Dimethyl 1,3-adamantanedicarboxylate

Base Information

• Chemical Name: Dimethyl 1,3-adamantanedicarboxylate
• CAS No.: 1459-95-6
• Molecular Formula: C14H20O4
• Molecular Weight: 252.31
• Hs Code.: 2917209090
• NSC Number: 632548
• DSSTox Substance ID: DTXSID70327115
• Nikkaji Number: J802.719F
• Wikidata: Q72468778
• ChEMBL ID: CHEMBL2003609
• Mol file: 1459-95-6.mol

Synonyms:1459-95-6;dimethyl adamantane-1,3-dicarboxylate;Dimethyl 1,3-adamantanedicarboxylate;NSC632548;1,3-DIMETHYL (1S,3S,5S,7S)-ADAMANTANE-1,3-DICARBOXYLATE;Tricyclo[3.3.1.13,7]decane-1,3-dicarboxylic acid, dimethyl ester;MFCD00167791;Maybridge3_000989;Oprea1_551832;SCHEMBL163027;1,3-dimethoxycarbonyladamantane;CHEMBL2003609;DTXSID70327115;HMS1433M21;1,3-bis(methoxycarbonyl)adamantane;BAA45995;CCG-48453;GEO-01144;STK366104;AKOS002323020;AKOS005257621;NSC-632548;IDI1_012376;BS-21416;NCI60_010661;1,3-dimethyl adamantane-1,3-dicarboxylate;Dimethyl 1,3-adamantanedicarboxylate, 98%;FT-0727549;1,3-Adamantanedicarboxylic acid dimethyl ester;A884560;SR-01000637992-1;W-200120;dimethyl tricyclo[3.3.1.1~3,7~]decane-1,3-dicarboxylate

Chemical Property of Dimethyl 1,3-adamantanedicarboxylate

Chemical Property:

• Appearance/Colour: off-white power
• Vapor Pressure: 0.000327mmHg at 25°C
• Melting Point: 60-61 ºC
• Refractive Index: 1.538
• Boiling Point: 320 °C at 760mmHg
• Flash Point: 152.7 °C
• PSA: 52.60000
• Density: 1.235 g/cm³
• LogP: 1.91900
• Storage Temp.: 2-8°C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 252.13615911
• Heavy Atom Count: 18
• Complexity: 353

Purity/Quality:

99% ^*data from raw suppliers

Dimethyl 1,3-adamantanedicarboxylate 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C12CC3CC(C1)CC(C3)(C2)C(=O)OC

Technology Process of Dimethyl 1,3-adamantanedicarboxylate

There total 9 articles about Dimethyl 1,3-adamantanedicarboxylate 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%

methanol (67-56-1) + adamantane-1,3-dicarboxylic acid (39269-10-8) → adamantane-1,3-dicarboxylic acid dimethyl ester (1459-95-6)

Guidance literature:

With thionyl chloride; for 6h; Reflux;

DOI:10.1021/jacs.9b09127

Reference yield: 95.0%

adamantane-1,3-dicarboxylic acid (39269-10-8) → adamantane-1,3-dicarboxylic acid dimethyl ester (1459-95-6)

Guidance literature:

With thionyl chloride; triethylamine; In methanol; N,N-dimethyl-formamide;

Reference yield:

1,3-dibromoadamantane (876-53-9) → adamantane-1,3-dicarboxylic acid dimethyl ester (1459-95-6)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂SO₄, Ag₂SO₄

With sulfuric acid; silver sulfate;

upstream raw materials:

diazomethane

adamantane-1,3-dicarboxylic acid

adamantane

1,3-dibromoadamantane

Downstream raw materials:

1,3-bis(2-hydroxymethyl)adamantane

1,3-Adamantane bis(α,α-dimethylmethyl) diol

Refernces

• 1、 Odinokov et al.. "". . . Retrieved 1979.
• 2、 Sartucci, Jenna L.,Maity, Arindam,Mohanan, Manikandan,Bertke, Jeffery,Kertesz, Miklos,Gavvalapalli, Nagarjuna. "Molecular tetrominoes: selective masking of the donor π-face to control the configuration of donor–acceptor complexes". supporting information. p. 375 - 386. Retrieved 2022/01/20.
• 3、 Lillis, Ryan,Thomas, Maximillian R.,Mohanan, Manikandan,Gavvalapalli, Nagarjuna. "Enhancing Insulated Conjugated Polymer Fluorescence Quenching by Incorporating Dithia[3.3]paracyclophanes". . p. 3112 - 3119. Retrieved 2021/05/05.