[1,1'-Binaphthalene]-2,2'-diamine

Base Information

• Chemical Name: [1,1'-Binaphthalene]-2,2'-diamine
• CAS No.: 4488-22-6
• Molecular Formula: C₂₀H₁₆N₂
• Molecular Weight: 284.36
• Hs Code.: 29215900
• European Community (EC) Number: 626-241-7,627-240-4,628-471-3
• NSC Number: 519704
• UNII: XI03TW52AO,7OL97NN4U4,TL35MU1249
• DSSTox Substance ID: DTXSID70196328
• Nikkaji Number: J36.105D,J83.320G,J82.768A
• Wikidata: Q27290008
• Mol file: 4488-22-6.mol

Synonyms:1,1'-binaphthyl-2,2'-diamine

Chemical Property of [1,1'-Binaphthalene]-2,2'-diamine

Chemical Property:

• Melting Point: 242-244oC(lit.)
• Refractive Index: 1.6450 (estimate)
• Boiling Point: 416.85°C (rough estimate)
• PKA: 3.79±0.10(Predicted)
• PSA: 52.04000
• Density: 1.249
• LogP: 5.98680
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Water Solubility.: Insoluble in water
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 284.131348519
• Heavy Atom Count: 22
• Complexity: 346

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-41-22
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC(=C2C3=C(C=CC4=CC=CC=C43)N)N
• Description: 1,1'-Binaphthalene]-2,2'-diamine is an axially asymmetric binaphthyl ligand mainly used in enantioselective catalysis.
• Uses: Novel axially chiral Rh N-heterocyclic carbene complexes were prepared from axially dissymmetric 1,1'-Binaphthalene]-2,2'-diamine and applied in the Rh-catalyzed enantioselective hydrosilylation of methyl ketones. The enantioselective direct aldol reaction, organocatalyzed by recoverable BINAM- prolinamide derivatives can be highly accelerated by a catalytic amount of a carboxylic acid without a detrimental of the obtained enantioselectivities.

Technology Process of [1,1'-Binaphthalene]-2,2'-diamine

There total 49 articles about [1,1'-Binaphthalene]-2,2'-diamine 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: 92.0%

naphthalen-2-ylamine (91-59-8) → 1,1'-binaphthalene-2,2'-diamine (4488-22-6,18531-95-8)

Guidance literature:

With iron(III) chloride hexahydrate; at 100 ℃; for 72h; Ionic liquid;

Reference yield: 90.0%

1,1'-bi-2-naphthol (602-09-5) → 1,1'-binaphthalene-2,2'-diamine (4488-22-6,18531-95-8)

Guidance literature:

With ammonia; sodium hydrogencarbonate; In water; at 150 ℃; Large scale;

Reference yield: 80.1%

1,2-di(naphthalen-2-yl)hydrazine (613-64-9) → 7H-dibenzo[c,g]carbazole (194-59-2) + 1,1'-binaphthalene-2,2'-diamine (4488-22-6,18531-95-8) + 2,2'-azonaphthalene (582-08-1)

Guidance literature:

With lithium perchlorate; perchloric acid; In 1,4-dioxane; water; at 0 ℃; for 24h;

DOI:10.1021/ja00297a030

upstream raw materials:

2-nitronaphthalene

2,2'-dinitro-[1,1']binaphthyl

naphthalen-2-ylamine

β-naphthol

Downstream raw materials:

4,5-diphenyl-dinaphtho[2,1-e;1',2'-g][1,4]diazocine

2,2′-bis-(isothiocyanato)binaphthyl

Refernces

• 1、 -. "AROMATIC COMPOUNDS AND ORGANIC ELECTRONIC DEVICE USING THE SAME". Paragraph 0384; 0389; 0390. . Retrieved 2017/01/09.
• 2、 Takeda, Youhei,Okazaki, Masato,Minakata, Satoshi. "Oxidative skeletal rearrangement of 1,1′-binaphthalene-2,2′- diamines (BINAMs) via C-C bond cleavage and nitrogen migration: A versatile synthesis of U-shaped azaacenes". supporting information. p. 10291 - 10294. Retrieved 2014/08/18.