(R)-1,1'-bi-2-Naphthol dibenzoate

Base Information

• Chemical Name: (R)-1,1'-bi-2-Naphthol dibenzoate
• CAS No.: 291772-40-2
• Molecular Formula: C₃₄H₂₂O₄
• Molecular Weight: 494.546
• DSSTox Substance ID: DTXSID50366224
• Nikkaji Number: J2.228.065A
• Wikidata: Q82151355
• Mol file: 291772-40-2.mol

Synonyms:291772-40-2;(R)-1,1'-bi-2-Naphthol dibenzoate;1,1'-binaphthyl-2,2'-diyl dibenzoate;[1,1'-Binaphthalene]-2,2'-diyl dibenzoate;(S)-[1,1'-Binaphthalene]-2,2'-diyl dibenzoate;Oprea1_174608;SCHEMBL16236952;DTXSID50366224;AKOS015918477;FT-0644358;(S)-[1,1'-Binaphthalene]-2,2'-diyldibenzoate;Bisbenzoic acid 1,1'-binaphthalene-2,2'-diyl ester;2'-(BENZOYLOXY)-[1,1'-BINAPHTHALEN]-2-YL BENZOATE;53545-44-1

Chemical Property of (R)-1,1'-bi-2-Naphthol dibenzoate

Chemical Property:

• Melting Point: 163-166 °C
• Boiling Point: 729.2°Cat760mmHg
• Flash Point: 380.6°C
• PSA: 52.60000
• Density: 1.268g/cm³
• LogP: 8.09840
• XLogP3: 8.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 494.15180918
• Heavy Atom Count: 38
• Complexity: 730

Purity/Quality:

98%min ^*data from raw suppliers

(R)-1,1'-BI-2-NAPHTHOL DIBENZOATE 95.00% ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)OC2=C(C3=CC=CC=C3C=C2)C4=C(C=CC5=CC=CC=C54)OC(=O)C6=CC=CC=C6

Technology Process of (R)-1,1'-bi-2-Naphthol dibenzoate

There total 7 articles about (R)-1,1'-bi-2-Naphthol dibenzoate 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%

benzoic acid (65-85-0,8013-63-6) + 1,1'-bi-2-naphthol (602-09-5) → (±)-1,1′-binaphthyl-2-2′-diyl dibenzoate (53545-44-1,291772-40-2)

Guidance literature:

With phosphoric acid; trifluoroacetic anhydride; In water; at 20 ℃; for 0.25h;

DOI:10.1080/00397911.2013.774017

Reference yield: 98.0%

benzoic acid anhydride (93-97-0) + 1,1'-bi-2-naphthol (602-09-5) → (±)-1,1′-binaphthyl-2-2′-diyl dibenzoate (53545-44-1,291772-40-2)

Guidance literature:

With bismuth(lll) trifluoromethanesulfonate; In dichloromethane; water; at 25 ℃; for 1h;

DOI:10.1021/jo0107453

Reference yield: 95.0%

N-benzyl-N-(tert-butoxycarbonyl)-benzamide (85909-02-0) + 1,1'-bi-2-naphthol (602-09-5) → (±)-1,1′-binaphthyl-2-2′-diyl dibenzoate (53545-44-1,291772-40-2)

Guidance literature:

With sodium t-butanolate; In toluene; at 150 ℃; for 36h; Sealed tube;

DOI:10.1007/s11426-020-9883-3

upstream raw materials:

benzoyl chloride

1,1'-bi-2-naphthol

benzoic acid anhydride

benzoic acid

Refernces

• 1、 Qu, Shen,Greenhalgh, Mark D.,Smith, Andrew D.. "Isothiourea-Catalysed Regioselective Acylative Kinetic Resolution of Axially Chiral Biaryl Diols". supporting information. p. 2816 - 2823. Retrieved 2019/02/05.
• 2、 Costantino, Andrea R.,Ocampo, Romina A.,Schneider, Maria G. Montiel,Fernandez, Gustavo,Koll, Liliana C.,Mandolesi, Sandra D.. "Efficient routes to racemic and enantiomerically pure (s)-binol diesters". supporting information. p. 3192 - 3202. Retrieved 2014/01/06.