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Chemical Structure| 1001911-28-9 Chemical Structure| 1001911-28-9

Structure of 1001911-28-9

Chemical Structure| 1001911-28-9

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Product Details of [ 1001911-28-9 ]

CAS No. :1001911-28-9
Formula : C28H23Br
M.W : 439.39
SMILES Code : CC1(C)C2=C(C3=CC(C(C)(C)C4=C5C6=CC=CC=C6C(Br)=C4)=C5C=C31)C=CC=C2

Safety of [ 1001911-28-9 ]

Application In Synthesis of [ 1001911-28-9 ]

* 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 [ 1001911-28-9 ]

[ 1001911-28-9 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 19616-28-5 ]
  • [ 1001911-28-9 ]
  • C44H41N [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With tri-tert-butyl phosphine; n-hexyllithium; palladium diacetate; In hexane; toluene; for 1h;Reflux; Hexyllithium (2.5 M in hexane, 1.2 eq.) is added dropwise to a solution of <strong>[19616-28-5]bis(2,4-dimethylphenyl)amine</strong> (1.25 eq), 1,2-benzo-3-bromo-6,6,12,12-tetramethyl-6,12-dihydroindeno[1,2-b]fluorene (1 eq), Pd(OAc)2 (0.02 eq) and 2-(dicyclohexylphosphino)-2?,6?-dimethoxy)biphenyl (S-Phos, 0.04 eq) in toluene, and the mixture is subsequently heated under reflux for 1 h. After cooling to room temperature, water is added, the organic phase is separated off, dried using MgSO4 and filtered through silica gel. The solvent is removed, and the residue is washed with acetonitrile and isopropanol. Yield: 90percent; purity; 99.2percent (HPLC). The purity can be increased to 99.95percent by Soxhlett extraction and sublimation. [0122] Further Examples with Hexyllithium or LDA as Base:
  • 2
  • [ 19616-28-5 ]
  • [ 1001911-28-9 ]
  • [ 865-48-5 ]
  • C44H41N [ No CAS ]
  • 5-tert-butoxy-7,7,13,13-tetramethyl-7H,13H-benzo[g]indeno[3,2-b]fluorene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With di(tert-butyl)chlorophosphine; palladium diacetate; In toluene; for 2h;Reflux; A mixture of sodium tert-butoxide (1.2 eq.), <strong>[19616-28-5]bis(2,4-dimethylphenyl)amine</strong> (1.25 eq), 1,2-benzo-3-bromo-6,6,12,12-tetramethyl-6,12-dihydroindeno-[1,2-b]fluorene (1 eq), Pd(OAc)2 (0.02 eq) and 2-(dicyclohexylphosphino)-2?,6?-dimethoxy)biphenyl (S-Phos, 0.04 eq) in toluene is heated under reflux for 2 h. After cooling to room temperature, water is added, the organic phase is separated off, dried using MgSO4 and filtered through silica gel. The solvent is removed. The 1H-NMR spectrum of the residue shows product type A: by-product type NA=17:80. [0118] Further examples with variation of ligand and starting-material type:
  • 3
  • [ 1257220-47-5 ]
  • [ 1001911-28-9 ]
  • C49H39N [ No CAS ]
YieldReaction ConditionsOperation in experiment
14% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); In toluene; at 105℃;Sealed tube; Inert atmosphere; 5-Bromo-7, 13-dihydro-7,7, 13,1 3-tetramethyl-benzo[g]indeno[i,2-b]fluorene (400 mg, 0.86 mmol,95.4%), 5,7-dihydro-7,7-dimethylindeno-[2, i-b]carbazole(292.4 mg, 1.03 mmol, 1.2 equiv.), Pd2(dba)3 (16.07 mg,0.017 mmol, 2 mol %) and SPhos (14.12 mg, 0.034 mmol,4 mol %) are weighed into a vial, provided with protectivegas atmosphere and sealed a septum, and 8 mL of toluene are added. Subsequently, at RT, K3P04 (583.3 mg, 2.69 mmol, 3.1 equiv.) is added to the reaction mixture while stirring. The reaction mixture is heated overnight at 105 C. for 8 d in a heating block while stirring. After allowing it to cool to room temperature, distilled H20 is added to the reaction solution and the aqueous phase is extracted with toluene. The organic phase is dried over Mg504 and concentrated, and the crude product is purified by column chromatography (eluent:heptane:DCM vol/vol. 15:1-1:1) on silica gel. The product is obtained as a pale yellow solid (78 mg, 14%). MS (El) mlz calculated for C49H39N: 641.3, found [M]+: 641.4. Elemental analysis calculated (%) for C49H39N: C,91.69, H, 6.12, N, 2.18, found: C, 91.62, H, 6.55, N, 2.07.
 

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