(2S,4S)-(-)-2,4-Bis(diphenylphosphino)pentane

Base Information

• Chemical Name: (2S,4S)-(-)-2,4-Bis(diphenylphosphino)pentane
• CAS No.: 77876-39-2
• Molecular Formula: C₂₉H₃₀P₂
• Molecular Weight: 440.505
• Hs Code.: 29310099
• European Community (EC) Number: 623-772-6
• DSSTox Substance ID: DTXSID90370365
• Nikkaji Number: J736.733C
• Wikidata: Q76146173
• Mol file: 77876-39-2.mol

Synonyms:77876-39-2;(2S,4S)-(-)-2,4-BIS(DIPHENYLPHOSPHINO)PENTANE;(2S,4S)-Pentane-2,4-diylbis(diphenylphosphine);(S,S)-BDPP;(2S,4S)-2,4-BIS(DIPHENYLPHOSPHINO)PENTANE;[(2S,4S)-4-diphenylphosphanylpentan-2-yl]-diphenylphosphane;Phosphine, [(1S,3S)-1,3-dimethyl-1,3-propanediyl]bis[diphenyl-;MFCD00058923;SCHEMBL30277;DTXSID90370365;CTYPJIUQROQJBG-DQEYMECFSA-N;AKOS015840641;(s,s)-2,4-bis(diphenylphosphino)pentane;AS-67190;BP-12276;CS-0086027;D94678;A865133;(2S,4S)-2,4-Bis(diphenylphosphino)pentane, 97%;[(2S,4S)-4-(DIPHENYLPHOSPHANYL)PENTAN-2-YL]DIPHENYLPHOSPHANE

Chemical Property of (2S,4S)-(-)-2,4-Bis(diphenylphosphino)pentane

Chemical Property:

• Vapor Pressure: 2.47E-11mmHg at 25°C
• Melting Point: 81°C
• Boiling Point: 543.8°C at 760 mmHg
• Flash Point: 300.7°C
• PSA: 27.18000
• LogP: 6.41930
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive.: air sensitive
• Solubility.: Benzene (Slightly), Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: 7.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 8
• Exact Mass: 440.18227495
• Heavy Atom Count: 31
• Complexity: 401

Purity/Quality:

97% ^*data from raw suppliers

(2S,4S)-2,4-Bis(diphenylphosphino)pentane ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC(C)P(C1=CC=CC=C1)C2=CC=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4
• Isomeric SMILES: C[C@@H](C[C@H](C)P(C1=CC=CC=C1)C2=CC=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4
• Uses: Ligand used for asymmetric hydrogenation of ketones and alkenes

Technology Process of (2S,4S)-(-)-2,4-Bis(diphenylphosphino)pentane

There total 14 articles about (2S,4S)-(-)-2,4-Bis(diphenylphosphino)pentane 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: 58.0%

(4R,6R)-4,6-dimethyl-(1,3,2)-dioxathian-2,2-dioxide (190671-79-5) + lithiumdiphenylphosphide*dioxane → (2S,4S)-2,4-bis(diphenylphosphino)pentane (96183-46-9,103021-94-9,77876-39-2)

Guidance literature:

(4R,6R)-4,6-dimethyl-(1,3,2)-dioxathian-2,2-dioxide; In tetrahydrofuran; at 20 ℃; for 2h;

lithiumdiphenylphosphide*dioxane; In tetrahydrofuran; at 60 ℃; for 5h;

DOI:10.1016/S0957-4166(01)00498-0

Reference yield: 54.0%

(S,S)-Skewphos-borane complex → (2S,4S)-2,4-bis(diphenylphosphino)pentane (96183-46-9,103021-94-9,77876-39-2)

Guidance literature:

With diethylamine; In toluene; at 60 ℃; for 5h; Inert atmosphere; Schlenk technique;

Reference yield:

bromobenzene (108-86-1,52753-63-6) → (2S,4S)-2,4-bis(diphenylphosphino)pentane (96183-46-9,103021-94-9,77876-39-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: magnesium; iodine / tetrahydrofuran / 5 h / 0 °C

1.2: 12 h / 0 - 80 °C

2.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / -78 - 20 °C

2.2: 2 h / 0 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 20 °C

4.1: tetrahydrofuran; hexane / 12 h / 20 °C

5.1: 1,4-diaza-bicyclo[2.2.2]octane / toluene / 18 h / 90 °C

With 1,4-diaza-bicyclo[2.2.2]octane; n-butyllithium; iodine; diisobutylaluminium hydride; magnesium; In tetrahydrofuran; hexane; toluene;

DOI:10.1039/d1cc04996h

upstream raw materials:

(2S,4S)-pentane-2,4-diyl bis-(4-methylbenzenesulfonate)

sodium diphenylphosphide

potassium diphenylphosphine

triphenylphosphine

Downstream raw materials:

(S,S)-2,4-bis(diphenylmethylphosphonium)pentane iodide