (t, = 6.8 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With caesium carbonate; In N,N-dimethyl-formamide; at 85℃; | Example 1: 4-((7-((cis-4-methylcyclohexyl)oxy)-8-(trifluoromethyl)naphthalen-2-yl)methyl)morphol ine -bromo-7-(cis-4-methyl-cyclohexyloxy)-naphthalene To a mixture of <strong>[116230-30-9]2-bromo-7-hydroxynaphthalene</strong> (1.2 g, 0.0053 mol) and cesium carbonate (3.440 g, 0.01056 mol) in N,N-dimethylformamide (10 mL, O.lmol) was added methanesulfonic acid cis-4-methyl-cyclohexyl ester (2 g, 0.01 mol) in two portion. The resulting mixture was heated at 85 C overnight, and cooled to room temperature, diluted with Et20, washed with water, brine and dried over Na2S04. The crude mixture was then purified by silica gel (EtO Ac/heptane gradient 0% to 30%) to give product 2-bromo-7-(cis-4-methyl-cyclohexyloxy)-naphthalene as a solid (778 mg, 46%). LCMS RT = 2.53 min, m/z = 319.10 [M+]. 1H NMR (400 MHz, CHLOROFORM-d) delta 7.86 (s, 1H), 7.71 (d, J = 8.97 Hz, 1H), 7.62 (d, J = 8.66 Hz, 1H), 7.38 (d, J = 8.66 Hz, 1H), 7.17 (d, J = 8.85 Hz, 1H), 7.06 (s, 1H), 4.65 (br. s., 1H), 2.08 (d, J = 13.55 Hz, 2H), 1.34 - 1.73 (m, 8H), 0.97 (d, J = 4.71Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.6% | Weigh TiCl4 (797mg, 4.2mmol) and 1,1-dichloromethyl methyl ether (253mg, 2.2mmol) in 2ml of dichloromethane, at 0 C and stirred 15min. Weigh <strong>[116230-30-9]2-hydroxy-7-bromo-naphthalene</strong> (446mg, 2mmol) in 6ml of dichloromethane was added dropwise to the reaction solution, stirred at room temperature 12h, was added a hydrochloric acid solution 20ml1N After the reaction, ethyl acetate, dried over anhydrous sodium sulfate, the product obtained directly 440mg, yield 87.6%. | |
General procedure: 6-Bromo-2-hydroxynaphthalene-1-carbaldehyde (AstaTech, Bristol, PA, USA). A solution of TiCl4 (1.0 Min CH2Cl2, 27 mmol, 27 mL) in dichloromethane was treated with a solution of dichloromethyl methylether (13.5 mmol) in 1,2-dichloroethane or dichloromethane (3 mL) at 0 C for 15 min. A solution of6-bromo-2-hydroxy naphthalene (13.5 mmol) in CH2Cl2 (30 mL) was added dropwise, and thereaction was allowed to stir overnight with gradual warm up to the room temperature. The reactionwas quenched by adding 1 M HCl (10 mL). The aqueous layer was extracted with CH2Cl2 (×3) andthe organic layers were then combined, dried over Na2SO4, and reduced to dryness to afford areddish-brown residue which was further purified using medium pressure chromatography using agradient EtOAc/hexane solvent system (1-10% EtOAc) to yield 1.4 g (1.20 g, 5.8 mmol, 43%) of thedesired product as a white powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With toluene-4-sulfonic acid; at 125℃; for 24h; | To a mixture of benzaldehyde (1 mmol) and bromo-naphthol 101 (2 mmol), p-TSA (0.02 mmol) was added. The reaction mixture was stirred magnetically at 125 0C for about 24 h and the reaction followed by TLC. After completetion of the reaction, the mixture was washed with EtOH-H20 (1:3). The crude product was purified by recrystallization from EtOH to give target compound 107. White needles (yield = 86%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With tetrakis(triphenylphosphine) palladium(0); barium hydroxide octahydrate; In 1,4-dioxane; water; at 20℃; for 24h;Reflux; Inert atmosphere; | Phenylboronic acid (0.24 g, 2.0 mmol)Ba (OH) 2 · 8H2O (0.9 g, 2.8 mmol)Pd (PPh3) 4 (0.06 g, 0.05 mmol)1,4-dioxane (10 mL),H2O (3 mL) and 7-bromo-2-naphthol (1.5 mmol) were refluxed under nitrogen24h,Cooled to room temperature,Remove 1,4-dioxane,The resulting phase was dissolved in DCM (30 mL)1 M hydrochloric acid (20 mL x 3), saturated brine (20 mL x 2), dried over Na2SO4,Removing the solvent,The residue was purified by silica gel column chromatography (PE / DCM = 2/1) to give the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With C38H40O6; In dichloromethane; at -78℃; for 24h; | To a solution of <strong>[116230-30-9]7-bromonaphthalen-2-ol</strong> (0.12 mmol)And chiral phosphoric acid C1 (5 mol%) were dissolved in anhydrous DCM (1 mL)The resulting solution was stirred for 15min at -78 ,Then, 2-ethoxycarbonyl-1,4-benzoquinone (0.10 mmol) was dissolved in 1 mL of dichloromethane,The reaction was stirred at -78 ,With TLC monitoring,After 24 hours the reaction solution was concentrated,Purification by silica gel column chromatography gave ethyl (R) -3,6-dihydroxy-2- (2-hydroxy-7-bromonaphthalen-1-yl) benzoate.TLC developing agent:DCM / EA = 30/1 (volume ratio);82% yield;91% ee; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With stannic bromide; In dichloromethane; at 20℃; for 24h;Inert atmosphere; | General procedure: To a solution of SnBr4 (2.7 mg. 6.16 mumol) in CH2Cl2 (1.3 mL) at room temperature wassuccessively added benzhydrol (1a) (22.6 mg. 0.123 mmol), and 2-naphthol (28.3 mg, 0.196mmol). The reaction mixture was stirred for 24 h at room temperature and then it was quenchedwith saturated aqueous NaHCO3 at 0 C. The organic layer was separated and the aqueous layerwas extracted with CH2Cl2. The combined organic layer was dried over Na2SO4. After filtrationof the mixture and evaporation of the solvent, the crude product was purified by preparative thinlayer chromatography on silica (toluene) to afford the desired compound 2a (36.6 mg, 96%yield) as a pale-brownish solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | General procedure: Reaction of 7-bromo-2-naphthol III-2 as a substrate yields the product (R) -7- bromo-2-methylene- 1 -phenyl-1,2-dihydronaphtho [2,1-b ] Furan I-2.Naphthol III-1 in Example 2 was replaced with 7-bromo-2-naphthol III-2,The rest with Example 2,(R) -7-bromo-2-methylene-1-phenyl-1,2-dihydronaphtho [2,1-b] furan I-2 in 82% yield,95% ee.Example 2- L-2-2 is prepared as a ligand (R) -2-Methylene-1-phenyl-1,2-dihydronaphtho [2,1-b] furan I-1.The ligand L-2-1 in Example 1 is replaced with ligand L-2-2,The rest with Example 1.The reaction gives compound I-1,92% yield,93% ee.Example 1- Cu (OAc) 2.H2O and L-2-1 as a catalyst for catalytic reaction, The product (R) -2-methylene-1-phenyl-1,2-dihydronaphtho [2,1-b] furan was obtained-1. Cu (OAc) 2.H2O (0.015 mmol, 5 mol%) and chiral ligand L-2-1 (0.0165 mmol, 5.5 mol%) were added to the reaction flask, Nitrogen gas was added 1.0 ml of anhydrous methanol, Stir at room temperature for 1 hour. Propargyl alcohol ester IV-1 (0.3 mmol, 1 equiv),Naphthol III-1 (0.36 mmol, 1.2 equiv) and N, N-diisopropylethylamine (0.36 mmol, 1.2 equiv) were dissolved in 2.0 ml of anhydrous methanol,The solution was then added under nitrogen to the above stirred catalyst solution,-40 stirring reaction 24h.The reaction is completed,Rotate to 0.5 ml under reduced pressure,The silica gel column was separated (petroleum ether / ethyl acetate = 150: 1)Concentrated under reduced pressure to no volatile solvents,Vacuum dried,Compound I-1 was obtained,White solid,86% yield,90% ee. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With C37H31F6N3S; In diethyl ether; at -78℃; for 0.25h; | General procedure: 0. 12mmol compound of Shulun Ke in the tube 2 and the chiral catalyst dissolved in an organic solvent, the resulting solution was stirred for lOmin at -78 C, then added 0. lOmmol compound 1, the reaction to the disappearance of the red, the completion of the reaction was monitored by TLC after the reaction solution was acidified with 6N hydrochloric acid, concentrated, silica gel column chromatography (CH2C12~CH2C12 / acetone = 10/1) to yield the product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In N,N-dimethyl-formamide; at 160℃; for 3h;Inert atmosphere; | Weigh 7-bromo-2-naphthol (2.22g, 10mmol), CuCN (1.08g, 12mmol) was dissolved in 3ml of DMF. Under an argon atmosphere and heated to 160 reflux 3h, track after the reaction of the reaction was cooled to room temperature, 20ml of water, extracted with ethyl acetate. Ethanol - water system recrystallization brown powder 1.4g, 83% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 1h;Reflux; | 7-bromo-2-naphthol (21g, 94.1mmol) and amine boron acid (45.6g, 103.5mmol) andWas dissolved in potassium carbonate (K2CO3) (39g, 282mmol) in tetrahydrofuran (THF) (300mL), water (H2O) (100ml) was heated to 90 . After addition of tetrakis (triphenylphosphine) palladium (Pd (PPh3) 4) (2.17g, 1.88mmol) was refluxed for 1 hour. After cooling to room temperature to remove the water layer. After loading the hwangsang magnesium (MgSO4) the organic layer was filtered. After concentration is purified by column chromatography to obtain a formula 2A (40g, yield 79%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 1h;Reflux; | 7-bromo-2-naphthol (21g, 94.1mmol) and carbazole boron acid(29.7g, 103.5mmol) and Was dissolved in potassium carbonate (K2CO3) (39g, 282mmol) in tetrahydrofuran (THF) (300mL), water (H2O) (100ml) was heated to 90 .After addition of tetrakis (triphenylphosphine) palladium (Pd (PPh3) 4) (2.17g, 1.88mmol) was refluxed for 1 hour. After cooling to room temperature to remove the water layer. After the insert was the hwangsang magnesium (MgSO4) the organic layer was filtered. After concentration is purified by column chromatography to obtain the compound of Formula 1A (30g, 85% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 12h;Reflux; Inert atmosphere; | Reagent 8-1 (50.0 g, 114.94 mmol) and Reagent 9-2 (25.6 g, 206.43 mmol) were put into 1,000 ml of tetrahydrofuran under a nitrogen atmosphere, and the resulting mixture was stirred and refluxed. Thereafter, potassium carbonate (71.2 g, 515.11 mmol) was dissolved in 200 ml of water, the resulting solution was introduced into the mixture, the resulting mixture was sufficiently stirred, and then tetrakistriphenyl-phosphinopalladium (8.9 g, 7.73 mmol) was introduced thereinto. After the reaction for 12 hours, the temperature of the product was lowered to normal temperature and a produced solid was filtered. After the filtration, the solid was washed with 100 ml of tetrahydrofuran, 500 ml of ethyl acetate, 500 ml of water, and 300 ml of ethanol. The resulting product was dried to prepare Compound 9A (42 g, 81%). Reagents 8-1 and 9-2 were purchased from Aldrich and TCI, respectively. |
71% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 1h;Reflux; | 7-bromo-2-naphthol (21g, 94.1mmol) and the triazine-dioxoborane (50g, 114.9mmol) and potassium carbonate (K2CO3) (39g, 282mmol) in tetrahydrofuran (THF) (300mL), H2O dissolved in (100ml) it was heated to 90C . After addition of tetrakis (triphenylphosphine) palladium (Pd (PPh3) 4) (2.17g, 1.88mmol) was refluxed for 1 hour. After cooling to room temperature to remove the water layer. After loading the hwangsang magnesium (MgSO4) the organic layer was filtered. After concentration and purification by column chromatography the formula 1A (30g, yield 71%) was obtained. |
