S-1,1'-BINAPHTHYL-2,2'-DICARBOXYLIC ACID

Base Information

• Chemical Name: S-1,1'-BINAPHTHYL-2,2'-DICARBOXYLIC ACID
• CAS No.: 18531-96-9
• Molecular Formula: C22H14O4
• Molecular Weight: 342.351
• Hs Code.: 2917399090
• Mol file: 18531-96-9.mol

Synonyms:[1,1'-Binaphthalene]-2,2'-dicarboxylicacid, (S)-(-)- (8CI);(-)-1,1'-Binaphthyl-2,2'-dicarboxylic acid;(S)-(-)-Binaphthyl-2,2'-dicarboxylicacid;(S)-1,1'-Binaphthyl-2,2'-dicarboxylic acid;2,2'-Dicarboxylic acid, 1,1'-binaphthyl-;1-(2-Carboxynaphth-1-yl)-2-naphthoic acid;1-(2-Carboxynaphthyl)naphthalene-2-carboxylic acid;

Chemical Property of S-1,1'-BINAPHTHYL-2,2'-DICARBOXYLIC ACID

Chemical Property:

• Boiling Point: 493.3 °C at 760 mmHg
• PKA: 3.66±0.30(Predicted)
• Flash Point: 266.2 °C
• PSA: 74.60000
• Density: 1.38 g/cm³
• LogP: 5.05640

Purity/Quality:

99% ^*data from raw suppliers

1-(2-carboxynaphthalen-1-yl)naphthalene-2-carboxylicacid 95%+ ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (S)-1,1''-Binaphthyl-2,2''-Dicarboxylic Acid is an intermediate used to prepare optically active 1,1''-binaphthyl quaternary ammonium salts as chiral phase-transfer catalysts.

Technology Process of S-1,1'-BINAPHTHYL-2,2'-DICARBOXYLIC ACID

There total 110 articles about S-1,1'-BINAPHTHYL-2,2'-DICARBOXYLIC 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: 100.0%

carbon dioxide (124-38-9,18923-20-1) + 2,2'-dibromo-1,1'-binaphthyl (74866-28-7,86688-08-6,150024-49-0) → 1,1'-binaphthyl-2,2'-dicarboxylic acid (18531-96-9,80703-23-7,99827-46-0)

Guidance literature:

2,2'-dibromo-1,1'-binaphthyl; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 ℃; for 1h;

carbon dioxide; In tetrahydrofuran; pentane; at -78 - 20 ℃; for 12.05h;

Reference yield: 91.0%

[1,1′-binaphthalene]-2,2′-dicarboxaldehyde (161146-88-9) → 1,1'-binaphthyl-2,2'-dicarboxylic acid (18531-96-9,80703-23-7,99827-46-0)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; dihydrogen peroxide; In acetonitrile; at 50 ℃; for 0.75h;

DOI:10.1021/ja066462f

Reference yield: 90.0%

[1,1']binaphthyl-2,2'-dicarboxylic acid dimethyl ester (85464-88-6,113567-15-0,113567-21-8) → 1,1'-binaphthyl-2,2'-dicarboxylic acid (18531-96-9,80703-23-7,99827-46-0)

Guidance literature:

With potassium hydroxide; In methanol; for 14h; Heating;

DOI:10.1021/ja00050a011

upstream raw materials:

1,1'-binaphthalene-2,2'-diamine

[1,1']binaphthyl-2,2'-dicarboxylic acid dimethyl ester

Methyl 1-chloro-2-naphthoate

2,2'-bis[2-(4,4-dimethyl-Δ²-oxazolinyl)]-1,1'-binaphthyl

Downstream raw materials:

anthanthrone

(R)-1,1'-binaphthyl-2,2'-dicarboxylic acid

3,3'-diphenyl-[1,1'-binaphthalene]-2,2'-dicarboxylic acid

Refernces

• 1、 Kanoh, Shigeyoshi,Hongoh, Yukihiko,Motoi, Masatoshi,Suda, Hiroshi. "Convenient Optical Resolution of Axially Chiral 1,1'-Binaphthyl-2,2'-dicarboxylic Acid". . p. 1032 - 1034. Retrieved 1988.
• 2、 Konishi, Hideyuki,Hoshino, Fumika,Manabe, Kei. "Practical synthesis of axially chiral dicarboxylates via Pd-catalyzed external-CO-free carbonylation". . p. 1438 - 1441. Retrieved 2016.
• 3、 Hoshi, Takashi,Nozawa, Eiji,Katano, Masayoshi,Suzuki, Toshio,Hagiwara, Hisahiro. "Practical synthetic protocols of enantiopure 1,1′-binaphthyl-2, 2′-dicarboxylic acid and 2,2′-dicyano-1,1′-binaphthyl starting from optically active dibromide precursor". . p. 3485 - 3487. Retrieved 2004.
• 4、 Itoh, Toshiyuki,Chika, Jun-ichi. "New Method of Kinetic Resolution of Axially Chiral Biaryl Compounds Using a Sugar Template". . p. 4968 - 4969. Retrieved 1995.
• 5、 Di Bari, Lorenzo,Pescitelli, Gennaro,Marchetti, Fabio,Salvadori, Piero. "Anomalous CD/UV exciton splitting of a binaphthyl derivative: The case of 2,2′-diiodo-1,1′-binaphthalene". . p. 6395 - 6398. Retrieved 2000.
• 6、 Oi,Matsunaga,Hattori,Miyano. "Convenient synthesis of 1,1'-binaphthyl-2,2'-dicarboxylic acid". . p. 895 - 899. Retrieved 1993.
• 7、 Zhang, Huaiyuan,Cormanich, Rodrigo A.,Wirth, Thomas. "Chiral Ligands in Hypervalent Iodine Compounds: Synthesis and Structures of Binaphthyl-Based λ3-Iodanes". supporting information. . Retrieved 2021/12/22.
• 8、 -. "Synthesis method of axially chiral dinaphthalene ligand precursor (s)-2,2'-dinaphthyl-1,1'-dicarboxylic acid". Paragraph 0020; 0029; 0038; 0047; 0056; 0065; 0074; 0083. . Retrieved 2016/10/10.