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[ CAS No. 16523-54-9 ] {[proInfo.proName]}

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Chemical Structure| 16523-54-9
Chemical Structure| 16523-54-9
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Product Details of [ 16523-54-9 ]

CAS No. :16523-54-9 MDL No. :MFCD00014294
Formula : C12H22ClP Boiling Point : -
Linear Structure Formula :(C6H11)2ClP InChI Key :AKJFBIZAEPTXIL-UHFFFAOYSA-N
M.W : 232.73 Pubchem ID :2734135
Synonyms :

Safety of [ 16523-54-9 ]

Signal Word:Danger Class:8
Precautionary Statements:P264-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P363-P405-P501 UN#:3265
Hazard Statements:H314 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 16523-54-9 ]

* 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 [ 16523-54-9 ]

[ 16523-54-9 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 101-84-8 ]
  • [ 16523-54-9 ]
  • [ 434336-16-0 ]
  • 2
  • [ 15469-97-3 ]
  • [ 16523-54-9 ]
  • 2-dicyclohexylphosphanyl-1-trityl-1H-imidazole [ No CAS ]
  • 3
  • [ 599-66-6 ]
  • [ 16523-54-9 ]
  • dicyclohexyl[5-methyl-2-(toluene-4-sulfonyl)phenyl]phosphane [ No CAS ]
  • 4
  • [ 55577-25-8 ]
  • [ 16523-54-9 ]
  • N-(dicyclohexylphosphino)-2-(4'-tolyl)-1H-indole [ No CAS ]
  • 5
  • [ 1293-65-8 ]
  • [ 16523-54-9 ]
  • [ 952586-77-5 ]
YieldReaction ConditionsOperation in experiment
84% 120 ml (0.3 mol) of n-BuLi (2.5 M in hexane) are added dropwise at a temperature of <-30C to a solution of 103 g (0.3 mol) of 1 ,1 '-<strong>[1293-65-8]dibromoferrocene</strong> in 300 ml of THF. The mixture is stirred further at this temperature for 1.5 hours. The mixture is then cooled to -500C, and 66.2 ml (0.3 mol) of dicyclohexylphosphine chloride are slowly added dropwise at such a rate that the temperature does not rise above -45C. After stirring for a further 10 minutes, the temperature is allowed to rise to room temperature and the mixture is stirred for another one hour. After adding 150 ml of water, the reaction mixture is extracted by shaking with hexane. The organic phases are dried over sodium sulphate, and the solvent is distilled off under reduced pressure on a rotary evaporator. The residue is crystallized in ethanol. The product 13 is obtained with a yield of 84% (yellow solid). 1H NMR (300 MHz, C6D6): delta 1.20-2.11 (m, 22H), 3.97 (m, 2H), 4.23 (m, 2H), 4.26 (m, 2H), 4.41 (m, 2H). 31P NMR (121.5 MHz, C6D6): delta -8.3 (s).
84% To a solution of 103 g (0.3 mol) of 1 ,1 '-<strong>[1293-65-8]dibromoferrocene</strong> in 300 ml of THF are added dropwise, at a temperature of < -300C, 120 ml (0.3 mol) of n-BuLi (2.5 M in hexane). <n="34"/>The mixture is stirred at this temperature for a further 1.5 hour. The mixture is then cooled to -500C, and 66.2 ml (0.3 mol) of dicyclohexylphosphine chloride are added dropwise sufficiently slowly that the temperature does not rise above -45C. After stirring for a further 10 minutes, the temperature is allowed to rise to room temperature and the mixture is stirred for another hour. After 150 ml of water have been added, the reaction mixture is extracted by shaking with hexane. The organic phases are dried over sodium sulphate and the solvent is distilled off under reduced pressure on a rotary evaporator. The residue is crystallized in ethanol. The product A2 is obtained with a yield of 84% (yellow solid).31P NMR (121.5 MHz, C6D6): delta -8.3 (s); 1H NMR (300 MHz, C6D6): delta 4.41 (m, 2H), 4.26 (m, 2H), 4.23 (m, 2H), 3.97 (m, 2H), 1.20-2.11 (m, 22H).
  • 6
  • [ 21524-34-5 ]
  • [ 36321-73-0 ]
  • [ 16523-54-9 ]
  • [ 1070663-80-7 ]
YieldReaction ConditionsOperation in experiment
28% EXAMPLE TEN: Synthesis of Ligand 7; An oven-dried three-neck 250 mL round bottom flask, which was equipped with a magnetic stir bar and charged with magnesium shavings (559 mg, 24.3 mmol), was fitted with a reflux condenser, addition funnel, and glass stopper. The flask was purged with argon and then THF (15 mL) and 2,4,6-triisopropylbromobenzene (2.83 g, 10 mmol) were added via syringe. The reaction mixture was heated to reflux and 1 ,2-dibromethane (40 uL) was added via syringe. The reaction was allowed to stir at reflux for 1 h and then the addition funnel, which was charged with l,2-dibromo-3,4,5,6-tetramethylbenzene (2.92 g, 10 mmol) in 40 mL of THF, was opened and the solution was added over a 1 h period. The mixture was stirred for 5 h at reflux and then cooled to room temperature where CuCl (1.0 g, 10 mmol) was added quickly to the reaction mixture. Next, ClPCy2 (2.65 mL, 10 mmol) was then added in a dropwise fashion and the reaction mixture was heated to 75 0C for 60 h. The reaction mixture was then cooled to room temperature, diluted with EtOAc, washed 3 times with 30% NH4OH, dried over MgSO4, and concentrated under reduced pressure. The crude material was recrystallized from benzene to yield the product as a white solid (1.507 g, 28% yield). 