1-(2-Aminonaphthalen-1-yl)naphthalen-2-ol

Base Information

• Chemical Name: 1-(2-Aminonaphthalen-1-yl)naphthalen-2-ol
• CAS No.: 137848-28-3
• Molecular Formula: C20H15NO
• Molecular Weight: 285.345
• Hs Code.: 29222990
• European Community (EC) Number: 633-701-0,635-060-2
• UNII: 3Y5S695XXC
• DSSTox Substance ID: DTXSID30929912
• Nikkaji Number: J1.136.269I,J1.136.270B,J461.875K
• Wikipedia: NOBIN
• Wikidata: Q6954850
• Mol file: 137848-28-3.mol

Synonyms:137848-28-3;137848-29-4;(R)-NOBIN;(S)-NOBIN;(S)-2'-Amino-[1,1'-binaphthalen]-2-ol;134532-03-9;(S)-(-)-NOBIN;(R)-2-Amino-2'-hydroxy-1,1'-binaphthyl;NOBIN;(R)-(+)-NOBIN;1-(2-aminonaphthalen-1-yl)naphthalen-2-ol;(R)-(+)-2-Amino-2'-hydroxy-1,1'-binaphthyl;(R)-2'-amino-[1,1'-binaphthalen]-2-ol;2'-Amino-1,1'-binaphthalen-2-ol;2'-Amino-[1,1'-binaphthalen]-2-ol;2'-Amino[1,1'-binaphthalen]-2-ol;(S)-2'-Amino-1,1'-binaphthalen-2-ol;(S)-2/'-Amino-1,1/'-binaphthalen-2-ol;(R)-(+)-2'-Amino-1,1'-binaphthalen-2-ol;(R)-(+)-1-(2-Amino-1-naphthyl)-2-naphthol;(S)-(-)-1-(2-Amino-1-naphthyl)-2-naphthol;2-AMINO-2/'-HYDROXY-1 1/'-BINAPHTHALENE;(S)-(-)-2'-Amino-1,1'-binaphthalen-2-ol;2-AMINO-2'-HYDROXY-1 1'-BINAPHTHALENE;(S)-(-)-2-Amino-2'-hydroxy-1,1'-binaphthyl;2-Amino-2'-hydroxy-1,1'-binaphthyl;3Y5S695XXC;SCHEMBL2068058;DTXSID30929912;HIXQCPGXQVQHJP-UHFFFAOYSA-N;2-Amino[1,1-binaphthalen]-2-ol;2-Amino-2-hydroxy-1,1-binaphthyl;AC-986;MFCD01882346;AKOS005145751;AKOS015920332;AKOS015920468;AC-1624;CS-W012228;SB82217;[1,1-Binaphthalen]-2-ol, 2-amino-;(R)-2'-amino-1,1'-binaphthyl-2-ol;(S)-2'-amino-1,1'-binaphthyl-2-ol;2-Amino-2'-hydroxy-1,1'-binaphthalene;BS-15318;[1,1'-Binaphthalen]-2-ol, 2'-amino-;(aR)-2'-Amino-1,1'-binaphthalene-2-ol;(aS)-2'-Amino-1,1'-binaphthalene-2-ol;(+/-)-2-Amino-[1,1-binaphthalen]-2-ol;FT-0600413;FT-0649596;R-(+)-2-Amino-2'-hydroxy-1,1'-binaphtyl;S-(-)-2-Amino-2'-hydroxy-1,1'-binaphtyl;E87854;F11541;F11546;(R)-(+)-2-Amino-2'-Hydoxy-1,1'-Binaphthol;A807312;[1,1'-Binaphthalen]-2-ol, 2'-amino-, (1R)-;J-007066;J-007067;Q6954850;(R)-(+)-2'-Amino-1,1'-binaphthalen-2-ol, 97%;(S)-(-)-2'-Amino-1,1'-binaphthalen-2-ol, 97%;(S)-2-Amino-2'-hydroxy-1,1'-binaphthyl

Chemical Property of 1-(2-Aminonaphthalen-1-yl)naphthalen-2-ol

Chemical Property:

• Melting Point: 239 ºC
• Boiling Point: 471.5 ºC at 760 mmHg
• PKA: 8.90±0.50(Predicted)
• PSA: 46.25000
• Density: 1.275 g/cm³
• LogP: 5.52900
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 285.115364102
• Heavy Atom Count: 22
• Complexity: 384

Purity/Quality:

97% ^*data from raw suppliers

(R)-(+)-2-Amino-2''-hydroxy-1,1''-binaphthyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,N
• Hazard Codes: Xi,N
• Statements: 41-50/53
• Safety Statements: 26-39-60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC(=C2C3=C(C=CC4=CC=CC=C43)O)N
• General Description: (R)-NOBIN, also known as (R)-2-amino-2'-hydroxy-1,1'-binaphthyl, is an axially chiral 1,1'-binaphthyl derivative widely used as a chiral building block in asymmetric synthesis. It can be synthesized through various methods, including transition-metal-free O-arylation of arylhydroxylamines, Cu(II)-mediated cross-coupling of 2-aminonaphthalene and 2-naphthol, and stereoselective oxidative cross-coupling with a chiral auxiliary. Additionally, enantiomerically pure (R)-NOBIN can be obtained via resolution of racemic mixtures or direct conversion from (R)-BINAM without racemization. Its structural versatility allows for further functionalization, making it valuable in catalytic asymmetric reactions and the preparation of chiral ligands.

Technology Process of 1-(2-Aminonaphthalen-1-yl)naphthalen-2-ol

There total 55 articles about 1-(2-Aminonaphthalen-1-yl)naphthalen-2-ol 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: 93.0%

C28H23NO → (R)-2-amino-2'-hydroxy-1,1'-binaphthyl (137848-28-3)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; at 20 ℃; under 760.051 Torr;

DOI:10.1021/acs.orglett.8b00800

Reference yield: 91.0%

1,1'-bi-2-naphthol (602-09-5) → 2-amino-2’-hydroxy-1,1’-binaphthyl (134532-03-9,137848-28-3,137848-29-4)

Guidance literature:

With ammonium hydroxide; ammonium bisulfite; at 200 ℃; for 120h;

DOI:10.1016/S0040-4039(02)01674-X

Reference yield: 85.0%

1,1'-bi-2-naphthol (602-09-5) → 7H-dibenzo[c,g]carbazole (194-59-2) + 2-amino-2’-hydroxy-1,1’-binaphthyl (134532-03-9,137848-28-3,137848-29-4)

Guidance literature:

With ammonium hydroxide; ammonium sulfite monohydrate; at 200 ℃; for 5h; Temperature; Reagent/catalyst; Autoclave;

upstream raw materials:

naphthalen-2-ylamine

β-naphthol

2-amino-2’-hydroxy-1,1’-binaphthyl

(R)-1,1'-Bi-2-naphthol

Downstream raw materials:

(S)-(-)-2'-amino-[1,1'-binaphthalene]-2-ol

7H-dibenzo[c,g]carbazole