(R)-(+)-2,2'-Diamino-1,1'-binaphthalene

Base Information

• Chemical Name: (R)-(+)-2,2'-Diamino-1,1'-binaphthalene
• CAS No.: 18741-85-0
• Molecular Formula: C20H16N2
• Molecular Weight: 284.36
• Hs Code.: 29215900
• Mol file: 18741-85-0.mol

Synonyms:[1,1'-Binaphthalene]-2,2'-diamine,(+)- (8CI);[1,1'-Binaphthalene]-2,2'-diamine, (R)-;(+)-1,1'-Binaphthyl-2,2'-diamine;(+)-2,2'-Diamino-1,1'-binaphthyl;(R)-(+)-1,1'-Binaphthyl-2,2'-diamine;(R)-(+)-2,2'-Diamino-1,1'-binaphthyl;(R)-1,1'-Binaphthalene-2,2'-diamine;(R)-1,1'-Binaphthyl-2,2'-diamine;(R)-2,2'-Diamino-1,1'-binaphthyl;(R)-BINAM;

Chemical Property of (R)-(+)-2,2'-Diamino-1,1'-binaphthalene

Chemical Property:

• Appearance/Colour: off-white to brown powder
• Melting Point: 242-244 °C(lit.)
• Refractive Index: 1.6450 (estimate)
• Boiling Point: 480.839 °C at 760 mmHg
• PKA: 3.79±0.10(Predicted)
• Flash Point: 293.854 °C
• PSA: 52.04000
• Density: 1.25 g/cm³
• LogP: 5.98680
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Water Solubility.: slightly soluble

Purity/Quality:

99.9% ^*data from raw suppliers

(R)-(+)-1,1'-Binaphthyl-2,2'-diamine >98.0%(HPLC)(T) ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Physical properties: (R)-(+)-2,2'-Diamino-1,1'-binaphthalene is a off-white to brown powder.
• Uses: (R)-(+)-1,1'-Bi(2-naphthylamine) derivatives have been used for asymmetric hydrogenations, cyclopropanations and formation of chiral lactones. It can be used for the synthesis of sterically hindered binaphthalene-based monophosphane ligands.

Technology Process of (R)-(+)-2,2'-Diamino-1,1'-binaphthalene

There total 28 articles about (R)-(+)-2,2'-Diamino-1,1'-binaphthalene 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: 99.0%

hydrogenchloride (7647-01-0,15364-23-5) + (R,R)-(2,2'-bis(diphenylphosphanyl)biphenyl)(2,2'-damine-1,1'-binaphthyl)platinum(II) hexafluoroantimonate → (R),(+)-1,1'-binaphthalene-2,2'-diamine (18531-95-8,18741-85-0,4488-22-6) + (R)-(2,2'-bis(diphenylphosphanyl)biphenyl)dichloroplatinum(II) (308084-79-9,170940-43-9,372077-28-6)

Guidance literature:

In dichloromethane; raction with concd. HCl at room temp. for 1 h;

DOI:10.1002/anie.200502682

Reference yield: 97.0%

(1R,2S,5R)-(2-isopropyl-5-methylcyclohexyl) [2'-amino-1,1'-binaphthalen-2-yl]carbamate → (R)-1,1'-binaphthyl-2,2'-diamine (18741-85-0)

Guidance literature:

With potassium hydroxide; In ethanol; water; for 12h; Reagent/catalyst; chemoselective reaction; Inert atmosphere; Reflux;

DOI:10.1016/j.tetasy.2014.06.006

Reference yield: 84.0%

C30H22N2O2S → (R)-1,1'-binaphthyl-2,2'-diamine (18741-85-0)

Guidance literature:

With titanium(IV) isopropylate; chloro-trimethyl-silane; magnesium; In tetrahydrofuran; at 50 ℃; for 24h; Inert atmosphere;

DOI:10.1002/anie.201310562

upstream raw materials:

naphthalen-2-ylamine

β-naphthol

2,2'-azonaphthalene

1,1'-binaphthalene-2,2'-diamine

Refernces

• 1、 Takishima, Ryo,Nishii, Yuji,Miura, Masahiro. "Synthesis and Optical Properties of Axially Chiral Bibenzo[ b]carbazole Derivatives". supporting information. p. 1349 - 1354. Retrieved 2021/02/20.
• 2、 Jiang, Qianwen,Liu, Wei,Yang, Xiaoyu. "A Versatile Method for Kinetic Resolution of Protecting-Group-Free BINAMs and NOBINs through Chiral Phosphoric Acid Catalyzed Triazane Formation". supporting information. p. 23598 - 23602. Retrieved 2020/10/23.