(2R,3R,11R,12R)-1,4,7,10,13,16-Hexaoxacyclooctadecane-2,3,11,12-tetracarboxylic acid

Base Information

• Chemical Name: (2R,3R,11R,12R)-1,4,7,10,13,16-Hexaoxacyclooctadecane-2,3,11,12-tetracarboxylic acid
• CAS No.: 61696-54-6
• Molecular Formula: C16H24O14
• Molecular Weight: 440.35
• Hs Code.: 2932990090
• European Community (EC) Number: 636-402-3
• DSSTox Substance ID: DTXSID60152559
• Nikkaji Number: J524.153G
• Wikidata: Q83019215
• ChEMBL ID: CHEMBL2375078
• Mol file: 61696-54-6.mol

Synonyms:(18-crown-6)-2,3,11,12-tetracarboxylic acid;18-crown-6 2,3,11,12-tetracarboxylic acid;18-crown-6 2,3,11,12-tetracarboxylic acid, (2R-(2R*,3R*,11r*,12R*))-isomer;18-crown-6 4COOH;18-crown-6 tetracarboxylic acid;18C6H4

Chemical Property of (2R,3R,11R,12R)-1,4,7,10,13,16-Hexaoxacyclooctadecane-2,3,11,12-tetracarboxylic acid

Chemical Property:

• Vapor Pressure: 5.06E-28mmHg at 25°C
• Melting Point: 210-212 °C(lit.)
• Refractive Index: 1.48
• Boiling Point: 798.9 °C at 760 mmHg
• PKA: 1.95±0.70(Predicted)
• Flash Point: 283.6 °C
• PSA: 204.58000
• Density: 1.399g/cm³
• LogP: -2.08760
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: -2.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 4
• Exact Mass: 440.11660544
• Heavy Atom Count: 30
• Complexity: 480

Purity/Quality:

98%,99%, ^*data from raw suppliers

(+)-(18-Crown-6)-2,3,11,12-tetracarboxylic acid ^*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: C1COC(C(OCCOCCOC(C(OCCO1)C(=O)O)C(=O)O)C(=O)O)C(=O)O
• Isomeric SMILES: C1CO[C@H]([C@@H](OCCOCCO[C@H]([C@@H](OCCO1)C(=O)O)C(=O)O)C(=O)O)C(=O)O
• Uses: Derived tetracarboxylic acid chloride of this crown ether reacts with meta- and para-xylylene diamines to form chiral captands in high yields. Used as a chiral selector in capillary zone electrophoresis for the separation of a variety of optically active amines. Synthesis of monoamides. (+)-(18-CROWN-6)-2,3,11,12-TETRACARBOXYLIC ACID is a calcium and barium chelator. A useful chiral NMR discriminating agent for underivatized amino acids

Technology Process of (2R,3R,11R,12R)-1,4,7,10,13,16-Hexaoxacyclooctadecane-2,3,11,12-tetracarboxylic acid

There total 4 articles about (2R,3R,11R,12R)-1,4,7,10,13,16-Hexaoxacyclooctadecane-2,3,11,12-tetracarboxylic 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: 95.0%

(2R,3R,11R,12R)-(+)-(N,N,N',N',N,N,N',N'-octamethyl-1,4,7,10,13,16-hexaoxacyclooctadecane-2,3,11,12-tetracarboxamide) (57207-22-4) → (2R,3R,11R,12R)-(+)-18-crown-6-2,3,11,12-tetracarbonic acid (61696-54-6)

Guidance literature:

With hydrogenchloride; at 80 ℃; for 24h;

DOI:10.1002/hlca.19800630736

Reference yield:

L-Tartaric acid (87-69-4,138508-61-9) → (2R,3R,11R,12R)-(+)-18-crown-6-2,3,11,12-tetracarbonic acid (61696-54-6)

Guidance literature:

DOI:10.1021/ja00381a007

Reference yield:

dianhydride [18]-crown-6-R,R-tartaric acid (76777-45-2) + benzylamine (100-46-9) → (2R,3R,11R,12R)-(+)-18-crown-6-2,3,11,12-tetracarbonic acid (61696-54-6) + N-benzyl-2-carbamoyl-(2R,3R,11R,12R)-1,4,7,10,13,16-hexaoxacyclooctadecane-3,11,12-tricarboxylic acid + (2R,3R,11R,12R)-3,11-Bis-benzylcarbamoyl-1,4,7,10,13,16-hexaoxa-cyclooctadecane-2,12-dicarboxylic acid + (2R,3R,11R)-3,12-Bis-benzylcarbamoyl-1,4,7,10,13,16-hexaoxa-cyclooctadecane-2,11-dicarboxylic acid

Guidance literature:

With water; triethylamine; Yield given. Multistep reaction. Yields of byproduct given; 1) THF, rt, 2 d; 2) THF, rt, 2 h;

DOI:10.1021/jo970707c

upstream raw materials:

(2R,3R,11R,12R)-(+)-(N,N,N',N',N,N,N',N'-octamethyl-1,4,7,10,13,16-hexaoxacyclooctadecane-2,3,11,12-tetracarboxamide)

L-Tartaric acid

dianhydride [18]-crown-6-R,R-tartaric acid

benzylamine

Refernces

• 1、 Behr, Jean-Paul,Dumas, Philippe,Moras, Dino. "The H3O+ Cation: Molecular Structure of an Oxonium-Macrocycle Polyether Complex". . p. 4540 - 4543. Retrieved 1982.
• 2、 Behr, Jean-Paul,Girodeau, Jean-Marc,Hayward, Rodney C.,Lehn, Jean-Marie,Sauvage, Jean-Pierre. "Molecular Receptors. Functionalized and Chiral Macrocyclic Polyethers Derived from Tartaric Acid". . p. 2096 - 2111. Retrieved 2007/10/02.