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[ CAS No. 13991-08-7 ] {[proInfo.proName]}

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Chemical Structure| 13991-08-7
Chemical Structure| 13991-08-7
Structure of 13991-08-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 13991-08-7 ]

CAS No. :13991-08-7 MDL No. :MFCD00014081
Formula : C30H24P2 Boiling Point : -
Linear Structure Formula :- InChI Key :NFRYVRNCDXULEX-UHFFFAOYSA-N
M.W : 446.46 Pubchem ID :498379
Synonyms :

Calculated chemistry of [ 13991-08-7 ]

Physicochemical Properties

Num. heavy atoms : 32
Num. arom. heavy atoms : 30
Fraction Csp3 : 0.0
Num. rotatable bonds : 6
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 143.85
TPSA : 27.18 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -3.85 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.47
Log Po/w (XLOGP3) : 7.29
Log Po/w (WLOGP) : 5.2
Log Po/w (MLOGP) : 7.27
Log Po/w (SILICOS-IT) : 8.92
Consensus Log Po/w : 6.63

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -7.5
Solubility : 0.0000142 mg/ml ; 0.0000000317 mol/l
Class : Poorly soluble
Log S (Ali) : -7.69
Solubility : 0.00000918 mg/ml ; 0.0000000206 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -12.56
Solubility : 0.0000000001 mg/ml ; 0.0 mol/l
Class : Insoluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 5.36

Safety of [ 13991-08-7 ]

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

Application In Synthesis of [ 13991-08-7 ]

* 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 [ 13991-08-7 ]

[ 13991-08-7 ] Synthesis Path-Downstream   1~84

  • 1
  • [ 1079-66-9 ]
  • [ 35035-62-2 ]
  • [ 13991-08-7 ]
YieldReaction ConditionsOperation in experiment
(i) nBuLi, (ii) /BRN= 512032/; Multistep reaction;
  • 2
  • [ 603-35-0 ]
  • [ 35035-62-2 ]
  • [ 13991-08-7 ]
YieldReaction ConditionsOperation in experiment
With ammonia; sodium 1.) -70 deg C, 90 min; 2.) THF, 3h; Yield given. Multistep reaction;
  • 3
  • [ 13991-08-7 ]
  • chloro(diphenylphosphanyl)diphenylphosphonium tetrachlorogallate [ No CAS ]
  • triphenyl-[2-(1,2,2-triphenyl-diphosphanyl)-phenyl]-phosphonium; GENERIC INORGANIC ANION [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% In dichloromethane at 20℃; for 12h;
55% In dichloromethane (N2); drybox; C6H4(PPh2)2 in CH2Cl2 was added to soln. of Ga compd. in CH2Cl2; mixt. was stirred at room temp. for 12 h; solvent removed (vac.); pentane added; elem. anal.;
  • 4
  • [ 13991-08-7 ]
  • [ 78605-35-3 ]
YieldReaction ConditionsOperation in experiment
100% With dihydrogen peroxide In chloroform at 20℃; for 1h;
99% With dihydrogen peroxide In water at 20℃; for 0.5h;
82% With dihydrogen peroxide In tetrahydrofuran at 20℃; for 2h; Synthesis of the phosphine oxides General procedure: Synthesis of the phosphine oxidesThe phosphine oxides were synthesized by oxidation ofthe corresponding phosphines. Calculated amounts of H2O2(30%) were added slowly to the vigorously stirred THF solutionof the respective phosphine. Stirring was maintainedat room temperature for 2 h. After evaporation of THF, theresidue was treated with acetone-ethyl acetate to obtain therespective phosphine oxide product as a precipitate. The precipitatesthus obtained were filtered off and dried in a vacuum.All melting points were above 360 C with decomposition. OPPO: 1H NMR (250 MHz, CDCl3): d = 7:19 (m, 8H,Phen-H), 7.35 (m, 12H, Phen-H), 7.57 (t, 2H, Phen-H), 7.75(m, 2H, Phen-H). - MS (EI): m=z = 478. Yield 82%.
