Segphos

Base Information

• Chemical Name: Segphos
• CAS No.: 210169-54-3
• Molecular Formula: C₃₈H₂₈O₄P₂
• Molecular Weight: 610.585
• European Community (EC) Number: 811-741-1,812-649-4
• DSSTox Substance ID: DTXSID101145953
• Nikkaji Number: J2.201.579F,J2.233.087J,J1.672.856J
• Wikipedia: SEGPHOS
• Wikidata: Q1089190
• Mol file: 210169-54-3.mol

Synonyms:210169-54-3;244261-66-3;SEGPHOS;(R)-SEGPHOS;(S)-SEGPHOS;(S)-(-)-SEGPHOS;(R)-5,5'-Bis(diphenylphosphino)-4,4'-bibenzo[d][1,3]dioxole;(R)-(+)-SEGPHOS;(R)-(+)-5,5'-BIS(DIPHENYLPHOSPHINO)-4,4'-BI-1,3-BENZODIOXOLE;(S)-(-)-5,5'-BIS(DIPHENYLPHOSPHINO)-4,4'-BI-1,3-BENZODIOXOLE;(S)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole;5,5'-Bis(diphenylphosphino)-4,4'-bibenzo[d][1,3]dioxole;[4-(5-diphenylphosphanyl-1,3-benzodioxol-4-yl)-1,3-benzodioxol-5-yl]-diphenylphosphane;244261-75-4;(S)-DM-SEGPHOS;MFCD09753005;(R)-5,5'-Bis(diphenylphosphanyl)-4,4'-bibenzo[d][1,3]dioxole;(S)-(-)-4,4'-Bis(diphenylphosphino)-3,3'-bi(1,2-methylenedioxybenzene);(S)-5,5'-bis(diphenylphosphanyl)-4,4'-bibenzo[d][1,3]dioxole;SCHEMBL27899;5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole;(R)-(+)-SEGPHOS(regR);(S)-(-)-SEGPHOS(regR);RZZDRSHFIVOQAF-UHFFFAOYSA-N;5,5'-Bis(diphenylphosphanyl)-4,4'-bibenzo[d][1,3]dioxole;DTXSID101145953;AKOS025213718;(R)-SEGPHOS(R), >=94%;(S)-SEGPHOS(R), >=94%;CS-W020802;SC11508;AS-70766;SY074111;CS-0035252;S0929;S0930;D70708;D70709;A877918;J-015520;Q1089190;(aS)-5,5'-Bis(diphenylphosphino)-4,4'-bi[1,3-benzodioxole];(-)-5,5'-bis(diphenylphosphanyl)-4,4'-bi[benzo-1,3-dioxolyl];(S)-5,5'-bis(diphenylphosphaneyl)-4,4'-bibenzo[d][1,3]dioxole;(R)-(+)-4,4'-Bis(diphenylphosphino)-3,3'-bi(1,2-methylenedioxybenzene);(R)-(+)-5,5?-Bis(diphenylphosphino)-4,4?-bi-1,3-benzodioxole, [4(R)-(4,4?-bi-1,3-benzodioxole)-5,5?-diyl]bis[diphenylphosphine];(S)-(-)-5,5 inverted exclamation mark -Bis(diphenylphosphino)-4,4 inverted exclamation mark -bi-1,3-benzodioxole;{4-[5-(diphenylphosphanyl)-2H-1,3-benzodioxol-4-yl]-2H-1,3-benzodioxol-5-yl}diphenylphosphane

Chemical Property of Segphos

Chemical Property:

• Melting Point: 231-235 °C
• Boiling Point: 715.4±60.0 °C(Predicted)
• PSA: 64.10000
• LogP: 6.32740
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 8.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 610.14628337
• Heavy Atom Count: 44
• Complexity: 787

Purity/Quality:

98% ^*data from raw suppliers

(S)-(-)-SEGPHOS? ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1OC2=C(O1)C(=C(C=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)C5=C(C=CC6=C5OCO6)P(C7=CC=CC=C7)C8=CC=CC=C8
• Uses: (S)-(-)-SEGPHOS? is a chelating ligand used to prepare coordination complex catalysts, such as its use in Pd catalysts for the enantioselective synthesis of spiro- or benzofused hetereocycles with exocyclic olefins via enantioselective intramolecular dearomative Heck reaction of indoles, benzofurans, pyrroles and furans.

Technology Process of Segphos

There total 1 articles about Segphos 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: 85.0%

→ 5,5’-bis(diphenylphosphino)-4,4’-bi-1,3-benzodioxole (210169-54-3,244261-66-3,244261-75-4)

Guidance literature:

Reference yield: 99.0%

5,5’-bis(diphenylphosphino)-4,4’-bi-1,3-benzodioxole (210169-54-3,244261-66-3,244261-75-4) + PtCl(8-O-quinoline)(dmso) → C47H34NO5P2Pt(1+)*Cl(1-)

Guidance literature:

In chloroform; at 60 ℃; for 24h; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.inorgchem.0c01326

Reference yield: 92.0%

bis(1,5-cyclooctadiene)diiridium(I) dichloride (12112-67-3) + Allyl acetate (591-87-7) + (S)-SEGPHOS (210169-54-3,244261-66-3,244261-75-4) + 2-nitro-4-carboxybenzonitrile (153775-42-9) → [(S)-(+)-5,5'-bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole][4-cyano-3-nitrobenzenecarboxylato] [1,2,3-eta-2-propenyl Ir(III)] (1208092-27-6,1221768-92-8)

Guidance literature:

With Cs₂CO₃; In tetrahydrofuran; Cs2CO3, THF, 80°C; isolated by pptn.;

DOI:10.1021/ja1082798

Downstream raw materials:

[((R)-segphos)Ni(C₆H₄-4-CN)(Br)]

[Rh(CO)Cl((C₆H₂OCH₂OP(C₆H₅)2)2)]

Ir(allyl)((S)-SEGPHOS)(m-nitrobenzoate(-H)-kappa.C,O)

[(S)-(+)-5,5'-bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole][4-cyano-3-nitrobenzenecarboxylato] [1,2,3-eta-2-propenyl Ir(III)]

Refernces

• 1、 -. "Chiral diphosphine compound intermediate for preparing the same transition metal complex having the same diphosphine compound as ligand and asymmetric hydrogenation catalyst". . . Retrieved 2008/06/13.