1H NMR (300 MHz, CDCl3) δ: 7.36 (s, 5H), 7.15 (s, 2H), 2.99 (septet, J= 7.0 Hz, IH), 2.44 (s, 3H), 2.35-2.14 (m, HH), 1.98 (s, 2H), 1.80-1.44 (m, 14H), 1.39-1.04 (m, 22H), 0.91 (d, J= 6.5 Hz, 6H) ppm. 13C NMR (75 MHz, CDCl3) δ: 150.9, 145.8, 145.4, 144.6, 140.0, 138.5, 135.8, 135.6, 135.5, 135.5, 128.6, 124.3, 40.2, 39.9, 35.4, <n="123"/>35.2, 34.5, 30.7, 29.5, 27.8, 27.7, 27.4, 27.2, 25.9, 25.0, 24.6, 21.2, 20.8, 17.7, 17.3 ppm (Observed complexity is due to P-C splitting). 31P NMR (121 MHz, CDCl3) δ: 16.33 ppm.
  • 7
  • [ 902518-11-0 ]
  • [ 16523-54-9 ]
  • [ 1308652-64-3 ]
YieldReaction ConditionsOperation in experiment
88.3% (Setting-Up and Reaction) To a 200 mL four-necked round-bottomed flask, a three-way stopcock, a Teflon-coated magnetic stirring bar, a 20 mL dropping funnel, and a thermometer were attached, and the inside was purged with nitrogen. To this flask, <strong>[902518-11-0]N-(2-bromophenyl)carbazole</strong> (7) (8.8 g, 27.3 mmol, 1.0 eq.) obtained in the first step and anhydrous tetrahydrofuran (hereinafter, abbreviated as THF) (54.6 mL) were sequentially added, and the obtained reactant solution was cooled to -70C by use of a dry ice/acetone bath. Subsequently, a n-butyllithium (hereinafter, abbreviated as n-BuLi)/n-hexane solution (1.60 mol/L, 17. 9 mL, 28. 6 mmol, 1.05 eq.) was placed in the dropping funnel, and added dropwise over 15 minutes, while the reactant solution was being stirred, and the inside temperature was being kept at -50C or below. Then, the dropping funnel was rinsed with anhydrous n-hexane (1 mL) . The obtained cream-colored suspension was stirred at -70C for 1 hour. Then, an anhydrous THF (14 mL) solution of chlorodicyclohexylphosphine (hereinafter, abbreviated as Cy2PCl) (7.0 g, 30.1 mmol, 1.1 eq.) was placed in the dropping funnel, and added dropwise over 15 minutes, while the suspension was being stirred, and the inside temperature was being kept at -50 C or below (the suspension was dissolved rapidly). After completion of the dropwise addition, the dry ice/acetone bath was taken out, and the temperature of the reaction solution was raised to room temperature over 30 minutes, followed by stirring for further 30 minutes. (Post Treatment and Purification) After the reaction solution had been concentrated under reduced pressure, toluene and an aqueous solution of sodium hydrogen carbonate (2.3 g, approximately 1 eq.) were added to the residue. The mixture was transferred to a separating funnel, shaken and allowed to stand, and the layers were separated (Aqueous Layer 1: pH=9). Then, the organic layer was further washed with water (Aqueous Layer 2: pH=7). The solvent was distilled off from the organic layer under reduced pressure, and toluene and silica gel (0.7 g) were added to the obtained light brown residue. The mixture was stirred at room temperature for 10 minutes and filtered by use of diatomaceous earth, and the residue was washed with toluene. The filtrate was concentrated, until crystals were precipitated. Then, methanol was added, and the obtained white suspension was filtered. The product obtained by the filtration was washed with methanol, and then dried under reduced pressure to give 10.6 g of title compound (2-1) as a colorless powder. Isolated Yield: 88.3%. 1H NMR (300 MHz, CDCl3): delta=8.12 (d, J=7.5 Hz, 2H), 7.76 (dt, J=1.5, 4.8 Hz, 1H), 7.57-7.47 (m, 2H), 7.38-7.28 (m, 3H), 7.23 (dt, J=0.9, 6.9 Hz, 2H), 7.02 (d, J=8.1 Hz, 2H), 1.85-1.38 (m, 12H), 1.22-0.90 (m, 10H). 31P NMR (121 MHz, CDCl3): delta=-14.5.
  • 8
  • [ 16523-54-9 ]
  • [ 103099-52-1 ]
  • 9
  • [ 1293-65-8 ]
  • [ 13292-87-0 ]
  • [ 16523-54-9 ]
  • C22H33BBrFeP [ No CAS ]
  • 10
  • [ 827-08-7 ]
  • [ 16523-54-9 ]
  • (2-bromo-3,4,5,6-tetrafluorophenyl)dicyclohexylphosphine [ No CAS ]
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