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[ CAS No. 7650-91-1 ] {[proInfo.proName]}

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Chemical Structure| 7650-91-1
Chemical Structure| 7650-91-1
Structure of 7650-91-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 7650-91-1 ]

CAS No. :7650-91-1 MDL No. :MFCD00014083
Formula : C19H17P Boiling Point : -
Linear Structure Formula :(C6H5CH2P(C6H5)2) InChI Key :UZCPNEBHTFYJNY-UHFFFAOYSA-N
M.W : 276.31 Pubchem ID :603920
Synonyms :

Calculated chemistry of [ 7650-91-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.05
Num. rotatable bonds : 4
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 89.42
TPSA : 13.59 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.76 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.28
Log Po/w (XLOGP3) : 4.54
Log Po/w (WLOGP) : 4.17
Log Po/w (MLOGP) : 5.4
Log Po/w (SILICOS-IT) : 5.85
Consensus Log Po/w : 4.65

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.82
Solubility : 0.00423 mg/ml ; 0.0000153 mol/l
Class : Moderately soluble
Log S (Ali) : -4.55
Solubility : 0.00783 mg/ml ; 0.0000283 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -7.94
Solubility : 0.00000314 mg/ml ; 0.0000000114 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 4.06

Safety of [ 7650-91-1 ]

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

Application In Synthesis of [ 7650-91-1 ]

* 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 [ 7650-91-1 ]

