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Chemical Structure| 168618-44-8 Chemical Structure| 168618-44-8

Structure of 168618-44-8

Chemical Structure| 168618-44-8

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Product Details of [ 168618-44-8 ]

CAS No. :168618-44-8
Formula : C14H12O2
M.W : 212.24
SMILES Code : CC1=C(C=CC=C1)C2=CC(=CC=C2)C(=O)O
MDL No. :MFCD03424589
Boiling Point : No data available
InChI Key :IAZJDWZUCUHVPQ-UHFFFAOYSA-N
Pubchem ID :2759814

Safety of [ 168618-44-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501

Application In Synthesis of [ 168618-44-8 ]

* 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 [ 168618-44-8 ]

[ 168618-44-8 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 585-76-2 ]
  • [ 16419-60-6 ]
  • [ 168618-44-8 ]
  • 2
  • [ 16419-60-6 ]
  • [ 535-80-8 ]
  • [ 168618-44-8 ]
  • 4
  • [ 168618-44-8 ]
  • [ 1092543-06-0 ]
  • C37H37Cl2N7O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In water; N,N-dimethyl-formamide; at 20℃; for 18h; A mixture of intermediate 9 (1 g, 0.002 mol), 2'-methyl-[l,l'-biphenyl]-3-carboxylic acid (0.43 g, 0.002 mol), EDCI (0.38 g, 0.002 mol), 1 -hydroxy- lH-benzotriazo Ie hydrate (0.31 g, 0.002 mol), Et3N (0.28 ml, 0.002 mol) and DMF (10 ml) was stirred at room temperature for 18 hours. Then the solvent was evaporated. The residue was stirred in water and extracted with DCM. The organic layer was dried, filtered and the solvent was evaporated. The residue was purified over silica gel using a mixture of DCM and CH3OH (90/10) as eluent. The fractions containing the product were collected and the solvent was evaporated, yielding 1.1 g of residue. This residue was purified by HPLC method A. The pure fractions were collected and the solvent was evaporated. The residue was stirred in DIPE. The product was filtered off and dried. Yield: 0.638 g of compound 6.
  • 5
  • [ 269409-73-6 ]
  • [ 95-46-5 ]
  • [ 168618-44-8 ]
YieldReaction ConditionsOperation in experiment
78% With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; In 1,4-dioxane; water; at 95℃;Inert atmosphere; General procedure: The halo aryl (1.0 equiv) was dissolved in a mixture of water:dioxane (1:1). The boronic acid or ester(1.5 equiv) and potassium phosphate (5.0 equiv) were added. The solution was degassed byvacuum/argon cycles (10 times) before addition of PdCl2(PPh3)2 (10 mol%) and further degassed (5times). The resulting mixture was stirred at 95 C under argon atmosphere for 16-20 hours. Thereaction mixture was filtered through Celite and diluted with water (approx. 30 mL) before washingwith chloroform (3 x 30 mL). If not stated otherwise, the aqueous phase was concentrated underreduced pressure and applied to a C18 precolumn before purification on a 10g or 60 g C18 column witha gradient of acetonitrile in water (10-100%) to yield the desired product.
  • 6
  • [ 95-46-5 ]
  • [ 99769-19-4 ]
  • [ 168618-44-8 ]
YieldReaction ConditionsOperation in experiment
General procedure: Step 1: Bromobenzene derivatives 20a-b (1.0 equiv), 21a (1.3 equiv) , Pd(PPh3)4 (0.03 equiv) and Na2CO3 (3 equiv) were dissolved in toluene: ethanol: H2O = 3: 1: 3 and then nitrogen is replaced three times at 80 C for 12 h. and then cooled to room temperature. The mixture was poured into 50mL H2O, a one third volume of ethyl acetate was added, and phases were separated. The aqueous layer was extracted three times with ethyl acetate, the combined organic layers were dried over Na2SO4, and solvent was evaporated in vacuum. Further purification was performed by column chromatography using ether/ethyl acetate as mobile phase to get 23a-b. The product was precipitated by addition of 2 M HCl until a pH of ≤ 2 was reached, filtered off, and dried in vacuum to get 22a-b.
  • 7
  • [ 168618-44-8 ]
  • [ 4518-10-9 ]
  • 3-(2'-methyl-[1,1'-biphenyl]-3-carboxamido)benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: 4-phenoxybenzoic acid (1.0 equiv) were dissolved in CH2Cl2 (15mL) and SOCl2 (3.0 equiv), DMF (0.1 equiv) was added. The mixture reacted at room temperature for 4-7 h, and the solvent was evaporated in vacuo to give the crude. The crude was slowly added dropwise to the flask containing 5a-d (1.0 equiv), N(Et)3 (3.0 equiv) and DMAP (0.1equiv) at -5C, After the addition is completed, the reaction is carried out at room temperature for 12 h. The mixture was poured into 20 mL H2O, an equal volume of CH2Cl2 was added, and phases were separated. The aqueous layer was extracted three times with ethyl acetate, the combined organic layers were dried over Na2SO4, and solvent was evaporated in vacuum. Further purification was performed by column chromatography using petroleum ether/ethyl (15:1, v/v) acetate as mobile phase. The respective ester was dissolved in THF: CH3OH: H2O (3:3:1), and aqueous LiOH solution (1.0 equiv) was added slowly. The mixture was then stirred at room temperature for 2 h. The solvent was evaporated in vacuum, the product was precipitated by addition of 2 M HCl until a pH ≤ 2 was reached, filtered off, and dried in vacuum to afford the target compounds 7-8, 12 as white solid.
 

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