39269-10-8

Basic information

• Product Name: 1,3-Adamantanedicarboxylic acid
• Synonyms: tricyclo(3.3.1.1(sup3,7))decane-1,3-dicarboxylicacid;Tricyclo[3.3.1.13,7]decane-1,3-dicarboxylic acid;ADAMANTANE-1,3-DICARBOXYLIC ACID;AKOS BC-0656;1,3-ADAMANTANEDICARBOXYLIC ACID;1,3-DICARBOXYADAMANTANE;(1s,3s,5r,7r)-AdaMantane-1,3-dicarboxylic acid;1,3-AdaMantanedicarboxylic acid SynonyMs AdaMantane-1,3-dicarboxylic acid
• CAS NO: 39269-10-8
• Molecular Formula: C₁₂H₁₆O₄
• Molecular Weight: 224.25
• EINECS: 254-395-1
• Product Categories: Adamantane derivatives;Carboxylic Acids;Adamantanes;Carboxylic Acids;Fused Ring Systems;Alicyclic/Etch-Resistant MonomersPolymer Science;Carboxylic Acid Monomers;Lithography Monomers;Monomers;Self Assembly&Contact Printing
• Mol File: 39269-10-8.mol

Chemical Properties

• Melting Point: 276-278 °C(lit.)
• Boiling Point: 380.6 °C at 760 mmHg
• Flash Point: 198.2 °C
• Appearance: /
• Density: 1.461 g/cm³
• Vapor Pressure: 7.6E-07mmHg at 25°C
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Sparingly), Methanol (Slightly, Heated)
• PKA: 4.24±0.40(Predicted)
• CAS DataBase Reference: 1,3-Adamantanedicarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Adamantanedicarboxylic acid(39269-10-8)
• EPA Substance Registry System: 1,3-Adamantanedicarboxylic acid(39269-10-8)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• RTECS: YD1994000
• Hazardous Substances Data: 39269-10-8(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
1,3-Adamantanedicarboxylic acid is used as a key intermediate for the synthesis of various drugs, particularly in the development of antidepressants and antiparkinsonic medications. Its unique structure and properties make it a valuable component in the creation of these therapeutic agents.
2. Used in Polymer Synthesis:
In the field of polymer chemistry, 1,3-adamantanedicarboxylic acid serves as an essential building block for the development of new polymer materials. Its adamantane core and carboxylic acid groups provide specific characteristics that can be exploited to create polymers with tailored properties for various applications.
3. Used in Fine Chemicals:
1,3-Adamantanedicarboxylic acid is also utilized in the production of fine chemicals, which are high-purity chemicals used in various industries, including pharmaceuticals, agriculture, and materials science. Its unique structure and reactivity make it a valuable component in the synthesis of these specialized chemicals.

Preparation

1,3-Adamantanedicarboxylic acid was synthesized from 1-adamantane carboxylic acid by one-pot method. In this process, the ratio of mixed acid (nitric acid and sulfuric acid) have important effect on the yield, the role of sulfuric acid not only is solvent, but also can improve the oxidate ability of nitric acid.Efficient Synthesis of 1,3-Adamantanedicarboxylic Acid and 1,3-DiaminoadamantaneReaction: 1-Adamantane carboxylic acid (20 g), nitric acid (65 %, 20 mL) and sulfuric acid (98 %, 160 mL) were placed in a three-necked roundbottom flask fitted with an efficient magnetic stirrer and a thermometer. Cooled to 0 oC and held at 0 oC, anhydrous formic acid (80 %, 70 mL) was added dropwise in 5 h and reacted for 1 h. poured to crushed ice, filtered and then washed the precipitate several times with water to give a white solid. Then the white solid was dissolved in aqueous NaOH solution and the upper clear solution was separated and acidified by HCl to pH = 3. Filtered, washed with water, dried in vacuum, recrystallized from ethanol. White solid, yield 22.9 g (92 %). m.p.: 275- 276 oC1H NMR (DMSO-d6, 400 MHz) δ: 1.616 (m, 2H), 1.691-1.727 (m, 4H), 1.759-1.791 (m, 4H), 1.850-1.882 (m, 2H), 2.059 (m, 1H), 12.062 (br, s, 2H, COOH); 13C NMR (100 MHz, DMSO-d6) δ 27.37 (C-5, C-7), 34.98 (C-6), 37.66 (C-4, C-8, C-9, C-10), 39.78 (C-2), 39.89 (C-2, C-3), 177.76 (COOH). IR (KBr, νmax, cm-1) : 2913, 2851, 2636, 1691, 1451, 1410, 1344, 1249, 1103, 1084, 952, 743, 670, 528; Anal. calcd for C12H16O4: C 64.29, H 7.14; found C 64.55, H 7.22.