55% | With bis(tri-t-butylphosphine)palladium(0); potassium carbonate; In tetrahydrofuran; water; for 12h;Inert atmosphere; Reflux; | In a nitrogen atmosphere 2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl)1,3,5-triazine(2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,5-triazine (reagent 13-1, 30 g, 69 mmol)And <strong>[116230-30-9]7-bromonaphthalene-2-ol</strong>(<strong>[116230-30-9]7-bromonaphthalen-2-ol</strong>) (reagent 13-2, 15 g, 69 mmol)Was dissolved in 300 ml of tetrahydrofuranAnd stirred and refluxed.After this, potassium carbonate (29 g, 206 mmol) was dissolved in 90 ml of water, And then bis (tri-tert-butylphosphine) palladium (0.4 g, 0.7 mmol) was added thereto.After 12 hours of reaction, the temperature was lowered to room temperature and filtered.The filtrate was extracted with chloroform and water, and then the organic layer was dried with magnesium sulfate. The organic layer was then distilled under reduced pressure and recrystallized using ethyl acetate.The resulting solid was filtered and dried to give Intermediate 13-1 (17 g, 55%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With boron trifluoride diethyl etherate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In chloroform; toluene; at 80℃; for 1h;Inert atmosphere; | General procedure: An oven dried Schlenk tube of 25 mL equipped with a magnetic stir bar was charged with naphthalen-2-ol 1 (0.2 mmol) and DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone, 0.6 mmol, 3.0 equiv.), after charging nitrogen for three times, alkene 2 (0.4 mmol, 2 equiv.), BF3xEt2O (10 mol %), toluene (1.4 mL), and CHCl3 (0.6 mL) were added. The reaction mixture was heated at 80 C for 1 h. After completion of the reaction, the reaction mixture was cooled to room temperature and the volatiles were removed under reduced pressure. The crude reaction mixture was purified over silica-gel (300-400 mesh) column chromatography using petroleum ether-ethylacetate as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With 1-Chloromethyl-4-methyl-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate); In acetonitrile; at 20℃; for 72h; | To a solution of 7-bromo-2-naphthol (0.22g, 1mmol) in acetonitrile (7mL) was added F-TEDA-BF4 (0.71g, 2mmol) in small portions under vigorous stirring. The resulting mixture was stirred at room temperature for 3days. The solution was diluted with EtOAc (7mL) and washed with brine (3×5mL). The organic phase was separated, dried over MgSO4. Solvent was removed under reduced pressure. The residue was purified by column chromatography (silica gel, chloroform). Yield 210mg (96%). Yellow solid. Chromatography: chloroform. Mp 92.2-96.7C. 1 NMR (300MHz, CDCl3), delta: 6.24 (dt, J=10.1 Hz, J=2.8 Hz, 1, H3), 7.22 (m, 1, H6), 7.38 (d, J=10.1 Hz, 1, H4), 7.67 (m, 1, H5), 7.94 (m, 1, H8). 13C NMR (75MHz, CDCl3), delta: 104.7 (t, J=245.9Hz, C1), 123.6 (t, J=2.6Hz, C3), 125.6 (t, J=2.2Hz, C7), 129.0 (t, J=5.3Hz, C10), 130.9 (t, J=3.5Hz, C8), 131.1 (s, C5), 134.6 (t, J=23.9Hz, C9), 135.3 (s, C6), 144.6 (s, C4), 186.4 (t, J=24.7Hz, C2). 19F NMR (282MHz, CDCl3), delta: -101.4 (br. s, 1F). Calcd for C10H5BrF2O (257.95): , 46.36; , 1.95; F, 14.67; Br, 30.85. Found: , 46.40; , 1.99; F, 14.39; Br, 31.00. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19% | With tris(2,2'-bipyridyl)ruthenium dichloride; lipase B Candida antarctica In water; acetonitrile at 20℃; Irradiation; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | A solution of <strong>[116230-30-9]7-bromonaphthalen-2-ol</strong> (4.43 g, 20 mmol) in DME (30 mmol) was added dropwiseto a suspension of NaH (60% oil dispersion, 1.4 g, 30 mmol) in DME (15 mL) at 0 C, and themixture was stirred at room temperature for 10 min. Et2NCOCl (4.1 g, 30 mmol) and DMAP (24mg, 1 mol%) was then added to the reaction mixture and stirred at room temperature for 2 h. Thesolvent was removed in vacuo to give a residue, which was dissolved in EtOAc and filtered througha pad of silica gel. The filtrate was then concentrated in vacuo to give the crude product, which waspurified by flash column chromatography over silica gel (eluent: hexane/EtOAc = 10/1) to give 1k(6.3 g, 98%) as a colorless oil.Rf 0.39 (hexane/EtOAc = 5/1). Colorless oil (6.3 g, 98%).1H NMR (CDCl3, 400 MHz): delta 7.94 (d, J = 1.8 Hz, 1H), 7.79 (d, J = 9.2 Hz, 1H), 7.68 (d, J = 8.7Hz, 1H), 7.50 (dd, J = 8.9, 2.1 Hz, 2H), 7.30 (dd, J = 8.7, 2.3 Hz, 1H), 3.45 (m, 4H), 1.26 (m, 6H).13C NMR (CDCl3, 100 MHz): delta 154.1, 150.0, 135.0, 129.50, 129.47, 129.3, 129.1, 128.7, 122.2,120.5, 117.6, 42.3, 42.0, 14.3, 13.4.IR (ATR): 2974 w, 2930 w, 1716 s, 1629 w, 1504 w, 1473 w, 1415 m, 1381 w, 1358 w, 1272 m,1237 m, 1199 s, 1160 s, 1097 w, 1065 w, 973 w, 913 m, 838 w, 745 m.HRMS (EI): Calcd for C15H16BrNO2 321.0364, Found 321.0362. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With caesium carbonate; In N,N-dimethyl acetamide; at 20℃; | To a solution of <strong>[116230-30-9]7-bromonaphthalen-2-ol</strong> (2.0 g, 9.0 mmol) in dimethyl acetamide (40 mL) was added chloro(methoxy)methane (1.4 g, 18 mmol) and cesium carbonate (5.8 g, 18 mmol) and the reaction mixture was stirred overnight at room temperature. The reaction was diluted with water and the aqueous layer washed with ethyl acetate. The combined organic layers were washed with water and brine, dried over magnesium sulfate and concentrated under vacuum. The crude material was purified by normal phase chromatography using 5-50% ethyl acetate/hexanes as the eluent to give 2-bromo-7-(methoxymethoxy)naphthalene (1.0 g, 3.7 mmol, 42 % yield). |
