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. : | 1948-40-9 | MDL No. : | MFCD00014670 |
Formula : | C7H4I2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WHLUEIMENHLCMY-UHFFFAOYSA-N |
M.W : | 373.91 | Pubchem ID : | 74760 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 59.29 |
TPSA : | 37.3 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) : | -6.33 cm/s |
Log Po/w (iLOGP) : | 1.72 |
Log Po/w (XLOGP3) : | 3.17 |
Log Po/w (WLOGP) : | 2.41 |
Log Po/w (MLOGP) : | 2.57 |
Log Po/w (SILICOS-IT) : | 3.44 |
Consensus Log Po/w : | 2.66 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.49 |
Solubility : | 0.012 mg/ml ; 0.0000321 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -3.62 |
Solubility : | 0.0889 mg/ml ; 0.000238 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.61 |
Solubility : | 0.0909 mg/ml ; 0.000243 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.66 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic anhydride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium acetate; acetic anhydride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-hexanoic anhydride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With propionic acid anhydride Behandeln des Reaktionsprodukts mit wss. HCl; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; hydroxylamine hydrochloride | ||
With hydroxylamine hydrochloride; sodium acetate In ethanol for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium acetate Erwaermen des Reaktionsprodukts mit wss. NaOH; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide | ||
With potassium hydroxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With sodium periodate; sulfuric acid; iodine; potassium iodide; sodium sulfite In water; acetic acid at 25℃; for 2h; | Iodination of phenol (1d) in the presence of Na2SO3 (typical procedure). General procedure: Iodination of phenol (1d) in the presence of Na2SO3 (typical procedure). A 100-mL round-bottom flask was charged with a solution of 3 mmol of phenol in 10 mL of acetic acid, and a solution of KI3 and Na2SO3 (prepared preliminarily by addition of 3 mmol of iodine and 3 mmol of Na2SO3 to a solution of 3 mmol of potassium iodide in 3 mL of water) was added rapidly. At the same time, a solution of 3 mmol of NaIO4 in 5 mL of water was added, and 0.5 mL of sulfuric acid was rapidly added using a pressure-equalizing dropping funnel. The mixture was stirred at 25°C, the progress of the reaction being monitored by TLC. When the reaction was complete, the mixture was poured into ice-cold water, and the solid product was separated by vacuum filtration, washed twice with deionized water, and dried. |
95% | With sodium periodate; potassium iodide; sodium chloride In water; acetic acid at 25℃; for 0.25h; | |
95% | Stage #1: 4-hydroxy-benzaldehyde With sodium periodate; acetic acid; sodium chloride In water at 20℃; for 0.166667h; Stage #2: With potassium iodide In water at 20℃; for 96h; Stage #3: With sodium dithionite In water; ethyl acetate for 0.25h; | Preparation of 4-(3,5-diiodo-4-methoxybenzyl)-7-ethoxyisoquinolin-8-ol hydrochloride 704-Hvdroxy-3,5-diiodobenzaldehvde RBO 40102In a 100 mL round bottom flask 4-hydroxybenzaldehyde (1 .0 g, 8.19 mmol), sodium periodate (1 .75 g, 8.19 mmol), and NaCI (957 mg, 16.38 mmol) were dissolved in acetic acid (30 mL) and H2O (3 mL) at RT. The reaction mixture was stirred at RT for 10 min, then potassium iodide (2.72 g, 16.4 mmol) was added and the reaction mixture was stirred at RT for 96 h. The reaction mixture was diluted with EtOAc (25 mL) and a 1 M sodium thiosulfate aq. solution (25 mL) was added the resulting mixture was stirred for 15 min. This solution was poured into a 250 mL Erlenmeyer with EtOAc (50 mL) and a 1 M sodium thiosulfate aq. solution (50 mL) and the resulting solution stirred for another 15 min. The organic layer was separated and the aqueous phase was further extracted with EtOAc (3x50 mL). The combined organic layers were washed with brine (100 mL), dried over Na2SO4, filtered and concentrated to dryness to give 4-hydroxy-3,5-diiodobenzaldehyde RBO 40102 (2.91 g, 95% yield) as a pale yellow solid.RBO 40102MW: 373.92; Yield: 95%; Pale yellow solid.1H-NMR (CDCIs, δ): 8.20 (s, 2H, ArH), 9.74 (s, 1 H, CHO).MS-ESI m/z (% rel. Int.): 374 ([MH] 10), 361 (100).HPLC: Method A, XBridge column, detection UV 254 nm, RT = 5.20 min, peak area 99.0%. |
94% | With N-chloro-N-(benzenesulfonyl)benzenesulfonamide; potassium iodide In N,N-dimethyl-formamide at 25 - 30℃; | |
86% | With pyridine iodine monochloride In methanol Reflux; regioselective reaction; | |
83% | With N-iodosaccharine In acetonitrile at 20℃; for 2h; | |
83% | With water; iodine; iodic acid for 0.333333h; neat (no solvent); regioselective reaction; | |
70% | With 2,2'-azinobis(3-ethylbenzthiazolinesulfonate); laccase; potassium iodide In dimethyl sulfoxide at 20℃; for 15h; Enzymatic reaction; | |
68% | With iodine; potassium carbonate; potassium iodide In dichloromethane; water for 14h; | |
