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2,2'-bis(diphenylphosphino)biphenyl
(R)-(5,5'-Dichloro-6,6'-dimethoxy-[1,1'-biphenyl]-2,2'-diyl)bis(diphenylphosphine)
Chemistry
Catalysts Ligands
Organic Building Blocks
Chiral phosphine ligands
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MeOBIPHEP Ligands
2,2'-bis(diphenylphosphino)biphenyl

[ CAS No. 185913-97-7 ] {[proInfo.proName]}

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Chemical Structure| 185913-97-7
Chemical Structure| 185913-97-7
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Quality Control of [ 185913-97-7 ]

COA NMR CNMR HPLC LC-MS

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Alternatived Products of [ 185913-97-7 ]

Product Details of [ 185913-97-7 ]

CAS No. :185913-97-7 MDL No. :MFCD03426987
Formula : C38H30Cl2O2P2 Boiling Point : -
Linear Structure Formula :- InChI Key :GCBRCSSVOVNEIX-UHFFFAOYSA-N
M.W : 651.49 Pubchem ID :5165044
Synonyms :

Safety of [ 185913-97-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 185913-97-7 ]

* 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 [ 185913-97-7 ]

[ 185913-97-7 ] Synthesis Path-Downstream   1~6

YieldReaction ConditionsOperation in experiment
wherein the bisphosphine of formula (B3) is selected from the group consisting of (5,5'-dichloro-6,6'-dimethoxybiphenyl-2,2'-diyl)-bisdiphenylphosphine, (4,4',6,6'-tetramethyl-5,5'-dimethoxybiphenyl-2,2'-diyl)-bis(diphenyl-phosphine), (4,4',6,6'-tetramethyl-5,5'-dimethoxybiphenyl-2,2'-diyl)-bis(di-p-methoxyphenylphosphine), (4,4',6,6'-tetratrifluoromethylbiphenyl-2,2'-diyl)-bis(diphenylphosphine) (4,6-ditrifluoromethyl-4',6'-dimethyl-5'-methoxybiphenyl-2,2'-diyl)-bis-(diphenyl-phosphine), (2-dicyclohexyl-2'-diphenylphosphino-4,4',6,6'-tetramethyl-5,5'-dimethoxybiphenyl-2,2'-diyl)-bis(diphenylphosphine), (6,6'-dimethyl-2,2'-biphenylene)-bis(diphenylphosphine), (4,4',6,6'-tetramethyl-2,2'-biphenylene)-bis(diphenylphosphine), (3,3',6,6'-tetramethyl-2,2'-biphenylene)-bis(diphenylphosphine), ...
6 Preparation of (5,5'-dichloro-6,6'-dimethoxybiphenyl-2,2'-diyl)-bis(diphenylphosphine) Example 6 Preparation of (5,5'-dichloro-6,6'-dimethoxybiphenyl-2,2'-diyl)-bis(diphenylphosphine) 220 mg of Pd(PPh3)4 were added with 75 mg of diphenylphosphinopropane to 10 ml of dimethyl sulfoxide under argon, and the mixture was stirred for 3 hours at room temperature, during which time an orange-colored suspension formed. To this suspension were added 0.99 g of diphenylphosphine, 0.85 g of N,N-diisopropylethylamine, 1.00 g of (5,5'-dichloro-6,6'-dimethoxybiphenyl-2,2'-diyl)-bistrifluoromethanesulfonic acid ester, and a further 10 ml of dimethyl sulfoxide, and the clear, yellow solution was then stirred at 100° C. for 79 hours. When the reaction was complete, the solvent was removed under reduced pressure at 100° C., and 10 ml of methanol were added to the residue and left to crystallize at -25° C. The resulting fine precipitate was filtered off and washed with methanol. Yield: 0.70 g (62% of theory). The NMR data were identical to those given in EP-A 749,973.
  • 2
  • [ 185913-95-5 ]
  • [ 185913-97-7 ]
YieldReaction ConditionsOperation in experiment
89% With sodium hydroxide; tributyl-amine; trichlorosilane In 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane; water 5 Reduction of the (+)-(5,5'-dichloro-6,6'-dimethoxybiphenyl-2,2'-diyl)-bis(diphenylphosphine oxide) obtained in Example 4 to give the corresponding phosphine Reduction of the (+)-(5,5'-dichloro-6,6'-dimethoxybiphenyl-2,2'-diyl)-bis(diphenylphosphine oxide) obtained in Example 4 to give the corresponding phosphine 32 ml of tributylamine were added to a solution of 13.5 mmol of (+)-(5,5'-dichloro-6,6'-dimethoxybiphenyl-2,2'-diyl)-bis(diphenylphosphine oxide) in 100 ml of xylene (purified isomer mixture), the mixture was heated to 110° C. under an argon atmosphere and, at this temperature, a solution of 13.6 g of trichlorosilane in 50 ml of xylene (purified isomer mixture) was added dropwise over the course of half an hour. The mixture was refluxed for 3 hours. The solution was then cooled to room temperature, 290 ml of methylene chloride were added, then the mixture was cooled to 0° C., and, at this temperature, sufficient 10% strength by weight aqueous sodium hydroxide solution was added to achieve a pH of 10. The resulting suspension was filtered under a protective-gas frit that had been filled with 5 g of aluminum oxide. The organic phase was transferred to a second flask and the aqueous phase was extracted with 290 ml of methylene chloride. The combined methylene chloride phases were washed twice with 250 ml of water under argon. The organic phase was then concentrated by evaporation in a vacuum to a volume of 100 ml. Even upon concentration, the product started to crystallize. The suspension was stored overnight at 5° C., then filtered with suction, and the solid product was dried in a vacuum. 