[ 7650-91-1 ] Synthesis Path-Downstream   1~100

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YieldReaction ConditionsOperation in experiment
85% 1.86 g (10 mmol) of diphenyl phosphane and 10 ml of tetrahydrofuran were introduced into a four-neck flask of 100 ml in capacity that had been fully replaced with nitrogen. Into this mixture, 7.63 g of 1.4 mol/kg isopropyl magnesium chloride/lithium chloride-THF solution was dripped over 30 minutes at a constant temperature between 0 C. and 2 C. After the entire solution had been dripped, the mixture was agitated for 4 hours at a temperature of 0 C., to manufacture a diphenyl phosphanyl magnesium chloride/lithium chloride complex. Into this complex, a solution prepared from 0.99 g (7.8 mmol) of benzoyl chloride and 5 ml of tetrahydrofuran was dripped over 1 hour at a constant temperature of 0 C. After the entire solution had been dripped, the mixture was agitated for 8 hours at a temperature of 0 C. Thereafter, 8.5 g of toluene was added to the reaction liquid, after which 10 ml of 5% aqueous sulfuric acid solution was added to the reaction liquid to separate out the organic layer which was then washed with 10 g of water, 10 g of 5% sodium bicarbonate water, and 10 g of water, in this order. The solvent was distilled away from the obtained organic layer under reduced pressure and the residue was dissolved in 5 ml of methanol at 50 C., after which the solution was cooled to 0 C., and thus 1.83 g of benzyl diphenyl phosphine (purity: 98%) was obtained as white crystal. The yield was 85%.
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  • Benzyl-diphenyl-β-phenoxyethyl-phosphonium-bromid [ No CAS ]
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  • N-Methyl-2-(diphenylphosphino)-2-phenylthioacetamid [ No CAS ]
  • 17
  • C40H36P2(2+) [ No CAS ]
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  • [ 607-01-2 ]
  • 18
  • [ 2219-66-1 ]
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  • C42H38P2(2+)*2Br(1-) [ No CAS ]
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  • C40H36P2(2+)*2Br(1-) [ No CAS ]
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  • [ 124730-76-3 ]
  • 24
  • [ 124-38-9 ]
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  • 2-phenyl-2-diphenylphosphinoacetic acid [ No CAS ]
  • 25
  • [ 16714-23-1 ]
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  • 26
  • [ 91271-31-7 ]
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  • 1-(5-carbethoxynaphthyl)-benzyl-diphenylphosphoniumbromid [ No CAS ]
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  • [ 134580-17-9 ]
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  • 28
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  • 29
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  • C43H40P2(2+)*2Br(1-) [ No CAS ]
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  • [ 74-88-4 ]
  • [ 63832-87-1 ]
  • 35
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  • C19H17Br2P [ No CAS ]
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  • [ 103-29-7 ]
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  • 40
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  • C19H17P*2C4H10O*Li [ No CAS ]
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  • C22H20O [ No CAS ]
  • [ 7650-91-1 ]
  • 8-exo-(S)-diphenylphosphanyl-9-endo-(R)-(2'-benzoxyphenyl)deltacyclane [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 4 Preparation of Benzyldiphenylphosphine from Benzyl Bromide To a solution of 2.7 ml benzyl bromide (20 mmol) in 40 ml DMF, was added 0.436 g NiCl2 (dppe) (0.826 mmol). The reaction mixture was cooled to 5 C. and 3.6 ml ClPPh2 (20 mmol) was added dropwise followed by the portionwise addition of 1.74 g zinc (27 mmol) while the internal temperature was kept at 814 C. The reaction mixture was heated to 83 C. for 45 minutes at which time 81% conversion to the title compound was observed by gas chromatographic analysis.
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  • [ 7650-91-1 ]
  • trisodium salt of the bis(m-sulfonatophenyl)-p-sulfonatobenzylphosphaneborane adduct [ No CAS ]
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  • [ 27546-82-3 ]
YieldReaction ConditionsOperation in experiment
With selenium; In chloroform-d1; at 60℃; for 3h;Inert atmosphere; Schlenk technique; General procedure: The selenides of the phosphines 1-8 were prepared by heating (60 C) each phosphine in CDCl3 (0.5 mL) with a three-fold excess of selenium in an NMR tube under nitrogen for 3 hours. Upon cooling to room temperature, the 31P{1H} NMR spectrum of each solution was recorded, and in each case revealed quantitative conversion to the corresponding phosphine selenide. The 31P{1H} NMR chemical shifts and 1JPSe coupling constants of the selenides are provided in Table 1.
  • 51
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  • magnesium chloride diphenylphosphanide [ No CAS ]
  • [ 7650-91-1 ]
  • 52
  • magnesium chloride diphenylphosphanide [ No CAS ]
  • [ 620-05-3 ]
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  • 55
  • [ 7650-91-1 ]
  • C26H30NO3P [ No CAS ]
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  • 1-(5-carbethoxynaphthyl)-diphenylphosphin [ No CAS ]
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  • [ 2959-74-2 ]
YieldReaction ConditionsOperation in experiment