With air; tin(IV) iodide In dichloromethane

  • 5
  • [ 13991-08-7 ]
  • [ 14074-80-7 ]
  • C118H78N8P2(2-)*2Zn(2+)*2PF6(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With 2,6-dimethylpyridine; tetraethylammonium hexafluorophosphate In 1,2-dichloro-ethane; acetonitrile for 6h; Electrochemical reaction;
  • 6
  • [ 367-11-3 ]
  • [ 1079-66-9 ]
  • [ 13991-08-7 ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: chloro-diphenylphosphine With potassium In tetrahydrofuran Heating; Stage #2: ortho-difluorobenzene In tetrahydrofuran; toluene for 24h; Further stages.;
  • 7
  • (n-Bu4N)2Re2Br8 [ No CAS ]
  • [ 13991-08-7 ]
  • trans-{ReBr2(1,2-bis(diphenylphosphino)benzene)2}Br [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% In ethanol N2 atmosphere; refluxing (4 d), cooling (room temp.); filtration, evapn., recrystn. (CH2Cl2/Et2O), filtration, washing (H2O, hexane and Et2O), drying;
40% With aq. HBr In methanol N2 atmosphere; refluxing (4 d), cooling (room temp.); filtration, evapn., recrystn. (CH2Cl2/Et2O), filtration, washing (H2O, hexane and Et2O), drying; elem. anal.;
28% In methanol N2 atmosphere; refluxing (4 d), cooling (room temp.); filtration, evapn., recrystn. (CH2Cl2/Et2O), filtration, washing (H2O, hexane and Et2O), drying;
  • 8
  • [ 60576-58-1 ]
  • [ 13991-08-7 ]
  • [ 138924-56-8 ]
YieldReaction ConditionsOperation in experiment
49% In dichloromethane Addn. of odppb at -78°C to soln. of Rh-complex under Ar, stirring (-78°C, 20 min), warming to 25°C, stirring (2 h).; Addn. of hexane, filtn., recrystn. (CH2Cl2), drying in a stream of air.;
  • 9
  • [ 38333-35-6 ]
  • [ 13991-08-7 ]
  • [ 119654-85-2 ]
YieldReaction ConditionsOperation in experiment
64% In tetrahydrofuran under N2; soln. of complex treated with a slight excess of ligand, stirred for 24 h at room temp.; filtered, solvent removed (vac.), oily residue dissolved in CH2Cl2, chromy. (alumina, CH2Cl2/hexanes 1:3), collected, evapd. (vac.), recrystn. by dissolving in CH2Cl2, layered with 10-fold vol. of hexanes, cooled to -20°C for 24 h;
  • 10
  • [ CAS Unavailable ]
  • [ 13991-08-7 ]
  • [ 101566-80-7 ]
YieldReaction ConditionsOperation in experiment
With Fe In ethanol; dichloromethane refluxing FeCl2*4H2O in ethanol with iron filings; filtration into a stirred soln. of ligand in ethanol/CH2Cl2; slowly reducing of solvent volume (vac., 0°C); filtration; washing (ethanol); drying in vac.; elem. anal.;
In ethanol for 12h; Reflux; Inert atmosphere;
  • 11
  • [ 109-99-9 ]
  • {trimethylplatinum(IV) iodide}4 [ No CAS ]
  • [ 13991-08-7 ]
  • [ 563-63-3 ]
  • fac-[o-bis(diphenylphosphino)benzene]PtMe3(OAc)*THF [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% In tetrahydrofuran byproducts: AgI; stirred under N2 overnight; filtd., volatiles removed in vacuo, residue recrystd. from THF/pentane at -35°C; elem. anal.;
  • 12
  • [PtMe3OTf]4 [ No CAS ]
  • [ 13991-08-7 ]
  • [ 5633-96-5 ]
  • [ 335630-44-9 ]
YieldReaction ConditionsOperation in experiment
70% In tetrahydrofuran byproducts: CF3SO3K; stirred under N2 at room temp. for 24 h; filtd., solvent removed in vacuo, residue recrystd. from toluene/pentaneat -35°C; elem. anal.;
  • 13
  • [PtMe3OTf]4 [ No CAS ]
  • [ 13991-08-7 ]
  • potassium 4-trifluoromethylphenoxide [ No CAS ]
  • [ 335630-42-7 ]
YieldReaction ConditionsOperation in experiment
60% In tetrahydrofuran byproducts: CF3SO3K; stirred under N2 at room temp. for 24 h; filtd., solvent removed in vacuo, residue recrystd. from toluene/pentaneat -35°C; elem. anal.;
  • 14
  • [PtMe3OTf]4 [ No CAS ]
  • [ 13991-08-7 ]
  • [ 1192-96-7 ]
  • [ 335630-34-7 ]
YieldReaction ConditionsOperation in experiment
70% In tetrahydrofuran byproducts: CF3SO3K; stirred under N2 at room temp. for 24 h; filtd., solvent removed in vacuo, residue recrystd. from toluene/pentaneat -35°C; elem. anal.;
  • 15
  • [PtMe3OTf]4 [ No CAS ]
  • [ 13991-08-7 ]
  • [ 100-67-4 ]
  • [ 335630-36-9 ]
YieldReaction ConditionsOperation in experiment
76% In tetrahydrofuran byproducts: CF3SO3K; stirred under N2 at room temp. for 24 h; filtd., solvent removed in vacuo, residue recrystd. from toluene/pentaneat -35°C; elem. anal.;
  • 16
  • [PtMe3OTf]4 [ No CAS ]
  • [ 13991-08-7 ]
  • [ 1121-74-0 ]
  • [ 335630-40-5 ]
YieldReaction ConditionsOperation in experiment
56% In tetrahydrofuran byproducts: CF3SO3K; stirred under N2 at room temp. for 24 h; filtd., solvent removed in vacuo, residue recrystd. from toluene/pentaneat -35°C; elem. anal.;
  • 17
  • [PtMe3OTf]4 [ No CAS ]
  • [ 13991-08-7 ]
  • [ 1122-93-6 ]
  • [ 335630-38-1 ]
YieldReaction ConditionsOperation in experiment
63% In tetrahydrofuran byproducts: CF3SO3K; stirred under N2 at room temp. for 24 h; filtd., solvent removed in vacuo, residue recrystd. from toluene/pentaneat -35°C; elem. anal.;
