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. : | 34771-45-4 | MDL No. : | MFCD00234616 |
Formula : | C10H8N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LVXOXXGCJHYEOS-UHFFFAOYSA-N |
M.W : | 156.18 | Pubchem ID : | 817373 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 47.47 |
TPSA : | 25.78 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.95 cm/s |
Log Po/w (iLOGP) : | 1.84 |
Log Po/w (XLOGP3) : | 1.83 |
Log Po/w (WLOGP) : | 2.14 |
Log Po/w (MLOGP) : | 1.32 |
Log Po/w (SILICOS-IT) : | 2.55 |
Consensus Log Po/w : | 1.94 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.64 |
Solubility : | 0.362 mg/ml ; 0.00232 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.99 |
Solubility : | 1.59 mg/ml ; 0.0102 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -4.16 |
Solubility : | 0.0109 mg/ml ; 0.00007 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.45 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
97% | With potassium carbonate; In ethanol; water; at 60℃; for 1h; | General procedure: In a thermostatted bath at 25C (or 60C for compounds 18 and 28), a 25 mL Schlenk flask was charged in air with a magnetic stir bar, arylbromide (0.5 mmol), arylboronic acid (0.6 mmol), K2CO3 (0.6 mmol), 1 (26.6 mg, 1mol-%), ethanol (1.5 mL), and water (0.5 mL). The reaction mixture was kept under vigorous stirring until the GC control showed no residual aryl bromide in solution. Water (10 mL) was added to the suspension and the organics were extracted with dichloromethane (3×10 mL). The solution was dried over Na2SO4 and then passed through a column filled with silica gel (diatomaceous earths were used in the case of compound 28). Elimination of the solvent under vacuum gave the desired biaryl as white microcrystalline solid. Purity (96÷99%) was established by GC and 1H NMR. 1H and 13C{1H} NMR data of compounds 8-28. Spin multiplicity is given by s=singlet, br s=broad singlet, q=quartet, st=septet, qq=quartet of quartets, ddd=doublet of doublets of doublets, m=unresolved multiplet. 5-Phenylpyrimidine (28). Yield 97%. C10H8N2 (156.19) calcd. C 76.90, H 5.16, N 17.94; found C 76.76, H 5.21, N 17.89. 1H NMR (CDCl3): delta = 9.19 (1H, s), 8.94 (2H, s), 7.60-7.31 (5H, m) ppm. 13C NMR (CDCl3): delta = 157.4, 154.8, 134.2, 134.1, 129.3, 128.9, 126.9 ppm. |
96% | With C14H19NO3*C6H15N; potassium hydroxide; palladium dichloride; In ethanol; water; at 80℃; for 4h;Green chemistry; | General procedure: In the first step,reference solution (CPd=0.5×10-4mmol/mL,CLigand=1.0×10-4mmol/mL) was prepared. A single-neckedground tube (rinner=1.1 cm, L=17.5 cm) was equipped with a magnetic stirbar. 0.5 mmol of aryl halides, 0.75 mmol of phenyl boronic acid and 1 mmol basewere added into the tube under atmospheric condition. Then, appropriate amountof reference solution and solventwere added into the tube. The reaction mixture was stirredat the pre-arranged temperature for appropriate reaction time in oil bath. Afterthe reaction was completed, 3 mL water was added, and the mixture was extractedwith EtOAc(10 mL×4). Then the organic phase was dried with Na2SO4and concentrated under reduced pressure. The residue was then purified by columnchromatography on silica gel. The pure product was obtained and was analyzed by1H NMR spectroscopy. |