42% | With caesium carbonate; In N,N-dimethyl acetamide; at 20℃; | To a solution of <strong>[116230-30-9]7-bromonaphthalen-2-ol</strong> (2.0 g, 9.0 mmol) in dimethyl acetamide (40 mL) was added chloro(methoxy)methane (1.4 g, 18 mmol) and cesium carbonate (5.8 g, 18 mmol) and the reaction mixture was stirred overnight at room temperature. The reaction was diluted with water and the aqueous layer washed with ethyl acetate. The combined organic layers were washed with water and brine, dried over magnesium sulfate and concentrated under vacuum. The crude material was purified by normal phase chromatography using 5-50% ethyl acetate/hexanes as the eluent to give 2-bromo-7-(methoxymethoxy)naphthalene (1.0 g, 3.7 mmol, 42% yield). |
42% | With caesium carbonate; In N,N-dimethyl acetamide; at 20℃; | To a solution of <strong>[116230-30-9]7-bromonaphthalen-2-ol</strong> (2.0 g, 9.0 mmol) in dimethyl acetamide (40 mL) was added chloro(methoxy)methane (1.4 g, 18 mmol) and cesium carbonate (5.8 g, 18 mmol) and the reaction mixture was stirred overnight at room temperature. The reaction was diluted with water and the aqueous layer washed with ethyl acetate. The combined organic layers were washed with water and brine, dried over magnesium sulfate and concentrated under vacuum. The crude material was purified by normal phase chromatography using 5-50% ethyl acetate/hexanes as the eluent to give 2-bromo-7-(methoxymethoxy)naphthalene (1.0 g, 3.7 mmol, 42 % yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With iron(III) trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 90℃; for 12h;Sealed tube; | General procedure: The mixture of phenols (1a-l, 1.0 mmol), ketones (2a-l, 2.5 mmol) and Fe(OTf)3 (98%, 25.1 mg, 0.05 mmol) in 1,2-dichloroethane (DCE, 1 mL) was stirred at 90 C (sealed tube) for 12 hours, cooled to room temperature, quenched with saturated sodium bicarbonate solution (20 mL), and extracted with ethyl acetate (3 × 20 mL). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by column chromatography over silica gel to afford the 4H-chromene 3a-y. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With [Yb(CH3CN)9]3+[(AlCl4)3]3-.CH3CN In chlorobenzene for 72h; Reflux; Inert atmosphere; Schlenk technique; stereoselective reaction; | 4.3 Typical procedure for the synthesis of 2,8-dioxabicyclo[3.3.1]nonanes (product 3aa as an example) General procedure: A mixture of 2-hydroxychalcone (112mg, 0.5mmol), β-naphthol (87mg, 0.6mmol) and [Yb(CH3CN)9]3+[(AlCl4)3]3-·CH3CN (16mg, 0.015mmol) in anhydrous chlorobenzene (4.0mL) was stirred under reflux for 72h. The reaction was cooled to room temperature. Water was added, and the mixture was extracted with ethyl acetate. The combined organic layer was dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 20:1) to afford the desired 3aa as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | 2-Benzyloxy-1,1-diphenyl-2,3-dienol (0.75 mmol, 1.5 equiv.) And 7-methoxynaphthol (0.5 mmol) was added to dichloroethane DCE (5 mL) and stirred until both substrates dissolved. The catalyst phosphonic acid (5 mmol%) was added and reacted at room temperature for 30 minutes. The temperature was raised to 80 C and stirring was continued for 8 h. After cooling to room temperature, p-toluenesulfonic acid TsOH (5 mmol%) was added, and the mixture was stirred at 80 C for 30 min. After completion of the reaction, the mixture was cooled to room temperature, and the product was isolated on a silica gel column to give the product 6-bromo-3-diphenylmethylenenaphthylpyran. The yield was 69%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With nickel(II) triflate; C43H46N2O2; sodium hydrogencarbonate; In chloroform; at 15℃; for 6h;Green chemistry; | General procedure: A mixture of Ni(OTf)2 (3.6 mg, 0.01 mmol), a chiral bisoxazoline ligand L12 (9.3 mg, 0.015 mmol) and NaHCO3 (4.2 mg, 0.05 mmol) in CHCl3 (4 mL) Stir at room temperature under a nitrogen atmosphere overnight. Then, azonaphthalene compound 1 (0.1 mmol, Compound A) and 2-naphthol derivative 2 (0.12 mmol, Compound B) were added to the reaction tube. The mixture was stirred at room temperature until TLC showed the disappearance of azo compound 2. The reaction mixture was directly purified by flash chromatography on silica gel to afford product 3 (ie Compound C) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With titanium tetrachloride; In 2,2,2-trifluoroethanol;Reflux; Inert atmosphere; | A 50 mL two-necked flask equipped with a reflux condenser and under a nitrogen atmosphere was charged with beta-naphthol Ic (2 mmol) and trifluoroethanol (10 mL), and heated to reflux with stirring. After the beta-naphthol Ic is completely dissolved, titanium tetrachloride (3 mmol) is added, and finally a mixed solution of alpha-haloketone IIf (3 mmol) and trifluoroethanol (2 mL) is slowly added dropwise to continue the reflux reaction. Monitored with TLC. After completion of the reaction, it was quenched with EtOAc EtOAc (EtOAc) The methylene chloride solution obtained by the mixed extraction was concentrated under reduced pressure, and then subjected to silica gel column chromatography to give the object product IIIp as a yellow oil, yield 76%. |