  • 18
  • [ 13991-08-7 ]
  • palladium dichloride [ No CAS ]
  • [ 58465-93-3 ]
YieldReaction ConditionsOperation in experiment
91% With NaCl In ethanol under Ar, Schlenk techniques; mixt. of PdCl2 and NaCl in EtOH was stirred at room temp. for 1 h, filtered, addn. of the diphosphane to filtrate,stirred for 0.5 h; ppt. filtered off and recrystd. from CH2Cl2/EtOH; elem. anal.;
  • 19
  • [ 69861-71-8 ]
  • [ 106-38-7 ]
  • [ 13991-08-7 ]
  • [ 460717-98-0 ]
  • 20
  • [ 69861-71-8 ]
  • [ 3972-65-4 ]
  • [ 13991-08-7 ]
  • [ 351531-25-4 ]
  • 21
  • [ 69861-71-8 ]
  • [ 95-46-5 ]
  • [ 13991-08-7 ]
  • [ 351531-26-5 ]
  • 22
  • [ 351531-13-0 ]
  • [ 13991-08-7 ]
  • [ 85318-49-6 ]
YieldReaction ConditionsOperation in experiment
In toluene byproducts: C2H5C(O)CH2C6H4-2-Me; under N2; in NMR tube; react. of Pd complex and ligand (excess) in toluene at 90°C; monitored by UV-vis spectra;
  • 23
  • [ 351531-13-0 ]
  • [ 13991-08-7 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
In benzene-d6 byproducts: (CH3C6H4)CH2C(O)CH2CH3; at 90°C;
  • 24
  • [ 351531-17-4 ]
  • [ 13991-08-7 ]
  • [ 85318-49-6 ]
YieldReaction ConditionsOperation in experiment
In toluene byproducts: t-BuOC(O)CH2C6H4-2-Me; under N2; in NMR tube; react. of Pd complex and ligand (excess) in toluene at 90°C; monitored by UV-vis spectra;
  • 25
  • [ 351531-17-4 ]
  • [ 13991-08-7 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
In benzene-d6 byproducts: (CH3C6H4)CH2C(O)OC4H9; at 90°C;
  • 26
  • [ 351531-11-8 ]
  • [ 13991-08-7 ]
  • [ 85318-49-6 ]
YieldReaction ConditionsOperation in experiment
In toluene byproducts: C6H5C(O)CH(CH3)C6H4-2-Me; under N2; in NMR tube; react. of Pd complex and ligand (excess) in toluene at 90°C; monitored by UV-vis spectra;
  • 27
  • [ 351531-11-8 ]
  • [ 13991-08-7 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
In benzene-d6 byproducts: (CH3C6H4)CH(CH3)C(O)C6H5; at 90°C;
  • 28
  • [ 351531-10-7 ]
  • [ 13991-08-7 ]
  • [ 85318-49-6 ]
YieldReaction ConditionsOperation in experiment
In toluene byproducts: 4-MeC6H4C(O)CH2C6H4-2-Me; under N2; in NMR tube; react. of Pd complex and ligand (excess) in toluene at 90°C; monitored by UV-vis spectra;
  • 29
  • [ 351531-10-7 ]
  • [ 13991-08-7 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
In benzene-d6 byproducts: (CH3C6H4)CH2C(O)C6H4CH3; at 90°C;
  • 30
  • [ 351531-08-3 ]
  • [ 13991-08-7 ]
  • [ 85318-49-6 ]
YieldReaction ConditionsOperation in experiment
In toluene byproducts: C6H5C(O)CH(CH3)C6H4-4-t-Bu; under N2; in NMR tube; react. of Pd complex and ligand (excess) in toluene at 90°C; monitored by UV-vis spectra;
  • 31
  • [ 351531-08-3 ]
  • [ 13991-08-7 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
In benzene-d6 byproducts: (C4H9C6H4)CH(CH3)C(O)C6H5; at 90°C;
  • 32
  • [ 351531-07-2 ]
  • [ 13991-08-7 ]
  • [ 85318-49-6 ]
YieldReaction ConditionsOperation in experiment
In toluene byproducts: 4-CH3C6H4C(O)CH2C6H4-4-t-Bu; under N2; in NMR tube; react. of Pd complex and ligand (excess) in toluene at 90°C; monitored by UV-vis spectra;
  • 33
  • [ 351531-07-2 ]
  • [ 13991-08-7 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
In benzene-d6 byproducts: (C4H9C6H4)CH2C(O)C6H4CH3; at 90°C;
  • 34
  • [ 351531-16-3 ]
  • [ 13991-08-7 ]
  • [ 85318-49-6 ]
YieldReaction ConditionsOperation in experiment
In toluene byproducts: 4-CF3C6H4C(O)CH2C6H4-2-Me; under N2; in NMR tube; react. of Pd complex and ligand (excess) in toluene at 90°C; monitored by UV-vis spectra;
  • 35
  • [ 351531-16-3 ]
  • [ 13991-08-7 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
In benzene-d6 byproducts: (CH3C6H4)CH2C(O)C6H4CF3; at 90°C;
  • 36
  • [ 13991-08-7 ]
  • [ 13510-35-5 ]
  • [ 203911-92-6 ]
  • 37
  • [ 13991-08-7 ]
  • [ 13510-35-5 ]
  • [ 203911-96-0 ]
  • 38
  • [ 13991-08-7 ]
  • [ 13465-09-3 ]
  • [ 203911-91-5 ]
  • 39
  • [ 13991-08-7 ]
  • [ 13465-09-3 ]
  • [ 203911-94-8 ]
  • 40
  • [ 106-39-8 ]
  • [ 69861-71-8 ]
  • [ 13991-08-7 ]
  • [ 727722-34-1 ]
  • 41
  • [ 69861-71-8 ]
  • [ 402-43-7 ]
  • [ 13991-08-7 ]
  • [ 727722-37-4 ]
  • 42
  • [ 108-86-1 ]
  • [ 69861-71-8 ]
  • [ 13991-08-7 ]
  • [ 727722-32-9 ]
  • 43
  • [ 104-92-7 ]
  • [ 69861-71-8 ]
  • [ 13991-08-7 ]
  • [ 727722-36-3 ]
  • 44
  • [ 69861-71-8 ]
  • [ 623-00-7 ]
  • [ 13991-08-7 ]
  • [ 727722-33-0 ]
  • 45
  • [ 108-37-2 ]
  • [ 69861-71-8 ]
  • [ 13991-08-7 ]
  • [ 727722-35-2 ]
  • 46
  • [ 2055-46-1 ]
  • [ 13991-08-7 ]
  • [ 7787-70-4 ]
  • [ 861892-43-5 ]
YieldReaction ConditionsOperation in experiment
92% In methanol; acetonitrile phosphane added to suspn. of copper compd. in CH3CN (1:1), stirred for 2h at 50°C, pptd., methanolic soln. of thione (1 equiv.) added, r efluxed for 2 h to nearly complete dissolution of precipitate, soln. filtered; crystd. on storage at room temp., filtered off, dried (vac.), elem. anal.;
