1459-95-6

Basic information

• Product Name: Dimethyl 1,3-adamantanedicarboxylate
• Synonyms: DIMETHYL 1,3-ADAMANTANEDICARBOXYLATE;1,3-ADAMANTANE DICARBOXYLIC ACID DIMETHYL ESTER;DIMETHYL 1,3-ADAMANTANEDICARBOXYLATE, 98 %;dimethyl 1,3-adamatanedicarboxylate;DiMethyl 1,3-adaMentanedicarboxylate;DMADC
• CAS NO: 1459-95-6
• Molecular Formula: C₁₄H₂₀O₄
• Molecular Weight: 252.31
• Product Categories: Adamantane derivatives;Alicyclic/Etch-Resistant Monomers;Lithography Monomers;Self Assembly&Contact Printing
• Mol File: 1459-95-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 60-61 °C(lit.)
• Boiling Point: 320 °C at 760mmHg
• Flash Point: 152.7 °C
• Appearance: off-white power
• Density: 1.235 g/cm³
• Vapor Pressure: 0.000327mmHg at 25°C
• Refractive Index: 1.538
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Dimethyl 1,3-adamantanedicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethyl 1,3-adamantanedicarboxylate(1459-95-6)
• EPA Substance Registry System: Dimethyl 1,3-adamantanedicarboxylate(1459-95-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1459-95-6(Hazardous Substances Data)

Usage

General Description

Dimethyl 1,3-adamantanedicarboxylate is a chemical compound that is categorized under the family of bridged compounds. Its molecular formula is C16H22O4, and it is known by its other name, 1,3-Adamantanedicarboxylic Acid Dimethyl Ester. Its systematic name is dimethyl bicyclo[3.3.1]nonane-1,3-dicarboxylate. Most often, it is used in the manufacturing sector, especially in chemical laboratories and research, predominantly for the synthesis of other chemicals or as a reactant in specific chemical reactions. Dimethyl 1,3-adamantanedicarboxylate is typically solid at room temperature and poses hazards if inhaled, swallowed, or in contact with human skin.

InChI:InChI=1/C14H20O4/c1-17-11(15)13-4-9-3-10(5-13)7-14(6-9,8-13)12(16)18-2/h9-10H,3-8H2,1-2H3

Upstream product

• 39269-10-8 adamantane-1,3-dicarboxylic acid 
• 67-56-1 methanol 
• 768-90-1 1-Adamantyl bromide 
• 201230-82-2 carbon monoxide 
• 876-53-9 1,3-dibromoadamantane 
• 281-23-2 adamantane 
• 186581-53-3 diazomethane 

Downstream Products

• 101725-90-0 1,3-Adamantane bis(α,α-dimethylmethyl) diol 
• 17071-62-4 1,3-bis(2-hydroxymethyl)adamantane 

Relevant articles and documents

Synthesis and cytotoxicity of novel simplified eleutherobin analogues as potential antitumour agents

Mixed simplified structures containing the paclitaxel and eleutherobin pharmacophore moieties were analyzed using molecular docking techniques and synthesized based on adamantane and 8-oxabicyclo[3.2.1]octane scaffolds. The crucial role of substituents' stereochemistry in biological activity is discussed. At micromolar concentrations the selected analogues interfered with tubulin dynamics in vitro and in a living organism. Furthermore, new compounds were cytotoxic against human tumour cell lines. The simplified eleutherobin analogues may be considered as prototypes of a new class of antitumour agents.

Facile synthesis and antimycobacterial activity of isoniazid, pyrazinamide and ciprofloxacin derivatives

Several rationally designed isoniazid (INH), pyrazinamide (PZA) and ciprofloxacin (CPF) derivatives were conveniently synthesized and evaluated in vitro against H37Rv Mycobacterium tuberculosis (M. tb) strain. CPF derivative 16 displayed a modest activity

Histidine-Specific Peptide Modification via Visible-Light-Promoted C-H Alkylation

Histidine (His) carries a unique heteroaromatic imidazole side chain and plays irreplaceable functional roles in peptides and proteins. Existing strategies for site-selective histidine modification predominantly rely on the N-substitution reactions of the moderately nucleophilic imidazole group, which inherently suffers from the interferences from lysine and cysteine residues. Chemoselective modification of histidine remains one of the most difficult challenges in peptide chemistry. Herein, we report peptide modification via radical-mediated chemoselective C-H alkylation of histidine using C4-alkyl-1,4-dihydropyridine (DHP) reagents under visible-light-promoted conditions. The method exploits the electrophilic reactivity of the imidazole ring via a Minisci-type reaction pathway. This method exhibits an exceptionally broad scope for both peptides and DHP alkylation reagents. Its utility has been demonstrated in a series of important peptide drugs, complex natural products, and a small protein. Distinct from N-substitution reactions, the unsubstituted nitrogen groups of the modified imidazole ring are conserved in the C-H alkylated products.