62% | With titanium tetrachloride; In 2,2,2-trifluoroethanol; at 70℃;Inert atmosphere; | General procedure: To a 25 mL two-necked flask equipped with a reflux condenser, fresh distilled 2,2,2-trifluoroethanol(1.0 mL), phenol (1.0 mmol), and titanium tetrachloride (1.0 mmol) were added under nitrogenatmosphere. Then, a mixture of alpha-haloketone (1.2 mmol) in 2,2,2-trifluoroethanol (1.0 mL) was droppedinto the reaction mixture under refluxing temperature. After completion of the reaction (monitored byTLC), the mixture was quenched with a saturated aqueous solution of NH4Cl (20 mL). After filtration ofthe mixture, the water layer was extracted by dichloromethane (3 x 10 mL) and dried with anhydroussodium sulphate. The organic mixture was concentrated under reduced pressure, and separated bysilica-gel column chromatography using ethyl acetatehexane as eluent in increasing polarity to yieldthe desired furan compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With titanium tetrachloride; In 2,2,2-trifluoroethanol; at 70℃;Inert atmosphere; | General procedure: To a 25 mL two-necked flask equipped with a reflux condenser, fresh distilled 2,2,2-trifluoroethanol(1.0 mL), phenol (1.0 mmol), and titanium tetrachloride (1.0 mmol) were added under nitrogenatmosphere. Then, a mixture of alpha-haloketone (1.2 mmol) in 2,2,2-trifluoroethanol (1.0 mL) was droppedinto the reaction mixture under refluxing temperature. After completion of the reaction (monitored byTLC), the mixture was quenched with a saturated aqueous solution of NH4Cl (20 mL). After filtration ofthe mixture, the water layer was extracted by dichloromethane (3 x 10 mL) and dried with anhydroussodium sulphate. The organic mixture was concentrated under reduced pressure, and separated bysilica-gel column chromatography using ethyl acetatehexane as eluent in increasing polarity to yieldthe desired furan compound. |
78% | With titanium tetrachloride; In 2,2,2-trifluoroethanol;Reflux; Inert atmosphere; | A 50 mL two-necked flask equipped with a reflux condenser and under a nitrogen atmosphere was charged with beta-naphthol Ic (2 mmol) and trifluoroethanol (10 mL), and heated to reflux with stirring. After the beta-naphthol Ic is completely dissolved, titanium tetrachloride (3 mmol) is added, and finally a mixed solution of alpha-haloketone IIg (3 mmol) and trifluoroethanol (2 mL) is slowly added dropwise to continue the reflux reaction. Monitored with TLC. After completion of the reaction, it was quenched with EtOAc EtOAc (EtOAc) The methylene chloride solution obtained by the mixed extraction was concentrated under reduced pressure, and then subjected to silica gel column chromatography to give the object product IIIq as a yellow oil, yield 78%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With titanium tetrachloride; In 2,2,2-trifluoroethanol;Reflux; Inert atmosphere; | A 50 mL two-necked flask equipped with a reflux condenser and under a nitrogen atmosphere was charged with beta-naphthol Ic (2 mmol) and trifluoroethanol (10 mL), and heated to reflux with stirring. After the beta-naphthol Ic is completely dissolved, titanium tetrachloride (2 mmol) is added, and finally a mixed solution of alpha-haloketone IIh (2 mmol) and trifluoroethanol (2 mL) is slowly added dropwise to continue the reflux reaction. Monitored with TLC. After completion of the reaction, it was quenched with EtOAc EtOAc (EtOAc) The methylene chloride solution obtained by the mixed extraction was concentrated under reduced pressure, and then subjected to silica gel column chromatography to give the objective product IIIr as a yellow oil, yield 70%. |
68% | With titanium tetrachloride; In 2,2,2-trifluoroethanol; at 70℃;Inert atmosphere; | General procedure: To a 25 mL two-necked flask equipped with a reflux condenser, fresh distilled 2,2,2-trifluoroethanol(1.0 mL), phenol (1.0 mmol), and titanium tetrachloride (1.0 mmol) were added under nitrogenatmosphere. Then, a mixture of alpha-haloketone (1.2 mmol) in 2,2,2-trifluoroethanol (1.0 mL) was droppedinto the reaction mixture under refluxing temperature. After completion of the reaction (monitored byTLC), the mixture was quenched with a saturated aqueous solution of NH4Cl (20 mL). After filtration ofthe mixture, the water layer was extracted by dichloromethane (3 x 10 mL) and dried with anhydroussodium sulphate. The organic mixture was concentrated under reduced pressure, and separated bysilica-gel column chromatography using ethyl acetatehexane as eluent in increasing polarity to yieldthe desired furan compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With titanium tetrachloride; In 2,2,2-trifluoroethanol;Reflux; Inert atmosphere; | A 50 mL two-necked flask equipped with a reflux condenser and under a nitrogen atmosphere was charged with beta-naphthol Ic (2 mmol) and trifluoroethanol (10 mL), and heated to reflux with stirring. After the beta-naphthol Ic is completely dissolved, titanium tetrachloride (3 mmol) is added, and finally a mixed solution of alpha-haloketone IIi (3 mmol) and trifluoroethanol (2 mL) is slowly added dropwise to continue the reflux reaction. Monitored with TLC. After completion of the reaction, it was quenched with EtOAc EtOAc (EtOAc) The methylene chloride solution obtained by the mixed extraction was concentrated under reduced pressure, and then subjected to silica gel column chromatography to give the object product IIIs as a yellow oil, yield 72%. |