98% With water; Selectfluor; In acetonitrile; at 20℃; for 0.166667h; General procedure: To a solution of 1 (0.2 mmol) in 2 mL of CH3CN/H2O(v/v = 100/1) was added Selectfluor (71 mg, 0.2 mmol). The mixture was stirred at room temperature for 5-60minutes. After removal of the solvent, the residue was then purified by flash column chromatography on silica gel with petroleum ether/ethyl acetate to give the desired product 2.
  • 61
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  • Diphenyl-<(((1S,2R,3R)-pinan-3-yl)-methylamino)-ethyl>-phosphin [ No CAS ]
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  • Diphenyl-<(?)-2-<((1S,2R,3R)-pinan-3-yl)-methylamino>-propyl>-phosphin [ No CAS ]
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  • C34H41N2P [ No CAS ]
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  • C22H25NP(1+)*Br(1-) [ No CAS ]
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  • C24H29NP(1+)*Br(1-) [ No CAS ]
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  • Benzyl-diphenyl-<(((1S,2R,3R)-pinan-3-yl)-methylamino)-ethyl>-phosphonium-bromid [ No CAS ]
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  • Benzyl-diphenyl-<2-(1'-methoxycarbonyl-3'-methyl-butyl-amino)-ethyl>-phosphonium-bromid [ No CAS ]
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  • Benzyl-diphenyl-<(?)-2-((1S,2R,3R)-pinan-3-yl)-methylamino>-propylphosphonium-bromid [ No CAS ]
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  • Benzyl-diphenyl-<(?)-2-(R)-1-methoxycarbonyl-3-methyl-butyl-amino-propyl>-phosphonium-bromid [ No CAS ]
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  • Benzyl-{2-[((1S,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amino]-ethyl}-diphenyl-phosphonium; bromide [ No CAS ]
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  • Benzyl-diphenyl-<2-((R)-1-phenyl-ethylamino)-ethyl>-phosphonium-bromid [ No CAS ]
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  • Benzyl-diphenyl-<2-((S)-1-phenyl-ethylamino)-ethyl>-phosphonium-bromid [ No CAS ]
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  • Benzyl-diphenyl-<(?)-2-((R)-1-phenyl-ethylamino)-propyl>-phosphonium-bromid [ No CAS ]
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  • Benzyl-diphenyl-<(?)-2-((S)-1-phenyl-ethylamino)-propyl>-phosphonium-bromid [ No CAS ]
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  • Diphenyl-<(?)-2-((R)-1-phenyl-ethylamino)-propyl>-phosphin [ No CAS ]
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  • Diphenyl-<(?)-2-((S)-1-phenyl-ethylamino)-propyl>-phosphin [ No CAS ]
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  • N-Methyl-2-(diphenylthiophosphoryl)-2-phenylthioacetamid [ No CAS ]
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  • C42H38P2(2+)*2Br(1-) [ No CAS ]
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  • 2-benzylpyridine iridium(III) chloro dimer [ No CAS ]
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  • mer-iridium(III) tris(diphenylbenzylphosphine) [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With sodium carbonate; In 2-ethoxy-ethanol; at 135℃; for 6h; A 100 mL round-bottomed flask was charged with 2.4 g of benzyl diphenyl phosphine, 1.4 g of benzylpyridine iridium(III) dichloro bridge dimer, 1.83 g of sodium carbonate and 100 mL of 2-ethoxyethanol. The reaction was stirred and heated at 135 C. for 6 h under nitrogen while protected from light with aluminum foil. The reaction mixture was cooled to ambient temperature and concentrated under reduced pressure(20 mmHg). A light brown solution was obtained and further purified by flash column chromatography on silica gel using dichloromethane and hexanes mixture as the eluent yielding 2 g (78%) of pure mer isomer was obtained.
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  • 1,2-Bis[2-(diphenylphosphino)-2-phenyl ethyl]-benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In tetrahydrofuran; hexane; water; toluene; EXAMPLE 9 Preparation of 1,2-Bis[2-(diphenylphosphino)-2-phenyl ethyl]-benzene A 500-mL three-necked flask was equipped with a mechanical stirrer, pressure equalizing dropping funnel, thermometer, and a nitrogen atmosphere. This was charged with 75 mL of THF and diphenylbenzylphosphine (6.0 grams, 21.7 mmole), and the mixture was then cooled to -5 C. N-Butyl lithium (1.55 molar in hexane, 14 mL, 21.7 mmole) was added dropwise to the cold mixture. The resulting dark red solution was stirred at -5 C. for an additional hour. The mixture was then cooled to -78 C. A solution of alpha,alpha'-dichloro-o-xylene (1.75 grams, 10 mmole) in 50 mL of THF was added dropwise to the cold anion solution over 40 minutes. The mixture was stirred at -78 C. for an additional 2 hours, and then it was warmed to 25 C. for 2 more hours. The mixture was quenched with 2 mL of water. The crude mixture was warmed to 70 C. and swept with argon to remove solvent. The residue was treated with a mixture of 200 mL of toluene and 75 ml of 5 percent aqueous hydrochloric acid. The aqueous phase was separated from the toluene layer and discarded. The toluene layer was washed once with 100 mL of water. The toluene solvent was removed by heating to 70 C. at 100 torr under an argon stream. The residue was purified by removing the volatile impurities by distillation with the base temperature reaching 210 C. at 1 torr. The base product (2.6 grams) was an amorphous yellow solid analyzing as follows: 1 H NMR (CDCl3)delta: 2.37-2.93 (multiplet 14H); 3.33-3.78 (multiplet, 2H); 6.33-8.00 (multiplet 34H); 31 P NMR (CDCl3): Two peaks at 0 ppm (Relative to 85 Percent H3 PO4 diasteriomeric pair).
