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Chemical Structure| 691905-26-7 Chemical Structure| 691905-26-7
Chemical Structure| 691905-26-7

2',6'-Dimethylbiphenyl-3-carbaldehyde

CAS No.: 691905-26-7

4.5 *For Research Use Only !

Cat. No.: A304825 Purity: 98%

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Product Details of [ 691905-26-7 ]

CAS No. :691905-26-7
Formula : C15H14O
M.W : 210.27
SMILES Code : O=CC1=CC(C2=C(C)C=CC=C2C)=CC=C1
MDL No. :MFCD11895278
InChI Key :SCADEVWRJSJBOM-UHFFFAOYSA-N
Pubchem ID :23082866

Safety of [ 691905-26-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 691905-26-7 ]

* 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.

  • Downstream synthetic route of [ 691905-26-7 ]

[ 691905-26-7 ] Synthesis Path-Downstream   1~29

  • 1
  • [ 691905-26-7 ]
  • [ 35418-07-6 ]
  • C25H25NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In toluene; at 20℃; for 55h;molecular sieves; To a solution of <strong>[35418-07-6]methyl 3-(4-aminophenyl)propanoate</strong> (3.33 g, 18.6 mmol) and 2',6'-dimethylbiphenyl-3-carbaldehyde (3.91 g, 18.6 mmol) in toluene (40 mL) were added molecular sieves (0.4 nm, beads, 7.2 g), and the mixture was stirred at room temperature for 55 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in tetrahydrofuran (100 mL). Sodium cyanoborohydride (2.53 g, 40.3 mmol) and acetic acid (2.31 mL, 40.3 mmol) were successively added, and the mixture was stirred under a nitrogen atmosphere at room temperature for 3 hr. Aqueous citric acid solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (10%-40% ethyl acetate/hexane) to give the title compound (4.24 g, yield 61%) as a colorless oil. MS m/z 374 (MH+).
  • 2
  • [ 3132-99-8 ]
  • [ 100379-00-8 ]
  • [ 691905-26-7 ]
YieldReaction ConditionsOperation in experiment
97% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 80℃; for 20h; 3-Bromobenzaldehyde (18.5 g, 100 mmol) and 2,6-dimethylphenylboronic acid (21.0 g, 140 mmol) were dissolved in a mixture of 1 M aqueous sodium carbonate solution (200 mL), ethanol (100 mL) and toluene (200 mL). The air was substituted with argon gas, and tetrakis(triphenylphosphine)palladium(0) (5.78 g, 5.00 mmol) was added. The reaction mixture was stirred under an argon atmosphere at 80C for 20 hr. After cooling the reaction mixture, water was added and the mixture was diluted with ethyl acetate. The insoluble material was filtered off through celite. The organic layer in the filtrate was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-10% ethyl acetate/hexane) to give the title compound (20.4 g, yield 97%) as a colorless oil. MS m/z 211 (MH+).
96% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 80℃;Inert atmosphere; 3-Bromobenzaldehyde (1.8 g, 10 mmol) and (2,6-dimethylphenyl)boronic acid (2.1 g, 14 mmol) were dissolved in a mixture of 1 M aqueous sodium carbonate solution (20 mL), EtOH (10 mL), and toluene (20 mL). After argon substitution, tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. The reaction mixture was stirred under argon atmosphere at 80 C for 20 h. The reaction mixture was cooled, and water was added to the reaction mixture. The mixture was diluted with AcOEt, and the insoluble material was filtered through Celite. The organic layer of the filtrate was washed with brine, dried over anhydrous magnesium sulfate, and concentrated. The crude residue was purified by silica gel chromatograph using a mixture of petroleum ether/ethyl acetate (20 : 1, v/v) as eluent to afford the product 7a (2.1 g, 96%) as a colorless oil. 1H NMR (300 MHz, DMSO-d6) δ: 10.06 (s, 1H), 7.86-7.90 (m, 1H), 7.67-7.69 (m, 1H), 7.61 (t, J = 7.6 Hz, 1H), 7.42-7.46 (m, 1H), 7.11-7.23 (m, 3H), 2.02 (s, 6H).
83% With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate; In ethanol; toluene; at 80℃; for 22h;Inert atmosphere; 3-bromo-benzaldehyde (370.4 mg, 2.002 mmol), 2,6- dimethyl phenyl boronic acid (420.5 mg, 2.804 mmol), saturated aqueous sodium hydrogen carbonate solution (1M solution, 4 mL, 4.001 mmol) ethanol (2.2 mL) of and in a mixed solution of toluene (4 mL), tetrakis (triphenylphosphine) palladium (0) (114.9 mg, 0.099 mmol) was added, under an argon atmosphere and stirred for 22 hours at 80 C.. The reaction mixture was cooled, water (5 mL) and ethyl acetate (10 mL) was added and filtered over Celite (registered trademark). Was separated into aqueous and organic layers, the aqueous layer was extracted twice with ethyl acetate (20 mL), the combined organic layers were extracted with brine (30 mL), further sedge aqueous layer of ethyl acetate (20 and extracted with mL). The combined organic layers were dried over sodium sulfate, the solvent was evaporated, and the residue was purified by column chromatography to give the title compound (hexane: diethyl ether = 60:: 1 ~ 50 1) (347.8 mg, 1.655 mmol, 83 %, to give a colorless oil).
83% With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate; In ethanol; water; toluene; at 80℃; for 22h;Inert atmosphere; 3-bromobenzaldehyde (370.4 mg, 2.002 mmol), 2,6- dimethyl phenyl boronic acid (420.5 mg, 2.804 mmol), saturated aqueous sodium hydrogen carbonate solution (1M solution, 4 mL, 4.001 mmol) ethanol (2.2 mL) of and in a mixed solution of toluene (4 mL), tetrakis (triphenylphosphine) palladium (0) (114.9 mg, 0.099 mmol) was added, under an argon atmosphere and stirred for 22 hours at 80 C.. The reaction mixture was cooled, water (5 mL) and ethyl acetate (10 mL) was added and filtered over Celite (registered trademark). Was separated into aqueous and organic layers, the aqueous layer was extracted twice with ethyl acetate (20 mL), the combined organic layers were extracted with brine (30 mL), further sedge aqueous layer of ethyl acetate (20 and extracted with mL). The combined organic layers were dried over sodium sulfate, the solvent was evaporated, and the residue was purified by column chromatography (hexane: diethyl ether = 60: 1 to 50: 1) toRi purified title compound (347.8 mg, 1.655 mmol, 83%, colorless oil) was obtained.
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; at 100℃; for 16h; To a degassed solution of 3-bromobenzaldehyde (500 mg, 2.70 mmol) , (2, 6-dimethylphenyl) boronic acid (608 mg, 4.05 mmol) , and Pd (PPh3) 4 (156 mg, 0.14 mmol) in dioxane (5 mL) was added K2CO3 (2N, 4.05 mL, 8.11 mmol) . The reaction was heated to 100. After 16 h, the mixture was poured into NH4Cl (sat, 25 mL) and extracted with EtOAc (2 x 25 mL) . The combined organic layers were dried over MgSO4 and concentrated. The resulting residue was purified by HPLC (ISCO 40 gram silica gel cartridge, 0 to 40EtOAc/Hex) to give the title compound.

