Adamantane-1,3,5,7-tetracarboxylic acid

Base Information

• Chemical Name: Adamantane-1,3,5,7-tetracarboxylic acid
• CAS No.: 100884-80-8
• Molecular Formula: C14H16 O8
• Molecular Weight: 312.276
• DSSTox Substance ID: DTXSID80347521
• Nikkaji Number: J662.564I
• Wikidata: Q82121519
• Mol file: 100884-80-8.mol

Synonyms:Adamantane-1,3,5,7-tetracarboxylic acid;100884-80-8;1,3,5,7-Adamantanetetracarboxylic acid;Tricyclo[3.3.1.13,7]decane-1,3,5,7-tetracarboxylic acid;YSZC054;AMY262;SCHEMBL1648486;DTXSID80347521;Adamantane-1,3,5,7-tetracarboxylicacid;1,3,5,7-Adamantanetetracarboxylic acid #;CS-0110078;E84226

Chemical Property of Adamantane-1,3,5,7-tetracarboxylic acid

Chemical Property:

• Melting Point: 395 °C (decomp)(Solv: acetic acid (64-19-7))
• Boiling Point: 403.6±40.0 °C(Predicted)
• PKA: 3.29±0.70(Predicted)
• PSA: 149.20000
• Density: 1.864±0.06 g/cm3(Predicted)
• LogP: 0.65180
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 312.08451746
• Heavy Atom Count: 22
• Complexity: 460

Purity/Quality:

≥99% ^*data from raw suppliers

Adamantane-1,3,5,7-tetracarboxylicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2(CC3(CC1(CC(C2)(C3)C(=O)O)C(=O)O)C(=O)O)C(=O)O

Technology Process of Adamantane-1,3,5,7-tetracarboxylic acid

There total 11 articles about Adamantane-1,3,5,7-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: 96.0%

1,3,5,7-tetrakis(phenyl)adamantane (16004-75-4) → adamantane-1,3,5,7-tetracarboxylic acid (100884-80-8)

Guidance literature:

With ruthenium trichloride; periodic acid; In tetrachloromethane; water; acetonitrile; at 20 ℃; for 168h;

DOI:10.1002/ejoc.200701003

Reference yield: 90.0%

tetramethyl adamantane-2,6-dione-1,3,5,7-tetracarboxylate (53120-57-3) → adamantane-1,3,5,7-tetracarboxylic acid (100884-80-8)

Guidance literature:

With sodium methylate; hydrazine hydrate; In methanol; 1.) heating slowly to 200 deg C, 2.) 240-250 deg C, 8 h;

DOI:10.1021/jo00027a061

Reference yield: 90.0%

tetramethyl 2,6-dioxoadamantane-1,3,5,7-tetracarboxylate → adamantane-1,3,5,7-tetracarboxylic acid (100884-80-8)

Guidance literature:

With sodium methylate; hydrazine hydrate; In methanol; at 240 ℃; for 8h;

DOI:10.1002/anie.202016225

upstream raw materials:

tetramethyl adamantane-2,6-dione-1,3,5,7-tetracarboxylate

tetramethyl adamantane-1,3,5,7-tetracarboxylate

1-Adamantanecarboxylic acid

adamantane-1,3-dicarboxylic acid

Downstream raw materials:

1,3,5,7-tetrakis(hydroxymethyl)adamantane

1,3,5,7-tetrakis-hydroxymethyl-adamantane

1,3,5,7-tetramethyl-adamantane

1,3,5,7-Tetrabenzoyl-adamantan

Refernces

• 1、 Newkome, George R.,Nayak, Ashutosh,Behera, Rajani K.,Moorefield, Charles N.,Baker, Gregory R.. "Cascade Polymers: Synthesis and Characterization of Four-Directional Spherical Dendritic Macromolecules Based on Adamantane". . p. 358 - 362. Retrieved 1992.
• 2、 Nasr, Khaled,Pannier, Nadine,Frangioni, John V.,Maison, Wolfgang. "Rigid multivalent scaffolds based on adamantane". . p. 1056 - 1060. Retrieved 2008.
• 3、 Hetzer, Constantin,Basel, Bettina S.,Kopp, Sebastian M.,Hampel, Frank,White, Fraser J.,Clark, Timothy,Guldi, Dirk M.,Tykwinski, Rik R.. "Chromophore Multiplication To Enable Exciton Delocalization and Triplet Diffusion Following Singlet Fission in Tetrameric Pentacene". . p. 15263 - 15267. Retrieved 2019.
• 4、 Al-Enizi, Abdullah M.,Fan, Ziwen,Forrest, Katherine A.,Ma, Shengqian,Niu, Zheng,Pham, Tony,Space, Brian,Thallapally, Praveen K.,Verma, Gaurav. "Self-Adjusting Metal–Organic Framework for Efficient Capture of Trace Xenon and Krypton". supporting information. . Retrieved 2022/02/01.