65% | With potassium dichloroiodate monohydrate In water at 50℃; for 0.166667h; Sealed tube; | Iodination of Thiophenes and Benzene Derivatives with KICl2*H2O; General Procedure General procedure: The conditions for the iodination of thiophene derivatives were optimized by repeating the reaction for different times, substrates and reagent ratios, and temperatures (Table 1). The progress of the reaction was monitored by TLC. The substrate (1 mmol) was dissolved or suspended in the solvent (5 mL). Next, KICl2*H2O (510 mg, 2 mmol) was added to the mixture. The mixture was stirred for the time and at the temperature specified in Tables 1-5. The r.t. reactions were carried out in a glass vial, and the elevated temperature reactions were carried out in a pressure tube sealed with a screw cap, in an oil bath. The progress of the reaction was monitored by TLC. An aliquot of aq Na2S2O3 (5 mL, 5% v/v) was added to quench the reaction. The mixture was then washed with H2O (3 5 mL) in a separatory funnel. The reaction mixtures carried out in H2O first were extracted with CH2Cl2 (3 5 mL) and then washed with H2O (3 5 mL). The combined organic layers were dried (MgSO4) and filtered through Whatman filter paper (diameter 9 cm, pore size 11 m). The iodinated product was obtained by evaporation of the filtrate. The purified product was obtained by column chromatography or recrystallization. For p-hydroxybenzaldehyde, 0.5 mmol of the substrate was dissolved in H2O (5 mL), and then KICl2*H2O (510 mg, 2 mmol) was added to the mixture. Next, the mixture was allowed to stir for 10 min at 50 °C. The precipitate was filtered through Whatman filter paper (diameter 9 cm, pore size 11 m) and purified by recrystallization from CH2Cl2. The solid-state reactions were performed by mixing of the substrate and reagent in a mortar and grinding with a pestle for the time specified in Tables 5 and 6, to obtain a homogeneous mixture. The aqueous solution of Na2S2O3 (5 mL, 5% v/v) was used to quench the reaction. The product was collected by filtration through Whatman filter paper (diameter 9 cm, pore size 11 m). |
23% | With iodine; sodium nitrite In methanol; water at 20℃; for 6h; | |
With potassium iodate; ethanol; sulfuric acid; iodine | ||
With hydrogenchloride; Iodine monochloride | ||
With ethanol; water; iodine; iodic acid | ||
With ethanol; iodine; mercury(II) oxide | ||
With hydrogenchloride; Iodine monochloride In water at 55 - 75℃; | 3 [00277] A solution of p-hydroxybenzaldehyde (31.0 grams, 0.25 mol) was prepared in 450 ml 20% HQ by heating to 75 °C in a stirred reaction vessel. A second iodinating solution was prepared by dissolving 81.25 grams IC1 to 125 ml 20% HC1. This solution was added to the first solution over about 5 minutes (no exotherm). The reaction temperature was raised to 55 °C for about 90 minutes as the reaction becomes clear and yellow. The reaction was poured into 4 L of ice-cold water and allowed to precipitate overnight. The product was isolated by filtration, washed with water, dried down in vacuuo with rubber dam (50 °C). Yield was 79.1 grams of off- white powder (85% of theoretical yield). The diiodo product can be purified by dissolving as a 10% solution in hot ethanol and precipitation by addition of hot water and cooling on ice with stirring. Melting Point (M.P).: at 201-203 °C. A second crop containing monoiodinated product can be obtained by adding cold water and storage at 4 °C. | |
With sodium periodate; potassium iodide; sodium chloride In water; acetic acid at 25℃; for 48h; | ||
With hydrogenchloride; Iodine monochloride In water at 55℃; for 1.58333h; | 3 Example 3 This synthesis was adapted and extended from prior works. See, e.g., Salamonczyk, G. M. et al., Tetrahedron Letters, 38(40): 6965-6968 (1997), the entire contents and disclosure of which are incorporated by reference. (0269) P-hydroxy benzaldehyde was diiodinated, followed by reduction of the aldehyde to the benzyl alcohol product. The alcohol was oxidized to the epoxy and purified to yellow orange crystals by removal of hydrophilic components by silica gel chromatography: (0270) A solution of p-hydroxybenzaldehyde (31.0 grams, 0.25 mol) was prepared in 450 ml 20% HCl by heating to 75° C. in a stirred reaction vessel. A second iodinating solution was prepared by dissolving 81.25 grams ICl to 125 ml 20% HCl. This solution was added to the first solution over about 5 minutes (no exotherm). The reaction temperature was raised to 55° C. for about 90 minutes as the reaction becomes clear and yellow. The reaction was poured into 4 L of ice-cold water and allowed to precipitate overnight. The product was isolated by filtration, washed with water, dried down in vacuuo with rubber dam (50° C.). Yield was 79.1 grams of off-white powder (85% of theoretical yield). The diiodo product can be purified by dissolving as a 10% solution in hot ethanol and precipitation by addition of hot water and cooling on ice with stirring. Melting Point (M.P).: at 201-203° C. A second crop containing monoiodinated product can be obtained by adding cold water and storage at 4° C. (0271) The benzyl alcohol product was formed by reaction of a solution of 3,5-Diiodo-4-Hydroxy-Benzaldehyde (49.6 grams, 0.133 mol) in 0.665 L isopropanol. Sodium borohydride (8 grams) was added with stirring, and the reaction was warmed to 82° C. over about 10 minutes to become homogeneous. The entire reaction was treated with 3 N HCl (58 ml) to pH=5. The precipitate was not removed. Water was added all at once at ambient temperature with stirring. The boric acid will dissolve, and the desired benzyl alcohol product will form over about 10 minutes. The reaction was cooled on ice to less than 15° C. to fully precipitate and isolate the product by