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. : | 5122-99-6 | MDL No. : | MFCD01319014 |
Formula : | C6H6BIO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PELJYVULHLKXFF-UHFFFAOYSA-N |
M.W : | 247.83 | Pubchem ID : | 151254 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 48.98 |
TPSA : | 40.46 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.76 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.48 |
Log Po/w (WLOGP) : | -0.03 |
Log Po/w (MLOGP) : | 1.21 |
Log Po/w (SILICOS-IT) : | 0.24 |
Consensus Log Po/w : | 0.58 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.69 |
Solubility : | 0.51 mg/ml ; 0.00206 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.94 |
Solubility : | 2.87 mg/ml ; 0.0116 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.24 |
Solubility : | 1.41 mg/ml ; 0.0057 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.37 |
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 |
---|---|---|
62% | With di-tert-butyl peroxide In acetonitrile at 120℃; for 12 h; Sealed tube | General procedure: Arylboronic acid (1.0 mmol), dimethyldisulfide (2.0 mmol), DTBP (3.0 mmol) andCH3CN (2.0 mL) were taken in a sealed tube. The reaction mixture was stirred at120 °C for 12 hours in air. After cooling to room temperature, the product was dilutedwith H2O (5 mL) and extracted with EtOAc (4×10 mL). The extracts were combinedand washed by brine (3×10 mL), dried over MgSO4, filtered, and evaporated, andpurified by chromatography on silica gel to obtain the desired products with ethylacetate/hexane (v/v=1:301:100). The products were characterized by their spectraland analytical data and compared with those of the known compounds (Seesupporting information). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With magnesium sulfate; In dichloromethane; at 20℃;Product distribution / selectivity; | Method 3; 4-((4-(5,5-dimethyl-l,3,2-dioxaborinan-2-yl)phenyl)ethynyl)benzaldehyde; A. 2-(4-iodophenyl)-5,5-dimethyl-l ,3,2-dioxaborinane; 2-(4-iodophenyl)-5,5-dimethyl-l,3,2-dioxaborinane was prepared following the method described in Method 2 step A to yield 5.4 g (86% yield) of the title compound as an off-white solid.LC-MS: [M+H]+ 316.12 Mass: calculated for C11H14BIO2, 315.95 |
In diethyl ether; at 20℃;Inert atmosphere; Molecular sieve; | General procedure: To a Et2O solution of anorganoboronic acid (1.00 equiv) and 2,2-dimethylpropane-1,3-diol (neopentyl glycol)(1.02 equiv), 4A molecular sieves was added and the reaction mixture was stirred atroom temperature. After the reaction finished, the reaction mixture was filtered andconcentrated in vacuo. The residue was subjected to flash column chromatography(eluent: petroleum ether/ethyl acetate) or recrystallization to obtain the desired product |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With oxygen; sodium acetate In water at 23℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With toluene-4-sulfonic acid; In toluene; for 3h;Heating / reflux; | Intermediate 6; 2-(4-lodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; A mixture of <strong>[5122-99-6](4-iodophenyl)boronic acid</strong> (2.4 g), 2,3-dimethyl-2,3-butanediol (6.6 g), toluenesulphonic acid monohydrate (110 mg) and in dry toluene (75 ml.) was heated under reflux for 3 h in a Dean Stark apparatus. The reaction mixture was cooled to room temperature, washed with water (100 ml_), brine, and then dried over magnesium sulphate and filtered. The solvent was evaporated to give the title compound. 1H NMR (CDCI3): delta 7.73 (2H, d), 7.52 (2H, d), 1.34 (12H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With sodium acetate; acetic acid;palladium diacetate; antimony(III) chloride; at 25℃; for 24h; | A.: 3-(4-iodophenyI)cyclopentanone (1) 0.23g palladium(II) acetate (0.1 eq) and 0.23g antimony(III) chloride (0.1 eq) were added to 80 mL acetic acid solution of 2-cyclopenten-l-one 0.82g (10 mmol), 4- iodophenylboronic acid-2.48g (10 mmol) and sodium acetate 1.6g (20 mmol) under N2 atmosphere. After being stirred for 24 hours at 250C, the black precipitation was filtered off and the filtrate was diluted with 250 mL of brine, and then extracted twice with 50 mL methylene chloride. The organic extraction was stirred with saturated NaHCO3 solution for 30 minutes, then washed with brine and dried over MgSO4. Removal of solvent resulted in a yellow oil, further purification by flash column (chloroform) gave 1.92g (67%) product as a white solid. J. Org. Chem., 1995, 60, 883-888.1H NMR (CDCl3) delta 7.63 (d, 2H, ArH), 7.00 (d, 2H, ArH), 3.35 (m, IH, ArCHCC), 2.7-1.8 (m, 6H, cyclo-pentyl);13C NMR (CDCl3) 6218, 143, 138, 129, 95, 46, 42, 39, 31. |
67% | With sodium acetate; antimony(III) chloride;palladium diacetate; In acetic acid; at 25℃; for 24h; | O.23g palladium(II) acetate (0.1 eq) and 0.23g antimony(III) chloride (0.1 eq) were added to 80 mL acetic acid solution of 2-cyclorhoenten-l-one 0.82g (10 mmol), <strong>[5122-99-6]4-iodophenylboronic acid</strong> 2.48g <n="26"/>(10 mmol) and sodium acetate 1.6g (20 mmol) under N2 atmosphere. After being stirred for 24 hours at 250C, the black precipitation was filtered off and the filtrate was diluted with 250 mL of brine, and then extracted twice with 50 mL methylene chloride. The organic extract was stirred with saturated NaHCO3 solution for 30 minutes, then washed with brine and dried over MgSO4. Removal of solvent resulted in a yellow oil, further purification by flash column (chloroform) gave 1.92g (67%) product as a white solid. J. Org. Chem., 1995, 60, 883-888. 1H NMR (CDCl3) delta 7.63 (d, 2H, ArH), 7.00 (d, 2H, ArH), 3.35 (m, IH, ArCHCC), 2.7-1.8 (m, 6H, cyclo- pentyl); 13C NMR (CDCl3) 5218, 143, 138, 129, 95, 46, 42, 39, 31. |
