(S,S)-(-)-1-(1-Naphthyl)-2-(2-naphthyl)-1,2-ethanediol

Base Information

• Chemical Name: (S,S)-(-)-1-(1-Naphthyl)-2-(2-naphthyl)-1,2-ethanediol
• CAS No.: 229185-00-6
• Molecular Formula: C₂₂H₁₈O₂
• Molecular Weight: 314.384
• DSSTox Substance ID: DTXSID60569729
• Wikidata: Q82456939
• Mol file: 229185-00-6.mol

Synonyms:229185-00-6;(S,S)-(-)-1-(1-Naphthyl)-2-(2-naphthyl)-1,2-ethanediol;(1S,2S)-1-(Naphthalen-1-yl)-2-(naphthalen-2-yl)ethane-1,2-diol;(s s)-(-)-1-(1-Naphthyl)-2-(2-naphthyl)&;DTXSID60569729;(1S,2S)-1-naphthalen-1-yl-2-naphthalen-2-ylethane-1,2-diol;AKOS015913255;J-014902

Chemical Property of (S,S)-(-)-1-(1-Naphthyl)-2-(2-naphthyl)-1,2-ethanediol

Chemical Property:

• Vapor Pressure: 6.47E-13mmHg at 25°C
• Melting Point: 100-105 °C(lit.)
• Refractive Index: 1.731
• Boiling Point: 549.7°Cat760mmHg
• Flash Point: 258.5°C
• PSA: 40.46000
• Density: 1.269g/cm³
• LogP: 4.76000
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 314.130679813
• Heavy Atom Count: 24
• Complexity: 409

Purity/Quality:

98% ^*data from raw suppliers

(S,S)-(-)-1-(1-NAPHTHYL)-2-(2-NAPHTHYL)-1,2-ETHANEDIOL 95.00% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C=C(C=CC2=C1)C(C(C3=CC=CC4=CC=CC=C43)O)O
• Isomeric SMILES: C1=CC=C2C=C(C=CC2=C1)[C@@H]([C@H](C3=CC=CC4=CC=CC=C43)O)O

Technology Process of (S,S)-(-)-1-(1-Naphthyl)-2-(2-naphthyl)-1,2-ethanediol

There total 8 articles about (S,S)-(-)-1-(1-Naphthyl)-2-(2-naphthyl)-1,2-ethanediol 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:

trans-1-(1-naphthyl)-2-(2-naphthyl)ethylene (2633-11-6) → (S,S)-(-)-1-(1-Naphthyl)-2-(2-naphthyl)ethane-1,2-diol (229185-00-6) + (R,R)-(+)-1-(1-Naphthyl)-2-(2-naphthyl)ethane-1,2-diol (229185-00-6)

Guidance literature:

With osmium(VIII) oxide; dihydroquinidine 9-O-(4-chlorobenzoate); 4-methylmorpholine N-oxide; In water; acetone; acetonitrile; at 0 ℃; for 27h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00103a035

Reference yield:

trans-1-(1-naphthyl)-2-(2-naphthyl)ethylene (2633-11-6) → (S,S)-(-)-1-(1-Naphthyl)-2-(2-naphthyl)ethane-1,2-diol (229185-00-6) + (R,R)-(+)-1-(1-Naphthyl)-2-(2-naphthyl)ethane-1,2-diol (229185-00-6)

Guidance literature:

With osmium(VIII) oxide; dihydroquinidine 9-O-(4-chlorobenzoate); 4-methylmorpholine N-oxide; In water; acetone; acetonitrile; at 0 ℃; for 27h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00103a035

Reference yield:

1-(1-Naphthyl)-2-(2-naphthyl)ethylene (10243-52-4) → (S,S)-(-)-1-(1-Naphthyl)-2-(2-naphthyl)ethane-1,2-diol (229185-00-6)

Guidance literature:

Multi-step reaction with 2 steps

1: I₂ / o-xylene / 24 h / Heating

2: OsO₄, N-methylmorpholine N-oxide, dihydroquinidine 9-O-(4-chlorobenzoate) / acetone; acetonitrile; H₂O / 27 h / 0 °C

With osmium(VIII) oxide; dihydroquinidine 9-O-(4-chlorobenzoate); iodine; 4-methylmorpholine N-oxide; In o-xylene; water; acetone; acetonitrile;

DOI:10.1021/jo00103a035

upstream raw materials:

trans-1-(1-naphthyl)-2-(2-naphthyl)ethylene

1-(1-Naphthyl)-2-(2-naphthyl)ethylene

1-naphthylmethyltriphenylphosphonium chloride

1-Chloromethylnaphthalene

Refernces