filtration, which was then washed with minimal cold water. The filter cake was dried in vacuo at 50° C. Yield was 40 grams of off-white crystals. Melting Point (M.P.) at 139-140° C. (0272) The epoxide function was formed from the alcohol (16 grams, 0.425 mol) by dissolving in a mixture of ethyl acetate (128 ml), acetic acid (102 ml) and water (13 ml) and treating with sodium bismuthate (23.9 grams, 0.085 mol) at 36° C. for 4 hours. The boric acid precipitate was filtered off, and 200 ml of toluene was added to the filtrate. The phases were separated, and the organic phase was dried with anhydrous sodium sulfate. The organic phase was filtered through anhydrous silica, and the filtrate was dried down to form the crystalline diiodo-epoxy product. Yield 8.9 gm (42% of theoretical yield) containing less than 8% of the mono-iodo substituted epoxy product. | |
With sodium periodate; acetic acid; potassium iodide; sodium chloride In water at 20℃; for 96h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine at 110℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With sodium acetate for 2h; Heating; | |
With sodium acetate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With sodium acetate for 2h; Heating; | |
With sodium acetate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With acetic acid; 3-amino propanoic acid for 24h; Heating; | |
46% | With acetic acid; triethylamine In ethyl acetate at 85℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | In chloroform for 24h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With sodium tetrahydridoborate In ethanol for 2h; | |
97% | With sodium tetrahydridoborate; ethanol; calcium(II) chloride at 25℃; for 18h; Cooling with ice; Large scale; | 1-1 (Synthesis Example 1-1) Synthesis of M1 Dissolve 128g (0.78mol) of calcium chloride and 91.3g (2.4mol) of NaBH4 in 2.8L of ethanol,Under ice cooling, 410 g (1.1 mol) of 4-hydroxy-3,5-diiodobenzaldehyde was added. After stirring at 25°C for 18 hours to make the reaction, add 10L of water, and adjust the pH to 2.5 with hydrochloric acid.The sediment is filtered, washed with water and dried,401 g of 4-hydroxy-3,5-diiodobenzyl alcohol shown below was obtained (yield 97%). |
97% | With sodium tetrahydridoborate; calcium chloride | S.3.1 (Synthesis Example 3-1) Synthesis of MAC-4H35I (Synthesis Example 3-1) Synthesis of MAC-4H35I In 2.8 L of ethanol, 128 g (0.78 mol) of calcium chloride and 91.3 g (2.4 mol) of NaBH4 were dissolved, and 410 g (1.1 mol) of 4-hydroxy-3,5-diiodobenzaldehyde was added thereto under ice-cooling. After the reaction was carried out by stirring at 25° C. for 18 hours, 10 L of water was added to the mixture, the pH was adjusted to 2.5 with hydrochloric acid, and the precipitate was filtered, washed with water, and dried to obtain 401 g (97%: yield) of 4-hydroxy-3,5-diiodobenzyl alcohol shown below. |
With sodium hydroxide; sodium tetrahydridoborate | ||
40 g | Stage #1: 3,5-diiodo-4-hydroxy-benzaldehyde With sodium tetrahydridoborate; isopropanol at 82℃; for 0.166667h; Stage #2: With hydrogenchloride In lithium hydroxide monohydrate | 3 [00278] The benzyl alcohol product was formed by reaction of a solution of 3,5-Diiodo-4- Hydroxy-Benzaldehyde (49.6 grams, 0.133 mol) in 0.665 L isopropanol. Sodium borohydride (8 grams) was added with stirring, and the reaction was warmed to 82 °C over about 10 minutes to become homogeneous. The entire reaction was treated with 3 N HC1 (58 ml) to pH=5. The precipitate was not removed. Water was added all at once at ambient temperature with stirring. The boric acid will dissolve, and the desired benzyl alcohol product will form over about 10 minutes. The reaction was cooled on ice to less than 15 °C to fully precipitate and isolate the product by filtration, which was then washed with minimal cold water. The filter cake was dried in vacuo at 50 °C. Yield was 40 grams of off-white crystals. Melting Point (M.P.) at 139-140 °C. |
40 g | With sodium tetrahydridoborate; isopropanol at 82℃; for 0.166667h; | 3 Example 3 This synthesis was adapted and extended from prior works. See, e.g., Salamonczyk, G. M. et al., Tetrahedron Letters, 38(40): 6965-6968 (1997), the entire contents and disclosure of which are incorporated by reference. (0269) P-hydroxy benzaldehyde was diiodinated, followed by reduction of the aldehyde to the benzyl alcohol product. The alcohol was oxidized to the epoxy and purified to yellow orange crystals by removal of hydrophilic components by silica gel chromatography: (0270) A solution of p-hydroxybenzaldehyde (31.0 grams, 0.25 mol) was prepared in 450 ml 20% HCl by heating to 75° C. in a stirred reaction vessel. A second iodinating solution was prepared by dissolving 81.25 grams ICl to 125 ml 20% HCl. This solution was added to the first solution over about 5 minutes (no exotherm). The reaction temperature was raised to 55° C. for about 90 minutes as the reaction becomes clear and yellow. The reaction was poured into 4 L of ice-cold water and allowed to precipitate overnight. The product was isolated by filtration, washed with water, dried down in vacuuo with rubber dam (50° C.). Yield was 79.1 grams of off-white powder (85% of theoretical yield). The diiodo product can be purified by dissolving as a 10% solution in hot ethanol and precipitation by addition of hot water and cooling on ice with stirring. Melting Point (M.P).: at 