96% | With potassium carbonate; In water; at 80℃; for 6h;Green chemistry;Catalytic behavior; | General procedure: Forthe Suzuki-Miyaura reaction, a 50 mL round-bottomed flask was charged with aryl halide(0.5 mmol), arylboronic acid (0.65 mmol), K2CO3 (1 mmol), catalyst (0.002 g; 0.0005 mmol ofPd) and water (4 mL) and stirred at appropriate temperature. The progress of the reaction wasmonitored by thin layer chromatography using aluminum coated TLC plates (Merck) underUV light. At the end of reaction, the mixture was cooled down to room temperature and theproduct diluted with water (10 mL) and extracted with ether (3 x 15 mL). The combinedextract was washed with brine (3 x 15 mL) and dried over Na2SO4. After evaporation of the solventunder reduced pressure, the residue was subjected to column chromatography with ethylacetate/hexane (1:9) as eluent to get the desired product. |
95% | With potassium phosphate tribasic heptahydrate; C18H24N3O2Pd; In ethanol; water; at 60℃; for 4h; | General procedure: The reaction vessel was charged with heteroaryl bromides (1.0mmol), arylboronic acid (1.2mmol), K3PO4·7H2O (1.5mmol), and the catalyst 1 (0.5mol%) in EtOH/H2O (1:2, v/v 3mL). The reaction mixture was heated at 60C in air and the progress of the reaction was monitored by TLC. At the end of the reaction, the reaction mixture was diluted with water (20mL) and then extracted with EtOAc (2×20mL). The combined organic layers were washed with brine (10mL) and then dried over anhydrous Na2SO4. After removal of the solvent, the crude product was purified by flash chromatography over silica gel using ethyl acetate/hexane as an eluent to afford the pure product. |
95% | With cetyltrimethylammonim bromide; potassium carbonate; sodium L-ascorbate; In water; at 80℃; for 10h;Inert atmosphere; Green chemistry; | In a two-necked round bottom flask equipped with a magnet, the catalyst PdMgAl-LDH-1 (43 mg, 0.20 mol% Pd) was added, sodium ascorbate (2 mg, 0.01 mmol), potassium carbonate (256 mg, 2.00 mmol), CTAB (36 mg, 0.10 mmol), phenylboronic acid (134 mg, 1.00 mmol), N2 gas replacement, iodobenzene (0.11 mL, 1.00 mmol) was added in that order, water (3.0 mL). N2 atmosphere slowly heated to 80 C , TLC tracking reaction. after 2 hours of reaction, the catalyst was filtered off with a sand core funnel, the catalyst was washed with ethyl acetate, the organic phases were combined and washed with saturated brine to neutral, dried over anhydrous MgSO4, the solvent was evaporated under reduced pressure, the residue column chromatography (ethyl acetate / petroleum ether = 1: 20, Rf = 0.6), to give 144 mg of a white solid, yield 93%. The preparation method was the same as in example 4, 5-bromopyrimidine (158 mg, 1.00 mmol) was used as substrate. After 10 hours of reaction, column chromatography (ethyl acetate / petroleum ether = 2: 3, Rf = 0.5), a light yellow solid 148 mg, Yield 95%. |
94% | With 2Na(1+)*C26H18N2O8PdS2(2-); potassium carbonate; In water; at 20℃; for 8h;Catalytic behavior; | General procedure: The Suzuki reaction was performed in a 50 mL round-bottomed flask, aryl halide (0.5 mmol), arylboronic acid (0.65 mmol), K2CO3 (1 mmol), Complex 1 (0.2-1 mol%) and water (4 mL) were charged and stirred for the required time at room temperature for aryl bromides or at 100 C for aryl chlorides. After completion, the mixture was cooled down to room temperature, diluted with water (10 mL) and extracted with diethyl ether (3 × 15 mL). The organic layer was washed with brine (3 × 15 mL), dried over anhydrous Na2SO4. The crude products were chromatographed on silica gel (ethyl acetate/hexane). |