  • 47
  • [ 1450-85-7 ]
  • [ 13991-08-7 ]
  • [ 7787-70-4 ]
  • [ 861892-42-4 ]
  • 48
  • [ 727722-22-7 ]
  • [ 13991-08-7 ]
  • [ 85318-49-6 ]
YieldReaction ConditionsOperation in experiment
In toluene byproducts: 4-t-BuC6H4C(O)CH2C6H5; under N2; in NMR tube; react. of Pd complex and ligand (excess) in toluene at 90°C; monitored by UV-vis spectra;
  • 49
  • [ 727722-23-8 ]
  • [ 13991-08-7 ]
  • [ 85318-49-6 ]
YieldReaction ConditionsOperation in experiment
In toluene byproducts: 4-t-BuC6H4C(O)CH2C6H4-4-Me; under N2; in NMR tube; react. of Pd complex and ligand (excess) in toluene at 90°C; monitored by UV-vis spectra;
  • 50
  • [ 727722-25-0 ]
  • [ 13991-08-7 ]
  • [ 85318-49-6 ]
YieldReaction ConditionsOperation in experiment
In toluene byproducts: 4-t-BuC6H4C(O)CH2C6H4-4-Cl; under N2; in NMR tube; react. of Pd complex and ligand (excess) in toluene at 90°C; monitored by UV-vis spectra;
  • 51
  • [ 727722-26-1 ]
  • [ 13991-08-7 ]
  • [ 85318-49-6 ]
YieldReaction ConditionsOperation in experiment
In toluene byproducts: 4-t-BuC6H4C(O)CH2C6H4-3-Cl; under N2; in NMR tube; react. of Pd complex and ligand (excess) in toluene at 90°C; monitored by UV-vis spectra;
  • 52
  • [ 727722-27-2 ]
  • [ 13991-08-7 ]
  • [ 85318-49-6 ]
YieldReaction ConditionsOperation in experiment
In toluene byproducts: 4-t-BuC6H4C(O)CH2C6H4-4-OMe; under N2; in NMR tube; react. of Pd complex and ligand (excess) in toluene at 90°C; monitored by UV-vis spectra;
  • 53
  • [ 13991-08-7 ]
  • [ 7787-70-4 ]
  • [(1,2-bis(diphenylphosphino)benzene)Cu(μ-Br)]2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% In acetonitrile dppbz (1 mmol) added to suspn. of Cu compd. (1 mmol) in CH3CN; refluxed for 4 h, evapd. at room temp., crystd., filtered off, dried (vac.), elem. anal.;
75% In acetonitrile for 4h; Inert atmosphere; Reflux;
58% In toluene suspn. CuBr and ligand in toluene was stirred at room temp. for 5 h; ppt. was filtered, washed with toluene, MeCN, and MeOH, and dried in vacuo;
18% In toluene suspn. CuBr and ligand in toluene was stirred at room temp. for 5 h; ppt. was filtered, washed with toluene, MeCN, and MeOH, and dried in vacuo, sublimation with Ar stream under 330-360°C and 1E-3 Torr; elem. anal.;

  • 54
  • [ 2001-93-6 ]
  • [ 13991-08-7 ]
  • [ 7787-70-4 ]
  • [ 902121-38-4 ]
YieldReaction ConditionsOperation in experiment
70% In methanol; acetonitrile dppbz (0.5 mmol) added to suspn. of Cu compd. (0.5 mmol) in CH3CN, stirred for 2 h at 50°C, pptd., methanolic. soln. of 2,4-dtucH2 (0.5 mmol) added; refluxed for 2 h, soln. filtered, evapd., crystd., filtered off, dried (vac.), elem. anal.;
  • 55
  • [ 2001-93-6 ]
  • [ 13991-08-7 ]
  • copper(l) chloride [ No CAS ]
  • [ 902121-37-3 ]
YieldReaction ConditionsOperation in experiment
70% In methanol; acetonitrile dppbz (0.5 mmol) added to suspn. of Cu compd. (0.5 mmol) in CH3CN, stirred for 2 h at 50°C, pptd., methanolic. soln. of 2,4-dtucH2 (0.5 mmol) added; refluxed for 2 h, soln. filtered, evapd., crystd., filtered off, dried (vac.), elem. anal.;
  • 56
  • [ 2637-34-5 ]
  • silver(I) bromide [ No CAS ]
  • [ 13991-08-7 ]
  • [ 942481-15-4 ]
YieldReaction ConditionsOperation in experiment
85% With pyridine In ethanol suspension of AgBr and the appropriate diphosphane in ethanol refluxed for 2 h until a white precipitate formed; soln. of pyridine-2-thione in ethanol treated with a small portion pyridine and added dropwise to the hot suspension; refluxed for 2 h; soln. filtered off; soln. kept at room temp.; slow evaporation of the solvent at room temp. gave microcrystalline solid, which filtered off and dried in vacuo; elem. anal.;
  • 57
  • silver(I) bromide [ No CAS ]
  • [ 13991-08-7 ]
  • [Ag(μ-Br)(1,2-bis(diphenylphosphano)benzene)]2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% In acetone suspension of AgBr and appropriate diphosphane in acetone refluxed for 2h; resulting mixture filtered off; clear soln. kept at room temp.; slow evaporation of the solvent at room temp. gave microcrystalline solid which was filtered off and dried in vacuo;, elem. anal.;
In dichloromethane at 40℃; for 10h; 2 Experiment 2: The experimental multi-tooth phosphine coordination silver complex double emitting dye synthesis method according to the following steps:1 mmol of multidentate phosphine ligand, 1 mmol of AgBr, 5 ml of DCM were mixed and reacted at 40 ° C. for 10 hours. The mixture was spin-dried and purified by column chromatography with DCM and PE to obtain a multidentate phosphine coordination silver complex.Wherein the ratio of multidentate phosphine ligand to AgBr is 1: 1.The volume ratio of DCM to PE in the mixed solvent of DCM and PE is 1:20.
