(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
• General Description: (+)-(18-CROWN-6)-2,3,11,12-TETRACARBOXYLIC ACID is a chiral macrocyclic polyether ligand with four carboxylic acid groups positioned at the 2, 3, 11, and 12 positions of the crown ether ring. It forms stable complexes with cations such as H₃O⁺, where the oxonium ion is centrally anchored within the cavity via hydrogen bonds to the crown ether oxygen atoms. The carboxylic acid groups extend outward from the macrocycle, contributing to interactions with counterions. This ligand exhibits a pseudoplanar conformation in its complexes, and its structural features make it suitable for selective ion recognition and binding applications.

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

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