92% | With potassium phosphate; trans-diacetylpalladium(II) bis(dicyclohexylamine); In ethanol; at 20℃; for 24h; | General procedure: Method A: K3PO4 (531 mg, 2.5 mmol) was added to a solution of 5-bromopyrimidine (1) (159 mg, 1.0 mmol), phenylboronic (2a)[2-fluorobenzeneboronic acid (2b), 3-fluorobenzeneboronic (2c), 4-fluorobenzeneboronic (2d), 2,4-difluorobenzeneboronic (2e), 3,5-difluorobenzeneboronic (2f), 2-(trifluoromethyl)benzeneboronic (2g), 3-(trifluoromethyl)benzeneboronic (2h), 4-(trifluoromethyl)benzeneboronic (2i), 2,4-bis(trifluoro-methyl)benzeneboronic (2j), or 3,5-bis(trifluoro-methyl)benzeneboronic (2k) acids] (1.2 mmol) and trans-bis(dicyclohexylamine)palladium(II) acetate (29 mg, 0.05 mmol) in EtOH (10 mL). The resulting suspension was stirred at ambient temperature for 24 h. EtOH wasevaporated under a reduced pressure and the residue was suspendedin CH2Cl2 (20 mL) and filtered from inorganic salts. After that solvent was distilled off under a reduced pressure, and theresidue was purified by flash column chromatography on silicagel (hexane/ethyl acetate, 1:3) to afford the desired cross-coupling products (3a-k). |
92% | With potassium phosphate; trans-diacetylpalladium(II) bis(dicyclohexylamine); In ethanol; for 2h;Reflux; | General procedure: Phenylboronic (2a)(1.0 mmol), [or 4-tert-butylphenylboronic (2b), 4-(trifluoromethyl)phenylboronic (2c), 2-thienylboronic (2d), 3-thienylboronic (2e), 1-benzothien-2-ylboronic (2f) or 1-benzothien-3-ylboronic (2g)] was added to trans-bis(dicyclohexylamine)palladium(II) acetate (29 mg, 0.05mmol) in EtOH (10 mL). The resulting suspension was kept at reflux for 2 h. EtOH was evaporated under reduced pressure and the residue was suspended in CH2Cl2 (20 mL), and then filtered from inorganic salts. Solvent was then distilled off under reduced pressure, and the residue was purified by flash column chromatography on silica gel (hexane/ethyl acetate, 1:3) to afford the desired cross-coupled products (3a-g). Compounds 3d-g were identified on the basis of their NMR spectra and comparison with authentic materials. For spectral data of compounds 3d-g synthesized earlier,see ref 21. 5-Phenylpyrimidine (3a). 29 Yield (see Table 1, entry 1), white solid; mp 38-40 C. 1H NMR (400MHz, CDCl3): delta 7.45-7.49 (m, 1H, Ph), 7.51-7.55 (m, 2H, Ph), 7.58-7.60 (m, 2H, Ph), 8.92 (s, 2H,H-4 and H-6), 9.17 (s, 1H, H-2) ppm. GC tR 15.76 min; MS m/z (rel intensity) 156 (M+, 100). Anal.Calcd for C10H8N2 (156.19): C, 76.90; H, 5.16; N, 17.94. Found: C, 76.81; H, 5.23; N, 17.87%. |
88% | With C28H40Br4N4Pd2; potassium carbonate; In water; acetone; at 40℃; for 24h; | General procedure: A mixture of aryl halide (1 mmol), arylboronic acid (1.2 mmol), catalyst A (1 mol %, 0.0096 g), K2CO3 (2 mmol), and (1:1) acetone/water mixed solvent (3 mL) were taken in 25 mL round bottom flask and the mixture was stirred at room temperature (40 C for heteroaryl halides) until the completion of reaction (required time given in Tables 3-5). The reaction mixture was then diluted with water (20 mL) and extracted three times with dichloromethane (3×10 mL). The combined organic layer was washed with brine (20 mL) and dried over anhydrous Na2SO4. After that it was concentrated under reduced pressure and the crude product was purified by column chromatography on silica gel (60-120 mesh) using petroleum ether (60-80 C) and ethyl acetate were as the eluent. |
