(11aS)-1,11-Bis(diphenylphosphino)dibenzo[d,f][1,3]dioxepine

Base Information

• Chemical Name: (11aS)-1,11-Bis(diphenylphosphino)dibenzo[d,f][1,3]dioxepine
• CAS No.: 486429-92-9
• Molecular Formula: C₃₇H₂₈O₂P₂
• Molecular Weight: 566.576
• DSSTox Substance ID: DTXSID20443915
• Nikkaji Number: J1.470.253I,J2.243.634A
• Wikidata: Q82261903
• Mol file: 486429-92-9.mol

Synonyms:486429-92-9;(R)-C4-TunePhos;(11aS)-1,11-Bis(diphenylphosphino)dibenzo[d,f][1,3]dioxepine;(11aS)-Dibenzo[d,f][1,3]dioxepin-1,11-diylbis[diphenylphosphine];1,11-Bis(diphenylphosphino)dibenzo[d,f][1,3]dioxepine;905714-07-0;(R)-C1-TunaPhos;1,1'-(11aS)-dibenzo[d,f][1,3]dioxepin-1,11-diylbis[1,1-diphenylphosphine;SCHEMBL3136653;DTXSID20443915;CS-0108765;CS-0108766;FT-0726683;F88717;1,11-Bis(diphenylphosphino)dibenzo[d,f][1,3]dioxepin;(aR)-2,2'-Bis(diphenylphosphino)-6,6'-(methylenebisoxy)biphenyl;(1-diphenylphosphanylbenzo[d][1,3]benzodioxepin-11-yl)-diphenylphosphane

Chemical Property of (11aS)-1,11-Bis(diphenylphosphino)dibenzo[d,f][1,3]dioxepine

Chemical Property:

• XLogP3: 8.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 566.15645413
• Heavy Atom Count: 41
• Complexity: 682

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1OC2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)C5=C(O1)C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7

Technology Process of (11aS)-1,11-Bis(diphenylphosphino)dibenzo[d,f][1,3]dioxepine

There total 3 articles about (11aS)-1,11-Bis(diphenylphosphino)dibenzo[d,f][1,3]dioxepine 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: 80.0%

chlorobromomethane (74-97-5) + (6,6′-dihydroxybiphenyl-2,2′-diyl)bis(diphenylphosphine) (270253-34-4,151395-61-8,151395-62-9) → 1,11-bis-diphenylphosphanyl-5,7-dioxa-dibenzo[a,c]cycloheptene (486429-92-9,301847-87-0)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 60 ℃; for 72h;

DOI:10.1021/jo000462v

Reference yield:

(RS)-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis(diphenylphosphine) (133545-16-1,133545-17-2,133577-92-1) → 1,11-bis-diphenylphosphanyl-5,7-dioxa-dibenzo[a,c]cycloheptene (486429-92-9,301847-87-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / BBr₃ / CH₂Cl₂ / -78 - 20 °C

2: 80 percent / K₂CO₃ / dimethylformamide / 72 h / 20 - 60 °C

With boron tribromide; potassium carbonate; In dichloromethane; N,N-dimethyl-formamide; 1: demethylation / 2: Alkylation;

DOI:10.1021/jo000462v

Reference yield:

(RS)-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis(diphenylphosphine oxide) (133545-15-0,133577-82-9,133577-84-1) → 1,11-bis-diphenylphosphanyl-5,7-dioxa-dibenzo[a,c]cycloheptene (486429-92-9,301847-87-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / Bu₃N; HSiCl₃ / xylene / 3 h / Heating

2: 84 percent / BBr₃ / CH₂Cl₂ / -78 - 20 °C

3: 80 percent / K₂CO₃ / dimethylformamide / 72 h / 20 - 60 °C

With tributyl-amine; trichlorosilane; boron tribromide; potassium carbonate; In dichloromethane; N,N-dimethyl-formamide; xylene; 1: Reduction / 2: demethylation / 3: Alkylation;

DOI:10.1021/jo000462v

upstream raw materials:

chlorobromomethane

(6,6′-dihydroxybiphenyl-2,2′-diyl)bis(diphenylphosphine)

(RS)-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis(diphenylphosphine)

(RS)-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis(diphenylphosphine oxide)