  • 3
  • [ 691905-26-7 ]
  • [ 691905-27-8 ]
YieldReaction ConditionsOperation in experiment
17% With methanol; sodium tetrahydroborate; at 0 - 20℃; for 3.16667h; To a stirred solution of Compound l-2a in methanol (7.5 g, 35.68mmol), NaBH (4.06g, 107.4mmol) was added portion-wise at 0C over a period of 10 min. The reaction temperature was raised to RT and stirred for additional 3 h. After completion of the reaction, the reaction mixture was quenched with saturated ammonium chloride solution, then distilled out methanol completely and diluted with water and extracted with ethyl acetate for 2 times. The organic layer was washed with sat. NaCl solution, dried over Na2S04 and concentrated to afford the crude product. The crude compound was purified by column chromatography on silica gel (100- 200 mesh) using 8-10% of ethyl acetate in pet ether as an eluent to afford Compound l-2b(1.3g, 17%). NMR (400 MHz, CDC13): d 7.45-7.40 (m, 1H), 7.38-7.32 (m, 1H), 7.18-7.05 (m, 5H), 4.74 (d, 2H), 2.02 (s, 6H), 1.64 (t, 1H)
  • 4
  • [ 691905-26-7 ]
  • [ 74-89-5 ]
  • [ 1218910-02-1 ]
  • 5
  • [ 691905-26-7 ]
  • [ 691902-33-7 ]
  • 6
  • [ 691905-26-7 ]
  • methyl 3-{4-[[(2',6'-dimethylbiphenyl-3-yl)methyl](methyl)amino]phenyl}propanoate [ No CAS ]
  • 7
  • [ 691905-26-7 ]
  • [ 1269763-57-6 ]
  • 8
  • [ 691905-26-7 ]
  • [ 1269763-58-7 ]
  • 9
  • [ 691905-26-7 ]
  • [ 1269763-59-8 ]
  • 10
  • [ 691905-26-7 ]
  • [ 1269763-60-1 ]
  • 11
  • [ 691905-26-7 ]
  • [ 691902-31-5 ]
  • 12
  • [ 691905-26-7 ]
  • [ 691902-35-9 ]
  • 13
  • [ 691905-26-7 ]
  • [ 691902-74-6 ]
  • 15
  • [ 691905-26-7 ]
  • 3-(4-[(2',6'-dimethylbiphenyl-3-yl)methyl]amino}phenyl)propanoic acid [ No CAS ]
  • 16
  • [ 691905-26-7 ]
  • 3-{4-[[(2',6'-dimethylbiphenyl-3-yl)methyl](methyl)amino]phenyl}propanoic acid [ No CAS ]
  • 17
  • [ 691905-26-7 ]
  • C25H26O2S [ No CAS ]
  • 18
  • [ 691905-26-7 ]
  • C26H27FO3 [ No CAS ]
  • 19
  • [ 691905-26-7 ]
  • C27H30O3 [ No CAS ]
  • 20
  • [ 691905-26-7 ]
  • C27H30O3 [ No CAS ]
  • 21
  • [ 691905-26-7 ]
  • [ 691902-32-6 ]
  • 22
  • [ 691905-26-7 ]
  • [ 691902-30-4 ]
  • 23
  • [ 691905-26-7 ]
  • [ 691902-34-8 ]
  • 24
  • [ 691905-26-7 ]
  • [ 691902-73-5 ]
  • 25
  • [ 691905-26-7 ]
  • [ 805248-55-9 ]
  • 26
  • [ 691905-26-7 ]
  • [ 805248-48-0 ]
  • 27
  • [ 691905-26-7 ]
  • [ 805248-71-9 ]
  • 28
  • [ 691905-26-7 ]
  • [ 805248-53-7 ]
  • 29
  • [ 691905-26-7 ]
  • [ 805248-47-9 ]
 

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