88% | With C22H20N4O6Pd; potassium carbonate; In water; at 100℃; for 6h;Green chemistry; | General procedure: Aryl halide (1 mmol), phenylboronic acid (1.5 mmol), palladium complex (1 mol%), K2CO3 (1.5 mmol), and water (1.5 mL) were added to 5 mL flask and mixture was stirred at 100 C for appropriate reaction time. The progress of the reaction to completion was monitored by TLC or GC analysis. After the completion of reaction, the aqueous layer was extracted with ethyl acetate or diethyl ether (51 mL). Organic extracts were combined to gether and dried over anhydrous Na2SO4 and purified by flash chromatographyusing hexane/EtOAc to give the desired coupling product. |
86% | With palladium; potassium carbonate; In methanol; acetonitrile; at 20℃; for 5h; | General procedure: To a freshly prepared solution of PdNPs (10 mL, 0.02 mmol), K2CO3 (0.276 g, 2 mmol) was added followed by arylhalide (1 mmol) and arylboronic acid (1.5 mmol). Then, the reaction mixture was stirred at room temperature in open atmosphere. The reaction was monitored by TLC and was stopped after the complete consumption of starting material. Then the mixture was centrifuged and filtered. The filtrate was evaporated to get the product in crude form and afterwards purified by column chromatography using hexane as the eluent. Characterization of products was done by 1H, 13C NMR and ESI-MS (see SI). |
84% | With potassium carbonate; In ethanol; water; at 30℃; for 17h;Green chemistry; | General procedure: Aryl halide (0.5 mmol), arylboronic acid (0.75 mmol), K2CO3 (104 mg, 0.75 mmol), catalyst (3.6 mg, containing 0.1 mol% Pd) and 2 mL solvent (1:1, EtOH:H2O for aryl bromides and PEG200 for arylchlorides) were added to a 5 mL flask, and the mixture was stirred mechanically at 30 C for aryl bromides and at 120 C for arylchlorides. The progress of the reaction was monitored by GC. After completion of the reaction, the crude product was extracted using ethyl acetate. The pure products were obtained by column chromatography on silica gel using hexane and ethyl acetate as eluent. |
82% | With potassium carbonate; In water; at 50℃; for 8h; | General procedure: For Suzuki-Miyaura reaction, appropriate amount of the catalyst, PdNP-NMe2SiO2, was added to a mixture of aryl halide (0.5 mmol), arylboronic acid (0.65 mmol), K2CO3 (1.5 mmol) in 6 mL solvent. The reaction was then stirred under desired temperature for the required time. The initial progress of the reaction was monitored by TLC using aluminum coated TLC plates (Merck) under UV light and the product formation was determined using GC-MS. After completion, the catalyst was collected by filtration and washed with isopropanol-water. The filtrate was diluted with water and extracted with ether and then dried over Na2SO4. After evaporation of the solvent under reduced pressure, the residue was chromatographed (silica gel, ethyl acetate-hexane, 1:9) to obtain the desired product. |
80% | With potassium phosphate; PdPt(2-diphenylphosphinopyridine)2Cl2; In water; at 25℃; for 20h; | General procedure: Aryl halide (1mmol), arylboronic acid (1.5mmol), catalyst (0.8mol%), K3PO4 (1.5mmol) and distilled water (2mL) were added to a 5mL flask. The mixture was stirred for appropriate reaction time at 25C for aryl iodides, 60C for aryl bromides and 80C for aryl chlorides. The progress of the reaction was monitored by GC. After completion of the reaction, the aqueous layer was extracted with ethyl acetate or hexane (5×1mL) and further purified by column chromatography using hexane and ethyl acetate as an eluant. 1a. |
