CID 11979534

Base Information

• Chemical Name: CID 11979534
• CAS No.: 12150-46-8
• Molecular Formula: C34H28FeP2
• Molecular Weight: 556.407
• Hs Code.: HOSPHINO)FERROCENE PRODUCT IDENTIFICATION
• NSC Number: 238923
• Mol file: 12150-46-8.mol

Synonyms:NSC238923

Chemical Property of CID 11979534

Chemical Property:

• Appearance/Colour: deep yellow crystalline powder
• Melting Point: 181-182 °C (dec.)(lit.)
• Boiling Point: 363.8oC at 760mmHg
• Flash Point: 182.8oC
• PSA: 27.18000
• LogP: 6.38890
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Solubility.: Chloroform, Ethyl Acetate
• Water Solubility.: Soluble in chloroform, dichloromethane, alcohol and pentane. Insoluble in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 6
• Exact Mass: 546.038960
• Heavy Atom Count: 37
• Complexity: 622

Purity/Quality:

98% ^*data from raw suppliers

1,1’-Bis(diphenylphosphino)ferrocene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xn,Xi
• Hazard Codes: T,Xi,Xn
• Statements: 25-36/37/38-20/21/22
• Safety Statements: 22-24/25-45-28A-36-26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)P([C-]2[C-]=[C-][C-]=[C-]2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2[C-]=[C-][C-]=[C-]2)C3=CC=CC=C3.[Fe]
• Uses: suzuki reaction 1,1'-Bis(diphenylphosphino)ferrocene used coordination compound in synthesis, readily forms complexes with various metals, i.e. when reacting with the acetonitrile or benzonitrile complexes of PdCl2 it forms (dppf)PdCl2, which i s a popular reagent for palladium-catalyzed coupling reactions. 1,1'-Bis(diphenylphosphino)ferrocene acts as a ligand in homogeneous catalysis. It is used as a ligand for ruthenium-catalyzed greener amine synthesis from amines and alcohols by hydrogen-borrowing. It is also employed as a ligand for Buchwald-Hartwig cross coupling. Further, it is used in the synthesis of coordination compound as well as the formation of complexes with various metals such as palladium chloride. In addition to this, it serves as a reagent for palladium-catalyzed coupling reactions and also plays an important role in Suzuki reaction.

Technology Process of CID 11979534

There total 14 articles about CID 11979534 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

[Fe(η5-C5H4P(OPh)2)2] (405164-68-3) → 1,1'-bis-(diphenylphosphino)ferrocene (12150-46-8)

Guidance literature:

With tributylphosphine; iodine; In tetrahydrofuran; acetonitrile; at 20 ℃; for 0.166667h; Inert atmosphere;

Reference yield: 92.0%

1,1'-bis(diphenylphosphino)ferrocene tetrafluoroborate → 1,1'-bis-(diphenylphosphino)ferrocene (12150-46-8)

Guidance literature:

In methanol; for 8h; Reflux;

Reference yield: 84.0%

lithium diphenylphosphinocyclopentadienyl (83272-80-4) + iron(II) chloride + 1,2-bis(diphenylphosphanyl)-4-tert-butylcyclopentadienyl lithium → 1,1'-bis-(diphenylphosphino)ferrocene (12150-46-8) + 1,1′,2,2′-tetrakis(diphenylphosphino)-4,4′-di-tert-butylferrocene (403815-19-0) + 1,1',2'-tris(diphenylphosphino)-4-tert-butylferrocene (878190-65-9)

Guidance literature:

In tetrahydrofuran; (Ar); dropwise addn. of a soln. of trisubstituted lithium compd. in THF to a suspn. of iron salt in THF at -40°C, stirring for 2 h at room temp., addn. of a soln. of monosubstituted lithium salt in THF at -40°C; evapn., reflux in toluene for 3 h, cooling, filtration, column chromy. (SiO2, toluene/hexane 4:1); elem. anal.;

DOI:10.1021/om050882g

upstream raw materials:

1,1'-dilithioferrocene

phenylthiodiphenylphosphine

phenyllithium

chloro-diphenylphosphine

Downstream raw materials:

2-(4-cyano-2-nitrophenylmethyl)benzoic Acid Methyl Ester

1-[3-(methylsulfanylmethyl)phenyl]-pyrrolidine

5-[2-(4-methoxybenzylamino)pyridin-6-yl]pentanoic acid ethyl ester

3-ethoxypropanal

Refernces

• 1、 Buonomo, Joseph A.,Eiden, Carter G.,Aldrich, Courtney C.. "Chemoselective Reduction of Phosphine Oxides by 1,3-Diphenyl-Disiloxane". supporting information. p. 14434 - 14438. Retrieved 2017/10/23.
• 2、 -. "A ferrocene diphosphine ligand preparation method". Paragraph 0006; 0015; 0016. . Retrieved 2017/08/31.