201-203° C. A second crop containing monoiodinated product can be obtained by adding cold water and storage at 4° C. (0271) The benzyl alcohol product was formed by reaction of a solution of 3,5-Diiodo-4-Hydroxy-Benzaldehyde (49.6 grams, 0.133 mol) in 0.665 L isopropanol. Sodium borohydride (8 grams) was added with stirring, and the reaction was warmed to 82° C. over about 10 minutes to become homogeneous. The entire reaction was treated with 3 N HCl (58 ml) to pH=5. The precipitate was not removed. Water was added all at once at ambient temperature with stirring. The boric acid will dissolve, and the desired benzyl alcohol product will form over about 10 minutes. The reaction was cooled on ice to less than 15° C. to fully precipitate and isolate the product by filtration, which was then washed with minimal cold water. The filter cake was dried in vacuo at 50° C. Yield was 40 grams of off-white crystals. Melting Point (M.P.) at 139-140° C. (0272) The epoxide function was formed from the alcohol (16 grams, 0.425 mol) by dissolving in a mixture of ethyl acetate (128 ml), acetic acid (102 ml) and water (13 ml) and treating with sodium bismuthate (23.9 grams, 0.085 mol) at 36° C. for 4 hours. The boric acid precipitate was filtered off, and 200 ml of toluene was added to the filtrate. The phases were separated, and the organic phase was dried with anhydrous sodium sulfate. The organic phase was filtered through anhydrous silica, and the filtrate was dried down to form the crystalline diiodo-epoxy product. Yield 8.9 gm (42% of theoretical yield) containing less than 8% of the mono-iodo substituted epoxy product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In toluene at 50℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 37% 2: 2% 3: 5% | With sodium bismuthate In water; acetic acid; ethyl acetate for 4h; Title compound not separated from byproducts; | |
1: 5% 2: 2% 3: 37% | With sodium bismuthate In water; acetic acid; ethyl acetate for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With sodium acetate; acetic acid for 16h; Heating; | |
94% | With ammonium acetate In toluene at 110℃; for 24h; Inert atmosphere; Darkness; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-heptanoic anhydride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With octanoic acid anhydride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic anhydride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic anhydride at 110℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic anhydride at 110℃; | ||
With acetic anhydride at 110℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With potassium carbonate In tetrahydrofuran; N,N-dimethyl-formamide for 24h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In methanol at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With hydrogenchloride In 1,4-dioxane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With perchloric acid In 1,4-dioxane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With perchloric acid In 1,4-dioxane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In methanol at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In methanol at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With acetic acid; sodium nitrite at 80℃; for 15h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 80 percent / NaNO2; HOAc / 15 h / 80 °C 2: 80 percent / m-CPBA / CH2Cl2 / 15 h / 4 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: aq. NH2OH*HCl; AcONa / ethanol / 12 h 2: N-chlorosuccinimide; pyridine / CHCl3; tetrahydrofuran / 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: aq. NH2OH*HCl; AcONa / ethanol / 12 h 2.1: N-chlorosuccinimide; pyridine / CHCl3; tetrahydrofuran / 2 h 3.1: Kaiser oxime resin; DIEA / CH2Cl2 / 12 h 3.2: DIEA / CH2Cl2 / 12 h 3.3: AcOH / dimethylformamide / 12 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 93 percent / K2CO3 / tetrahydrofuran; dimethylformamide / 24 h / Heating 2: 76 percent / bis(triphenylphosphine)palladium(II) dichloride; diisopropylamine; CuI / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 99 percent / NaOAc, AcOH / 16 h / Heating 2: 47 percent / diisopropylethylamine / ethanol / 1.5 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: Cu2O, pyridine / 2 h / Heating 2: conc. HCOOH / 72 h / Heating 3: 87 percent / HCOONa, Pd(Ph3P)4 / dimethylformamide / 0.17 h / 120 °C 4: NaBH4 / methanol / 2 h / Ambient temperature 5: 53 percent / Et3SiH, TFA / CHCl3 / 5 h / 20 - 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: Cu2O, pyridine / 2 h / Heating 2: conc. HCOOH / 72 h / Heating 3: 87 percent / HCOONa, Pd(Ph3P)4 / dimethylformamide / 0.17 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: Cu2O, pyridine / 2 h / Heating 2: conc. HCOOH / 72 h / Heating 3: 87 percent / HCOONa, Pd(Ph3P)4 / dimethylformamide / 0.17 h / 120 °C 4: NaBH4 / methanol / 2 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: Cu2O, pyridine / 2 h / Heating 2: conc. HCOOH / 72 h / Heating 3: NaBBH4 / methanol / 2 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: toluene / 0.5 h / 50 °C 2: NaBH3CN / tetrahydrofuran; acetic acid / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: toluene / 0.5 h / 50 °C 2: NaBH3CN / tetrahydrofuran; acetic acid / Ambient temperature 3: 0.5M aq. NaHCO3 / CHCl3 / 0.5 h / Ambient temperature 4: dioxane / 22 h / 80 °C 5: 1M aq. oxalic acid / tetrahydrofuran / 