(-)-1,2-Bis((2R,5R)-2,5-diphenylphospholano)ethane

Base Information

• Chemical Name: (-)-1,2-Bis((2R,5R)-2,5-diphenylphospholano)ethane
• CAS No.: 528565-79-9
• Molecular Formula: C34H36P2
• Molecular Weight: 506.607
• Hs Code.: 2934999090
• European Community (EC) Number: 815-107-5
• DSSTox Substance ID: DTXSID70465304
• Nikkaji Number: J1.908.168K
• Mol file: 528565-79-9.mol

Synonyms:528565-79-9;(-)-1,2-Bis((2R,5R)-2,5-diphenylphospholano)ethane;1,2-Bis((2R,5R)-2,5-diphenylphospholan-1-yl)ethane;(2R,5R)-1-[2-[(2R,5R)-2,5-diphenylphospholan-1-yl]ethyl]-2,5-diphenylphospholane;(R,R)-Phenyl-BPE;MFCD07369027;(2R,5R)-1-[2-[(2R,5R)-2,5-diphenylphospholan-1-yl]ethyl]-2,5-diphenyl-phospholane;SCHEMBL903335;DTXSID70465304;AKOS030621895;PS-17813;D83185;(-)-1,2-Bis(2S,5R)-2,5-(diphenylphospholano)ethane;(-)-1,2-Bis((2R,5R)-2,5-diphenylphospholano)ethane, kanata purity

Chemical Property of (-)-1,2-Bis((2R,5R)-2,5-diphenylphospholano)ethane

Chemical Property:

• Melting Point: 144°C
• Boiling Point: 654.2±55.0 °C(Predicted)
• Flash Point: 373.1oC
• PSA: 27.18000
• LogP: 10.50300
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive.: Air Sensitive
• Water Solubility.: Sparingly soluble in water.(3.2E-5g/L) (25°C
• XLogP3: 6.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 7
• Exact Mass: 506.22922514
• Heavy Atom Count: 36
• Complexity: 530

Purity/Quality:

98%,99%, ^*data from raw suppliers

(-)-1,2-Bis((2R,5R)-2,5-diphenylphospholano)ethane, min. 95% (R,R)-Ph-BPE ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC(P(C1C2=CC=CC=C2)CCP3C(CCC3C4=CC=CC=C4)C5=CC=CC=C5)C6=CC=CC=C6
• Isomeric SMILES: C1C[C@@H](P([C@H]1C2=CC=CC=C2)CCP3[C@H](CC[C@@H]3C4=CC=CC=C4)C5=CC=CC=C5)C6=CC=CC=C6
• Uses: DuPhos and BPE Ligands: Highly Efficient Privileged Ligands

Technology Process of (-)-1,2-Bis((2R,5R)-2,5-diphenylphospholano)ethane

There total 4 articles about (-)-1,2-Bis((2R,5R)-2,5-diphenylphospholano)ethane 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: 95.0%

1,2-bis[(R,R)-2,5-diphenylphospholano]ethane oxide → (R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane (528565-79-9,824395-67-7)

Guidance literature:

With trichlorosilane; N,N-dimethyl-aniline; In toluene; Reagent/catalyst; Inert atmosphere; Reflux;

Reference yield: 92.0%

1,2-bis[(R,R)-2,5-diphenylphospholano]ethane-borane → (R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane (528565-79-9,824395-67-7)

Guidance literature:

With tetrafluoroboric acid dimethyl ether complex; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/ol0341952

Reference yield:

(R,R)-(+)-1-hydroxy-1-oxo-2,5-trans-diphenylphospholane (226393-33-5) → (R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane (528565-79-9,824395-67-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: PhSiH₃ / toluene / 16 h / 110 °C

1.2: 95 percent / BH₃*SMe₂ / tetrahydrofuran / 16 h / 20 °C

2.1: nBuLi / tetrahydrofuran; hexane / 1 h / -20 °C

2.2: 69 percent / tetrahydrofuran; hexane / 40 h / 20 °C

3.1: 92 percent / HBF₄*OMe₂ / CH₂Cl₂ / 16 h / 20 °C

With n-butyllithium; phenylsilane; tetrafluoroboric acid dimethyl ether complex; In tetrahydrofuran; hexane; dichloromethane; toluene;

DOI:10.1021/ol0341952

upstream raw materials:

(R,R)-(+)-1-hydroxy-1-oxo-2,5-trans-diphenylphospholane

Downstream raw materials:

rhodium(acac)(R,R-1,2-bis(2,5-diphenylphospholano)ethane)

1,2-bis(2,5-diphenylphospholano)ethane