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[ CAS No. 1321613-04-0 ]

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Chemical Structure| 1321613-04-0
Chemical Structure| 1321613-04-0
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Product Details of [ 1321613-04-0 ]

CAS No. :1321613-04-0 MDL No. :MFCD20441900
Formula : C14H17BCl2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :331.00 g/mol Pubchem ID :-
Synonyms :

Safety of [ 1321613-04-0 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501 UN#:
Hazard Statements:H302-H312-H332 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1321613-04-0 ]

  • Downstream synthetic route of [ 1321613-04-0 ]

[ 1321613-04-0 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 33863-76-2 ]
  • [ 1321613-04-0 ]
  • 2
  • [ 14920-87-7 ]
  • [ 73183-34-3 ]
  • [ 1321613-04-0 ]
YieldReaction ConditionsOperation in experiment
53% With 4,4'-di-tert-butyl-2,2'-bipyridine In n-heptane for 18h; Reflux; A.A-49A A-49A) 2,6-Dichloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoicacid methyl ester Bis(pinacolato)diboron [Pin2B2] (44.8 g, 176 mmol), 4,4'-Di-tert-butyl-[2,2']bipyridinyl (120 mg, 0.44 mmol), and [Ir(COD)(OMe)]2 (147 mg, 0.22 mmol) were added to a solution of compound H8 (45 g, 0.22 mol) in heptane (500 mL). The reaction mixture turned from yellow to forest green to brick red within the first minute. The reaction mixture was heated to reflux for 18 h and then partitioned between ethyl acetate and water. The organic extracts were combined, dried over Na2SO4 and concentrated under reduced pressure. The solid residue was purified by chromatography on silica gel (PE: EtOAc=50:1, detected by boric indicator) to afford the title compound (A-49A) as a white solid (41.0 g, 53%). Rf=0.4 (petrolether: ethylacetate=20:1).
  • 3
  • [ 320-31-0 ]
  • [ 73183-34-3 ]
  • [ 1321613-04-0 ]
YieldReaction ConditionsOperation in experiment
With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In N,N-dimethyl-formamide; at 80℃; for 2h; A-49B) 2-Trifluoromethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoicacid methyl ester A suspension of compound H10 (23.5 g, 83.3 mmol), Bis(pinacolato)diboron (21 g, 83.3 mmol), Pd(dppf)Cl2 (6 g, 8.3 mmol) and KOAc (24 g, 25 mmol) in DMF (400 mL) was heated to 80 C. quickly for 2 h. The solvent was evaporated in vacuo. The resulting residue was dissolved in PE, filtered and the filtrate was collected. The resulting filtrate was concentrated in vacuo to give crude product, crystallized in petrolether to give A-49B (10.8 g; 40%).
  • 4
  • [ 1321613-01-7 ]
  • [ 1321613-04-0 ]
  • 5
  • [ 14920-87-7 ]
  • [ 25015-63-8 ]
  • [ 1321613-04-0 ]
YieldReaction ConditionsOperation in experiment
71% With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine at 80℃; for 20h; Inert atmosphere; Schlenk technique; regioselective reaction; Borylation of Arenes; General Procedure General procedure: In a fume hood, an oven dried Schlenk flask equipped with a magnetic stirring bar was filled with N2 and evacuated (three cycles). Under N2 atmosphere [Ir(OMe)(COD)]2 (13.3 mg, 0.01 mmol, 1 mol%), 4,4-ditert-butyl-2,2′-bipyridyl (10.7 mg, 0.02 mmol, 2 mol%), and pinacolborane (HBPin) (436 μL, 384 mg, 3 mmol, 1.5 equiv) were added. The appropriate arene substrate (2 mmol, 1 equiv) was added via micropipette under N2 atmosphere. The Schlenk flask was closed and the reaction mixture was heated at 80 °C in an oil bath. The progress of reaction was monitored by GC-MS and TLC. Upon completion of reaction, Schlenk flask was cooled to r.t. and exposed to air. The contents of the flask were dissolved in CH2Cl2 (3-5 mL) and taken out in a round-bottomed flask. The volatile organics were removed under reduced pressure using a rotary evaporator. The crude product was purified by column chromatography (silica gel, hexanes-CH2Cl2 1:1).
  • 6
  • [ 73183-34-3 ]
  • [ 232275-53-5 ]
  • [ 1321613-04-0 ]
YieldReaction ConditionsOperation in experiment
57% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; at 80℃; To a solution of 0188-1 (500 mg, 1.76 mmol) in dioxane (10 mL) was added bis(pinacolato)diboron (894 mg, 3.52 mmol), K2CO3 (486 mg, 3.52 mmol) and Pd(dppf)Cl2 (132 mg, 0.18 mmol). The mixture was stirred at 80 C for overnight. Remove the solid by filtration, the filtrate was concentrated and purified by CC (5% to 10% ethyl acetate in petroleum ether) to get 0188-2 (330 mg, 57% yield) as a white solid.
  • 7
  • [ 232275-51-3 ]
  • [ 1321613-04-0 ]
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