  • 58
  • tetrakis(acetonitrile)copper(I)tetrafluoroborate [ No CAS ]
  • [ 13991-08-7 ]
  • bis(1,2-bis(diphenylphosphino)benzene)copper(I) tetrafluoroborate [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% In dichloromethane at 20℃; for 1h; Inert atmosphere; Schlenk technique;
In dichloromethane Cu complex and phosphorous ligand (1:2) reacted in CH2Cl2;
  • 59
  • [ 1295-35-8 ]
  • [ 13991-08-7 ]
  • [ 21119-30-2 ]
  • Ni(C6H4CONTol)(1,2-bis(diphenylphosphino)benzene) [ No CAS ]
  • 60
  • [ 829-85-6 ]
  • [ 583-53-9 ]
  • [ 13991-08-7 ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: diphenylphosphane With cesiumhydroxide monohydrate In N,N-dimethyl-formamide at 20℃; for 1h; Molecular sieve; Inert atmosphere; Stage #2: 2,3-dibromobenzene In N,N-dimethyl-formamide at 20℃; for 60h; Inert atmosphere; Molecular sieve; 7 Comparative Catalyst Preparation Example 7Preparation of (phenyl)2P(1,2-phenyl)P(phenyl)2 ligand; A (phenyl)2P(1,2-phenyl)P(phenyl)2 ligand was prepared by reacting diphenylphosphine with 2 equivalents of dibromoalkyl in dimethylfluoromethylene (DMF) and cesium hydroxide atmospheres, as disclosed in the document “R. N. Salvatore et al, Tetrahedron Letters 44 (2003) 8373”. First, 360 mg (2.14 mmol) of a cesium hydroxide monohydrate was added to 16.6 ml of an anhydrous N,N-dimethylformamide suspension mixed with 1.0 g of activated molecular sieve powder having a particle size of 4 , and was then stirred in a nitrogen atmosphere. Subsequently, 0.38 ml (2.14 mmol) of diphenyl phosphine was added thereto, and was then stirred at room temperature for 1 hour to form a dark reddish orange solution. 0.16 ml (1.29 mmol) of 1,2-dibromobenzene was dropped into the solution, which thus became white. The solution was reacted for 60 hours at room temperature, and 60 ml of distilled water was added thereto, and the solution was extracted three times using 60 ml of DMC to form an organic layer. The organic layer was washed three times with distilled water, and was dried using anhydrous sodium sulfate, the solvent was removed therefrom in a vacuum, and then the organic layer, from which the solvent had been removed, was recrystallized in a benzene solvent, thereby obtaining air-sensitive white crystals (358 mg, yield 75%).
  • 61
  • [ 578743-87-0 ]
  • [ 13991-08-7 ]
  • [ 2923-28-6 ]
  • [(IPR)Cu(dppbz)]OTf [ No CAS ]
YieldReaction ConditionsOperation in experiment
49.6% Chloro[l ,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I) (487.59 mg, 0.25 mmol) and silver triflate (64.2 mg, 0.25 mmol) were mixed under nitrogen in 25 mL flask and 10 mL of dry THF were added. Reaction mixture was stirred at RT for 30 minutes. Solution of 1 ,2-bis(diphenylphosphino)benzene (1 1 1.6 mg, 0.25 mmol) in dry THF (5 mL) was added. Reaction mixture was stirred at RT overnight. Resulting mixture was filtered through Celite and solvent was evaporated on rotovap. Recrystallization from CH2CI2 by vapor diffusion of Et20 gave 130 mg (49.6%) of white needle crystals. Structure confirmed by 1H-NMR spectrum of [(IPR)Cu(dppbz)]OTf (CDCb, 400MHz).
