1,1'-BIS(2-HYDROXY-3-NAPHTHOIC ACID)

Base Information

• Chemical Name: 1,1'-BIS(2-HYDROXY-3-NAPHTHOIC ACID)
• CAS No.: 47568-49-0
• Molecular Formula: C₂₂H₁₄O₆
• Molecular Weight: 374.35
• Mol file: 47568-49-0.mol

Synonyms:(?à)-2,2'-Dihydroxy-1,1'-binaphthyl-3,3'-dicarboxylicacid; 1,1'-Bis(2-hydroxy-3-naphthalenecarboxylic acid);2,2'-Dihydroxy-1,1'-binaphthalene-3,3'-dicarboxylic acid;2,2'-Dihydroxy-1,1'-binaphthyl-3,3'-dicarboxylic acid; NC 060

Chemical Property of 1,1'-BIS(2-HYDROXY-3-NAPHTHOIC ACID)

Chemical Property:

• Melting Point: 331-333 °C
• Boiling Point: 570.0±50.0 °C(Predicted)
• PKA: 2.42±0.30(Predicted)
• PSA: 115.06000
• Density: 1.528±0.06 g/cm3(Predicted)
• LogP: 4.46760

Purity/Quality:

≥99% ^*data from raw suppliers

[1,1''-Binaphthalene]-3,3''-dicarboxylicacid,2,2''-dihydroxy- 96% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,1'-BIS(2-HYDROXY-3-NAPHTHOIC ACID)

There total 31 articles about 1,1'-BIS(2-HYDROXY-3-NAPHTHOIC ACID) 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%

(S)-2,2'-dihydroxy-1,1'-binaphthyl-3-carboxylic acid (S)(-)-1-phenethylamine → (S)-2,2'-dihydroxy-[1,1'-binaphthalene]-3,3'-dicarboxylic acid (18531-92-5,42167-04-4,47568-49-0,65390-98-9)

Guidance literature:

With hydrogenchloride; In tert-butyl methyl ether; water; at 20 ℃; for 1h;

Reference yield: 90.0%

3-Hydroxy-2-naphthoic acid (92-70-6) → 2,2'-dihydroxy-1,1'-binaphthalene-3,3'-dicarboxylic acid (18531-92-5,42167-04-4,47568-49-0,65390-98-9)

Guidance literature:

With iron(III) chloride; at 60 ℃; for 25h;

DOI:10.1135/cccc19970925

Reference yield: 89.0%

dimethyl 2,2'-dihydroxy-1,1'-binaphthalene-3,3'-dicarboxylate (47644-69-9,69678-00-8,18531-91-4) → 2,2'-dihydroxy-1,1'-binaphthalene-3,3'-dicarboxylic acid (18531-92-5,42167-04-4,47568-49-0,65390-98-9)

Guidance literature:

With potassium hydroxide; In methanol; for 12h; Reflux;

DOI:10.1016/j.tetasy.2015.09.002

upstream raw materials:

3-Hydroxy-2-naphthoic acid

dimethyl 2,2'-dimethoxy-1,1'-naphthalene-3,3'-dicarboxylate

nitrobenzene

ethanol

Downstream raw materials:

(S)-2,2'-dihydroxy-[1,1'-binaphthalene]-3,3'-dicarboxylic acid

(S)-3,3′-bis[hydroxy(diphenyl)methyl]-1,1′-binaphthalene-2,2′-diol

C₃₆H₂₈N₂O₄

Refernces

• 1、 Someshwar, Nagamalla,Ramanathan, Chinnasamy Ramaraj. "Resolution of (±)-2,2′-dihydroxy-1,1′-binaphthyl-3,3′-dicarboxylic acid using (1R,2R)-trans-cyclohexane-1,2-diamine". . p. 1209 - 1213. Retrieved 2015/10/28.
• 2、 -. "SYNTHETIC METHOD OF ENANTIOMERICALLY PURE 2,2'-DIHYDROXY-1,1'-BINAPHTHYL-3-CARBOXYLIC ACID". Page/Page column 6-7. . Retrieved 2012/06/15.