12 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: toluene / 0.5 h / 50 °C 2: NaBH3CN / tetrahydrofuran; acetic acid / Ambient temperature 3: 0.5M aq. NaHCO3 / CHCl3 / 0.5 h / Ambient temperature 4: dioxane / 22 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: toluene / 0.5 h / 50 °C 2: NaBH3CN / tetrahydrofuran; acetic acid / Ambient temperature 3: 0.5M aq. NaHCO3 / CHCl3 / 0.5 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: propionic acid-anhydride / Behandeln des Reaktionsprodukts mit wss. HCl 2: aqueous NaOH |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: hexanoic acid anhydride 2: aqueous NaOH |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium acetate; acetic acid anhydride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: NaOAc 2: diethyl ether; CHCl3 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Combinatorial reaction / High throughput screening (HTS); | Libraries were prepared in a single compound per well format. Stock solutions of all aldehydes (0.5 M) and aryloxyamines (0.4 M) were prepared in DMSO. A Gilson 215 Liquid Handler equipped with a 1 mL syringe, 1.1 mL tubing, and a 13 mm I.D. probe was used to distribute all solutions into a 96 well (2 mL volume) polypropylene plate at a rate of 0.3 mL/min. To make 0.5 mL of a 0.1 M solution of each oxime ether, 100 muL (0.05 mmol, 1 eq.) of aldehyde, 156 muL (0.63 mmol, 1.25 eq.) of aryloxyamine, and 244 muL of 0.164 M acetic acid, were distributed to each well of the plate. The plate was covered and agitated for 24 h at room temperature using a dual action shaker. The reactions were diluted to 720 muM in DMSO and analyzed by LC-MS to determine yield, purity, and identity. Compounds were stored frozen at -20 C. after synthesis. Reaction yield was determined using the integrated value of aldehyde that remained in the reaction mixture. Calibration curves of all aldehydes were made and the yield of each oxime ether was calculated assuming all the aldehyde that reacted quantitatively formed oxime ether; i.e. if 5% of aldehyde remained in the reaction mixture the yield of oxime ether would be 95%. Yields ranged from 98-100% and >95% purity in all wells. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 98% 2: 98% 3: 98% 4: 98% 5: 98% 6: 98% 7: 98% 8: 98% 9: 98% 10: 98% 11: 98% 12: 98% 13: 98% 14: 98% 15: 98% 16: 98% 17: 98% 18: 98% 19: 98% 20: 98% 21: 98% 22: 98% 23: 98% 24: 98% 25: 98% | With acetic acid In water; dimethyl sulfoxide at 20℃; for 24h; Combinatorial reaction / High throughput screening (HTS); | Libraries were prepared in a single compound per well format. Stock solutions of all aldehydes (0.5 M) and aryloxyamines (0.4 M) were prepared in DMSO. A Gilson 215 Liquid Handler equipped with a 1 mL syringe, 1.1 mL tubing, and a 13 mm I.D. probe was used to distribute all solutions into a 96 well (2 mL volume) polypropylene plate at a rate of 0.3 mL/min. To make 0.5 mL of a 0.1 M solution of each oxime ether, 100 μL (0.05 mmol, 1 eq.) of aldehyde, 156 μL (0.63 mmol, 1.25 eq.) of aryloxyamine, and 244 μL of 0.164 M acetic acid, were distributed to each well of the plate. The plate was covered and agitated for 24 h at room temperature using a dual action shaker. The reactions were diluted to 720 μM in DMSO and analyzed by LC-MS to determine yield, purity, and identity. Compounds were stored frozen at -20° C. after synthesis. Reaction yield was determined using the integrated value of aldehyde that remained in the reaction mixture. Calibration curves of all aldehydes were made and the yield of each oxime ether was calculated assuming all the aldehyde that reacted quantitatively formed oxime ether; i.e. if 5% of aldehyde remained in the reaction mixture the yield of oxime ether would be 95%. Yields ranged from 98-100% and >95% purity in all wells. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80.7% | With hydrogenchloride In ethanol; isopropyl alcohol | 6 1-(n-butyl)-2-(4'-hydroxy-3',5'-diiodostyryl)-3,3-dimethylindoleninium iodide EXAMPLE 6 1-(n-butyl)-2-(4'-hydroxy-3',5'-diiodostyryl)-3,3-dimethylindoleninium iodide A mixture of 3,5-diiodo-4-hydroxybenzaldehyde (3.73, 10 mmole), 1-(n-butyl)-2,3,3-trimethylindoleninium iodide (D. P. Maisuradze et al., Soobschch. Akad. Nauk Gruz. SSR 50, 77-82 (1968); CA 69: 106526r) (4.46 g, 13 mmole) and piperidine (0.8 ml) in EtOH (40 ml) was maintained under an inert gas atmosphere. The solution was refluxed for 1 hour, and cooled to an ambient temperature. The solution was evaporated to dryness in vacuo, leaving a residue. The residue was taken up in EtOH (10 ml) and treated with 1.93M HCl in i-PrOH (3.0 ml). The solution was thereafter again evaporated to dryness in vacuo, leaving a residue. The residue was taken up in EtOH (4 ml). The solution was refrigerated and crystals spontaneously formed. The crystalline solids that separated were collected by filtration, washed with ice-cold EtOH and vacuum dried to give crude 1-(n-Butyl)-2-(4'-hydroxy-3',5'-diiodostyryl)-3,3-dimethylindoleninium iodide (4.90 g, 80.7%). The crude compound was taken up in hot EtOH (60 ml), filtered through paper and concentrated in vacuo to about 30 ml. |
