2,2'-DIBROMO-1,1'-BINAPHTHYL

Base Information

• Chemical Name: 2,2'-DIBROMO-1,1'-BINAPHTHYL
• CAS No.: 74866-28-7
• Molecular Formula: C₂₀H₁₂Br₂
• Molecular Weight: 412.123
• Hs Code.: 2903999090
• Mol file: 74866-28-7.mol

Synonyms:(?à)-2,2'-Dibromo-1,1'-binaphthalene;2,2'-Dibromo-1,1'-binaphthalene;2,2'-Dibromo-1,1'-binaphthyl;1,1'-Binaphthyl,2,2'-dibromo- (6CI);

Chemical Property of 2,2'-DIBROMO-1,1'-BINAPHTHYL

Chemical Property:

• Melting Point: 178-183 °C
• Boiling Point: 464.1 °C at 760 mmHg
• Flash Point: 273.6 °C
• PSA: 0.00000
• Density: 1.614 g/cm³
• LogP: 7.18500
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: soluble in Toluene
• Water Solubility.: Sparingly Soluble in water.

Purity/Quality:

98% ^*data from raw suppliers

2,2''-Dibromo-1,1''-binaphthyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Uses: The synthesis of this class of compounds relies on the lithiation of racemic 2,2'-dibromo-1,1'-binaphthyl with t-BuLi followed by addition of Ph 2 PCl.

Technology Process of 2,2'-DIBROMO-1,1'-BINAPHTHYL

There total 13 articles about 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:

2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl dioxide

(+/-)-2,2'-bis(dicyclohexylphosphinyl)-1,1'-binaphthyl

(R)-(-)-2,2'-bis(dicyclohexylphosphinoyl)-1,1'-binaphthyl

(S)-(+)-2,2'-bis(dicyclohexylphosphinoyl)-1,1'-binaphthyl

Refernces

• 1、 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.
• 2、 Meskova, Michaela,Putala, Martin. "Highly sterically hindered binaphthalene-based monophosphane ligands: Synthesis and application in stereoselective Suzuki-Miyaura reactions". . p. 894 - 902. Retrieved 2013/09/23.