Purification Methods

Dissolve the acid in aqueous NaOH, treat with charcoal, filter and acidify with dilute HCl. It crystallises from MeOH. [Stetter & Wulff Chem Ber 93 1366 1960, Beilstein 9 III 4066, 9 IV 2997.]

InChI:InChI=1/C12H16O4/c13-9(14)11-2-7-1-8(4-11)5-12(3-7,6-11)10(15)16/h7-8H,1-6H2,(H,13,14)(H,15,16)/p-2

Upstream product

• 201230-82-2 carbon monoxide 
• 281-23-2 adamantane 
• 1660-04-4 1-acetyladamantane 
• 16091-98-8 oxo-tricyclo[3.3.1.1^3,7]decan-1-yl-acetic acid 
• 33705-31-6 α-Hydroxymethyl 1-adamantyl ketone 
• 5122-81-6 2-((1r,3r,5r,7r)-adamantan-2-yl)-2-oxoacetaldehyde 
• 64558-01-6 dimethyl adamantane-2,6-dione-1,5-dicarboxylate 
• 41585-35-7 adamantane-2,6-dione-1,5-dicarboxylic acid 
• 124-41-4 sodium methylate 
• 876-53-9 1,3-dibromoadamantane 
• 64-18-6 formic acid 
• 5001-18-3 1,3-adamantandiol 
• 768-90-1 1-Adamantyl bromide 
• 80937-33-3 oxygen 

Downstream Products

• 281-23-2 adamantane 
• 62472-38-2 adamantane-1,3-dicarbonitrile 
• 29713-15-3 adamantane-1,3-dicarboxylic acid dichloroanhydride 
• 197707-05-4 Adamantane-1,3-dicarboxylic acid bis-[(S)-2-((S)-2-benzyloxycarbonylamino-3-methyl-butyrylamino)-2-methoxycarbonyl-ethyl] ester 
• 75534-58-6 1,3,5,7-tetrakis(hydroxymethyl)adamantane 
• 5001-18-3 1,3-adamantandiol 

Relevant articles and documents

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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.

Amantadine nitrate compounds with neural protective effect, and preparation and medical use thereof

The present invention relates to amantadine nitrate compounds having neural protective effect, and preparation method and medical use thereof. The compounds have the structure of the general formula (I). The compounds have multifunctional mechanisms, including inhibiting NMDA receptors, releasing NO, inhibiting calcium influxes, and having protective effects on cells particularly neurocytes. The compounds can be used in the preparation of medicaments having a cellular protective effect, for prevention or treatment of the diseases related to such as NMDA receptors and elevation of calcium anions in cells, including the diseases related to neurodegeneration such as Alzheimer's disease, Parkinson's disease, cerebral paralysis and glaucoma, and the diseases related to cardio-cerebral-vascular system such as Parkinson's syndrome combined with cerebral arteriosclerosis, as well as respiratory tract infections caused by influenza virus.

A 1, 3 - adamantane dicarboxylic acid preparation method

The invention belongs to the technical field of organic synthesis and relates to a preparation method of adamantane disubstituted derivates, in particular to a preparation method of 1,3-adamantanedicarboxylic acid. 1,3-adamantanedicarboxylic acid is directly prepared with a one-step method, and raw materials directly generate 1,3-adamantanedicarboxylic acid in a mixed acid solution of concentrated sulfuric acid and fuming nitric acid. The preparation method has the advantages that the raw materials are novel, a one-pot reaction step is short, a few reagents are used, the economic efficiency of the raw materials is good, the operation is simple and convenient, and the conversion rate is higher.

Synthesis and biological evaluation of memantine nitrates as a potential treatment for neurodegenerative diseases

A series of memantine nitrate derivatives, as dual functional compounds with neuroprotective and vasodilatory activity for neurodegenerative diseases, was designed and synthesized. These compounds combined the memantine skeleton and a nitrate moiety, and thus inhibited the N-methyl-d-aspartic acid receptor and released NO in the central nervous system. The biological evaluation results revealed that the new memantine nitrates were effective in protecting neurons against glutamate-induced injury in vitro. Moreover, memantine nitrates dilated aortic rings against phenylephrine-induced contraction. The structure-activity relationships of neuroprotection and vasodilation were both analyzed. In further studies, compound MN-05 significantly protected cortical neurons by inhibiting Ca2+ influx, reducing free radical production and maintaining the mitochondrial membrane potential. Further research on MN-05 is warranted.