72% | With C32H26NO2PPdS; potassium carbonate; In ethanol; N,N-dimethyl acetamide; water; at 100℃; for 12h;Catalytic behavior; | General procedure: To the catalyst (1.0 mol%) dissolved in 1 ml DMAc, aryl bromide (1.0 mmol), phenyl boronic acid (1.5 mmol) in 1 ml ethanol, K2CO3 (2.0 mmol) in 1 ml water and DMAc (5 ml) were all added. The mixture was heated at 100 C for 12 h. Then, the mixture was cooled, water was added and the product was extracted with ethylacetate. The organic layer was washed with brine, dried over Na2SO4, filtered, passed through celite, and analyzed by GC. Yields were based on corresponding aryl bromides. |
45% | With C28H37Cl2N3Pd; potassium carbonate; In methanol; water; at 20℃; for 24h; | General procedure: In the air condition, hexamethylbenzene (0.05 mmol, 0.0081 g,0.1 equiv), aryl halide (0.5 mmol, 1 equiv), aryl boronic acid(0.6 mmol, 1.2 equiv), base (1.1 mmol, 2.2 equiv) and solvent wassubsequently added into a 10 mL vial equipped with a magneticstir bar. The 5 mM Pd catalyst solution in MeOH was added asindicated in the table. The reaction vial was capped and vigorouslystirred at room temperature for desired time as indicated. Thereaction mixture was extracted with CH2Cl2 (3 10 mL), washedwith water (2 10 mL), brine (1 10 mL) and dried over Na2SO4.The combined organic phase was then concentrated to afford thecrude coupling product. The reaction was monitored by GC-FIDbased on integration relative to hexamethylbenzene as an internalstandard. The crude product was finally isolated by columnchromatography (0e10%: EtOAc/hexane) to afford the desiredproduct. |
General procedure: Catalyst (2 mol%), aryl halide (1 equiv.) and Na2CO3 (1.1 equiv.) were stirred in H2O (5 mL) taken in the round bottom flask. The aryl boronic acid (1.1 equiv.) was added to the stirring solution. Stirring was continued for required time at 45 C. After the requisite time, the reaction mixture was diluted with water and the product was extracted with ethyl acetate. The ethyl acetate extract was passed through celite bed and then analyzed by GC. Authentic samples of both reactant and product were used to verify the retention time and to confirm the product formation. The ethyl acetate extract was concentrated and chromatographed on a silica gel column using hexane and ethylacetate as eluent to afford coupled product. The products are characterized by NMR, GC MS and UPLC analyses. | ||
With potassium carbonate; In water; for 3h;Reflux;Catalytic behavior; | General procedure: To a mixture of Pd(II)-beta-CD (0.001mol%, based on palladium, 0.23mL from a solution of 1mg in 100mL water, see Table2 for amount of catalyst) in 2mL water was added aryl halide (0.2mmol), arylboronic acid (0.24mmol), and K2CO3 (0.3mmol). The resulting mixture was stirred at reflux for 1-12h (Table2). After cooling, the product was extracted with n-hexane (2×3mL) and dried over Na2SO4. The product was purified by flash chromatography and characterized with 1H and 13CNMR (in CDCl3 and DMSO solvents) to afford biaryls 3a-s in 56-100% yields. All products are known and most of them are commercially available (see supporting information). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With potassium acetate; tetra-(n-butyl)ammonium iodide; C25H34P2; palladium dichloride; In dimethyl sulfoxide; at 100℃; for 12h; | General procedure: In the reaction flask, arylsulfonylhydrazide (1 mmol), phenyldiazonium salt (1.1 mmol), TBAI (1.5 mmol), KOAc (2.0 mmol), PdCl 2 (0.05 mmol), ligand Dcypm (0.1 mmol) and 2 mL DMSO, then heated to 100 C The reaction was carried out. After 12 hours of reaction, the reaction was completely monitored by TLC, cooled to room temperature, and the solid was filtered, and 1 mL of water was added and then extracted with 2 mL of diethyl ether. After taking three times and combining the extracts to dry the solvent, the column was separated by using a mixed solvent of petroleum ether and ethyl acetate as an eluent. That is the product. The reaction formula and reaction results are as follows: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With palladium diacetate; potassium carbonate; In ethanol; water; at 80℃; for 2h; | General procedure: A mixture of aryl bromides (0.5 mmol), potassium aryltrifluoroborates (0.6 mmol), K2CO3 (0.5 mmol), Pd(OAc)2 (1 mol %), EtOH/H2O (2 mL/2 mL) was stirred at 25 C in air for the indicated time. The reaction mixture was added to brine (15 mL) and extracted with ethyl acetate (3×15 mL). The solvent was concentrated under vacuum, and the product was isolated by short-column chromatography on silica gel (200-300 mesh). |
96% | With 5%-palladium/activated carbon; oxygen; potassium carbonate; In ethanol; water; at 80℃; for 3h; | General procedure: A mixture of aryl halide (0.5 mmol), potassium aryltrifluoroborate (0.6 mmol), K2CO3 (1.0 mmol), Pd/C (5%; 0.5 mol%), ethanol (3 mL), and distilled water (1 mL) was stirred at 80 C in air for the time indicated. The reaction mixture was added to brine (15 mL) and extracted with ethyl acetate (4×15 mL). The organic solvent was removed under vacuum, and the product was isolated by short-column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A 100 mL round-bottom flask was charged with 5-chloropyrimidine (5 mmol), phenylboronic acid (1.22 g, 10 mmol), PPh3 (265 mg, 1 mmol) and Pd(OAc)2 (224 mg, 1 mmol) in dioxide (50 mL) under nitrogen at room temperature. After stirring for 30 minutes, Na2C03 (159 mg, 7.5 mmol) and H20 (10 mL) were added and the resulting mixture was heated at reflux for 3 h. After cooling to rt, the reaction mixture was poured into water and extracted with EtOAc (3 x 50 mL). The combined organic layers were washed with brine (3 x 50 mL) and dried over anhydrous Na2S04. After filtration and concentration, the crude product was purified by column chromatography to give the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With potassium acetate; palladium dichloride; at 110℃; for 0.8h; | General procedure: Phenyl iodide (1.0 mmol, 0.136 mL) was added to a stirring mixture of PdCl2/ Ph3P (0.15 mol%/0.62 mol%) in PEG 400. Then Ph3SnCl (0.5 mmol, 0.193 g) and KOAc (3.0 mmol, 0.294 g) were added. The reaction mixture was stirred in an oil bath at 110 C. Monitoring of the reaction with TLC analysis showed that the reaction was completed within 1h. Work-up the reaction mixture after completion of the reaction, afforded biphenyl in 87% yield (0.133 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis(2-phenylpyridinato)(2,2'-bipyridine)iridium(III) hexafluorophosphate; at 20℃; for 16h;Inert atmosphere; Irradiation; | General procedure: In an oven-dried 10 mL round-bottom flask equipped with a magnetic stirrer bar, Ph2IPF6 (2,130 mg, 0.30 mmol), Ir(ppy)2bpyPF6 (1, 2.4 mg, 3.0 mol), 1-methylpyrrole (1.0 mL) were placed. The mixture was degassed by freeze-pump-thaw cycles and filled with nitrogen. The flask was placed 3 cm above 14W white LED (lambda = 400-750 nm) and illuminated for 16 h. The mixture was evaporated, and