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Catalysts and Ligands
Chiral phosphine ligands
Binap Ligands
(S)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl
Catalysts and Ligands
Chiral phosphine ligands
Binap Ligands

[ CAS No. 100165-88-6 ]

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Chemical Structure| 100165-88-6
Chemical Structure| 100165-88-6
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COA NMR CNMR HPLC LC-MS

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Product Details of [ 100165-88-6 ]

CAS No. :100165-88-6 MDL No. :
Formula : - Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :- Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 100165-88-6 ]

* 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 [ 100165-88-6 ]

[ 100165-88-6 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 100227-70-1 ]
  • [ 100165-88-6 ]
YieldReaction ConditionsOperation in experiment
95% With trichlorosilane; triethylamine In xylene at 80 - 130℃; for 6.5h;
Reference： [1]Takaya, Hidemasa; Mashima, Kazushi; Koyano, Kinko [Journal of Organic Chemistry, 1986, vol. 51, # 5, p. 629 - 635]
  • 2
  • [ 100165-88-6 ]
  • [ 847984-87-6 ]
  • [ 554433-10-2 ]
YieldReaction ConditionsOperation in experiment
1: 59% 2: 240 mg With sulfur In tetrahydrofuran at 20℃; for 4h;
Reference： [1]Faller; Wilt, Jeremy C. [Organic Letters, 2005, vol. 7, # 4, p. 633 - 636]
  • 3
  • [ 126258-42-2 ]
  • [ 126613-06-7 ]
  • [ 100165-88-6 ]
YieldReaction ConditionsOperation in experiment
79.2% With 1,4-diaza-bicyclo[2.2.2]octane In DMF (N,N-dimethyl-formamide) at 20 - 110℃; for 73.5h; 11 Example 11; (S)-2,2'-bis[bis(4-methylphenyl)phosphino]-1,1'-binaphthyl Example 11 (S)-2,2'-bis[bis(4-methylphenyl)phosphino]-1,1'-binaphthyl Under an argon atmosphere, to a solution (5 ML) of [1,2-bis(diphenylphosphino)-ethane]dichloronickel (48 mg, 0.1 equivalent) and (S)-2,2'-bis(trifluoromethanesulfonyloxy)-1,1'-binaphthyl (500 mg, 0.91 MmoL) synthesised in Reference Example 1 and 1,4-diazabicyclo[2,2,2]octane (610 mg, 6.0 equivalents) in DMF was added bis(4-methylphenyl)phosphine-borane complex (0.476 g, 2.3 equivalents) synthesised in Reference Example 18 at room temperature and the mixture was stirred at room temperature for 30 min. and then at 110°C for 73 hrs. DMF was evaporated under reduced pressure and methanol was added to the residue to give the title compound (488 mg, white crystals).. yield 79.2%.1H-NMR (300 MHz, CDCl3, TMS) δ: 2.27 (s, 6H), 2.29 (s, 6H), 6.86-7.03 (m, 20H), 7.38-7.41 (m, 2H), 7.47-7.50 (m, 2H), 7.85 (d, 2H, J = 8.16 Hz), 7.89 (d, 2H, J = 8.48 Hz).31P-NMR (121 MHz, CDCl3, 85%H3PO4) δ: -15.73 (s).
Reference： [1]Current Patent Assignee: SPERA PHARMA - EP1452537, 2004, A1 Location in patent: Page 41
  • 4
  • [ CAS Unavailable ]
  • [ 100165-88-6 ]
  • [ 854274-96-7 ]
YieldReaction ConditionsOperation in experiment
In methanol; dichloromethane at 50℃; for 0.25h; 9 A Schlenk flask under nitrogen is charged with 110.8 mg of (S)-BINAP (0.1633 mmol) and 40.8 mg of [(benzene)RuCl2]2 (0.0816 mmol) and charged with 5ml of dry degassed dichloromethane and 0.625ml of dry degassed methanol. The solution is heated to 50°C for 15 minutes before removing the solvent in vacuo to give a yellow crystalline solid. 18.65mg of (i?,i?)-DACH (0.1633 mmol) are added with 5ml of dry degassed tetrahydrofuran and heated at 60°C for 4 hours. The reaction is cooled to room temperature. 31P NMR reveals essentially a single species and no starting materials. 31P NMR reveals >96% product and conversion. The solvent is removed in vacuo to give a pale yellow amorphous solid.31P NMR (162 MHz, CDCl3) δ44.79 ppm, singlet.