70% | With titanium tetrachloride; In 2,2,2-trifluoroethanol; at 70℃;Inert atmosphere; | General procedure: To a 25 mL two-necked flask equipped with a reflux condenser, fresh distilled 2,2,2-trifluoroethanol(1.0 mL), phenol (1.0 mmol), and titanium tetrachloride (1.0 mmol) were added under nitrogenatmosphere. Then, a mixture of alpha-haloketone (1.2 mmol) in 2,2,2-trifluoroethanol (1.0 mL) was droppedinto the reaction mixture under refluxing temperature. After completion of the reaction (monitored byTLC), the mixture was quenched with a saturated aqueous solution of NH4Cl (20 mL). After filtration ofthe mixture, the water layer was extracted by dichloromethane (3 x 10 mL) and dried with anhydroussodium sulphate. The organic mixture was concentrated under reduced pressure, and separated bysilica-gel column chromatography using ethyl acetatehexane as eluent in increasing polarity to yieldthe desired furan compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With titanium tetrachloride; In 2,2,2-trifluoroethanol;Reflux; Inert atmosphere; | A 50 mL two-necked flask equipped with a reflux condenser and under a nitrogen atmosphere was charged with naphthol Ic (2 mmol) and trifluoroethanol (10 mL), and heated to reflux with stirring. After the naphthol Ic was completely dissolved, titanium tetrachloride (3 mmol) was added, and finally a mixed solution of alpha-haloketone IIa (3 mmol) and trifluoroethanol (2 mL) was slowly added dropwise to continue the reflux reaction, and the reaction was carried out by TLC. monitor. After completion of the reaction, it was quenched with EtOAc EtOAc (EtOAc) The methylene chloride solution obtained by the mixed extraction was concentrated under reduced pressure, and then subjected to silica gel column chromatography to give the object product IIIc as a yellow oil, yield 72%. |
66% | With titanium tetrachloride; In 2,2,2-trifluoroethanol; at 70℃;Inert atmosphere; | General procedure: To a 25 mL two-necked flask equipped with a reflux condenser, fresh distilled 2,2,2-trifluoroethanol(1.0 mL), phenol (1.0 mmol), and titanium tetrachloride (1.0 mmol) were added under nitrogenatmosphere. Then, a mixture of alpha-haloketone (1.2 mmol) in 2,2,2-trifluoroethanol (1.0 mL) was droppedinto the reaction mixture under refluxing temperature. After completion of the reaction (monitored byTLC), the mixture was quenched with a saturated aqueous solution of NH4Cl (20 mL). After filtration ofthe mixture, the water layer was extracted by dichloromethane (3 x 10 mL) and dried with anhydroussodium sulphate. The organic mixture was concentrated under reduced pressure, and separated bysilica-gel column chromatography using ethyl acetatehexane as eluent in increasing polarity to yieldthe desired furan compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | Stage #1: 7-bromonaphthalen-2-ol With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 5h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; hexane at -50℃; for 1.5h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With piperidine; In ethanol; at 140℃; for 0.0333333h;Microwave irradiation; | General procedure: The reaction mixture of 7-bromo-2-naphthol (1) (2.23g, 0.01mol), different aromatic aldehydes (2a-m) (1.24, 1.4, 1.85, 1.42, 1.75, 2.93g, 0.01mol), malononitrile (3) (0.01mol), and piperidine (0.5ml) in absolute ethanol (30ml) was heated under microwave irradiation conditions for 2min at 140C. After the completion of the reaction, the mixture of the reaction was cooled to room temperature. The precipitated solid was filtered off, washed with methanol, and recrystallized from ethanol or ethanol/benzene. The physical and spectral data of compounds 4a-m are as follows: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With piperidine; In ethanol; at 140℃; for 0.0333333h;Microwave irradiation; | General procedure: The reaction mixture of 7-bromo-2-naphthol (1) (2.23g, 0.01mol), different aromatic aldehydes (2a-m) (1.24, 1.4, 1.85, 1.42, 1.75, 2.93g, 0.01mol), malononitrile (3) (0.01mol), and piperidine (0.5ml) in absolute ethanol (30ml) was heated under microwave irradiation conditions for 2min at 140C. After the completion of the reaction, the mixture of the reaction was cooled to room temperature. The precipitated solid was filtered off, washed with methanol, and recrystallized from ethanol or ethanol/benzene. The physical and spectral data of compounds 4a-m are as follows: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With piperidine; In ethanol; at 140℃; for 0.0333333h;Microwave irradiation; | General procedure: The reaction mixture of 7-bromo-2-naphthol (1) (2.23g, 0.01mol), different aromatic aldehydes (2a-m) (1.24, 1.4, 1.85, 1.42, 1.75, 2.93g, 0.01mol), malononitrile (3) (0.01mol), and piperidine (0.5ml) in absolute ethanol (30ml) was heated under microwave irradiation conditions for 2min at 140C. After the completion of the reaction, the mixture of the