(S,S)-Me-BPE

Base Information

• Chemical Name: (S,S)-Me-BPE
• CAS No.: 136779-26-5
• Molecular Formula: C14H28P2
• Molecular Weight: 258.32000
• Hs Code.: 29310099
• European Community (EC) Number: 621-504-2
• UNII: 23B6D1OYCY
• DSSTox Substance ID: DTXSID50420658
• Nikkaji Number: J922.961B
• Mol file: 136779-26-5.mol

Synonyms:(S,S)-Me-BPE;136779-26-5;Me-bpe, (S,S)-;(S,S)-Me-bpe [MI];(S,S)-Me-bpe, (-)-;UNII-23B6D1OYCY;23B6D1OYCY;(-)-1,2-Bis((2S,5S)-2,5-dimethylphospholano)ethane;Bpe ligands (S,S)-me-bpe [MI];(2S,5S)-1-[2-[(2S,5S)-2,5-dimethylphospholan-1-yl]ethyl]-2,5-dimethylphospholane;(-)-1,2-Bis((2S,5S)-2,5-(dimethylphospholan-1-yl))ethane;Phospholane, 1,1'-(1,2-ethanediyl)bis(2,5-dimethyl-, (2S,2'S,5S,5'S)-;1,2-Bis[(2S,5S)-2,5-dimethyl-1-phospholanyl]ethane;Phospholane, 1,1'-(1,2-ethanediyl)bis[2,5-dimethyl-, (2S,2'S,5S,5'S)-;(2S,5S)-1-{2-[(2S,5S)-2,5-DIMETHYLPHOSPHOLAN-1-YL]ETHYL}-2,5-DIMETHYLPHOSPHOLANE;MFCD01073771;SCHEMBL903337;DTXSID50420658;AKOS015910307;CS-0106015;F82480;(-)-1,2-Bis(2S,5S)-2,5-dimethylphospholano)ethane;Q27253738;1,2-Bis((2S,5S)-2,5-dimethylphospholan-1-yl)ethane;1,1'-Ethylenebis(2beta,5alpha-dimethyltetrahydro-1H-phosphole);(-)-1,2-Bis[(2S,5S)-2,5-dimethylphospholano]ethane, kanata purity

Chemical Property of (S,S)-Me-BPE

Chemical Property:

• Vapor Pressure: 0.000285mmHg at 25°C
• Refractive Index: n20/D 1.535
• Boiling Point: 64-67oC0.06 mm Hg
• Flash Point: 162.1oC
• PSA: 27.18000
• Density: 0.938 g/mL at 25oC
• LogP: 5.09180
• Sensitive.: Air Sensitive
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 258.16662489
• Heavy Atom Count: 16
• Complexity: 185

Purity/Quality:

99% ^*data from raw suppliers

(-)-1,2-Bis((2S,5S)-2,5-dimethylphospholano)ethane, 98+% (S,S)-Me-BPE ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F
• Statements: 11-17
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CCC(P1CCP2C(CCC2C)C)C
• Isomeric SMILES: C[C@H]1CC[C@@H](P1CCP2[C@H](CC[C@@H]2C)C)C

Technology Process of (S,S)-Me-BPE

There total 4 articles about (S,S)-Me-BPE 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:

(2R,5R)-2,5-hexanediol (17299-07-9) → 1,2-bis((2S,5S)-2,5-dimethylphospholano)ethane (136779-26-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) SOCl₂, 2.) RuCl₃, NaIO₄

With ruthenium trichloride; sodium periodate; thionyl chloride;

DOI:10.1021/ja00022a047

Reference yield:

(1R,4R)-4-methanesulfonyloxy-1-methylpentyl methanesulfonate (129705-31-3) → 1,2-bis((2S,5S)-2,5-dimethylphospholano)ethane (136779-26-5)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) 25 deg C, 16 h

2: 1.) Li / 1.) THF, 25 deg C, 10 h, 2.) THF, 25 deg C, 1 h

With lithium; In tetrahydrofuran;

DOI:10.1016/S0957-4166(00)86109-1

Reference yield:

1,2-diphosphinoethane (5518-62-7) + (4R,7R)-4,7-dimethyl-[1,3,2]dioxathiepane 2,2-dioxide (136779-29-8) → 1,2-bis((2S,5S)-2,5-dimethylphospholano)ethane (136779-26-5)

Guidance literature:

Multistep reaction;

DOI:10.1021/ja00022a047

upstream raw materials:

1,2-diphosphinoethane

(4R,7R)-4,7-dimethyl-[1,3,2]dioxathiepane 2,2-dioxide

1,2-bis-tosyloxyethane

(2S,5S)-2,5-dimethyl-1-phenylphospholane

Refernces

• 1、 Burk,Feaster,Harlow. "New chiral phospholanes; synthesis, characterization, and use in asymmetric hydrogenation reactions". . p. 569 - 592. Retrieved 2007/12/18.