  • 62
  • [ 13991-08-7 ]
  • [ 603-35-0 ]
  • silver(I) chloride [ No CAS ]
  • [ 1222527-35-6 ]
YieldReaction ConditionsOperation in experiment
Stage #1: o-phenylenebis(diphenylphosphine); silver(I) chloride In acetonitrile at 20℃; for 6h; Inert atmosphere; Reflux; Stage #2: triphenylphosphine In dichloromethane at 40℃; for 0.166667h; Inert atmosphere; 14 Under argon atmosphere, 25 mL of dry acetonitrile was added to silver(I) chloride (150 mg, 1.04 mmol) and 1,2-bis(diphenylphosphino)benzene (467 mg, 1.04 mmol), and the mixture was stirred at room temperature for one hour, followed by reflux for five hours. The reaction solution was allowed to reach room temperature, concentrated, and filtrated after being suspended in 7 mL of chloroform. The filtrated matter was subjected to thermal recrystallization from acetonitrile-chloroform and dried to obtain 258 mg of the colorless crystal complex. Under argon atmosphere, 3 mL of dry dichloromethane was added to the above obtained complex (80.0 mg, 0.0678 mmol) and triphenylphosphine (35.6 mg, 0.136 mmol), and the mixture was stirred at 40°C for 10 minutes. The reaction solution was concentrated, subjected to recrystallization by slow diffusion of chloroform-ether, and dried to provide 107 mg of the colorless crystal complex. The result of elemental analysis for the obtained complex is shown in Table 2-2, and the composition ratio of the complex was obtained. The present complex corresponds to the above composition formula (3). [Show Image] The NMR data of the obtained complex is provided below. 1H NMR (300 MHz, CDCl3) δ 7.48-7.17 (m, 31H), 7.06 (t, J = 7.0 Hz, 8H); 13C NMR (75 MHz, CDCl3) δ 134.9-134.8 (m), 134.5 (br), 134.4-134.1 (m), 130.1 (br), 129.7 (br), 129.8-129.7 (m), 129.0 (br), 128.9 (br), 128.8-128.7 (m); 31P NMR (122 MHz, CDCl3) δ 9.1 (br, W1/2 = 66 Hz), -14.8 (br, W1/2 = 390 Hz). The result of DART-MS measurement for the obtained complex is provided below. DART-MS (M/Z): found; 815.16. calcd; 815.13 (M-C1)+. Based on the DART-MS measurement of the obtained complex, it was confirmed that the obtained complex contained the following structure.
  • 63
  • [ 13991-08-7 ]
  • [ 603-35-0 ]
  • silver(I) iodide [ No CAS ]
  • [ 1228792-71-9 ]
YieldReaction ConditionsOperation in experiment
Stage #1: o-phenylenebis(diphenylphosphine); silver(I) iodide In acetonitrile for 7h; Reflux; Inert atmosphere; Stage #2: triphenylphosphine In dichloromethane at 20℃; for 0.5h; 1 Under argon atmosphere, silver(I) iodide (235 mg, 1.00 mmol) and 50 mL of the solution of 1,2-bis(diphenylphosphino)benzene (447 mg, 1.00 mmol) in acetonitrile were mixed and the mixture was heated to reflux with stirring for seven hours. The reaction solution was allowed to reach room temperature and the precipitated colorless crystal was filtrated. The obtained filtrated matter was washed with acetonitrile and dried to obtain 531 mg of the complex. The mixture of this complex (49.7 mg) and triphenylphosphine (19.2 mg, 0.0730 mmol) was dissolved in 3 mL of dichloromethane, and the resulting solution was stirred for 30 minutes at room temperature. The reaction solution was concentrated, subjected to recrystallization by slow diffusion of chloroform-diethylether, and dried to provide 30.9 mg of the colorless solid complex. The result of elemental analysis for the obtained complex is shown in Table 2-1, and the composition ratio of the complex was obtained. The present complex corresponds to the above composition formula (3). [Show Image] The NMR data of the obtained complex is provided below. 1H NMR (300 MHz, CDCl3) δ 7.44-7.14 (m, 31H), 7.03 (t, J= 7.2 Hz, 8H); 13C NMR (75 MHz, CDCl3) δ 141.2 (t, J= 22.7 Hz), 134.5 (t, J= 3.0 Hz), 134.2-134.0 (m), 133.3 (d, J= 22.2 Hz), 132.2 (t, J= 10.9 Hz), 129.6 (s), 129.3 (s), 128.5 (d, J= 9.0 Hz), 128.2 (t, J= 4.5 Hz); 31P NMR (122 MHz, CDCl3) δ 3.7 (br, W1/2=159 Hz), -14.8 (br, W1/2 = 450 Hz). The result of DART-MS measurement of the obtained complex is provided below. DART-MS (M/Z): found; 815.16. calcd; 815.13 (M-I)+. Based on the DART-MS measurement of the obtained complex, it was confirmed that the obtained complex contained the following structure.
  • 64
  • silver(I) bromide [ No CAS ]
  • [ 13991-08-7 ]
  • [ 603-35-0 ]
  • [ 1228792-91-3 ]
YieldReaction ConditionsOperation in experiment
Stage #1: silver(I) bromide; o-phenylenebis(diphenylphosphine) In acetonitrile at 20℃; for 8h; Inert atmosphere; Reflux; Stage #2: triphenylphosphine In dichloromethane at 40℃; for 0.166667h; Inert atmosphere; 13 Under argon atmosphere, 20 mL of dry acetonitrile was added to silver(I) bromide (170 mg , 0.904 mmol) and 1,2-bis(diphenylphosphino)benzene (404 mg, 0.904 mmol), and the mixture was stirred at room temperature for one hour and then heated to reflux for seven hours. The reaction solution was allowed to reach room temperature, concentrated, and filtrated after being suspended in 9 mL of chloroform. The filtrated matter was subjected to thermal recrystallization from acetonitrile-chloroform and dried to obtain 399 mg of the colorless crystal complex. Under argon atmosphere, 3 mL of dry dichloromethane was added to the above obtained complex (80.0 mg, 0.0631 mmol) and triphenylphosphine (33.1 mg, 0.126 mmol), and the mixture was stirred at 40°C for 10 minutes. The reaction solution was concentrated, subjected to recrystallization by slow diffusion of chloroform-ether, and dried to provide 108 mg of the complex. The result of elemental analysis for the obtained complex is shown in Table 2-2, and the composition ratio of the complex was obtained. The present complex corresponds to the above composition formula (3). The NMR data of the obtained complex is provided below. 1H NMR (300 MHz, CDCl3) δ 7.48-7.17 (m, 31H), 7.07-7.03 (m, 8H); 13C NMR (75 MHz, CDCl3) δ 134.8 (t, J = 2.4 Hz), 134.6-134.2 (m), 130.2-130.0 (m), 129.7 (br), 129.0 (br), 128.9 (br), 128.7-128.6 (m); 31P NMR (122 MHz, CDCl3) δ 8.1 (br, W1/2 = 87 Hz) , -14.8 (br, W1/2 = 340 Hz). The result of DART-MS measurement for the obtained complex is provided below. DART-MS (M/Z): found; 815.16. calcd; 815.13 (M-Br)+. Based on the DART-MS measurement of the obtained complex, it was confirmed that the obtained complex contained the following structure.
