Adamantane

Base Information

• Chemical Name: Adamantane
• CAS No.: 281-23-2
• Molecular Formula: C10H16
• Molecular Weight: 136.237
• Hs Code.: 29021990
• European Community (EC) Number: 206-001-4
• NSC Number: 527913
• UNII: PJY633525U
• DSSTox Substance ID: DTXSID5022017
• Nikkaji Number: J45.672A
• Wikipedia: Adamantane
• Wikidata: Q351461,Q83043490,Q83046187
• Metabolomics Workbench ID: 52251
• ChEMBL ID: CHEMBL1230831
• Mol file: 281-23-2.mol

Synonyms:Adamantane;Diamantane

Chemical Property of Adamantane

Chemical Property:

• Appearance/Colour: slightly beige crystals
• Melting Point: 209-212 °C (subl.)(lit.)
• Refractive Index: 1.517
• Boiling Point: 187.142 °C at 760 mmHg
• Flash Point: 48.858 °C
• PSA: 0.00000
• Density: 0.977 g/cm³
• LogP: 2.83260
• Storage Temp.: Store below +30°C.
• Solubility.: 0.00021g/l slightly soluble
• Water Solubility.: Insoluble in water.
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 136.125200510
• Heavy Atom Count: 10
• Complexity: 75.1

Purity/Quality:

99%, ^*data from raw suppliers

Adamantane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,N
• Statements: 36/37/38-50
• Safety Statements: 24/25-36-26-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Other Organic Compounds
• Canonical SMILES: C1C2CC3CC1CC(C2)C3
• Uses: Adamantane is a tetrahedral cyclic hydrocarbon containing 10 carbon atoms and 16 hydrogen atoms with its basic structure being the chair form of cyclohexane. It is a highly symmetric and very stable compound. Adamantane has the following characteristics: (1) very stable to light (2) good lubrication force; (3) highly lipophilic: (4) almost tasteless and is sublimate; (5) Although the reactivity is not as active as the reactivity of benzene, but synthesizing of its derivatives is very easy. It is mainly used for the synthesis of special drugs of anti-cancer and anti-tumor. It can also be used to prepare advanced lubricants, the surfactants of photosensitive material, pesticides, catalysts and the like. The hydrogen atom of its bridgehead carbon atoms (i. e. 1, 3, 5, and 7) is easy to have substitution reaction. E.g. adamantane has reaction with an excess amount of bromine, generating 1-bromo-adamantane; reaction with nitrogen dioxide at 175 °C can yield 1-Polynitroadamantanes; oxidation between chromium trioxide and acetic acid can form a 1-adamantyl alcohol. Adamantane can also be obtained through the isomerization between tetrahydro-dicyclopentadiene in the presence of anhydrous aluminum chloride. Its derivative can be used as medicaments, e.g., 1-amino-adamantane hydrochloride and 1-adamantyl triethylamine hydrochloride can prevent the influenza caused by the virus A2. Adamantane can be used for the synthesis of adamantane derivative. It can often be used as pharmaceutical intermediates as well as being used as the raw material of light-sensitive material, cosmetic and surfactant intermediates and also the epoxy curing agent. synthon for Amantadine, Rimantadine, Somantadine, Tromantadine The diamine as curing agent for epoxy resins [US 3053907 (1962 to du Pont)]. Adamantane is mainly used for the synthesis of medicine to treat influenza, serve as NMDA receptor channel blockers. Also be used for preparation of advanced lubricants, photographic material, surface active agents, catalysts and other products.
• Production method: Adamantane is presented in the petroleum with the content being about four millionths. Adamantane can be obtained through via the catalyzed hydrogenation of dicyclopentadiene into tetrahydro-dicyclopentadiene and further isomerization in the presence of anhydrous aluminum chloride. The technical process is as follows: 1. catalytic hydrogenation; put the dicyclopentadiene and nickel catalyst into the autoclave, use nitrogen to displace the air in the autoclave. Then start the mixing hydrogen reaction. The pressure during the first half stage should be 0.5-0.7MPa while the latter stages pressure should be 1.5-2MPa with the temperature being 120 ℃ and continued for about 12h until no hydrogen absorption occurs any more. Stand for 3-4h and have stratification, apply sampling tests and the olefin content should be less than 2%. 2. Isomerization; add the Tetrahydro-dicyclopentadiene to a dry glass-lined tank, then add anhydrous aluminum chloride, heat at 35°C, stir and dissolve. Add drop wise of water within 3 h and gradually raise the temperature to 75 °C with being cooled to 40 °C after 5 h of reaction. Add water to destroy the aluminum trichloride and start steam distillation, collect the distilled adamantane, drain and wash with a small amount of acetone to give adamantane.

