S-(-)-2,2-DIBROMO-1,1'-BINAPHTHYL

Base Information

• Chemical Name: S-(-)-2,2-DIBROMO-1,1'-BINAPHTHYL
• CAS No.: 150024-49-0
• Molecular Formula: C₂₀H₁₂Br₂
• Molecular Weight: 412.123
• Mol file: 150024-49-0.mol

Synonyms:1,1'-Binaphthalene,2,2'-dibromo-, (S)-

Chemical Property of S-(-)-2,2-DIBROMO-1,1'-BINAPHTHYL

Chemical Property:

• Boiling Point: 464.1±30.0 °C(Predicted)
• PSA: 0.00000
• Density: 1.614±0.06 g/cm3(Predicted)
• LogP: 7.18500
• Storage Temp.: 2-8°C

Purity/Quality:

98.5% ^*data from raw suppliers

(1S)-2,2'-Dibromo-1,1'-binaphthalene, min. 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of S-(-)-2,2-DIBROMO-1,1'-BINAPHTHYL

There total 13 articles about S-(-)-2,2-DIBROMO-1,1'-BINAPHTHYL 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: 94.0%

1,1'-binaphthalene-2,2'-diamine (4488-22-6,18531-95-8) → 2,2'-dibromo-1,1'-binaphthyl (74866-28-7,86688-08-6,150024-49-0)

Guidance literature:

1,1'-binaphthalene-2,2'-diamine; With hydrogen bromide; In water; at 20 ℃; Large scale;

With sodium nitrite; In water; at -5 ℃; for 0.5h; Large scale;

With hydrogen bromide; copper(I) bromide; In water; at 70 ℃; for 2.5h; Large scale;

Reference yield: 66.0%

(R)-1,1'-binaphthyl-2,2'-diamine (18741-85-0) → 2,2'-dibromo-1,1'-binaphthyl (74866-28-7,86688-08-6,150024-49-0)

Guidance literature:

With tert.-butylnitrite; copper(I) bromide; In acetonitrile; at 65 ℃; for 3h;

DOI:10.1016/j.tetasy.2013.06.007

Reference yield: 60.0%

triphenylphosphine (603-35-0) + 1,1'-bi-2-naphthol (602-09-5) → 2,2'-dibromo-1,1'-binaphthyl (74866-28-7,86688-08-6,150024-49-0)

Guidance literature:

With bromine; In acetonitrile; microwave irradiation;

DOI:10.1081/SCC-120022163

upstream raw materials:

2-bromonaphthalene

2,2'-bis(trimethylsiloxy)-1,1'-bi-2-naphthyl

dibromotriphenylphosphorane

1,1'-bi-2-naphthol

Downstream raw materials:

(+/-)-7-phenyldinaphtho<2,1-b;1',2'-d>phosphole

2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl

2,2’-bis(diphenylphosphinooxide)-1,1’-binaphthalene

1,1'-binaphthyl-2,2'-dicarboxylic acid

Refernces

• 1、 Dubois, Fabien,Gingras, Marc. "Syntheses of [5]-helicene by McMurry or carbenoid couplings". . p. 5039 - 5040. Retrieved 1998.
• 2、 Judice, J. Kevin,Keipert, Steven J.,Cram, Donald J.. "A Srongly Binding, Helically Chiral Ligand System". . p. 1323 - 1325. Retrieved 1993.
• 3、 Shuklov, Ivan A.,Dubrovina, Natalia V.,Jiao, Haijun,Spannenberg, Anke,Boerner, Armin. "A highly diastereoselective route to dinaphtho [c,e][1,2] oxaphosphinines and their application as ligands in homogeneous catalysis". . p. 1669 - 1680. Retrieved 2010.
• 4、 Ageshina, Alexandra A.,Sterligov, Grigorii K.,Rzhevskiy, Sergey A.,Topchiy, Maxim A.,Chesnokov, Gleb A.,Gribanov, Pavel S.,Nechaev, Mikhail S.,Asachenko, Andrey F.,Bermeshev, Maxim V.,Melnikova, Elizaveta K.. "Mixed er-NHC/phosphine Pd(ii) complexes and their catalytic activity in the Buchwald-Hartwig reaction under solvent-free conditions". supporting information. p. 3447 - 3452. Retrieved 2019/04/30.