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Chemical Structure| 56671-81-9 Chemical Structure| 56671-81-9

Structure of 56671-81-9

Chemical Structure| 56671-81-9

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Product Details of [ 56671-81-9 ]

CAS No. :56671-81-9
Formula : C6H7BrO
M.W : 175.02
SMILES Code : BrC(CCC1)=CC1=O
MDL No. :MFCD00015782

Safety of [ 56671-81-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501

Application In Synthesis of [ 56671-81-9 ]

* 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 [ 56671-81-9 ]

[ 56671-81-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 30413-58-2 ]
  • [ 56671-81-9 ]
  • [ 880292-10-4 ]
YieldReaction ConditionsOperation in experiment
82% With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; In DMF (N,N-dimethyl-formamide); at 55℃; for 1h; Example 1: 3- (6-METHYL-PYRIDIN-2-YLETHYNYL)-CYCLOHEX-2-ENONE O- ["C-METHYL]-OXIME 3- (6-METHYL-PYRIDIN-2-YIETHYNYL)-CYCLOHEX-2-ENONE 0- ["C-METHYL]-OXIME is synthesized by reacting ["C]-MEL with the sodium salt of 3- (6-METHYL-PYRIDIN-2-YLETHYNYL)-CYCLOHEX-2-ENONE oxime (1MG) in dry DMF (400 PL). ["C]-Mel is introduced via a slow stream of helium and when addition is completed the reaction mixture is heated to 120C for 10 min. Product purification is accomplished by reversed phase HPLC using a C-18 U-BONDAPAK column (7. 8X300MM) and a mobile phase consisting of CH3CN/0. 1% H3PO4 (70/30) at a flow rate of 5 ML/MIN. The retention time of the desired product is between 6 and 7 min. 3-(6-METHYL-PYRIDIN-2-YLETHYNYL)-CYCLOHEX-2-ENONE O-["C-METHYL]-OXIME is formulated in a solution containing polysorbatum (2%), ethanol (10%) and saline (0.9%). LogD = 2.5 (determined using the classical shake-flask method). The starting materials are prepared as described hereafter: a) 3-(6-Methyl-pyridin-2-ylethynyl)-cyclohex-2-enone A solution OF 2-ETHYNYL-6-METHYL-PYRIDINE (702 mg, 6 MMOL), 3-bromo-cyclohex-2-enone (1.26 g, 7.2 MMOL), BIS- (TRIPHENYLPHOSPHINE)-PALLADIUM-DICHLORIDE (168 mg, 0.24 MMOL), copper (L) iodide (93 mg, 0.48 mmol), triethylamine (4.8 ml, 34.4 MMOL) in 12MOI DMF is heated to 55C for 1 h. After that time the solution is diluted with ethyl acetate (500 ml) and washed with sat aq. NAHCO3 (1 X 150 ML). The water phase is extracted with ethyl acetate (1 X 150 ML) and the combined organic phases are dried over NA2SO4, filtered and concentrated in vacuo. The residue (1.88 g) is purified on column chromatography (silica gel, eluent hexane/ethyl acetate 3: 1 V/V) and the fractions containing the desired compound are collected and concentrated in vacuo to yield 1.05 g (yield = 82 %) of the title compound as a light yellow oil. b) 3- (6-Methyl-pyridin-2-ylethynyl)-cyclohex-2-enone oxime A solution of 3- (6-methyl-pyridin-2-ylethynyl)-cyclohex-2-enone (422 mg, 2 MMOL) and hydroxylamine hydrochloride (278 mg, 4 MMOL) in pyridine (20 ml) is stirred for 17 h at RT. After that time the solvent is evaporated in vacuo. The residue is dissolved in ethyl acetate (300 ml) and washed with sat NAHCO3 (1 X 50 ML). The water phase is extracted with ethyl acetate (1 X 50 ML). The combined organic phases are dried over NA2SO4, filtered and concentrated in vacuo. The residue (0.45 g) is purified on column chromatography (Silica gel, eluent hexane/ethyl acetate 2: 1 V/V) and the fractions containing the desired compound are collected and concentrated in vacuo to yield 0.192 g (yield = 42 %) of the title compound as light yellow crystals, m. p. 166-168C.
  • 2
  • [ 56671-81-9 ]
  • [ 42237-85-4 ]
  • 5-amino-5'-oxo-2',3',4',5'-tetrahydro[1,1'-biphenyl]-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
33.7% a) 5-amino-5'-oxo-2',3',4',5'-tetrahvdro-ri, 1 '-biphenyll-3-carboxylic acid. Bis(pinacolato)diboron (290 mg, 1.143 mmol) was added to a stirred solution of 3- bromocyclohex-2-enone (100 mg, 0.571 mmol), [1 , 1 '- bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (20.89 mg, 0.029 mmol) and potassium acetate (168 mg, 1 .714 mmol) in dry 1 ,4-dioxane (5 ml.) under nitrogen. The reaction was allowed to slowly warm to room temperature, and was stirred for an additional 3 hours. The solution was filtered. Potassium carbonate (158 mg, 1.143 mmol) in water (2 ml_), <strong>[42237-85-4]3-amino-5-bromobenzoic acid</strong> (61.4 mg, 0.286 mmol) and tetrakis(triphenylphosphine)palladium(0) (33.0 mg, 0.029 mmol) were added to the filtrate. The mixture was heated under reflux for 4 hours, filtered, concentrated and purified by reverse-phase preparative HPLC (ODS, 10- 90% acetonitrile/water + 0.1 % trifluoroacetic acid) to give 5-amino-5'-oxo-2',3',4',5'- tetrahydro-[1 , 1 '-biphenyl]-3-carboxylic acid (49 mg, 0.193 mmol, 33.7 % yield) as a pale yellow syrup. 1H NMR (METHANOL-d4) delta: 8.16 (t, J = 1 .5 Hz, 1 H), 7.93 - 7.99 (m, 1 H), 7.70 (t, J = 1.9 Hz, 1 H), 6.39 - 6.58 (m, 1 H), 2.82 - 2.94 (m, 2 H), 2.45 - 2.56 (m, 1 H), 2.20 (q, 3 H).
 

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