1,1'-Bi-2-naphthol

Base Information

• Chemical Name: 1,1'-Bi-2-naphthol
• CAS No.: 602-09-5
• Deprecated CAS: 41024-90-2
• Molecular Formula: C20H14O2
• Molecular Weight: 286.33
• Hs Code.: 29072900
• European Community (EC) Number: 606-050-5,210-014-0,606-048-4
• NSC Number: 27049
• UNII: M6IDZ128WT,54OT5RRV4C,25AB254328
• DSSTox Substance ID: DTXSID9060526
• Nikkaji Number: J1.031.260D,J1.031.261B,J1.055.781J,J1.055.782H,J134.638E,J166.096I,J54.937A
• Wikipedia: 1,1%E2%80%B2-Bi-2-naphthol
• Wikidata: Q161292,Q72443503,Q72443501
• ChEMBL ID: CHEMBL138718
• Mol file: 602-09-5.mol

Synonyms:1,1'-bi-2-naphthol

Chemical Property of 1,1'-Bi-2-naphthol

Chemical Property:

• Appearance/Colour: white to beige powder
• Melting Point: 215-218 °C
• Refractive Index: 1.7580 (estimate)
• Boiling Point: 462.104 °C at 760 mmHg
• PKA: 8.29±0.50(Predicted)
• Flash Point: 218.932 °C
• PSA: 40.46000
• Density: 1.303 g/cm³
• LogP: 5.07120
• Storage Temp.: 2-8°C
• Solubility.: dioxane: 50 mg/mL, clear
• Water Solubility.: insoluble
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 286.099379685
• Heavy Atom Count: 22
• Complexity: 346

Purity/Quality:

99% ^*data from raw suppliers

1,1'-Bi-2-naphthol >99.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, Xi
• Hazard Codes: T,Xi
• Statements: 25-36-36/37/38
• Safety Statements: 26-45-37/39-36

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)O)O
• Uses: 1,1'-Bi-2-naphthol is used as a chiral ligand in alkynylation, Diels-Alder and assymmetric Michael addition reactions. (+/-)-1,1'-Bi(2-naphthol) acts as chiral separation agents. It is widely used in chiral liquid crystal,medicines,spices etc,. Chiral ligand and auxiliary for asymmetric Michael addition reaction; enantioselective Diels-Alder reaction; alkynylation.

Technology Process of 1,1'-Bi-2-naphthol

There total 189 articles about 1,1'-Bi-2-naphthol 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: 98.0%

β-naphthol (135-19-3) + 1-diazo-2(1H)naphthalenone (773-90-0,860253-14-1) → 1,1'-bi-2-naphthol (602-09-5)

Guidance literature:

With palladium diacetate; In dichloromethane; at 20 ℃; for 36h; enantioselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1007/s11426-021-1003-9

Reference yield: 95.0%

(+)-1,1'-binaphthyl-2,2'-diyl N-<(S)-α-methylbenzyl>thiophosphoroamidate → 1,1'-bi-2-naphthol (602-09-5)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1021/jo00059a025

Reference yield: 84.0%

2,2'-dimethoxy-1,1'-binaphthyl (75685-01-7) → 1,1'-bi-2-naphthol (602-09-5)

Guidance literature:

With potassium tert-butylate; diphenylphosphane; In N,N-dimethyl-formamide; at 80 ℃; for 12h; Sealed tube;

DOI:10.1039/d1ob01286j

upstream raw materials:

1-bromo-2-naphthol

1,1'-thiobis(2-naphthol)

bis-(2-hydroxy-1-naphthyl)disulphide

sodium methylate

Downstream raw materials:

perixanthenoxanthene

2,2'-diacetoxy-1,1'-binaphthyl

9-phenyldibenzocarbazole

N-methyl-7H-dibenzo[c,g]carbazole

Refernces

• 1、 Hu,Vitharana,Pu. "An efficient and practical direct resolution of racemic 1,1'-bi-2-naphthol to both of its pure enantiomers". . p. 2123 - 2126. Retrieved 1995.
• 2、 Sridhar, Madabhushi,Vadivel, Subramanian K.,Bhalerao, Uday T.. "Novel horseradish peroxidase catalysed enantioselective oxidation of 2-naphthols to 1,1'-binaphthyl-2,2'-diols". . p. 5695 - 5696. Retrieved 1997.
• 3、 Shaikh, Melad,Sahu, Aanchal,Kiran Kumar,Sahu, Mahendra,Singh, Sunil. K.,Ranganath, Kalluri V. S.. "Metal-free carbon as a catalyst for oxidative coupling: Solvent-enhanced poly-coupling with regioselectivity". . p. 4533 - 4537. Retrieved 2017.
• 4、 Noshiranzadeh, Nader,Bikas, Rahman,Emami, Marzieh,Siczek, Milosz,Lis, Tadeusz. "Oxidative coupling of 2-naphthol catalyzed by a new methoxido bridged dinuclear oxidovanadium(V) complex". . p. 167 - 172. Retrieved 2016.
• 5、 Nakamura,Y. et al.. "-". . p. 1949 - 1977. Retrieved 1975.
• 6、 Meca, Ludek,Reha, David,Havlas, Zdenek. "Racemization barriers of 1,1′-binaphthyl and 1,1′-binaphthalene-2,2′-diol: A DFT study". . p. 5677 - 5680. Retrieved 2003.
• 7、 Zhang, Zhaoming,Wang, Yue,Nakano, Tamaki. "Photo racemization and polymerization of (R)-1,1′-Bi(2-naphthol)". . . Retrieved 2016.
• 8、 Guo, Jing,Xu, Yao-Wei,Li, Kang,Xiao, Li-Min,Chen, Sha,Wu, Kai,Chen, Xu-Dong,Fan, Yan-Zhong,Liu, Jun-Min,Su, Cheng-Yong. "Regio- and Enantioselective Photodimerization within the Confined Space of a Homochiral Ruthenium/Palladium Heterometallic Coordination Cage". . p. 3852 - 3856. Retrieved 2017.
• 9、 Koltunov, Konstantin Yu.,Chernov, Aleksey N.,Ostashevskaya, Ludmila A.,Gribov, Pavel A.. "Electrophilic dimerization of naphthols in the presence of aluminum halides". . p. 122 - 124. Retrieved 2014.
• 10、 Das, Sameeran Kr.,Mahanta, Sanjeev P.,Bania, Kusum K.. "Oxidative coupling of 2-naphthol by zeolite-Y supported homo and heterometallic trinuclear acetate clusters". . p. 51496 - 51509. Retrieved 2014.