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  • 2,2'-Bis(benzylphenylphosphinomethyl)-1,1'-biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
With naphthalene; In tetrahydrofuran; water; EXAMPLE 7 2,2'-Bis(benzylphenylphosphinomethyl)-1,1'-biphenyl Benzyldiphenylphosphine (9.74 grams, 35.3 mmol) was dissolved in THF (100 ml) under nitrogen in a 250 ml three-necked round-bottomed flask equipped with a magnetic stirrer, thermometer, and condenser with a nitrogen inlet. A small amount of naphthalene (0.12 gram) was added followed by the addition of lithium metal (0.49 gram, 70.6 mmol) in small pieces. The mixture quickly became dark reddish-brown and was heated at 40 C. for 6 hours. t-Butyl chloride (2.29 grams, 24.8 mmol) was added dropwise at room temperature, and the mixture was stirred for 0.5 hour. 2,2'-Bis(bromomethyl)-1,1'-biphenyl (4.71 grams, 13.9 mmol) in THF (20 ml) was added dropwise, whereupon the color changed from dark red-brown to medium orange. The mixture was allowed to stir overnight at room temperature and was then heated at reflux for 1 hour. Water (40 ml) was added and most of the THF was removed on the steam bath under a stream of nitrogen. The aqueous solution was extracted three times with diethyl ether. The combined organic solution was washed with water. The solvent was evaporated to leave an orange oily residue which was placed in a Kugelrohr distillation apparatus and heated at 220 C./1 mm Hg to remove low boiling components, leaving 9.20 grams of an orange glassy solid. 1 H NMR (benzene-d6): delta3.28 (br s, 8H benzylic); 6.33-7.33 (complex, 28H, aromatic). 31 P NMR (benzene-d6): delta+10.
With naphthalene; In tetrahydrofuran; water; EXAMPLE 7 2,2'-Bis(benzylphenylphosphinomethyl)-1,1'-biphenyl Benzyldiphenylphosphine (9.74 grams, 35.3 mmol) was dissolved in THF (100 ml) under nitrogen in a 250 ml three-necked round-bottomed flask equipped with a magnetic stirrer, thermometer, and condenser with a nitrogen inlet. A small amount of naphthalene (0.12 gram) was added followed by the addition of lithium metal (0.49 gram, 70.6 mmol) in small pieces. The mixture quickly became dark reddishbrown and was heated at 40 C. for 6 hours. t-Butyl chloride (2.29 grams, 24.8 mmol) was added dropwise at room temperature, and the mixture was stirred for 0.5 hour. 2,2'-Bis(bromomethyl)-1,1'-biphenyl (4.71 grams, 13.9 mmol) in THF (20 ml) was added dropwise, whereupon the color changed from dark red-brown to medium orange. The mixture was allowed to stir overnight at room temperaure and was then heated at reflux for 1 hour. Water (40 ml) was added and most of the THF was removed on the steam bath under a stream of nitrogen. The aqueous solution was extracted three times with diethyl ether. The combined organic solution was washed with water. The solvent was evaporated to leave an orange oily residue which was placed in a Kugelrohr distillation apparatus and heated at 220 C./l mm Hg to remove low boiling components, leaving 9.20 grams of an orange glassy solid. 1 H NMR (benzene-d6): delta3.28 (br s, 8H benzylic); 6.33-7.33 (complex, 28H, aromatic). - P NMR (benzene-d6): delta+10.
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  • nickel(II) chloride hexahydrate [ No CAS ]
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  • bis(μ-methyl-1,3-dimethyl-η3-allyl-nickel) [ No CAS ]
  • [ 7650-91-1 ]
  • π-C5H9Ni(P(C6H5)2CH2C6H5)CH3 [ No CAS ]
  • anti,syn-π-CH3CHCHCHCH3Ni(P(C6H5)2CH2C6H5)CH3 [ No CAS ]
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  • trans-{PtH(CF3)(PPh3)2} [ No CAS ]
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  • trans-{PtH(CF3)(P(CH2Ph)Ph2)2} [ No CAS ]
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  • nickel(II) bromide trihydrate [ No CAS ]
  • [ 7650-91-1 ]
  • [ 29977-31-9 ]
  • 91
  • bis[(benzyldimethylamino)chloropalladium(II)] [ No CAS ]
  • [ 7650-91-1 ]
  • di-μ-chlorobis{(2-diphenylphosphinomethylphenyl-C1,P)palladium(II)} * 1/6 benzene [ No CAS ]
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  • bis[(benzyldimethylamino)chloropalladium(II)] [ No CAS ]
  • [ 7650-91-1 ]
  • di-μ-chlorobis-[2-[(diphenylphosphino)methyl]phenyl-C,P]dipalladium(II) [ No CAS ]
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  • nickel(II) iodide [ No CAS ]
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  • [ 107308-16-7 ]
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  • [ 12080-32-9 ]
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  • [ 61586-06-9 ]
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  • PtMe((pyrazol-1-yl)2(C3H2N2)CH-N,C')(pyridine) [ No CAS ]
  • [ 7650-91-1 ]
  • PtMe((pyrazol-1-yl)2(C3H2N2)CH-C)(PPh2(CH2Ph))2 [ No CAS ]
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  • nickel(II) bromide trihydrate [ No CAS ]
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  • [ 29977-32-0 ]
  • 97
  • tetrafluoroboric acid [ No CAS ]
  • [ 38117-54-3 ]
  • [ 7650-91-1 ]
  • C5H5(CO)2FeP(C6H5)2(CH2C6H5)(1+)*BF4(1-)={C5H5(CO)2FeP(C6H5)2(CH2C6H5)}BF4 [ No CAS ]
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  • dicarbonyl(η5-indenyl)methyliron [ No CAS ]
  • [ 7650-91-1 ]
  • (C9H7)Fe(CO)(COCH3)(P(C6H5)2CH2C6H5) [ No CAS ]
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  • [ 21264-30-2 ]
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  • [ 61046-58-0 ]
  • 100
  • [ 12080-32-9 ]
  • [ 1571-33-1 ]
  • [ 7650-91-1 ]
  • {Pt(O2P(O)C6H5)(PCH2C6H5(C6H5)2)2}*H2O [ No CAS ]
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