7.4 g of a pale yellow solid with a content of 95.5% of (+)-(5,5'-dichloro-6,6'-dimethoxybiphenyl-2,2'-diyl)-bis(diphenylphosphine) were obtained. This corresponds to a yield of 89%.
Reference： [1]Current Patent Assignee: LANXESS AG - US2002/58814, 2002, A1
  • 3
  • [ 37366-09-9 ]
  • [ 185913-98-8 ]
  • [ 135875-04-6 ]
  • trans-RuCl2[(S)-Cl-MeO-BIPHEP][(S)-Me-bimaH] [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% Stage #1: dichloro(benzene)ruthenium(II) dimer; (S)-(-)-5,5'-dichloro-6,6'-dimethoxy-2,2'-bis(diphenylphosphino)-1,1'-biphenyl In N,N-dimethyl-formamide at 100℃; for 1h; Inert atmosphere; Stage #2: (S)-α-methyl-1H-benzimidazole-2-methanamine In dichloromethane at 20℃; for 5h; Inert atmosphere; 8 The complex [RuCl2(benzene)]2 (3.3 mg, 7μmol) and (S)-Cl-MeO-BIPHEP (8.5 mg, 0.013 mmol) were suspended in 3 ml of degassed DMF. After stirring for 1 hour at 100 0C, the solvent was removed under high vacuum at 50 0C for 2 hours. After (S)-Me-bimaH (2.1 mg, 0.013 mmol) and 3 ml of degassed CH2Cl2 were added following 5-hours stirring at room temperature, the volume of the solution was redued to about 0.5 ml and the complex was precipitated by adding 6 ml of hexane. The solid obtained was filtered off, washed twice with 3 ml of ethyl ether and dried under vacuum.Yield 11.7 mg (91 %). 31P(1H) NMR (162 MHz, CDCl3, 20 0C) δ 48.42 (d, J= 29.7 Hz), 46.18 (d, J= 29.7 Hz).
Reference： [1]Current Patent Assignee: ENANTIOTECH; CHINESE ACADEMY OF SCIENCES - WO2009/149670, 2009, A1 Location in patent: Page/Page column 13
  • 4
  • [ 37366-09-9 ]
  • [ 185913-98-8 ]
  • [ 135875-04-6 ]
  • trans-RuCl2[(S)-Cl-MeO-BIPHEP][(S)-Me-bimaH] [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% Stage #1: dichloro(benzene)ruthenium(II) dimer; (S)-(-)-5,5'-dichloro-6,6'-dimethoxy-2,2'-bis(diphenylphosphino)-1,1'-biphenyl In N,N-dimethyl-formamide at 100℃; for 1h; Degassed solvent; Stage #2: (S)-α-methyl-1H-benzimidazole-2-methanamine In dichloromethane at 20℃; for 5h; 8 The complex [RuCl2(benzene)]2 (3.3 mg, 7 μmol) and (S)-Cl-MeO-BIPHEP (8.5 mg, 0.013 mmol) were suspended in 3 ml of degassed DMF. After stirring for 1 hour at 100° C., the solvent was removed under high vacuum at 50° C. for 2 hours. After (S)-Me-bimaH (2.1 mg, 0.013 mmol) and 3 ml of degassed CH2Cl2 were added following 5-hours stirring at room temperature, the volume of the solution was redued to about 0.5 ml and the complex was precipitated by adding 6 ml of hexane. The solid obtained was filtered off, washed twice with 3 ml of ethyl ether and dried under vacuum.Yield 11.7 mg (91%). 31P{1H} NMR (162 MHz, CDCl3, 20° C.) δ 48.42 (d, J=29.7 Hz), 46.18 (d, J=29.7 Hz).
Reference： [1]Current Patent Assignee: ENANTIOTECH; CHINESE ACADEMY OF SCIENCES - US2011/92712, 2011, A1 Location in patent: Page/Page column 6
  • 5
  • chloro(1,5-cyclooctadiene)iridium(I) dimer [ No CAS ]
  • [ 591-87-7 ]
  • [ 185913-97-7 ]
  • [ 153775-42-9 ]
  • (NCC6H3(NO2)COO)Ir(((C6H5)2PC6H2ClOCH3)2)(CHCHCH2OCOCH3) [ No CAS ]
Reference： [1]Chemical Communications,2011,vol. 47,p. 10028 - 10030
  • 6
  • [ 12112-67-3 ]
  • [ 591-87-7 ]
  • [ 185913-97-7 ]
  • [ 153775-42-9 ]
  • (allyl)((Cl(MeO)(C6H2)PPh2)2)Ir(O2N(CN)(C6H2)COO) [ No CAS ]
Reference： [1]Chemical Communications,2012,vol. 48,p. 4692 - 4694

Tags: 185913-97-7 synthesis path| 185913-97-7 SDS| 185913-97-7 COA| 185913-97-7 purity| 185913-97-7 application| 185913-97-7 NMR| 185913-97-7 COA| 185913-97-7 structure

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Chemistry
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Aryls
2,2'-bis(diphenylphosphino)biphenyl
Catalysts Ligands
Chiral phosphine ligands
MeOBIPHEP Ligands
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[ 185913-97-7 ]

Chemical Structure| 185913-98-8

A341008[ 185913-98-8 ]

(S)-(-)-5,5'-Dichloro-6,6'-dimethoxy-2,2'-bis(diphenylphosphino)-1,1'-biphenyl

Reason: Optical isomers