6.5 g | With sodium acetate; antimony(III) chloride; palladium diacetate; acetic acid; at 25℃; for 2h;Inert atmosphere; | Intermediate 3A: 3 -(4-iodophenyl)cyclopentanoneTo a solution of cyclopent-2-enone (3.39 g, 0.0407 mol), sodium acetate (6.659 g, 0.08 13 mol) and <strong>[5122-99-6](4-iodophenyl)boronic acid</strong> (10 g, 0.0407 mol) in acetic acid (325 mL) was added palladium (II) acetate (0.9728 g, 0.00406 mol) and antimony (III) chloride (0.9279 g, 0.00406 mol) under a nitrogen atmosphere. After being stirred for 2 hours at 25 C, the black precipitation was filtered off and the filtrate was diluted with brine and then extracted twice with dichloromethane. The organic extraction was stirred with saturated sodium bicarbonate for 30 minutes, then washed with brine and dried over sodium sulfate. Removal of the solvent resulted in a yellow oil. Further purification (flash column, chloroform eluent) gave a 6.5 g of 3-(4-iodophenyl)cyclopentanone as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine;copper diacetate; In dichloromethane; at 20℃; for 16h; | Intermediate 44 EPO <DP n="53"/>Ethyl 1 -(^iodophenyO^HHfrans^-methylcyclohexyOcarbonyl^i -methylethyl)amino]- 1 H-pyrazole-4-carboxylateTo a solution of Intermediate 4 (4.0 g) in anhydrous DCM (300 ml_) at room temperature was added 4-iodophenyl boronic acid (4.6 g), copper (II) acetate (3.3 g) and pyridine (1.97 ml_). The reaction was stirred at room temperature for 16 h.The reaction was diluted with DCM (200 ml_) and washed with sat. aq. sodium bicarbonate solution, water, brine, dried (Na2SO4) and evaporated. This was purified by chromatography on silica gel using a cyclohexane/ethyl acetate gradient to give the title compound. MS calcd for (C23H3OlN3CVH)+ : 524 MS found (electrospray): (M+H)+ = 524 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
[0431] Step A: [0432] A solution of <strong>[5122-99-6]4-iodophenylboronic acid</strong> (19.8g, 80.0 mmol) and Pd(PPh3)4 (0.93 mg, 0.80 mmol) in pyrrolidine (100 mL) was stirred at room temperature for 5 min. The resulting solution was cooled to 0 C., and propargyl alcohol (9.4 mL, 161.5 mmol) was then added. The reaction was stirred at 0 C. for 1h before being warmed up to room temperature and stirred for 18 h. The mixture was concentrated and the residue was dissolved in 2 N NaOH (200 mL). The aqueous solution was washed with CH2Cl2 (100 mL×2) before being cooled to 0 C. and acidified with 10% aq. HCl. The resulting mixture was filtrated and the solid was washed with H2O and dried in vacuo. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With copper(II) choride dihydrate; sodium carbonate; In methanol; at 25℃; for 0.25h;Green chemistry; | General procedure: Arylboronic acid (0.3 mmol), CuCl2·2H2O (2.5 mg, 5 mol%), Na2CO3 (10 mol%),methanol (1 mL) were added to a vial. The reaction mixture was stirred at 25 C inthe air for 5-15 min and was monitored by TLC. Then the reaction was quenched withtwo drops of H2O, diluted with 2 mL of ethyl acetate, and filtered over a pad ofMgSO4 and silica. The pad was rinsed with additional ethyl acetate, and the solutionwas concentrated in vacuum. The crude material was loaded onto a silica gel columnand purified by flash chromatography. |
13% | With sodium tetrachloroaurate(III) dihyrate; potassium carbonate; In ethanol; at 50℃; for 24h; | Representative experimental procedure: A mixture of AuCl (11.6 mg, 0.050 mmol), phenylboronic acid (1a, 121.9 mg, 1.00 mmol), K2CO3 (152.0 mg, 1.10 mmol) in EtOH (8.0 mL) was heated at 50 C under open air for 24 h. The reaction mixture was filtered through a plug of Florisil washing with hexane-AcOEt (3:1). The filtrate was concentrated under reduced pressure, and the resulting residue was subjected to preparative thin-layer chromatography (hexane:AcOEt = 20:1) to afford biphenyl (2a, 58.6 mg, 76%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | Example 1.1; Preparation of the intermediate (4-Bromo-2-methyl-2H-pyrazol-3-yl)-(4-iodo-phenyl)- amine.A 500-mL round bottom flask was charged with toluene (80 mL), copper(II) acetate (0.83 g, 4.55 mmol), myristic acid (1.56 g, 6.82 mtnol), and/>-iodophenylboronic acid (10.14 g, 40.91 mmol) then stirred at room temperature for five minutes. While mixing, 2,6-lutidine (7.14 mL, 61.27 mmol) was added and allowed to stir for an additional 10 minutes. 3-Amino-4- bromo-2-methyl pyrazole (4.00 g, 22.73 mmol) was added then the reaction mixture was stirred at room temperature overnight. Ethyl acetate was added, washed with ammonium hydroxide, water and brine. The ammonium salt formed, suspended in the organic layer, was removed by filtration. The filtrate was washed with water twice, dried over MgSO4 and filtered. The solvent was removed under reduced pressure to yield a crude yellow oil, that was purified by column EPO <DP n="67"/>chromatography on silica gel (Biotage hexanes/ethyl acetate, gradient elution) to afford (4- bromo-2-methyl-2H-pyrazol-3-yl)-(4-iodo-phenyl)-amine as a yellow solid. Yield: 4.51 g (53 %). LCMS m/z (%) = 378 (M+Eta 79Br, 100), 380 (M+Eta 81Br, 97). 1H NMR (400MHz, DMSO- d6): delta 8.13 (s, IH), 7.59 (s, IH), 7.46 (dd, J=I 1.8, 3.0 Hz, 2H), 6.39 (dd, J=I 1.8, 3.0 Hz, 2H), 6.62 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; In dichloromethane; water; at 20℃; for 10h; | General procedure: To a solution of benzoquinone (0.5 mmol, 1.0 equiv) and [Cp*RhCl2]2 (0.025 mmol, 5 mol%) in CH2Cl2 (2 mL) was added the boronic acid (0.75 mmol, 1.5 equiv), H2O (1 mL). Then the solution was stirred vigorously at r.t. for 10 h. Upon completion, the reaction was diluted with CH2Cl2 (3 mL) and washed with 5% NaHCO3. The layers were separated, and the aqueous layer was extracted with CH2Cl2 (3 × 4 mL), dried over Na2SO4, and was evaporated to give the residue. The residue was then purified by column chromatography on silica gel (EtOAc-PE, 1:10) to provide the corresponding product. |
52% | With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; In dichloromethane; water; at 20℃; for 12h; | General procedure: To a solution of benzoquinone (0.5 mmol, 1.0 equiv.) and [Cp*IrCl2]2 (0.025mmol, 5%) in dichloromethane (2 mL) was added the phenylboronic acid (0.75 mmol, 1.5 equiv.) and water (2 mL) Then the solution was stirred vigorously at room temperature for 12 h. Upon completion, the reaction was diluted with dichloromethane (5 mL) and washed with 5% sodium bicarbonate. The layers were separated, and the aqueous layer was extracted with dichloromethane (10 X 3 mL), dried over sodium sulfate, and was evaporated to give the residue. The residue was then purified by column chromatography on silica gel (ethyl acetate / petroleumether = 1:10) to provide the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With copper(l) iodide; 8-quinolinol; sodium phosphate; In ethanol; at 80℃; for 24h; | General procedure: A 5.0 mL of reaction tube was charged with organoboron compound (1.0 mmol), alkynyl bromide (1.0 mmol), CuI (0.10 mmol), 8-hydroxyquinoline (0.20 mmol), ethanol (2.0 mmol). The mixture was stirred at 80 C for 24 h, and then washed with ethyl acetate (3.0 mL×3), the combined ethyl acetate was concentrated under reduced pressure. The obtained residue was purified by flash column chromatography on silica gel (petroleum ether as eluting agent) to give the corresponding pure cross-coupling product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With dihydrogen