Reference： [1]Current Patent Assignee: DR REDDY'S LABORATORIES LIMITED - WO2007/5550, 2007, A1 Location in patent: Page/Page column 11
  • 5
  • [ 100165-88-6 ]
  • [ 100227-70-1 ]
YieldReaction ConditionsOperation in experiment
97% With dihydrogen peroxide In dichloromethane; water for 0.0833333h;
96% With dihydrogen peroxide In dichloromethane; water at 0 - 20℃; for 2h;
With dihydrogen peroxide In acetone General procedure: Chiral phosphine oxides were prepared by oxidation of the corresponding phosphines with hydrogen peroxide in acetone.
Reference： [1]Petersson, Maria J.; Loughlin, Wendy A.; Jenkins, Ian D. [Chemical Communications, 2008, # 37, p. 4493 - 4494]
[2]Horibe, Takahiro; Nakagawa, Keita; Hazeyama, Takashi; Takeda, Kazuki; Ishihara, Kazuaki [Chemical Communications, 2019, vol. 55, # 91, p. 13677 - 13680]
[3]Kotani, Shunsuke; Furusho, Haruka; Sugiura, Masaharu; Nakajima, Makoto [Tetrahedron, 2013, vol. 69, # 14, p. 3075 - 3081]
  • 6
  • [ CAS Unavailable ]
  • [ 100165-88-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Stage #1: bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine] In dichloromethane for 0.5h; Inert atmosphere; Stage #2: With hydrogen In dichloromethane for 1h; 1.3 Under an argon atmosphere, a 1.0 ml of methylene chloride solution of (S)-tol-binap (3.4 mg, 0.0050 mmol) was added to a 1.0 ml of methylene chloride solution of [Rh(COD)2]BF4 (2.0 mg, 0.0050 mmol), and stirred for 30 minutes. Then, hydrogen gas was introduced into the schlenk tube, and the mixture was stirred for 1 hour. Successively, the reaction mixture was concentrated to dryness in vacuo, and 0.5 mL of methylene chloride was added thereto. To the mixture, a 1.5 ml of methylene chloride solution of hexayne compound obtained by above example 1 (2) (36.1 mg, 0.0500 mmol), then, the mixture was stirred at room temperature for 16 hours. Concentration of the reaction mixture and subsequent purification by thin-layer chromatography (ethyl acetate/methanol=20/1) gave 16.6 mg of the target material as a colorless solid in a yield of 46%. The optical purity of the obtained target material was 91% ee
Reference： [1]Current Patent Assignee: TAKASAGO INTERNATIONAL CORPORATION; TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY - US2011/218345, 2011, A1 Location in patent: Page/Page column 7
  • 7
  • [ 100165-88-6 ]
  • [ 2334327-36-3 ]
YieldReaction ConditionsOperation in experiment
95% Stage #1: 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine] With bis(1,5-cyclooctadiene)nickel (0); Phenyl triflate In N,N-dimethyl-formamide at 140℃; for 20h; Glovebox; Inert atmosphere; Sealed tube; Stage #2: With dihydrogen peroxide In water; N,N-dimethyl-formamide at 20℃; for 1h; Glovebox; Inert atmosphere; Sealed tube;
Reference： [1]Fujimoto, Hayato; Kusano, Momoka; Kodama, Takuya; Tobisu, Mamoru [Organic Letters, 2019, vol. 21, # 11, p. 4177 - 4181]

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A378477[ 99646-28-3 ]

(R)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthalene

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