the residue was purified by silica gel column chromatography with EtOAc/hexane (1/20) to give 1-methyl-2-phenyl-1H-pyrrole (41 mg, 88% yield) as a pale yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With caesium carbonate; In ethanol; at 80℃; for 12h; | General procedure: To a round-bottom flask, aryl electrophile (1.0mmol), Pdnanocatalyst (1.5 mol%), Cs2CO3(1.5 mmol), PhB(OH)2(1.3 mmol), and EtOH (3.0 mL) were added, stirred andheated at 80C. The progress of the reaction was checked using TLC. After the completion of the reaction, the mixturewas cooled down and the catalyst was isolated usingan external magnet. The solvent was evaporated and furtherpurification was achieved using column chromatography onsilica gel to deliver the desired biphenyl derivatives in highyields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | General procedure: 2,4-dibromothiophene (4) (224 muL, 2.0 mmol) was added to a solution of 5-(hetero)arylpyrimidines (3a-g) (1.0 mmol) in CF3COOH (5 mL). The reaction mixture was stirred at room temperature for an appropriate time (see Table 1) and evaporated. The solution of KOH (224 mg,4.0 mmol, 4 equiv) and K3Fe(CN)6 (658 mg, 2.0 mmol, 2 equiv) in 10 mL water was added to formed was filtered off, washed with H2O, and air-dried. The residue was purified by flash column chromatography (hexane/ethyl acetate, 1:3) or by semi-preparative HPLC to afford the desired SNH-product (5a-g). 4-(3,5-Dibromothien-2-yl)-<strong>[34771-45-4]<strong>[34771-45-4]5-phenylpyrimidin</strong>e</strong> (5a). Yield (see Table 1, entry 8), yellow semisolid; mp 108-110 C. 1H NMR (500 MHz, DMSO-d6): delta 7.30 (s, 1H, H-4'), 7.34-7.36 (m, 2H,Ph), 7.40-7.45 (m, 3H, Ph), 8.99 (s, 1H, H-6), 9.28 (s, 1H, H-2) ppm. 13C NMR (126 MHz, DMSOd6):delta 110.58, 115.40, 128.47, 128.74, 128.85, 133.12, 134.16, 134.72, 136.60, 154.93, 156.90,158.65 ppm. GC tR 25.74 min; MS m/z (rel intensity): 396 (+, 100). Anal. Calcd for C14H8Br2N2S(396.11): C 42.45, H 2.04, N, 7.07. Found: C 42.74; H, 1.99; N, 7.05 %. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30%Spectr.; 28%Spectr. | With 2-chloro-[1,10]phenanthroline; {Pd(2,2':6',2''-terpyridine)(acetonitrile)}(BF4)2; Selectfluor; In acetonitrile; at 50℃; for 14h; | A mixture of palladium complex SI (27.7 mg, 50.0 muiotaetaomicron, 5.00 mol%) and 2-chloro- phenanthroline (10.7 mg, 50.0 muiotaetaomicron, 5.00 mol%.) was dissolved in acetonitrile (5.0 mL). This mixture was added to a 20 mL vial containing a solution of Selectfluor (709 mg, 2.00 mmol, 2.00 equiv.) and <strong>[34771-45-4]<strong>[34771-45-4]5-phenylpyrimidin</strong>e</strong> (156 mg, 1.0 mmol, 1.0 equiv.) in acetonitrile (5.0 mL, final c = 0.10 M). The reaction mixture was stirred for 14 hours at 50 C and then transferred to a separately funnel. Ethyl acetate (50 mL) was added and the organic layer was washed with water (50 mL) with brine added (10 mL). The aqueous layer was extracted with dichloromethane (3 chi 50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo at 40 C to afford a pale yellow solid. The residue was dissolved in dichloromethane (2 mL), loaded onto a short plug of silica (20 g) and eluted with ethyl acetate/dichloromethane 20:80 (v/v) and concentrated in vacuo to afford a yellow- orange solid (123 mg) containing the title compounds (111 mg, 0.580, 58% yield, 3ia: 3ib (52:48)), <strong>[34771-45-4]<strong>[34771-45-4]5-phenylpyrimidin</strong>e</strong> and minor inseparable impurities. The yield and