peroxide; In neat (no solvent); at 30℃; for 0.0833333h;Green chemistry; | General procedure: A mixture of arylboronic acid (1.0 mmol), 30% H2O2 (2 mL), and Amberlite IR-120 resin (15 mg) was stirred at room temperature for the time indicated in Table 2. After completion of the reaction (indicated by TLC) the solid was separated by filtration,extracted with EtOAc (10 mL), washed with 10% NaHCO3 (2 5 mL), and the organic layer was evaporated to give the desired product without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With oxygen; palladium diacetate; acetic acid; copper(l) chloride In dimethyl sulfoxide at 50℃; for 20h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16% | With oxygen; triethylamine;copper diacetate; In dichloromethane; at 20℃; for 24h;Molecular sieve; Sealed tube; | A mixture of N, N-dimethylazetidin-3 -amine 2,2,2-trifluoroacetate ( 1.25 g, 5.84 mmol), <strong>[5122-99-6]4-iodophenylboronic acid</strong> (4.34 g, 17.5 mmol), Et3N (4.1 mL, 29 mmol), 4 A MS (1 g) and CH2CI2 (30 mL) was purged with oxygen gas for 10 min. Copper(II) acetate (1.06 g, 5.84 mmol) was added, the vial sealed and stirred at room temperature for 1 d. The mixture was diluted with CH2CI2, filtered through a cake of Celite and the filtrate was concentrated to give the crude product. The residue was purified by flash chromatography using MeOH/CH2Cl2 (2:98 to 10:90) to give a brown oil. Saturated NaHC03 was added to the brown oil and the resulting mixture was sonicated for 5 minutes. The desired product was collected by vacuum filtration as a pale brown solid (0.29 g, 16%). NMR (400 MHz, MeOD) delta 7.44 (d, J - 7.7 Hz, 2H), 6.31 (d, J = 8.4 Hz, 2H), 4.62 (s, 1H), 3.98 (t, J = 7.0 Hz, 2H), 3.61 (t, J = 7.0 Hz, 2H), 2.23 (s, 6H); MS ESI 303.0 [M + H]+, calcd for [CnHi5IN2+ H]+ 303.03. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Inert atmosphere 2: o-phenylenebis(diphenylphosphine); copper(II) acetate monohydrate; lithium tert-butoxide / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | IE (6.70 g, 33.7 mmol) and 2-fluoro-5-methoxyphenylboronic acid (6.29 g, 37.0 mmol) were combined in THF (100 mL) and a 2 M aq. solution of K2C03 (50 mL, 100 mmol) was added. The reaction mixture was purged with argon for 5 min and then Pd(Ph3P)4 (1.556 g, 1.346 mmol) was added. The reaction mixture was refluxed at 85 C for 4 h. The reaction mixture was cooled to rt, the layers were separated, and the aqueous layer was extracted with EtOAc (3 x 30 mL). The combined organic layers were washed with water and brine, dried (MgS04), filtered, and concentrated. The crude product was purified by silica chromatography to provide 2'-fluoro-5'-methoxy-3-methylbiphenyl-4-carbaldehyde (8.00 g, 29.5 mmol, 88% yield) as a yellow oil. To a solution of 2'-fluoro-5'-methoxy-3- methylbiphenyl-4-carbaldehyde (2.00 g, 8.19 mmol) in 1,4-dioxane (40 mL) was added 4-methylbenzenesulfonohydrazide (1.53 g, 8.19 mmol) and the resulting solution was heated at 80 C for 90 min with a reflux condenser. Then, <strong>[5122-99-6]4-iodophenylboronic acid</strong> (3.04 g, 12.3 mmol) and K2CO3 (1.70 g, 12.3 mmol) were added. The reaction mixture was refiuxed at 110 C for 2 h. The reaction mixture was diluted with EtOAc and water. The aqueous layer was further extracted with EtOAc (2 x 50 mL) and the combined extracts was washed with water and brine, dried over MgSC^, filtered, and concentrated. The crude product was purified via silica chromatography to afford IF (1.90 g, 4.40 mmol, 54% yield) as a colorless oil. 1H NMR (400 MHz, CDC13) delta 7.58 - 7.65 (2 H, m), 7.31 - 7.39 (2 H, m), 7.15 (1 H, d, J=7.5 Hz), 7.02 - 7.10 (1 H, m), 6.90 - 6.97 (3 H, m), 6.82 (1 H, dt, J=9.0, 3.4 Hz), 3.97 (2 H, s), 3.83 (3 H, s), 2.29 (3 H, s). | |
52% | [00283] 28D. 2-fluoro-4'-(4-iodobenzyl)-5-methoxy-3'-methylbiphenyl: To a 2 L round-bottom flask equipped with a reflux condenser was added 28C (37.6 g, 154 mmol), 1,4-dioxane (600 mL) and 4-methylbenzenesulfonylhydrazide (28.7 g, 154 mmol). The resulting solution was heated to 80 C for 20 min. The heating was stopped and (4- iodophenyl)boronic acid (38.1 g, 154 mmol) and K2CO3 (25.5 g, 185 mmol) were added. The reaction mixture was then heated to 90 C for 80 min to give a white suspension. The reaction mixture was cooled to rt and stored in a refrigerator overnight. The reaction mixture was diluted with EtOAc and water and the layers were separated. The aqueous layer was extracted with EtOAc (2 x 1.5 L) and the combined organic extracts were washed with water and brine, dried (MgSC^), filtered, and concentrated to give an orange oil. Upon standing at at rt, the residual 4-idophenylboronic acid precipitated as white crystals. The white solid was removed by filtration and washed with EtOAc. The filtrate was concentrated. The filtration and concentration were repeated (3x). The crude product was purified by flash chromatography to provide 28D (34.4 g, 80.0 mmol, 52% yield) as a white solid. lH NMR (400 MHz, CDC13) delta 7.58 - 7.65 (m, 2H), 7.31 - 7.39 (m, 2H), 7.15 (d, J= 7.5 Hz, 1H), 7.02 - 7.10 (m, 1H), 6.90 - 6.97 (m, 3H), 6.82 (dt, J = 9.0, 3.4 Hz, 1H), 3.97 (s, 2H), 3.83 (s, 3H), 2.29 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16% | With pyridine; copper diacetate; In N,N-dimethyl-formamide; at 90℃; for 0.5h; | A 100 mL flask was charged with <strong>[4928-88-5]methyl 1H-1,2,4-triazole-3-carboxylate</strong> (2.8 g, 16 mmol), 4-iodopheynylboronic acid (4.0 g, 16 mmol), Cu(OAc)2 (3.3 g, 18 mmol), pyridine (1.5 mL, 19 mmol), and DMF (30 mL). The mixture was stirred on a preheated oil bathe set to 90° C. for 30 minutes, during which time the solution changed color from a deep blue to a light green. The mixture was diluted in EtOAc (200 mL), filtered, and washed with 3:1 v/v saturated NH4Cl-30percent NH4OH. The organic phase was concentrated in vacuo and the resulting residue was purified by flash chromatography (SiO2, 20percent-60percent EtOAc/hexanes) to obtain a white powder of methyl 1-(4-iodophenyl)-1,2,4-triazole-3-carboxylate (830 mg, 16percent yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With copper(I) oxide; ammonium hydroxide; potassium carbonate; In water; for 0.166667h;Microwave irradiation; | General procedure: The microwave reaction tube was added with aromatic boronic acid 1 (0.5 mmol), ammonia (0.6 mmol, 25% aqueous solution) 2, propargyl halide 3 (0.5 mmol), K2CO3 (138 mg, 1 mmol), and H2O (2 mL). The mixture was conducted under 5 watt microwave for 10 minutes, and the reaction was monitored by TLC. The system was diluted with 30 mL of