(S,S)-Dipamp

Base Information

• Chemical Name: (S,S)-Dipamp
• CAS No.: 97858-62-3
• Molecular Formula: C₂₈H₂₈O₂P₂
• Molecular Weight: 458.477
• Hs Code.: 2919900090
• European Community (EC) Number: 678-214-4
• UNII: HS6F5EW3U6
• DSSTox Substance ID: DTXSID101027541
• Nikkaji Number: J1.534.935B
• Wikidata: Q411299
• Wikipedia: DIPAMP
• Mol file: 97858-62-3.mol

Synonyms:(S,S)-DIPAMP;97858-62-3;1,2-Bis((S)-(2-methoxyphenyl)(phenyl)phosphino)ethane;Dipamp, (S,S)-;HS6F5EW3U6;(S)-(2-methoxyphenyl)-[2-[(2-methoxyphenyl)-phenylphosphanyl]ethyl]-phenylphosphane;Phosphine, 1,1'-(1,2-ethanediyl)bis(1-(2-methoxyphenyl)-1-phenyl-, (1S,1'S)-;(S,S)-1,2-Bis[(2-methoxyphenyl)phenylphosphino]ethane;(S,S)-(+)-1,2-Bis[2-methoxyphenyl)(phenyl)phosphino]ethane;UNII-HS6F5EW3U6;(+)-DIPAMP;SCHEMBL259791;(S,S)-DIPAMP, 95%;DTXSID101027541;MFCD05863547;(S,S)-DIPAMP, >=95%;AKOS008901422;CS-W013836;GS-0007;(R,R)-DIPAMP (S,S)-FORM [MI];T71507;Q411299;(S,S)-1,2-Ethanediylbis[(2-methoxyphenyl)phenylphosphine];(S,S)-(+)-1,2-Bis[(2-methoxyphenyl)-(phenyl)phosphino]ethane;(S)-(2-methoxyphenyl)({2-[(S)-(2-methoxyphenyl)(phenyl)phosphanyl]ethyl})phenylphosphane

Chemical Property of (S,S)-Dipamp

Chemical Property:

• Vapor Pressure: 7.55E-13mmHg at 25°C
• Melting Point: 102-103°C
• Refractive Index: 85 ° (C=1, CHCl3)
• Boiling Point: 580.2°Cat760mmHg
• Flash Point: 383°C
• PSA: 45.64000
• Density: g/cm³
• LogP: 5.26940
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: soluble in Chloroform
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 9
• Exact Mass: 458.15645413
• Heavy Atom Count: 32
• Complexity: 472

Purity/Quality:

98% ^*data from raw suppliers

(S,?S)?-?DIPAMP ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC=C1P(CCP(C2=CC=CC=C2)C3=CC=CC=C3OC)C4=CC=CC=C4
• Isomeric SMILES: COC1=CC=CC=C1[P@@](CC[P@@](C2=CC=CC=C2)C3=CC=CC=C3OC)C4=CC=CC=C4
• Uses: (S,?S)?-?DIPAMP is a catalyst used in in the preparation of diphosphinobenzenes as well as in cross coupling reactions.

Technology Process of (S,S)-Dipamp

There total 38 articles about (S,S)-Dipamp 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: 97.0%

(RP,RP)-1,2-bis[(o-anisyl)(phenyl)phosphino-P-borane]ethane (131830-91-6,136844-63-8,162490-91-7,97764-56-2) → (RP,RP)-1,2-bis[(o-anisyl)(phenyl)phosphino]ethane (55739-58-7,63449-62-7,63589-61-7,97858-62-3)

Guidance literature:

With diethylamine; Reflux; Inert atmosphere;

DOI:10.1039/c1ob05364g

Reference yield: 94.0%

(S,S)-1,1'-(1,2-ethanediyl)bis[1-(2-methoxyphenyl)-1-phenyl]phosphine oxide (55739-59-8,63449-61-6,74713-67-0,85599-11-7) → (RP,RP)-1,2-bis[(o-anisyl)(phenyl)phosphino]ethane (55739-58-7,63449-62-7,63589-61-7,97858-62-3)

Guidance literature:

With trichlorosilane; triethylamine; In toluene; Inert atmosphere; Reflux;

Reference yield: 93.0%

2-bromoanisole (578-57-4) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → (S(P),S(P))-1,2-bis[(o-anisyl)(phenyl)phosphino]ethane (55739-58-7,63449-62-7,63589-61-7,97858-62-3)

Guidance literature:

1,2-bis-(diphenylphosphino)ethane; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 12h; Inert atmosphere;

2-bromoanisole; With (S,S)-(-)-2,2'-isopropylidenebis(4-tert-butyl-2-oxazoline); nickel dibromide; In tetrahydrofuran; at 70 ℃; for 10h; Concentration;

upstream raw materials:

(R,R)-1,2-Ethandiylbis-<(o-methoxyphenyl)-phenylphosphinoxid>

(R_p)-(2-methoxyphenyl)methylphenylphosphine oxide

(R_P,R_P)-1,2-bis[(o-anisyl)(phenyl)phosphino]ethane

(1R,1R')-(-)-1,1'-(1,2-ethanediyl)bis[1-(2-methoxyphenyl)-1-phenyl]phosphine oxide

Downstream raw materials:

(R,R)-1,2-Aethandiylbis<(o-methoxyphenyl)phenylphosphin>

(1R,1R')-(-)-1,1'-(1,2-ethanediyl)bis[1-(2-methoxyphenyl)-1-phenyl]phosphine oxide

[Rh(DIPAMP)(cod)]+

[Rh₂(DIPAMP)₂(μ₂-Cl)₂]

Refernces

• 1、 Landais, Yannick,Laye, Claire,Lusseau, Jonathan,Robert, Frédéric. "The Trityl-Cation Mediated Phosphine Oxides Reduction". . p. 3035 - 3043. Retrieved 2021/05/10.
• 2、 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.