80.7% | With hydrogenchloride In ethanol; isopropyl alcohol | 12 Example 12. Example 12. 1-(n-butyl)-2-(4'-hydroxy-3',5'-diiodostyryl)-3,3-dimethylindoleninium iodide. A mixture of 3,5-diiodo-4-hydroxybenzaldehyde (3.73, 10 mmole), 1-(n-butyl)-2,3,3-trimethylindoleninium iodide (D.P. Maisuradze et al., Soobschch. Akad. Nauk. Gruz. SSR 50, 77-82 (1968): CA 69 : 106526r) (4.46 g, 13 mmole) and piperidine (0.8 ml) in EtOH (40 ml) was maintained under an inert gas atmosphere. The solution was refluxed for 1 hour, and cooled to an ambient temperature. The solution was evaporated to dryness in vacuo, leaving a residue. The residue was taken up in EtOH (10 ml) and treated with 1.93 M HCl in i-PrOH (3.0 ml). The solution was thereafter again evaporated to dryness in vacuo,leaving a residue. The residue was taken up in EtOH (4ml). The solution was refrigerated and crystals spontaneously formed. The crystalline solids that separated were collected by filtration, washed with ice-cold EtOH and vacuum dried to give crude 1-(n-butyl)-2-(4'-hydroxy-3',5'-diiodostyryl)-3,3-dimethylindoleninium iodide (4.90 g, 80.7%). The crude compound was taken up in hot EtOH (60 ml), filtered through paper and concentrated in vacuoto about 30 ml. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In tetrahydrofuran; ethyl acetate | 169.1 step 1 step 1 3,5-diiodo-4-(2-methoxyethoxymethyloxy)-benzaldehyde To a stirred solution of 3,5-diiodo-4-hydroxybenzaldehyde (18.696 g, 50 mmol) in THF (360 ml) under nitrogen at ~0° C. was added sodium hydride (2.6 g, 1.3 mmol), portionwise. After the addition, the mixture was stirred for 20 minutes followed by the dropwise addition of MEMCl (9.966 g, 80 mmol). The mixture was stirred at ~4° C. for 20 minutes and then at room temperature for 24 h. The reaction mixture was then concentrated to dryness and the residue diluted with EtOAc (300 ml) and washed with 1N NaOH (3*50 ml), water (2*50 ml), brine (2*50 ml), dried over Na2SO4, filtered and the filtrate concentrated in vac and dried. The residue was purified by flash chromatography (Hex, 10% and 20% EtOAc/Hex) to give the product as a white solid (19.209 g, 83%); mp 68-72° C.; 1H NMR (400 MHz, DMSO-d6) δ3.27 (s, 3H), 3.54-3.56 (m, 2H), 4.00-4.04 (m, 2H), 5.24 (s, 2H), 8.34 (s, 2H), 9.85 (s, 1H); IR (KBr) 3410, 2880, 1700, 1540, 1360 cm-1; mass spectrum [EI], m/z 462 M+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With sodium hydroxide; NaH In tetrahydrofuran; ethyl acetate; Petroleum ether | 44.1 step 1 step 1 3,5-Diiodo-4-methoxyethoxymethoxybenzaldehyde To a stirred solution of 3,5-diiodo-4-hydroxybenzaldehyde (10.0 g, 26.7 mmol) in THF (267 mL) at 0° C. was added NaH (1.39 g, 34.7 mmol). After 0.5 h at this temperature, MEMCl (4.88 mL, 42.7 mmol) was added dropwise. The reaction mixture was stirred for another 15 min. at 0° C. and then at room temperature for 18 h. The resulting mixture was quenched with 0.1 N NaOH and extracted with Et2O (1000 mL). The organic layer was washed with 0.1 N NaOH (3*100 mL) and brine (100 mL) and then dried (MgSO4). After concentration, the residue was purified by flash chromatography (5 to 15% EtOAc/petroleum ether gradient) to afford the product (8.60 g, 69%) as a solid; 1H NMR (CDCl3) δ3.44 (s, 3H), 3.67 (t, J=5.5 Hz, 2H), 4.16 (t, J=5.5 Hz, 2H), 5.34 (s, 2H), 8.29 (s, 2H), 9.82 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With acetic acid; triethylamine In ethyl acetate at 85℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With palladium diacetate; potassium carbonate; tris-(o-tolyl)phosphine at 90℃; for 12h; Inert atmosphere; stereospecific reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With palladium diacetate; potassium carbonate; tris-(o-tolyl)phosphine at 90℃; for 12h; Inert atmosphere; regiospecific reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With palladium diacetate; potassium carbonate; tris-(o-tolyl)phosphine at 90℃; for 12h; Inert atmosphere; stereospecific reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With palladium diacetate; potassium carbonate; tris-(o-tolyl)phosphine at 90℃; for 12h; Inert atmosphere; stereospecific reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 13h; Inert atmosphere; | |
80% | Stage #1: 4-hydroxy-3,5-diiodobenzaldehyde With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 19h; Inert atmosphere; Darkness; | |
Stage #1: 4-hydroxy-3,5-diiodobenzaldehyde With potassium carbonate In acetone at 20℃; for 0.5h; Stage #2: methyl iodide In acetone for 5h; Reflux; | 3,5-Diiodo-4-methoxybenzaldehvde RBO 40112In a 100 mL round bottom flask 4-hydroxy-3,5-diiodobenzaldehyde RBO 40102 (1 .0 g, 2.67 mmol) was dissolved in acetone (15 mL) and K2CO3 (553 mg, 4.0 mmol) was added at RT. The mixture was stirred at RT for 30 min, then iodomethane (758 mg, 5.34 mmol) was added and reaction was stirred at reflux for 3.5 h. After this time iodomethane (2 eq, 758 mg, 5.34 mmol) was added and mixture was stirred at reflux for another 1 .5 h. Acetone was evaporated and the residue was taken back in EtOAc (40 mL) and water (60 mL). The aqueous layer was further extracted with EtOAc (3x40 mL). The combined organic layers were washed with brine (60 mL), dried over Na2SO4, filtered and concentrated to dryness to give a yellow oil. This oil was purified by column chromatography (S1O2, eluent cyclohexane:EtOAc = 100:0 to 90:10) to give, after evaporation and drying, 3,5-diiodo-4-methoxybenzaldehyde RBO 40112 (493 mg, 48% yield) as a white solidRBO 40112MW: 387.94; Yield: 48%; White solid.H-NMR (CDCI3, δ): 3.93 (s, 3H, OMe), 8.27 (s, 2H, 2xArH), 9.81 (s, 1 H, CHO).MS-ESI m/z (% rel. Int.): 388 ([MH]+, 10), 153 (100). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate / tetrahydrofuran; N,N-dimethyl-formamide / 24 h / Reflux 2.1: sodium tetrahydroborate / methanol; dichloromethane / 3 h / 0 - 20 °C 2.2: Saturated solution |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: potassium carbonate / tetrahydrofuran; N,N-dimethyl-formamide / 24 h / Reflux 2.1: sodium tetrahydroborate / methanol; dichloromethane / 3 h / 0 - 20 °C 2.2: Saturated solution 3.1: dmap / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: potassium carbonate / tetrahydrofuran; N,N-dimethyl-formamide / 24 h / Reflux 2.1: sodium tetrahydroborate / methanol; dichloromethane / 3 h / 0 - 20 °C 2.2: Saturated solution 3.1: dmap / dichloromethane / 20 °C 4.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine; triphenylphosphine / tetrahydrofuran / 10 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / tetrahydrofuran; N,N-dimethyl-formamide / 24 h / Reflux 2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine; triphenylphosphine / tetrahydrofuran / 10 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: potassium carbonate / tetrahydrofuran; N,N-dimethyl-formamide / 24 h / Reflux 2.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine; triphenylphosphine / tetrahydrofuran / 10 h / 20 °C / Inert atmosphere 3.1: sodium tetrahydroborate / methanol; dichloromethane / 3 h / 20 °C 3.2: 12 h / 20 °C / Saturated solution |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With potassium carbonate In tetrahydrofuran; N,N-dimethyl-formamide for 24h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | Stage #1: 4-methoxy-N-[(E)-phenylmethylidene]aniline With neopentylmagnesium bromide; cobalt(II) bromide; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In tetrahydrofuran at 0℃; Inert atmosphere; Stage #2: 4-methoxy-N-[(E)-phenylmethylidene]aniline In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; Stage #3: 4-hydroxy-3,5-diiodobenzaldehyde Further stages; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With sodium metabisulfite In N,N-dimethyl-formamide at 80℃; for 0.2h; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With sodium metabisulfite In N,N-dimethyl-formamide at 100℃; for 0.2h; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate; isopropyl alcohol / 0.17 h / 82 °C 1.2: pH 5 2.1: sodium bismuthate / water; ethyl acetate; acetic acid / 4 h / 36 °C | ||
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; isopropyl alcohol / 0.17 h / 82 °C 2: sodium bismuthate / ethyl acetate; water; acetic acid / 4 h / 36 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With toluene-4-sulfonic acid In toluene at 150℃; for 10h; Dean-Stark; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | With potassium <i>tert</i>-butylate; dihydrogen peroxide In water at 130℃; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h; | Synthesis of MG2I: (1) from Scheme 1: lOmmol 3, 5-Diiodo-4-hydroxybenzaldehyde was dissolved in dry 5ml DMF, added 1.1 eq of finely powdered K2CO3 and heated to 80°C for 3 hours, the reaction mixture was cooled to room temperature and filtered the precipitate, The solvent was then removed under reduced pressure to afford the crude product, which was purified by column chromatography on silica gel using hexane/Ethyl acetate (4/1), yield: 94%. NMR (300 MHz, CDCI3): δ 9.82(s, lH), 8.38(s, 2H), 4.17(q, 2H), 4.1 l(t, 2H), 2.72(t, 2H), 2.58(m, 2H), 1.29(t, 3H), 13C NMR (100 MHz, CDC13): δ 188.1, 173.3, 162.7, 141.6, 135.4, 91.7, 72.4, 60.4, 80.6, 25.3, 14.4, MS (ΕΓ): m/z (%): 488.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With perchloric acid In 1,4-dioxane; water for 2h; | Oxime ether cyclorearrangement procedures only: 70% HClO4in water (63.0mL, 0.733 mmol) was added to a stirring mixture of 3,5-diiodo-4-hydroxybenzaldehyde (304 mg, 0.814 mmol) and ethyl-N-(2,6-dichlorophenoxy)acetimidate (202 mg, 0.0.813 mmol) in 1,4-dioxane (8.0 mL) and the reaction was stirred for 2 h.The reaction was then concentrated and flash chromatographic purification over silica (4:1 hexanes:EtOAc) afforded the 3,5-diiodo-4-hydroxybenzaldehyde-O-(2,6-dichlorophenyl)oxime intermediate.A portion of this was then heated at 70°C in THF (10 mL), then was concentrated and flash chromatographic purification over silica (2:1-1:1 hexanes:EtOAc gradient elution) afforded 2-(3,5-diiodo-4-hydroxyphenyl)-7-chlorobenzoxazole (201) as a white solid. 1H-NMR (500 MHz,d6-DMSO)d10.5 (br s, 1H), 8.43 (s, 2H), 7.72 (dd,J=1.0, 7.9 Hz, 1H), 7.50 (dd,J=1.0, 8.0 Hz, 1H), 7.40 (t,J=8.0 Hz, 1H);13C-NMR (125 MHz,d6-DMSO)d160.01, 159.27, 146.55, 142.77, 137.98, 126.06, 125.39, 121.13, 118.62, 114.55, 86.96; ESI-MS 498m/z[MH]+, C13H7ClI2NO2requires 498, 497m/z[M-H+]-, C13H5ClI2NO2requires 497; RP-HPLC: 98% pure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | Stage #1: (3,5-bis-benzyloxy-benzyl)-triphenyl-phosphonium; chloride With n-butyllithium In hexane; toluene for 0.5h; Inert atmosphere; Stage #2: 4-hydroxy-3,5-diiodobenzaldehyde In hexane; toluene at 110℃; for 6h; Inert atmosphere; | 13.4 3.4 Synthesis of stilbene 17 The stirred solution of phosphorus ylide 15 (1.3 g, 2.2 mmol) in dry toluene (40 mL) under argon atmosphere was added to a solution of n-BuLi (2.2 mL, 12.0 mmol) in n-hexane. After stirring for 30 min, aldehyde 16 (0.7 g, 1.8 mmol) was added and then stirred for an additional 6 h under refluxing at 110 °C, after which ethanol (10 mL) was added. The reaction mixture was concentrated and extracted with EtOAc (50 mL) for three times, washed with water, brine and then dried over anhydrous MgSO4. The solvent was removed under reduced pressure and the residue was purified on a silica gel column chromatography (petroleum ether: EtOAc = 8:1) to give stilbene 17 (0.96 g, 81%) as a pale white solid. 