H2O after the reaction was completed, and the mixture was then extracted with EtOAc for three times. The organic layer was separated, washed with water and saturated brine, and dried over anhydrous Na2SO4. The evaporation of the solvent provided the crude product, which was subjected to column chromatography (silica gel, EtOAc-petroleum ether 1:8?1:3) to obtain arylaminomethyl acetylene 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With copper(I) oxide; ammonium hydroxide; potassium carbonate; In water; for 0.166667h;Microwave irradiation; | General procedure: The microwave reaction tube was added with aromatic boronic acid 1 (0.5 mmol), ammonia (0.6 mmol, 25% aqueous solution) 2, propargyl halide 3 (0.5 mmol), K2CO3 (138 mg, 1 mmol), and H2O (2 mL). The mixture was conducted under 5 watt microwave for 10 minutes, and the reaction was monitored by TLC. The system was diluted with 30 mL of H2O after the reaction was completed, and the mixture was then extracted with EtOAc for three times. The organic layer was separated, washed with water and saturated brine, and dried over anhydrous Na2SO4. The evaporation of the solvent provided the crude product, which was subjected to column chromatography (silica gel, EtOAc-petroleum ether 1:8?1:3) to obtain arylaminomethyl acetylene 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | General procedure: The 2,5-dibromo-3-hexylthiophene (1 mmol) and 4 mol % Pd(PPh3)4 were added in an organic solvent 1,4-dioxane (2 mmol) under inert (argon) atmosphere. The mixture was stirred in a Schlenkflask at 25 C for a duration of 30 min. After stirring, the arylboronic acids (1 mmol) and K3PO4 (1.75 mmol) were added along with water (0.5 mL) under the same atmosphere. The solution wasstirred again at 90 C for a duration of 12 h. After stirring for 12 h, the reaction mixture was cooled to room temperature. The organic layer in the reaction mixture was separated by using CH3COOC2H5 and desiccated above MgSO4. After that, the excess solvent was evaporated by applying reducedpressure on a rotary evaporator. The crude product thus obtained, and was purified using column chromatography. In chromatography, ethyl acetate and n-hexane were used in equal ratios to acquire the final compounds. The end products were characterized by different spectroscopic techniques [23]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | General procedure: Aryl boronic acid (1.0 mmol), CuI (5 mol%),amide (3.0 mmol), and DMSO (1.0 mL) were added to a reactionvial, and the mixture was stirred at room temperature for10 min. A 70% aqueous solution of TBHP (1.1 mmol) was addedto the reaction mixture dropwise over 5 min. The reaction vialwas then immersed in a preheated oil bath and the progress ofreaction was followed by TLC. Upon completion of reaction, thecooled mixture was partitioned between water and ethyl acetate.The aqueous layer was further extracted with ethyl acetate,and the combined organic layers were washed with brine,dried over Na2SO4, filtered, and concentrated in vacuo. Theresidue was purified by column chromatography on silica gel(hexane-ethyl acetate) to give the desired N-aryl lactam |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With potassium phosphate; 1,10-Phenanthroline; di-tert-butyl peroxide; trifluorormethanesulfonic acid; carbon dioxide; copper(II) bis(trifluoromethanesulfonate); silver carbonate; In N,N-dimethyl-formamide; at 80℃; | The substrate 1r (0.1 mmol, 24.2 mg) was added to a 25 mL test tube reactor under a carbon dioxide atmosphere, 2 r (0.15 mmol, 37.2 mg),Cu (OTf) 2 (0.02 mmol, 7.2 mg),1,10-phenanthroline (0.04 mmol, 7.2 mg),Ag2CO3 (0.12 mmol, 33.1 mg),K3PO4 (0.14 mmol, 29.7 mg),DTBP (0.1 mmol, 18.5 [mu] L) CF3SO3H (0.05 mmol, 5.0 [mu] L), and DMF (2.0 mL). The reaction was heated to 80 C to carry out the reaction. TLC detection reaction After the end, the system is cooled to room temperature. The reaction was quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate (3 * 10 mL) Column chromatography gave 20.5 mg (60%) of product 3r. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With 4,4'-bipyridine; copper(l) iodide; lithium carbonate; In diethylene glycol dimethyl ether; at 60℃; for 15h;Inert atmosphere; Sealed tube; | Procedure: Under argon conditions, 0.7 mmol <strong>[5122-99-6]4-iodophenylboronic acid</strong>, 0.84 mmol reagent 1,0.35 mmol carbon Lithium chloride, 0.035 mmol of cuprous iodide, 0.035 mmol of bipyridine (bpy) was placed in a 25 mL sealed tube and then added5mL diethylene glycol dimethyl ether (diglyme), 60 C for 15 hours. After completion of the reaction, the mixture was cooled to room temperature and added25 mL of water and 50 mL of ether, and the organic phase was washed three times with 20 mL of water, dried over anhydrous sodium sulfate, The solvent was removed by evaporation, and the residue was purified by flash silica gel column to obtain 134 mg of the corresponding product. The yield was 67% The hydrogen spectrum shows a purity greater than 98%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With potassium carbonate; triphenylphosphine; palladium dichloride; In N,N-dimethyl-formamide; at 90℃; | General procedure: The compounds 4-(4-bromophenyl)-2,5-dimethylthiazole (1)(1.5 mmol), arylboronic acid 2(a-l) (1 mmol), PdCl2 (0.3 mmol), PPh3 (0.5 mmol) and K2CO3 (2 mmol) were kept in DMF (20 mL) solvent for 4-5 h at 90 C. After, reaction mixture was cooled and filtered. The filtrate was diluted, extracted with dichloromethane and the organic layer was removed under vacuum. The resultantresiduewas purified by column chromatography (silica gel, 60-120 mesh) using hexane/EtOAc (4:1) as eluent. 4.3.11 4-(4'-Iodobiphenyl-4-yl)-2,5-dimethylthiazole (3k) Off white solid in (0.58 g, 83%), mp 159-161 C; 1H NMR (300 MHz, CDCl3+DMSO): delta 2.16 (s, 3H, (C5-CH3)), 2.28 (s, 3H, (C2-CH3)), 7.20-7.80 (m, 8H, Ar-H); 13C NMR (75 MHz, CDCl3+DMSO): delta 12.1 (C5-CH3), 18.1 (C2-CH3), 123.6, 125.8, 126.5, 128.1, 128.5, 131.2, 134.5, 137.0, 140.1 (C-5), 148.8 (C-4), 159.3 (C-2); HRMS: m/z calcd for C17H15INS (M+H)+ 392.0112; found 392.0124. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20%; 68% | With tert.