AMANTADINE NITRATE COMPOUND HAVING A NEUROPROTECTIVE EFFECT AND PREPARATION AND MEDICAL USE THEREOF

The present invention relates to amantadine nitrate compounds having neural protective effect, and preparation method and medical use thereof. The compounds have the structure of the general formula (I). The compounds have multifunctional mechanisms, including inhibiting NMDA receptors, releasing NO, inhibiting calcium influxes, and having protective effects on cells particularly neurocytes. The compounds can be used in the preparation of medicaments having a cellular protective effect, for prevention or treatment of the diseases related to such as NMDA receptors and elevation of calcium anions in cells, including the diseases related to neurodegeneration such as Alzheimer's disease, Parkinson's disease, cerebral paralysis and glaucoma, and the diseases related to cardio-cerebral-vascular system such as Parkinson's syndrome combined with cerebral arteriosclerosis, as well as respiratory tract infections caused by influenza virus.

Generation of liquid crystallinity from a Td-symmetry central unit

A series of new columnar liquid crystals containing an adamantane central unit with its four bridgehead positions partially or fully decorated with different numbers (1-4) of 3,4,5-tris(dodecyloxy)phenyl carbamoyl groups were designed and investigated carefully to explore the structure-property correlations. The molecular structures and mesomorphic properties of the DLCs were characterized by 1H-NMR, 13C-NMR, IR, UV-vis, POM, DSC and XRD. It was found that the mesophase symmetry and thermal stability were extremely dependent on the structures of the adamantane derivatives. No mesophase was observed for the 1-adamantanecarboxylic acid derivative ADLC1, while two different mesophases were observed for ADLC2, a 1,3-disubstituted derivative functionalized with two 3,4,5-tris(dodecyloxy)phenyl carbamoyl groups at two symmetric bridgehead positions. At lower temperature ADLC2 exhibited a rectangular columnar phase, which switched to a square columnar phase possessing a wide temperature range. Similarly, a hexagonal columnar mesophase was observed for the bridgehead trisubstituted adamantane molecule ADLC3. Interestingly, the fully bridgehead-functionalized 1,3,5,7-tetrasubstituted adamantane compound ADLC4 completely lost liquid crystallinity.

A manufacturing method of a carboxylic acids and polyadamantane hydroxyacid purification method

PROBLEM TO BE SOLVED: To provide an efficient manufacturing method of hydroxy adamantane carboxylic acids that have an adamantane skeleton, and that are the raw materials of a functional resin excellent in an optical characteristic and heat resistance or the like. SOLUTION: The manufacturing method of hydroxy adamantane carboxylic acids comprises as follows. Adamantane diols shown by general formula (1) is made to react with at most two equivalents of a carbon monoxide source based on one equivalent of a hydroxyl group of the adamantane diols in a liquid state protonic acid solvent, and then the crystal of hydroxy adamantane carboxylic acid shown by general formula (2) is filtered to be separated. COPYRIGHT: (C)2013,JPOandINPIT

Process for producing hydroxy adamantane carboxylic acid compounds

The present invention can provide a process for producing a hydroxy adamantane carboxylic acid compound represented by the above formula (2), which comprises (i) reacting an adamantane compound represented by the above formula (1) with carbon monoxide or with a carbon monoxide source in a proton acid solution prepared at a concentration of 90% by mass or more to thereby cause carboxylation of the OX group(s), and then (ii) adding an oxidizing agent to the reaction mixture to cause oxidation of the bridgehead C—H bond to thereby generate a hydroxyl group.

Efficient synthesis of 1,3-adamantanedicarboxylic acid and 1,3-diaminoadamantane

1,3-Adamantane dicarboxylic acid was efficiently synthesized from 1-adamantane carboxylic acid by one-pot method. 1,3- Diaminoadamantane was synthesized from 1,3-adamantane dicarboxylic acid via amidation reaction and Hofmann degradation. The structure was confirmed by NMR spectra, etc.

The first selective one-pot synthesis of 1,3-dicarbonyl adamantanes from adamantane and 1,3-dimethyladamantane

A new approach to a simple one-pot functionalization of adamantane and 1,3-dimethyladamantane with CO and various nucleophiles in the presence of the superelectrophilic complex, CBr4·2AlBr3 provides access to important 1,3-dicarbonyl adamantanes with two new functional groups at the bridge-head positions.