18741-85-0

Basic information

• Product Name: (R)-(+)-2,2'-Diamino-1,1'-binaphthalene
• Synonyms: (R)-(+)-1,1'-BINAPHTHYL-2,2'-DIAMINE, 99 % (99% EE/GLC);(R)-(+)-2,2'-Diamino-1,1'-binaphthyl,99%;(R)-(+)-1,1''-BINAPHTHALENE-2,2''-DIAMINE (R-BINAM) ((R)-(+) -2,2''-DIAMINO-1''1-BINAPHTHYL);(R)-(+)-1,1μ-Binaphthalene-2,2μ-diamine, (R)-(+)-2,2μ-Diamino-1,1μ-binaphthalene, (R)-(+)-DABN;(R)-(+)-1,1μ-Bi(2-naphthylamine), (R)-(+)-1,1μ-Binaphthalene-2,2μ-diamine, (R)-(+)-2,2μ-Diamino-1,1μ-binaphthalene, (R)-(+)-DABN;(aR)-1,1'-Binaphthalene-2,2'-diamine;(aR)-2,2'-Diamino-1,1'-binaphthalene;(R)-BINAM
• CAS NO: 18741-85-0
• Molecular Formula: C₂₀H₁₆N₂
• Molecular Weight: 284.35
• EINECS: -0
• Product Categories: BINAM Series;Achiral Nitrogen
• Mol File: 18741-85-0.mol
• Article Data: 28

Chemical Properties

• Melting Point: 242-244 °C(lit.)
• Boiling Point: 416.85°C (rough estimate)
• Flash Point: 293.854 °C
• Appearance: slightly beige/Powder
• Density: 1.0447 (rough estimate)
• Refractive Index: 1.6450 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 3.79±0.10(Predicted)
• Water Solubility: slightly soluble
• BRN: 5279621
• CAS DataBase Reference: (R)-(+)-2,2'-Diamino-1,1'-binaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-2,2'-Diamino-1,1'-binaphthalene(18741-85-0)
• EPA Substance Registry System: (R)-(+)-2,2'-Diamino-1,1'-binaphthalene(18741-85-0)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38
• Safety Statements: 26-39-37/39-36
• WGK Germany: 3
• RTECS: DU3090000
• F: 10
• Hazardous Substances Data: 18741-85-0(Hazardous Substances Data)

Usage

Synthesis

(R)-(+)-2,2'-Diamino-1,1'-binaphthalene can be 1a , 2b, potassium carbonate, potassium iodide, dimethyl sulfoxide as a reaction solvent, then react with adding potassium hydroxide, and finally extract with ethyl acetate And get.

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.

General Description

(R)-(+)-1,1′-Binaphthyl-2,2′-diamine is an axially dissymmetric binaphthyl ligand mainly used in enantioselective catalysis.

Upstream product

• 582-08-1 2,2'-azonaphthalene 
• 4488-22-6 1,1'-binaphthalene-2,2'-diamine 
• 66-99-9 β-naphthaldehyde 
• 1613472-71-1 C₃₀H₂₂N₂O₂S 
• 7647-01-0 hydrogenchloride 
• 970-62-7 2,2'-hydrazonaphthalene 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 13672-18-9 benzyl-2-naphthylamine 
• 128544-05-8 (R)-(-)-1,1'-bi-2-naphthol triflate 
• 3857-83-8 2-naphthyl triflate 
• 613-64-9 1,2-di(naphthalen-2-yl)hydrazine 
• 135-19-3 β-naphthol 
• 582-02-5 1,2-di(naphthalen-2-yl)diazene oxide 
• 581-89-5 2-nitronaphthalene 

Downstream Products

• 95241-24-0 C₃₄H₂₄N₂O₂ 
• 86688-06-4 (R_a)-2,2'-diiodo-1,1'-binaphthyl 
• 856908-93-5 (R)-[Rh(5-phenyldibenzo[a,e]cyclooctene)(R-(+)1,1'-binaphthyl-2,2'-diamine)](OTf) 
• 444759-14-2 N,N’-bis(salicylidene)-1,1’-binaphthyl-2,2’-diamine 

Relevant articles and documents

A miniaturized analytical method based on molecularly imprinted absorbents for selective extraction of (S)-1,1′-binaphthyl-2,2′-diamine and combinatorial screening of polymer precursors by computational simulation

Chiral resolution of binaphthylamine is often a toilful conundrum in the field of analytical chemistry and biomedicine. The work puts forward a selective, sensitive, and miniaturized analytical method based on molecularly imprinted polymers (MIPs) as adsorbent for miniaturized tip solid-phase extraction (MTSPE) in the separation of binaphthylamine enantiomer. This method combines the advantages of MIPs (high selectivity), MTSPE (low consumption), and high-performance liquid chromatography (HPLC, high sensitivity). A simple synthesis methodology of MIP (P2) was conducted through bulk polymerization with (S)-(?)-1,1′-binaphthyl-2,2′-diamine (S-DABN) as template together with methacrylic acid monomer, and ethylene glycol dimethacrylate as cross-linker in proper porogen, realizing a selective recognition and efficient enrichment for S-DABN. The method exhibited appreciable linearity (0.06–1.00 mg ml?1), low quantification limit (0.056 mg ml?1), good absolute recoveries (45.70%–69.29%), and high precision (relative standard deviations ≤ 3.54%), along with low consumption (0.50?ml sample solution and 25.0?mg adsorbent). Based on the density functional theory, computational simulation was used to make a preliminary prediction for rational design of MIPs and gave a reasonable elaboration involving the potential mechanism of templates interacting with functional monomers. The adsorption kinetics and thermodynamics were investigated to evaluate the recombination process of substrates. In addition, the selectivity of MIPs for S-DABN was obtained by MIP-MTSPE coupled with HPLC, which supports the feasibility of this convenient design process. The proposed method was employed for selective extraction of S-DABN and exhibited promising potential in the application of chiral analysis.

Method for resolving chiral compound

The invention relates to the field of organic chemistry, in particular to a method for resolving a chiral compound. The method for splitting the chiral compound provided by the invention comprises thestep of carrying out addition reaction on a racemic compound shown as a formula A and azodicarbonic acid ester in the presence of a catalyst so as to provide an S-configuration compound shown as theformula A and an S-configuration compound shown as the formula C. According to the method, chiral phosphoric acid is used as a catalyst; good catalytic effect is achieved, and very wide substrate applicability is also achieved; the product and the recovered raw material can be obtained with excellent enantioselectivity, the selectivity coefficient of kinetic resolution can reach 371, and the method has an excellent kinetic resolution effect on various N-monosubstituted and N-unsubstituted binaphthalene diamines, H8-binaphthalene diamines and biphenyl diamines.

Switchable Smiles Rearrangement for Enantioselective O-Aryl Amination

Asymmetric assembly of atropisomeric anilines from abundant and readily available precursors is one of the most challenging but valuable processes in organic synthesis. The use of highly efficient Smiles rearrangement to accomplish switchable enantioselec