-butylhydroperoxide; copper(l) iodide; In N,N-dimethyl-formamide; at 130℃; for 48h; | General procedure: To a 25 mL round flask was added the mixture of boronic acid (1) (0.3 mmol), ethyl2-cyano-3-ethoxyacrylate (2a, 0.6 mmol), CuI (0.3 mmol), t-BuOOH (0.6 mmol) in DMF (2 mL)successively. The mixture was stirred at 130 C for 24 h under air. After the reaction was completed, themixture was cooled to room temperature, diluted with water (15 mL) and then extracted withdichloromethane (5 mL × 3). The organic extract was washed with H2O (10 mL × 3) and dried overanhydrous Na2SO4. After removal of the CH2Cl2 in vacuum, the crude product thus obtained was purified bycolumn chromatography on silica gel using petroleum ether/ethyl acetate as eluent to give the desired product3 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With pyridine; pyridine N-oxide; oxygen; copper diacetate; In dichloromethane; at 20℃; for 72h;Molecular sieve; | General procedure: Compound 3g was obtained from 2 using the proceduredescribed above for 3e, using 4-iodophenyl boronic acid. The crudeproduct was purified by chromatography on silica gel with CHCl3/hexane/acetone = 1:8:1 to provide 3g (632.8 mg, 74.0%) as a beigesolid: mp: 155-156 C; 1H NMR (600 MHz, DMSO-d6) d ppm: 8.21(dd, J = 2.6, 8.8 Hz, 1H), 7.99 (dd, J = 3.1, 5.7 Hz, 2H), 7.93 (dd,J = 2.9, 5.5 Hz, 2H), 7.89 (d, J = 8.8 Hz, 1H), 7.79 (d, J = 2.6 Hz, 1H),7.71 (d, J = 6.6 Hz, 2H), 6.91 (d, J = 6.8 Hz, 2H); FTIR (KBr) cm1:3436, 1738, 1717; EI-MS m/z: 486 [M]+; HR-MS: calcd forC20H11IN2O5 [M]+: 485.9713; found 485.9723. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 8h;Inert atmosphere; | After 20 g (55.2 mmol) of Compound 1-4 was dissolved in 180 mL of tetrahydrofuran (THF) in a nitrogen atmosphere, 13.7 g (55.2 mmol) of <strong>[5122-99-6]4-iodophenylboronic acid</strong> and tetrakis (Triphenylphosphine) palladium (0.64 g, 0.55 mmol) were added and stirred. 19.1 g (138 mmol) of saturated potassium carbonate in water was added, and the mixture was refluxed by heating at 80 DEG C for 8 hours. After the completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM). The extract was dried over anhydrous MgSO 4, filtered and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain 18.1 g (75%) of the compound I-16 It was. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | General procedure: The substrate 2,5-dibromo-3-hexylthiophene (1 mmol) was taken in Schlenk flask and 6 mol% tetrakis(triphenylphosphine)palladium(0) was added along with 1,4-Dioxane (2 mL) under argon atmosphere. The mixture in the flask was stirred for half an hour at 25 C. After mixing, the aryl-boronic acids (2.5 mmol), K3PO4 (4 mmol) and water (0.5 mL) were added in the mixture under argon atmosphere. The reaction mixture was cooled to normal room temperature after stirring the solution for 12 h at 90 C. Ethyl acetate was used to separate the organic layer and then dried over magnesium sulfate. The excess solvent was evaporated using a rotary evaporator. The desired products were obtained from the purification of the crude residue using ethyl acetate and n-hexane in the same ratio by column chromatography. Spectroscopic techniques were applied for the characterization of the final products [18]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With di-tert-butyl peroxide; In acetonitrile; at 120℃; for 12h;Sealed tube; | General procedure: Arylboronic acid (1.0 mmol), dimethyldisulfide (2.0 mmol), DTBP (3.0 mmol) andCH3CN (2.0 mL) were taken in a sealed tube. The reaction mixture was stirred at120 C for 12 hours in air. After cooling to room temperature, the product was dilutedwith H2O (5 mL) and extracted with EtOAc (4×10 mL). The extracts were combinedand washed by brine (3×10 mL), dried over MgSO4, filtered, and evaporated, andpurified by chromatography on silica gel to obtain the desired products with ethylacetate/hexane (v/v=1:301:100). The products were characterized by their spectraland analytical data and compared with those of the known compounds (Seesupporting information). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With [2,2]bipyridinyl; ferrous(II) sulfate heptahydrate; copper(ll) sulfate pentahydrate; trifluorormethanesulfonic acid; oxygen; sodium carbonate; In ethanol; at 25℃; | Oxygen atmosphere,Substrate 4-iodobenzeneboronic acid (69.4 mg, 0.28 mmol, 1.4 equiv.) Was added to the reaction tube,2a (39.7 mg, 0.2 mmol, 1.0 equiv.),CuSO4.5H2O (2.5 mg, 0.01 mmol, 5.0 mol%),Bipy (6.3 mg, 0.04 mmol, 20 mol%),Na2CO3 (10.6 mg, 0.1 mmol, 0.5 equiv.),FeSO4 · 7H2O (11.1 mg, 0.04 mmol, 20 mol%),LiOTf (12.5 mg, 0.08 mmol, 40 mol%)And EtOH (2.0 mL),The reaction was carried out at 25 C,After the TLC detection reaction was completed,Adding silica gel,After removal of the solvent under reduced pressure,The product was purified by column chromatography to give 3h (62%) of product. (Eluent polarity: petroleum ether). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | General procedure: All compounds were synthesized by reported method [28]. N-[5-bromo-2-methylpyridine-3-yl]acetamide (3, 0.1 g), tetrakis(triphenylphosphine)-palladium (5 mol %) and 1,4-dioxane (2 mL) wereplaced in the Schlenk flask at room temperature and the mixture was stirred for 30 min . Then theappropriate arylboronic acid (1.1 mmol), potassium phosphate (1.5 mmol) and H2O (0.5 mL) were addedto the mixture, which was stirred and kept at 85-95 C for more than 15 h. After reaching roomtemperature, the mixture was filtered and then diluted with ethyl acetate (50 mL). The excess solvent wasevaporated by rotary evaporator in order to obtain a concentrated solution. Column chromatography(silica gel, n-hexane and ethyl acetate?) was applied to obtain the desired pure products. The finalproduct was dried and recrystallized and further analyzed using different spectroscopic techniques. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | General procedure: All compounds were synthesized following the previously reported method [28]. Briefly 5-bromo-2-methylpyridin-3-amine (1, 0.2 g with tetrakis(triphenylphosphine)palladium (5 mol %) and1,4-dioxane (2 mL) were mixed in a Schlenk flask. The reaction mixture was stirred at room temperaturefor 30 min and then the arylboronic acid (1.1759 mmol), potassium phosphate (2.318 mmol) and water(0.5 mL) were added and the mixture again stirred at 85-95 C for more than 15 h. After lowering thetemperature, the mixture was filtered and diluted with ethyl acetate (50 mL). The excess solvent in thesolution was evaporated by rotary evaporator in order to obtain a concentrated solution. Columnchromatography was applied to get the desired pure product (silica gel, n-hexane and ethyl acetate). Thefinal products were dried, recrystallized and then characterized using different spectroscopic techniques. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; cesium acetate; In dichloromethane; at 20℃;Inert atmosphere; Schlenk technique; | General procedure: The reaction of phenylboronic acid (1a) with N-(pivaloyloxy)benzamide (2a) is representative(Table 1, entry 11): [Cp*RhCl2]2 (3.1 mg, 0.0050 mmol), CsOAc (48 mg, 0.25 mmol), phenylboronicacid (1a; 46 mg, 0.38 mmol), N-(pivaloyloxy)benzamide (2a; 55 mg, 0.25 mmol), and dibenzyl (internalstandard, 25 mg) were placed in a 20 mL two-necked reaction flask, which was filled with nitrogen byusing the standard Schlenk technique. CH2Cl2 (1.0 mL) was then added to the flask, and the resultingsolution was stirred for 1 h at ambient temperature. The GC yield of N-phenylbenzamide (3aa) wasestimated to be 99% by comparison with integrated intensity of dibenzyl. The mixture was thenquenched with water and extracted with ethyl acetate three times. The combined organic layer wasdried over Na2SO4. Filtration and evaporation under reduced pressure formed the crude product. Theresidue was purified by column chromatography on silica gel with hexane/ethyl acetate (5/1, v/v) toafford an analytically pure N-phenylbenzamide (3aa; 49 mg, 0.25 mmol) in 99% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With pyridine; copper diacetate; sodium carbonate; In 1,2-dichloro-ethane; at 20℃; for 14h;Schlenk technique; Molecular sieve; Sealed tube; | General procedure: In a nitrogen-filled glove box, a 25 mL Schlenk tube equipped with a magnetic stir bar was charged with Cu(OAc)2 (9.3 mg,0.05 mmol, 0.1 equiv), aryl boronic acid 1 (0.5 mmol, 1.0 equiv),Na2CO3 (106.0 mg, 1.0 mmol, 2.0 equiv) and 4 A MS (250.0 mg). The vessel was sealed with a septum before removing from the glovebox. The tube was evacuated and backfilled with air for 3 times.Then DCE (5.0 mL), pyridine (39.6 mg, 0.5 mmol, 1.0 equiv) and CF3CH2OH (100.0 mg, 1.0 mmol, 2.0 equiv) were added respectivelyvia syringe. The mixture was stirred vigorously under a balloon ofair at room temperature for 14 h. Then the reaction solution was vacuum-filtered over a sintered-glass funnel with a tightly packedpad of Celite (1 cm thick), and the filter cake was rinsed with DCM(20 mL). The combined filtrates were concentrated. The residue was purified with silica gel column chromatography to provide the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | To a 10 mL reaction tube equipped with a magnetic carrier, 0.4 mg (0.8 mmol) of trimethylsilyl diazomethane (2M n-hexane solution) was added to 99 mg (0.4 mmol) of 4-iodobenzeneboronic acid, 1 mL of toluene was added to the system, The rubber stopper was stoppered and reacted on an electromagnetic heating stirrer at 50 C for 4 hours.Followed by the addition of 71 mg (0.6 mmol) of pinacol (dissolved in 1 mL of 1,4-dioxane), 0.2 mL of tetrabutylammonium fluoride (1 M tetrahydrofuran solution) and 200 uL of water at 50 C, On the reaction for 4 hours.After completion of the reaction, the organic solvent was removed by a rotary evaporator and purified by column chromatography4-iodobenzyl boronic acid pinacol ester, its structure is as follows:The compound was a colorless liquid in a yield of 56% with the following NMR data: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In dichloromethane at 20℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With sodium hydroxide; In toluene; at 100℃; for 2h;Schlenk technique; | General procedure: An oven-dried Schlenk flask, equipped with a magnetic stir bar, septum and a condenser was charged with acyl chloride (1.0 mmol), arylboronic acid (1.0 mmol), NaOH (4 mmol) and 5.0 mL of toluene. The flask was immersed and stirred in an oil bath at 100 C. Upon complete consumption of starting materials as determined by GC analysis, the water (10.0 mL) was added. The reaction mixture was extracted with diethyl ether (3 × 5.0 mL). The combined organic layer was collected, dried over anhydrous Na2SO4 and concentrated in vacuum to afford product which was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate = 9:1 or 8:2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide; In tetrahydrofuran; water; at 75℃; for 12h; | A 500 mL 2-neck round bottom flask was charged with intermediate 6-9 (50 mmol, 24.9 g) 4-Iodophenylboronic acid (50 mmol, 12.4 g), Pd (PPh3) 4 (1.5 mmol, 1.74 g), Sodium hydroxide (150 mmol, 6.0 g) , 200 mL of tedrahydrofuran and 50 mL of water are added, and the mixture is refluxed at 75 C. for 12 hours. When the reaction is completed, the temperature of the reaction solution is cooled to room temperature After extracting with dichloromethane, the organic solvent layer was dried over MgSO 4, and the solvent was removed by drying under reduced pressure. The reaction product thus obtained was recrystallized from dichloromethane and normal hexane, and then separated by silica gel column chromatography To obtain 23.9 g (Yield: 85%) of Intermediate 6-10 as a yellow solid. |
85% | With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide; In tetrahydrofuran; water; at 75℃; for 12h;Inert atmosphere; | A 500 mL 2-neck round bottom flask was charged with intermediate 6-9 (50 mmol, 24.9 g) 4-Iodophenylboronic acid (50 mmol, 12.4 g),Pd (PPh3) 4 (1.5 mmol, 1.74 g),Sodium hydroxide (150 mmol, 6.0 g)And 200 mL of tedrahydrofuran and 50 mL of water After filling with nitrogen, the mixture is refluxed at 75 DEG C for 12 hours.When the reaction is completed, the reaction solution is cooled to room temperature and extracted with dichloromethane. The organic solvent layer is dried using MgSO 4, and the solvent is removed by drying under reduced pressure. The reaction product thus obtained was recrystallized from dichloromethane and n-hexane and then purified by silica gel column chromatography to obtain 23.9 g (yield: 85%) of Intermediate 6-10 as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide; In tetrahydrofuran; water; at 75℃; for 12h;Inert atmosphere; | A 500 mL 2-neck round bottom flask was charged with intermediate 30-6 (50 mmol, 24.9 g)4-Iodophenylboronic acid (50 mmol, 12.4 g),Pd (PPh3) 4 (1.5 mmol, 1.74 g),Sodium hydroxide (150 mmol, 6.0 g) was added, and 200 mL of tetrahydrofuran and 50 mL of waterAfter filling with nitrogen, the mixture is refluxed at 75 DEG C for 12 hours. When the reaction is completed, the reaction solution is cooled to room temperature, extracted with dichloromethane, dried over MgSO 4, and then dried under reduced pressure to remove the solvent. The reaction product thus obtained is recrystallized from dichloromethane and normal hexane And then purified by silica gel column chromatographyTo obtain 23.9 g (yield: 86%) of Intermediate 30-7 as a yellow solid |