reaction was cooled to room temperature. The precipitated solid was filtered off, washed with methanol, and recrystallized from ethanol or ethanol/benzene. The physical and spectral data of compounds 4a-m are as follows: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With piperidine; In ethanol; at 140℃; for 0.0333333h;Microwave irradiation; | General procedure: The reaction mixture of 7-bromo-2-naphthol (1) (2.23g, 0.01mol), different aromatic aldehydes (2a-m) (1.24, 1.4, 1.85, 1.42, 1.75, 2.93g, 0.01mol), malononitrile (3) (0.01mol), and piperidine (0.5ml) in absolute ethanol (30ml) was heated under microwave irradiation conditions for 2min at 140C. After the completion of the reaction, the mixture of the reaction was cooled to room temperature. The precipitated solid was filtered off, washed with methanol, and recrystallized from ethanol or ethanol/benzene. The physical and spectral data of compounds 4a-m are as follows: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With piperidine; In ethanol; at 140℃; for 0.0333333h;Microwave irradiation; | General procedure: The reaction mixture of 7-bromo-2-naphthol (1) (2.23g, 0.01mol), different aromatic aldehydes (2a-m) (1.24, 1.4, 1.85, 1.42, 1.75, 2.93g, 0.01mol), malononitrile (3) (0.01mol), and piperidine (0.5ml) in absolute ethanol (30ml) was heated under microwave irradiation conditions for 2min at 140C. After the completion of the reaction, the mixture of the reaction was cooled to room temperature. The precipitated solid was filtered off, washed with methanol, and recrystallized from ethanol or ethanol/benzene. The physical and spectral data of compounds 4a-m are as follows: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With piperidine; In ethanol; at 140℃; for 0.0333333h;Microwave irradiation; | General procedure: The reaction mixture of 7-bromo-2-naphthol (1) (2.23g, 0.01mol), different aromatic aldehydes (2a-m) (1.24, 1.4, 1.85, 1.42, 1.75, 2.93g, 0.01mol), malononitrile (3) (0.01mol), and piperidine (0.5ml) in absolute ethanol (30ml) was heated under microwave irradiation conditions for 2min at 140C. After the completion of the reaction, the mixture of the reaction was cooled to room temperature. The precipitated solid was filtered off, washed with methanol, and recrystallized from ethanol or ethanol/benzene. The physical and spectral data of compounds 4a-m are as follows: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With piperidine; In ethanol; at 140℃; for 0.0333333h;Microwave irradiation; | General procedure: The reaction mixture of 7-bromo-2-naphthol (1) (2.23g, 0.01mol), different aromatic aldehydes (2a-m) (1.24, 1.4, 1.85, 1.42, 1.75, 2.93g, 0.01mol), malononitrile (3) (0.01mol), and piperidine (0.5ml) in absolute ethanol (30ml) was heated under microwave irradiation conditions for 2min at 140C. After the completion of the reaction, the mixture of the reaction was cooled to room temperature. The precipitated solid was filtered off, washed with methanol, and recrystallized from ethanol or ethanol/benzene. The physical and spectral data of compounds 4a-m are as follows: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With piperidine; In ethanol; at 140℃; for 0.0333333h;Microwave irradiation; | General procedure: The reaction mixture of 7-bromo-2-naphthol (1) (2.23g, 0.01mol), different aromatic aldehydes (2a-m) (1.24, 1.4, 1.85, 1.42, 1.75, 2.93g, 0.01mol), malononitrile (3) (0.01mol), and piperidine (0.5ml) in absolute ethanol (30ml) was heated under microwave irradiation conditions for 2min at 140C. After the completion of the reaction, the mixture of the reaction was cooled to room temperature. The precipitated solid was filtered off, washed with methanol, and recrystallized from ethanol or ethanol/benzene. The physical and spectral data of compounds 4a-m are as follows: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With piperidine; In ethanol; at 140℃; for 0.0333333h;Microwave irradiation; | General procedure: The reaction mixture of 7-bromo-2-naphthol (1) (2.23g, 0.01mol), different aromatic aldehydes (2a-m) (1.24, 1.4, 1.85, 1.42, 1.75, 2.93g, 0.01mol), malononitrile (3) (0.01mol), and piperidine (0.5ml) in absolute ethanol (30ml) was heated under microwave irradiation conditions for 2min at 140C. After the completion of the reaction, the mixture of the reaction was cooled to room temperature. The precipitated solid was filtered off, washed with methanol, and recrystallized from ethanol or ethanol/benzene. The physical and spectral data of compounds 4a-m are as follows: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With piperidine; In ethanol; at 140℃; for 0.0333333h;Microwave irradiation; | General procedure: The reaction mixture of 7-bromo-2-naphthol (1) (2.23g, 0.01mol), different aromatic aldehydes (2a-m) (1.24, 1.4, 1.85, 1.42, 1.75, 2.93g, 0.01mol), malononitrile (3) (0.01mol), and piperidine (0.5ml) in absolute ethanol (30ml) was heated under microwave irradiation conditions for 2min at 140C. After the completion of the reaction, the mixture of the reaction was cooled to room temperature. The precipitated solid was filtered off, washed with methanol, and recrystallized from ethanol or ethanol/benzene. The physical and spectral data of compounds 4a-m are as follows: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With piperidine; In