  • 65
  • [ 14104-20-2 ]
  • [ 119-91-5 ]
  • [ 13991-08-7 ]
  • Ag(1+)*BF4(1-)*C18H12N2*C30H24P2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: silver tetrafluoroborate; o-phenylenebis(diphenylphosphine) In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: 2,2'-biquinoline In dichloromethane at 20℃; for 1h; 9 Under argon atmosphere, 1,2-bis(diphenylphosphino)benzene (91.7 mg, 0.205 mmol) was added to 5 mL of the suspension of silver(I) tetrafluoroborate (40.0 mg, 0.205 mmol) in dry dichloromethane, and the mixture was stirred at room temperature for one hour. Then, 2,2'-biquinoline (52.7 mg, 0.205 mmol) was added to the reaction solution, which was stirred at room temperature for another one hour. The pale yellow reaction solution was filtrated, and the filtrate was concentrated, subjected to recrystallization by slow diffusion of chloroform-ether, and dried to provide 171 mg of the pale yellow solid complex. The result of elemental analysis for the obtained complex is shown in Table 2-2, and the composition ratio of the complex was obtained. The present complex corresponds to the above composition formula (5).
  • 66
  • [ 14104-20-2 ]
  • [ 13991-08-7 ]
  • [ 29176-55-4 ]
  • Ag(1+)*BF4(1-)*C12H6Cl2N2*C30H24P2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: silver tetrafluoroborate; o-phenylenebis(diphenylphosphine) In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: 2,9-dichloro-[1,10]phenanthroline In dichloromethane for 2h; Reflux; 20 Under argon atmosphere, 1,2-bis(diphenylphosphino)benzene (34.6 mg, 0.0776 mmol) was added to 5 mL of the solution of silver(I) tetrafluoroborate (15.1 mg, 0.0776 mmol) in dichloromethane, and the mixture was stirred at room temperature for 30 minutes. Then, 2,9-dichloro-1,10-phenanthroline (23.2 mg, 0.0931 mmol) was added to the reaction solution, which was heated to reflux with stirring for two hours. The reaction solution was filtrated, and the filtrate was concentrated, subjected to recrystallization by slow diffusion of dichloromethane-ether, and dried to provide 46.0 mg of the yellow solid complex. [Show Image] The NMR data of the obtained complex is provided below. 1H NMR (300 MHz, CDCl3) δ 8.80 (d, J = 8.1 Hz, 2H), 8.24 (s, 2H), 8.15 (d, J = 8.1 Hz, 2H), 7.62-7.51 (m, 4H), 7.39-7.29 (m, 20H); 31P NMR (122 MHz, CDCl3) δ -4.4 (d, J (31P-107Ag, 109Ag) = 325, 373 Hz). The composition of the obtained complex was determined according to the same method as in Example 15. The present complex corresponds to the above composition formula (5).
  • 67
  • [ 13991-08-7 ]
  • [ 1087-09-8 ]
  • [ 1254977-43-9 ]
YieldReaction ConditionsOperation in experiment
90% In toluene at 20℃; for 0.166667h; Inert atmosphere;
  • 68
  • [ 13991-08-7 ]
  • [ 762-21-0 ]
  • [ 1254977-42-8 ]
YieldReaction ConditionsOperation in experiment
98% In toluene at 20℃; for 0.166667h; Inert atmosphere;
  • 69
  • [ 13991-08-7 ]
  • [ 351531-13-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: benzene 2: toluene
  • 70
  • [ 13991-08-7 ]
  • [ 351531-17-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: benzene 2: toluene
  • 71
  • [ 13991-08-7 ]
  • [ 351531-11-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: benzene 2: toluene
  • 72
  • [ 13991-08-7 ]
  • [ 351531-10-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: benzene 2: toluene
  • 73
  • [ 13991-08-7 ]
  • [ 351531-08-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: benzene 2: toluene
  • 74
  • [ 13991-08-7 ]
  • [ 351531-07-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: benzene 2: toluene
  • 75
  • [ 13991-08-7 ]
  • [ 351531-16-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: benzene 2: toluene
  • 76
  • [ 13991-08-7 ]
  • [ 727722-23-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: benzene 2: toluene
  • 77