86% | With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide; In tetrahydrofuran; water; at 75℃; for 12h;Inert atmosphere; | To a 500 mL 2-necked round bottom flask were added intermediate 30-6 (50 mmol, 24.9 g), <strong>[5122-99-6]4-iodophenylboronic acid</strong> (50 mmol, 12.4 g)Pd (PPh3) 4 (1.5 mmol, 1.74 g) and sodium hydroxide (150 mmol, 6.0 g) were added, and 200 mL of tetrahydrofuran and 50 mL of water were added. The mixture was refluxed at 75 C for 12 hours. When the reaction is completed, the temperature of the reaction solution is cooled to room temperature After extracting with dichloromethane, the organic solvent layer is dried using MgSO 4, and the solvent is removed by drying under reduced pressure.The reaction product thus obtained was recrystallized from dichloromethane and n-hexane and purified by silica gel column chromatographyTo obtain 23.9 g (yield: 86%) of Intermediate 30-7 as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide; In tetrahydrofuran; water; at 90℃; for 12h;Inert atmosphere; | A 500 mL two-necked round bottom flask was charged with intermediate 47-6 (50 mmol, 21.9 g) 4-Iodophenylboronic acid (50 mmol, 12.4 g),Pd (PPh3) 4 (1.5 mmol, 1.74 g),Sodium hydroxide (150 mmol, 6.0 g)And 200 mL of tedrahydrofuran and 50 mL of waterAfter filling with nitrogen, the mixture is refluxed at 90 DEG C for 12 hours. When the reaction is completed, the reaction solution is cooled to room temperature, extracted with dichloromethane, dried over MgSO 4, and then dried under reduced pressure to remove the solvent. The reaction product thus obtained is recrystallized from dichloromethane and normal hexane And then purified by silica gel tube chromatography to obtain 22.7 g (yield: 81%) of Intermediate 47-7 as a yellow solid |
81% | With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide; In tetrahydrofuran; water; at 90℃; for 12h;Inert atmosphere; | To a 500 mL 2-necked round bottom flask was added intermediate 47-6 (50 mmol, 21.9 g), <strong>[5122-99-6]4-iodophenylboronic acid</strong> (50 mmol, 12.4 g)Pd (PPh3) 4 (1.5 mmol, 1.74 g),Add sodium hydroxide (150 mmol, 6.0 g), add 200 mL of tetrahydrofuran and 50 mL of water, fill with nitrogen, and reflux at 90 C for 12 hours. When the reaction is completed, the reaction solution is cooled to room temperature and extracted with dichloromethane. The organic solvent layer is dried using MgSO 4, and the solvent is removed by drying under reduced pressure. The reaction product thus obtained was recrystallized using dichloromethane and n-hexane, and then purified by silica gel column chromatography to obtain 22.7 g (yield: 81%) of Intermediate 47-7 as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | General procedure: In a glove box, an over-dried 50 mL Schlenk tube equipped with a magnetic stir bar was charged with 4A molecular sieves (250.0 mg) and K3PO4 (382.1 mg, 1.8 mmol, 3.0 equiv). The vessel was sealed with a septum and flame-dried under vacuum. After the tube was cooled to room temperature, CuSCN (73.0 mg, 0.6 mmol, 1.0 equiv), 2-fluoropyridine (57 muL, 0.6 mmol, 1.0 equiv), S8 (60.0 mg, 1.8 mmol, 6.0 equiv), aryl boronic acid (0.6 mmol, 1.0 equiv) and Ag2CO3 (330.9 mg, 1.2 mmol, 2.0 eqiuv) were added to the tube in a glove box. The tube was then evacuated and backfilled with N2. Freshly distilled DMF (25 mL) and CS2 (37 muL, 0.6 mmol, 1.0 eqiuv) were then added to the reaction tube, followed by the addition of TMSCF2CF3 (324 muL, 1.8 mmol, 3.0 equiv) or TMSCF2CF2CF3 (345 muL, 1.8 mmol, 3.0 equiv) after 30min. Then, the reaction mixture was then placed under a balloon of N2 and was stirred vigorously for 24h. Benzotrifluoride (75 muL, 0.6 mmol) was added as an internal standard, and the yield of the crude reaction was measured by 19F NMR before working up. The reaction solution was filtered by Celite on silica, eluted with diethyl ether, washed with brine and concentrated. The residue was purified with silica gel column chromatography to provide pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | General procedure: In a glove box, an over-dried 50 mL Schlenk tube equipped with a magnetic stir bar was charged with 4A molecular sieves (250.0 mg) and K3PO4 (382.1 mg, 1.8 mmol, 3.0 equiv). The vessel was sealed with a septum and flame-dried under vacuum. After the tube was cooled to room temperature, CuSCN (73.0 mg, 0.6 mmol, 1.0 equiv), 2-fluoropyridine (57 muL, 0.6 mmol, 1.0 equiv), S8 (60.0 mg, 1.8 mmol, 6.0 equiv), aryl boronic acid (0.6 mmol, 1.0 equiv) and Ag2CO3 (330.9 mg, 1.2 mmol, 2.0 eqiuv) were added to the tube in a glove box. The tube was then evacuated and backfilled with N2. Freshly distilled DMF (25 mL) and CS2 (37 muL, 0.6 mmol, 1.0 eqiuv) were then added to the reaction tube, followed by the addition of TMSCF2CF3 (324 muL, 1.8 mmol, 3.0 equiv) or TMSCF2CF2CF3 (345 muL, 1.8 mmol, 3.0 equiv) after 30min. Then, the reaction mixture was then placed under a balloon of N2 and was stirred vigorously for 24h. Benzotrifluoride (75 muL, 0.6 mmol) was added as an internal standard, and the yield of the crude reaction was measured by 19F NMR before working up. The reaction solution was filtered by Celite on silica, eluted with diethyl ether, washed with brine and concentrated. The residue was purified with silica gel column chromatography to provide pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.71 g | With pyridine; copper diacetate; In N,N-dimethyl acetamide; at 20℃; | A mixture of (4-iodophenyl)boronic acid (5 g), <strong>[5932-27-4]ethyl 1H-pyrazole-3-carboxylate</strong> (3.08 g), copper(II) acetate (4 g), pyridine (2.9 g) and DMA (50 ml) was stirred overnight at room temperature. The mixture was extracted with ethyl acetate and saturated aqueous ammonium chloride solution. The obtained organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (4.71 g). 1H NMR (300 MHz, DMSO-d6) delta 1.32 (3H, t, J = 7.1 Hz), 4.33 (2H, q, J = 7.1 Hz), 7.02 (1H, d, J = 2.6 Hz), 7.68-7.77 (2H, m), 7.85-7.96 (2H, m), 8.65 (1H, d, J = 2.6 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With chloro[tris(para-trifluoromethylphenyl)phosphine]gold (I); In methanol; at 20℃;Irradiation; Inert atmosphere; | General procedure: In a dried Pyrex screwtop reaction tube (4CF3C6H4)3PAuC (OO3 mmo, 10 mo %) and the corresponding boronic acid (0.3 mmo, 1.0 equiv.) were dissoved in 1.5 mL MeOH. After adding the corresponding diazonium saFt (1.2 mmo, 4.0 equiv.) the reac tion mixture was degassed under argon by sparging for 510 mm, The tubes were irra..diated at room temperature with 29 W bue LEDs for 1517 hours, The sovent was removed under reduced pressure and the resufting crude product was purified by cop. umn chromatography on Si02. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With nickel diacetate; potassium carbonate; In toluene; at 120℃; for 8h;Inert atmosphere; | Add 6 mmol of diphenylphosphonium chloride containing a bridge nitrogen atom ligand (R1, R2, R3, R4, R5, R6, in a 100 mL reaction tube).The R7, R8, R9, R10, R11, R12, and R13 groups are hydrogen),9mmol aryl boronic acid (R14, R15, R17, R18 groups are hydrogen, R16 is iodine),5 mol% nickel acetate, 2 equivalents of potassium carbonate, and vacuum-filled with nitrogen three times.40 ml of toluene was added under a nitrogen atmosphere.The reaction was carried out at 120 C for 8 h.After the reaction, the toluene was removed under reduced pressure.Recrystallization from ethyl acetate and n-hexane gave the desired product.The yield was 94%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With pyridine; copper diacetate; In dichloromethane; at 40℃; for 24h;Inert atmosphere; Molecular sieve; | General procedure: A 10 mL-round bottom flask was charged with 1 (0.143 mmol), aryl boronic acid 2 (0.429 mmol), Cu(OAc)2 (0.143 mmol), molecular sieves (0.15 g), pyridine (0.286 mmol) and CH2Cl2 (1.5 mL). The reaction mixture was stirred under air atmosphere at 40 C. After 24 h, the mixture was filtered through celite (eluting with ethyl acetate and CH2Cl2). The filtrate was concentrated under vacuum and the residue was purified by column chromatography on silica gel to give the desired product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With perchloric acid treated surface-modified sludge carbon; In 1,2-dichloro-ethane; at 20 - 70℃; for 8.5h;Schlenk technique; | At room temperature, weigh 1-p-chlorophenyldiazoacetate 1b (0.5 mmol),P-iodophenylboronic acid 2f (0.8 mmol), SW-I (50 mg) in a 25 mL Schlenk reaction tube,Under air atmosphere, add 5 mL of 1,2-dichloroethane, and stir at room temperature for 0.5 h.Move to 70 C oil bath magnetic stirring heater for 8 hours,TLC detects that the raw materials have reacted completely, stop the reaction, cool the reaction solution to room temperature, suction filter, wash the filter cake with dichloromethane until the filtrate is colorless, and concentrate under reduced pressure to remove volatile components.Silica gel column chromatography (eluent: petroleum ether (60-90 C) / ethyl acetate, v / v = 10: 1) to obtain 3l (98mg, yield 51%) of the target product as a colorless transparent viscous substance. ,The target product was confirmed by NMR spectrum and high resolution mass spectrometry. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With perchloric acid treated surface-modified sludge carbon; In 1,2-dichloro-ethane; at 20 - 70℃; for 8.5h;Schlenk technique; | At room temperature, weigh phenyldiazoacetate 1a (0.5 mmol),P-iodophenylboronic acid 2f (0.8 mmol), SW-I (50 mg) in a 25 mL Schlenk reaction tube,Under air atmosphere, add 5 mL of 1,2-dichloroethane, and stir at room temperature for 0.5 h.Move to 70 C oil bath magnetic stirring heater for 8 hours,TLC detects that the raw materials have reacted completely, stop the reaction, cool the reaction solution to room temperature, suction filter, wash the filter cake with dichloromethane until the filtrate is colorless, and concentrate under reduced pressure to remove volatile components.Silica gel column chromatography (eluent: petroleum ether (60-90 C) / ethyl acetate, v / v = 10: 1) to obtain the target product 3f (77 mg, yield 42%) as a colorless transparent viscous substance. ,The target product was confirmed by NMR spectrum and high resolution mass spectrometry. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); potassium methanolate; In N,N-dimethyl acetamide; at 70℃; for 24h;Schlenk technique; Sealed tube; | n the glove box, to a 50 mL Schlenk bottle with a stir bar was added <strong>[5122-99-6]4-iodophenylboronic acid</strong> (1 mmol, 247.8 mg), potassium methoxide (2 mmol, 2 equivalents, 140.2 mg), Cu(IPr)Cl (0.03 mmol, 0.03 equivalents, 14.6 mg) in this order. ), 5 mL of solvent N, N-dimethylacetamide. Remove the capped Schlenk bottle from the glove box, fully evacuate, fill the reaction system with carbon dioxide and seal it well, and then stir the reaction mixture at 70 C. for 24 hours. After cooling to room temperature, it was acidified by adding 1 mol / L hydrochloric acid, and extracted with ethyl acetate, and washed once with brine. The organic phase was collected and concentrated in vacuo. The liquid mixture was dropped on a silica gel column and purified by column chromatography. As petroleum ether / ethyl acetate, the desired product 4-iodobenzoic acid was obtained in a yield of 69%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With sodium hydrogencarbonate; copper(II) sulfate; In methanol; at 10 - 30℃; for 12h;Inert atmosphere; Sealed tube; | General procedure: Operation steps: Under the protection of argon gas, weigh 0.9mmol of boric acid, 0.5mmol of reagent, 0.05mmol of copper sulfate, 0.75mmol of sodium bicarbonate, 5mL of methanol in a 25mL sealed tube, and react at room temperature for 12h. After the reaction was completed, 10 mL of water was added, extracted with anhydrous ether, dried over anhydrous magnesium sulfate, filtered through celite, and concentrated. The residue was subjected to flash silica gel column chromatography to obtain 123 mg of a colorless oily liquid with a yield of 81%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With methanesulfonic acid; palladium(II) acetylacetonate; In N,N-dimethyl acetamide; at 110℃; for 24h;Sealed tube; | In an air atmosphere, add the raw material [1,1'-biphenyl]-2,2'-dinitrile (0.4mmol) to a 25ml sealed tube, p-iodophenylboronic acid (0.8 mmol), catalyst diacetylacetonate palladium (5mol%), N,N-dimethylacetamide (2 mL) and methanesulfonic acid (4 mmol), then it was reacted at 110C for 24 hours to obtain 7-(4-iodophenyl)-5H-dibenzo[c,e]aza-5-one; the final product yield is 80%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | With copper(l) iodide; E-pyridine-2-carbaldehyde 2-pyridylhydrazone; cobalt(II) chloride hexahydrate; potassium carbonate In acetonitrile at 20℃; Irradiation; Overall yield = 73 percent; |
Tags: 5122-99-6 synthesis path| 5122-99-6 SDS| 5122-99-6 COA| 5122-99-6 purity| 5122-99-6 application| 5122-99-6 NMR| 5122-99-6 COA| 5122-99-6 structure
[ 374790-98-4 ]
2-Fluoro-4-iodophenylboronic acid
Similarity: 0.73
[ 374790-98-4 ]
2-Fluoro-4-iodophenylboronic acid
Similarity: 0.73
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 :