ethanol; at 140℃; for 0.0333333h;Microwave irradiation; | General procedure: The reaction mixture of 7-bromo-2-naphthol (1) (2.23g, 0.01mol), different aromatic aldehydes (2a-m) (1.24, 1.4, 1.85, 1.42, 1.75, 2.93g, 0.01mol), malononitrile (3) (0.01mol), and piperidine (0.5ml) in absolute ethanol (30ml) was heated under microwave irradiation conditions for 2min at 140C. After the completion of the reaction, the mixture of the reaction was cooled to room temperature. The precipitated solid was filtered off, washed with methanol, and recrystallized from ethanol or ethanol/benzene. The physical and spectral data of compounds 4a-m are as follows: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With piperidine; In ethanol; at 140℃; for 0.0333333h;Microwave irradiation; | General procedure: The reaction mixture of 7-bromo-2-naphthol (1) (2.23g, 0.01mol), different aromatic aldehydes (2a-m) (1.24, 1.4, 1.85, 1.42, 1.75, 2.93g, 0.01mol), malononitrile (3) (0.01mol), and piperidine (0.5ml) in absolute ethanol (30ml) was heated under microwave irradiation conditions for 2min at 140C. After the completion of the reaction, the mixture of the reaction was cooled to room temperature. The precipitated solid was filtered off, washed with methanol, and recrystallized from ethanol or ethanol/benzene. The physical and spectral data of compounds 4a-m are as follows: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With piperidine; In ethanol; at 140℃; for 0.0333333h;Microwave irradiation; | General procedure: The reaction mixture of 7-bromo-2-naphthol (1) (2.23g, 0.01mol), different aromatic aldehydes (2a-m) (1.24, 1.4, 1.85, 1.42, 1.75, 2.93g, 0.01mol), malononitrile (3) (0.01mol), and piperidine (0.5ml) in absolute ethanol (30ml) was heated under microwave irradiation conditions for 2min at 140C. After the completion of the reaction, the mixture of the reaction was cooled to room temperature. The precipitated solid was filtered off, washed with methanol, and recrystallized from ethanol or ethanol/benzene. The physical and spectral data of compounds 4a-m are as follows: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With triethylamine; In chloroform; at 20℃; for 36h;Inert atmosphere; | General procedure: To a dry test tube with a magnetic stirring bar and chloroform (1.0 ml) were added 1a (0.20 mmol, 46.8mg), beta-naphthol 2a (0.24 mmol, 28.8 mg), followed by the addition of triethylamine (0.04 mmol, 15.2 mg). Then chloroform (1.00 mL) was introduced by syringe, and the mixture was stirred at room temperature for 36 h. Then the solvent was removed in vacuo. The residue was purified by column chromatography on silica gel (petroleum: ethyl acetate = 10:1 to 5:1) to afford 3aa (74.2 mg, 99% yield) as a colourless syrup. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With palladium diacetate; In 1,4-dioxane; at 130℃; for 16h;Inert atmosphere; | Under argon, 0.02 mmol palladium acetate, 0.3 mmol reactant 1a, 0.3 mmol reactant 2b,0.3 mmol reactant 3k, 0.4 mmol potassium phosphate, 2.0 mL 1,4-dioxane, then heated to 130 in an oil bath, and reacted for 16 hours. After the reaction, the reaction solution was directly spin-dried, and the target product was separated by column chromatography7'-Bromo-2,3-diphenyl-2'H-spiro[indene-1,1'-naphthalen]-2'-one (4j). Product data characterization: yellow solid (80.8 mg, yield: 85%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 1.2: 2 h / 20 °C / Inert atmosphere 2.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 16 h / -78 - 20 °C / Inert atmosphere 3.1: hydrogenchloride / methanol / 2 h / 50 °C / Inert atmosphere | ||
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 20 °C 1.2: 2 h / 20 °C 2.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 16 h / 20 °C / Inert atmosphere 3.1: hydrogenchloride / methanol / 50 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran at 80℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran at 90℃; Inert atmosphere; | 1 Under the protection of nitrogen, dissolve S1 (20mmol, 4460mg) in 60mL THF, and slowly add methylmagnesium bromide (3.0M inTHF, 34mL), [1,1'-bis(diphenylphosphino)ferrocene] dichloride Palladium was dissolved in 30 mL THF and slowly added dropwise to the reaction. After the end, the temperature was raised to 90°C. After the completion of the reaction was detected by TLC, saturated ammonium chloride was added for quenching, extracted with ethyl acetate, the organic phases were combined and dried with anhydrous sodium sulfate, the solvent was removed by rotary evaporation to obtain a residue, which was subjected to flash column chromatography (eluent: PE:EA=4:1) A yellow solid product S2 3122mg was obtained with a yield of 99%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran / 90 °C / Inert atmosphere 2.1: 2-bromo-propionic acid amide; potassium carbonate; potassium iodide / dimethyl sulfoxide / 50 °C 2.2: 150 °C 3.1: copper(l) chloride; rac-methylbenzylamine / isopropyl alcohol / 20 °C / Inert atmosphere |
Tags: 116230-30-9 synthesis path| 116230-30-9 SDS| 116230-30-9 COA| 116230-30-9 purity| 116230-30-9 application| 116230-30-9 NMR| 116230-30-9 COA| 116230-30-9 structure
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.
Home
* Country/Region
* Quantity Required :
* Cat. No.:
* CAS No :
* Product Name :
* Additional Information :