1H NMR (400 MHz, d-acetone): δ = 5.14 (s, 4H), 6.61 (t, J = 2.0 Hz, 1H), 6.96 (d, J = 2.0 Hz, 2H), 7.06 (d, J = 16.4 Hz, 1H), 7.14 (d, J = 16.4 Hz, 1H), 7.33-7.50 (m, 10H), 8.01 (br s, 2H) ppm; 13C NMR (100 MHz, d-acetone): δ = 74.8 (2C), 89.1, 106.8, 110.9 (2C), 130.8, 132.8 (5C), 133.0 (3C), 133.6 (5C), 133.8, 139.2, 142.6 (4C), 144.5, 159.8, 165.5 (2C) ppm; HRMS (ESI): m/z calcd. for C28H22I2O3+H: 660.9731; found: 660.9725. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With potassium carbonate In N,N-dimethyl-formamide at 65℃; for 18h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With piperidine In ethanol at 80℃; for 16h; Inert atmosphere; | 3-(3,5-difluoro-4-hydroxybenzylidene)-5-(furan-2-carbonyl)indolin-2-one (3): General procedure: Piperidine (8.7 µL, 0.088 mmol), 3,5-difluoro-4-hydroxybenzaldehyde (69.5 mg, 0.44 mmol) and S3 (100.0 mg, 0.44 mmol) were dissolved in EtOH (2.0 mL). The mixture was heated to 80 oC for 16 h. The orange solid was filtered and washed with 1N HCl and Et2O to afford 3 (114.0 mg, 70%, mixture of E/Z isomers). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With piperidine; acetic acid In acetonitrile at 85℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With piperidine; acetic acid In acetonitrile at 85℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38.8% | With pyridine In ethanol at 80℃; for 7h; Inert atmosphere; | 1-3 In a 2000ml three-necked flask, first add 182g (0.65mol) of light yellow powder, 196g (0.52mol) of 3,5-diiodo-4-hydroxybenzaldehyde, 1500ml of absolute ethanol, stir, add pyridine dropwise under the protection of nitrogen 41g (0.52mol), after dropping, the temperature was raised to 80 ° C for 7 hours, the reaction was completed, the solvent was concentrated under reduced pressure to remove the solvent, the residue was acidified with 5% hydrochloric acid to PH2.0, and an oily product was precipitated. Extraction, combined extracts, chromatographic column separation, eluting with a gradient of methanol and dichloromethane (1: 100, 1:80, 1:60, 1:40, 1:20, 1:10), collecting 1:20 ~ 1: 10 stage eluent, to obtain 165g rose red crystalline powder (main component SPDIB), the total yield was 38.8%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With dmap; dicyclohexyl-carbodiimide In acetonitrile at 0 - 20℃; for 1.5h; | 21 In a reaction vessel, after 5.0 mmol of triphenylsulfonium 3-((4-carboxybenzyl)oxy)-1,1,2,2-tetrafluoro-3-oxopropane-1-sulfonate, 5.5 mmol of 4-hydroxy-3,5-diiodobenzaldehyde, and 1.0 mmol of N,N-dimethyl-4-aminopyridine (DMAP) were dissolved in acetonitrile to adjust to 1 M, the solution was cooled to 0° C. After the cooling, 11 mmol of N,N'-dicyclohexylcarbodiimide (DCC) was gradually added over 0.5 hrs and then the solution was stirred at room temperature for 1 hour. After completion of the reaction, quenching with a saturated aqueous ammonium chloride solution was executed followed by addition of dichloromethane to permit extraction, and the organic layer was separated. After the organic layer thus obtained was dried over anhydrous sodium sulfate, the solvent was eliminated, and purification with a column gave triphenylsulfonium 1,1,2,2-tetrafluoro-3-((4-((4-formyl-2,6-diiodophenoxy)carbonyl)benzyl)oxy)-3-oxopropane-1-sulfonate with a yield of 77%. A thus resulting compound was used in the next reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With dmap; dicyclohexyl-carbodiimide In acetonitrile at 0 - 20℃; for 1.5h; | 30 In a reaction vessel, after 7.5 mmol of triphenylsulfonium 2-(8-carboxy-1,4-dioxaspiro[4.5]decan-2-yl)-1,1,2,2-tetrafluoroethane-1-sulfonate, 8.0 mmol of 4-hydroxy-3,5-diiodobenzaldehyde, and 1.5 mmol of N,N-dimethyl-4-aminopyridine (DMAP) were dissolved in acetonitrile to adjust to 1 M, the solution was cooled to 0° C. After the cooling, 16.5 mmol of N,N′-dicyclohexylcarbodiimide (DCC) was gradually added over 0.5 hrs and then the solution was stirred at room temperature for 1 hour. After completion of the reaction, quenching with a saturated aqueous ammonium chloride solution was executed followed by addition of dichloromethane to permit extraction, and the organic layer was separated. After the organic layer thus obtained was dried over anhydrous sodium sulfate, the solvent was eliminated, and purification with a column gave an acid generating agent (B-10) with a yield of 79%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With copper(l) iodide; 1,10-Phenanthroline; magnesium In N,N-dimethyl-formamide at 110℃; for 12h; Inert atmosphere; |
Tags: 1948-40-9 synthesis path| 1948-40-9 SDS| 1948-40-9 COA| 1948-40-9 purity| 1948-40-9 application| 1948-40-9 NMR| 1948-40-9 COA| 1948-40-9 structure
[ 131088-03-4 ]
2,4-Dihydroxy-5-iodobenzaldehyde
Similarity: 0.87
[ 131088-03-4 ]
2,4-Dihydroxy-5-iodobenzaldehyde
Similarity: 0.87
[ 131088-03-4 ]
2,4-Dihydroxy-5-iodobenzaldehyde
Similarity: 0.87
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 :