  • [ 13991-08-7 ]
  • [ 727722-25-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: benzene 2: toluene
  • 78
  • [ 108-86-1 ]
  • [ 13991-08-7 ]
  • [ 727722-22-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: benzene 2: toluene
  • 79
  • [ 104-92-7 ]
  • [ 13991-08-7 ]
  • [ 727722-27-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: benzene 2: toluene
  • 80
  • [ 108-37-2 ]
  • [ 13991-08-7 ]
  • [ 727722-26-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: benzene 2: toluene
  • 81
  • [ 14057-91-1 ]
  • [ 100125-12-0 ]
  • [ 75-09-2 ]
  • [ 13991-08-7 ]
  • [ 1360717-69-6 ]
  • 82
  • [ 425-75-2 ]
  • [ 13991-08-7 ]
  • [ 1415495-06-5 ]
YieldReaction ConditionsOperation in experiment
86% In 1,1,2,2-tetrachloroethane at 110℃; for 12h;
  • 83
  • [ 1426922-89-5 ]
  • [ 13991-08-7 ]
  • [RuCl(κ3-cis-1,3,5-triaminocyclohexane)(κ2-phenylene-1,2-bis(diphenylphosphane))]Cl*2H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% In methanol at 90℃; for 48h; Inert atmosphere; Sealed tube;
  • 84
  • [ 1426922-89-5 ]
  • [ 13991-08-7 ]
  • chloro[phenylene-1,2-bis(diphenylphosphane-κ2P,P,)](cis,cis-1,3,5-triaminocyclohexane-κ3N,N,,N")ruthenium(II) chloride hydrate [ No CAS ]
YieldReaction ConditionsOperation in experiment
68.6% In methanol at 90℃; for 48h; Inert atmosphere; 19 Example 19 chloro[phenylene-1,2-bis(diphenylphosphane-κ2P,P,)](cis,cis-1,3,5-triaminocyclohexane-κ3N,N,,N")ruthenium(II) chloride hydrate [19][Cl] ([RuCl(dppben)(tach)]Cl) A solution of [8][CI] (50.0 mg, 0.109 mmol) in methanol (5 mL) with phenylene-1,2- bis(diphenylphosphane) was heated at 90 °C in sealed ampoule under argon for 48 hours. The deep orange solution was allowed to cool, over which a white precipitate formed. The unreacted phosphine precipitate was removed by filtration and diethyl ether (90 mL) added to the solution, forming a cream precipitate. The mixture was cooled to -20 °C for 2 hours, the product isolated by filtration, and dried in vacuo. Yield: 58.6 mg (68.6 %, 0.0748 mmol of rRuCl(K2-dppben)(K -cis-tach)]C1.2H20). NMR Spectroscopy b Cs mirror planelH NMR (CD3OD, 500.2 MHz, 295K) δ 8.07 (ddd, HP = 1 1.0 Hz, HH = 7.5 Hz, HH = 1.2 Hz, 4H, PPh2, Ar211), 7.52 (m, 6H: 2H, PPh2, Ar4a; 4H, PC6H4P, Br2 + Br3), 7.44 (t, VHH = 7.5 HZ, 4H, VPh2, Ar3a), 7.39 (dd, VHH = 7.4 Hz, VHH = 7.2 Hz, 4H, PPhz, Ar3b), 7.34 (td, VHH = 7.2 Hz, HH = 1.4 Hz, 4H, PPh2, Ar b), 7.34 (ddd, VHP = 10.0 Hz, VHH = 7.4 Hz, VHH = 1.4 Hz, 4H, fPh2, Ar4b), 4.93 (d, HH = 11 8 HZ, 2H, NH2, N2), 3.87 (d, HH = Π.8 Hz, 2H, NH2> N2), 3.56 (s, 2Η, CH, Cy2), 2.72 (s, 1Η, CH, Cy1), 2.30 (d, VHH = 15.4 Hz, 1H, CH2, Cy4), 2.14 (d, VHH = 15.4 Hz, 1H, CH2, Cy4), 1.86 (d, HH = 15.2 Hz, 2H, CH2, Cy3), 1.74 (d, VHH = 15.2 Hz, 2H, CH2, Cy3), 1.39 (s, 2H, NH2, N2); 3Ρ{} NMR (CD3OD 202.5 Hz, 295K) δ 72.9 (s, 2P, Ph2); "( {} NMR (CD3OD, 125.8 MHz, 2950K) δ 145.6 (vt, |VPC + VP C| = 82 Hz, PC6H4P, Br1), 139.9 (t, |VRC + VP>c| = 10 Hz, ?Ph2, Ar2a), 133.6 (m, PP/z2, ArIa + Arlb), 133.5 (t, |VPC + VP| = 17 Hz, PC^P, Br2), 133.0 (t, |VPC + VP.C| = 9 Hz, PPki, Ar215), 131.8 (s, PC6P, Br3; s, PP/*2, Ar a), 131.1 (s, P A2, Ar4b), 130.5 (t, |VPC + Vp-c| = 9 Hz, VPh2, Ar3 ), 129.5 (t, |VPC + VFC| = 9 Hz, Pi, Ar a), 44.7 (s, CH, Cy2), 44.4 (s, CH, Cy1), 35.6 (s, CH2, Cy4), 34.3 (s, CH2, Cy3). Mass Spectrometry ESI-MS-. m/z 712.1372 ([RuCl(K2-dppben)(K3-cw-tach)]+, Calc 712.1352, 100 %). Elemental Analysis H20 C / % H / % N / % Found 55.50 5.44 5.33 0 57.83 5.26 5.62 1 56.47 5.40 5.49 2 55.18 5.53 5.36 Table 0.11: CH Elemental analysis for [RuCl(K2-dppben)(K3-cis-tach)]Cl, C36H39N3P2Cl2Ru, calculated with varying water content.3 Integrations of the 1H NMR spectrum recorded in anhydrous CD2CI2 indicates at least 1 equivalent of water present.
Same Skeleton Products
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