selectivity were determined by 19F using l,4-bis(trifluoromethyl)benzene as an internal standard (standard: delta -63.4 ppm, 6 F; compared with product peaks at delta -112.4 and -117.5 ppm; first relaxation time of 10 s to ensure accurate integration). The spectra matched the reported spectra for the title compound 5ib. See Liu et al., Chem. Commun., 2009, 6267-6269. (0419) R/= 0.45 (ethyl acetate/dichloromethane 20:80 (v/v)). HRMS-FIA(m/z) calculated for CioFN2 [M+H]+, 175.0666; found, 175.0667. (0420) [00210] NMR Spectroscopy: 13C NMR (125 MHz, CDC13, 23 C, delta): 163.5 (d, J= 249.7 Hz), 159.9 (d, J = 249.7 Hz), 157.7, 157.6, 157.6, 156.4 (d, J= 4.1 Hz), 155.0, 154.8, 134.4 (d, J = 8.3 Hz), 131.1 (d, 7= 8.3 Hz), 130.2 (d, 7= 2.9 Hz), 129.8 (d, 7= 1.8 Hz), 129.5, 129.1, 128.9 (d, J= 8.4 Hz), 127.1, 125.2, 125.1, 116.7 (d, J= 21.8 Hz), 116.6 (d, J= 22.0 Hz). 5- (2-fluorophenyl)pyrimidine (3ia): 1H MR (500 MHz, CDC13, 23 C, delta): 9.15 (s, 1H), 8.91 - 8.84 (m, 3H), 7.55 - 7.33 (m, 4H), 7.27 - 7.10 (m, 3H). 19F NMR (470 MHz, CDC13, 23 C, delta): -117.5 ppm. 5-(4-fluorophenyl)pyrimidine (3ib): 1H NMR (500 MHz, CDC13, 23 C, delta): 9.21 (d, J= 1.2 Hz, 1H), 8.96 (s, 1H), 8.92 (s, 1H), 7.62 - 7.51 (m, 3H), 7.50 - 7.44 (m, 1H), 7.22 (t, J= 8.6 Hz, 1H). 19F NMR (500 MHz, CDC13, 23 C, delta): -112.4 ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88%Chromat. | With 1,4-diaza-bicyclo[2.2.2]octane; In N,N-dimethyl-formamide; at 60℃; for 24h;Inert atmosphere; | General procedure: To a 5 mL flask, the catalyst MgO(at)PdCu (10 mg for ArI or 40 mgfor ArBr and ArCl), ArX (1 mmol), DABCO (168 mg, 1.5 mmol), andTBAB (322 mg, 1 mmol), for aryl chloride and DMF (2 mL) wereadded under argon atmosphere. The alkyne (1.5 mmol) was alsoadded and the resulting mixture was stirred at 60-120 C forappropriate reaction times (see Tables). Progress of reactions wasfollowed by GC. Then, the reaction mixture was cooled down toroom temperature and extracted with ethyl acetate (3 x 5 mL), the organic phase was washed with H2O (10 mL), dried and evaporated.The resulting residue was purified by column or plate chromatographyusing hexane and ethyl acetate as eluents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In neat (no solvent); at 110℃; for 10h; | General procedure: The metal-free arylations of N-heteroaromatic compounds 1 using (trimethoxybenzene)iodonium salts Iwere performed according to the literature procedure.10a In the case of pyrazine 1d, the iodonium salt Ia(104 mg, 0.2 mmol) and sodium hydroxide (ca. 60 mg, 7.5 equiv) were added to pyrazine solution (1 mL)in reflux tube. After stirring at 110 C for 10 h, the remaining pyrazine was distilled by rotary evaporatorunder reduced pressure. The resulting oily residue including the pheylation product 2da was diluted withEtOAc (20 mL), and washed with brine (15 mL) and water (15 mL), and then the organic layer was driedover anhydrous sodium sulfate. After removal of the solvent, the crude product was subjected to columnchromatography on silica-gel (hexane/EtOAc = 5/1) to give a pure 2-phenylpyrazine 2da (26.8 mg, 0.17mmol) in 86% yield as a colorless crystals. |
Tags: 34771-45-4 synthesis path| 34771-45-4 SDS| 34771-45-4 COA| 34771-45-4 purity| 34771-45-4 application| 34771-45-4 NMR| 34771-45-4 COA| 34771-45-4 structure
[ 640769-70-6 ]
3-(Pyrimidin-5-yl)benzaldehyde
Similarity: 0.85
[ 640769-70-6 ]
3-(Pyrimidin-5-yl)benzaldehyde
Similarity: 0.85
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 :