Technology Process of Adamantane

There total 373 articles about Adamantane 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: 90.0%

acetonitrile (75-05-8,26809-02-9) + trans-N,N'-bis(1-adamantyl)diazene (24325-56-2) → 1,1'-Biadamantane (3732-31-8) + adamantane (281-23-2) + N-(1-adamantyl)acetamide (880-52-4) + 1-acetyladamantane (1660-04-4)

Guidance literature:

With thianthrenium perchlorate; Further byproducts given; Ambient temperature;

DOI:10.1021/ja00294a066

Reference yield: 78.0%

1-chloroadamantane (935-56-8) → 1-Adamantyl bromide (768-90-1) + 2-adamantyl bromide (7314-85-4) + adamantane (281-23-2) + 1,3-dibromoadamantane (876-53-9)

Guidance literature:

With hydrogen bromide; ferric(III) bromide; In dichloromethane; at 25 ℃; for 0.3h;

DOI:10.1039/c39870001013

Reference yield: 69.5%

1-iodoadamantane (768-93-4) → 1,1'-Biadamantane (3732-31-8) + adamantane (281-23-2) + C10H15IMg (97580-88-6)

Guidance literature:

With magnesium; ethylene dibromide; In diethyl ether; at 35 ℃; Product distribution;

DOI:10.1021/jo00142a023

upstream raw materials:

1,3-dibromoadamantane

(3aR,4R,7S,7aS)-octahydro-1H-4,7-methanoindene

1-Adamantyl bromide

1,1-Dichloroethylene

Downstream raw materials:

1-Adamantanecarboxylic acid

2-Adamantanone

4-(1-adamantyl)pyridine

1-chloroadamantane

Refernces

• 1、 Kramer, Nina,Wadepohl, Hubert,Greb, Lutz. "Tris(dimethylamino)silylium ion: Structure and reactivity of a dimeric silaguanidinium". . p. 7764 - 7767. Retrieved 2019.
• 2、 Camps,Lukach,Rossi. "Synthesis of several halobisnoradamantane derivatives and their reactivity through the SRN1 mechanism". . p. 5366 - 5373. Retrieved 2001.
• 3、 Lin, Tzuen-Yeuan,Fuh, Ming-Ren,Chen, Yu-Yu. "Rate study of haloadamantane reduction by samarium diiodide". . p. 969 - 973. Retrieved 2002.
• 4、 Yamamoto,Y. et al.. "". . p. 2558 - 2559. Retrieved 1975.
• 5、 Olah, George A.,Farooq, Omar. "Superacid-Catalyzed Isomerization of endo-to exo-Trimethylenenorborane (Tetrahydrodicyclopentadiene) and to Adamantane". . p. 5410 - 5413. Retrieved 1986.
• 6、 Akhrem, I. S.,Orlinkov, A. V.,Bakhmutov, V. I.,Afanas'eva, L. V.,Vol'pin, M. E.. "NATURE OF THE SPECIES RESPONSIBLE FOR THE HIGH ACTIVITY OF RCOX*2AlX3 COMPLEXES IN REACTIONS WITH ALKANES AND CYCLOALKANES". . p. 2252 - 2256. Retrieved 1990.
• 7、 Webster,Sommer. "". . p. 3103. Retrieved 1964.
• 8、 Paquette et al.. "". . p. 6779,6783. Retrieved 1969.
• 9、 Johnston et al.. "". . p. 2798. Retrieved 1971.
• 10、 Curran,Gualtieri. "Synthesis and asymmetric hydrogermylation reactions of dithiogermanium hydrides derived from C2-symmetric dithiols". . p. 1038 - 1041. Retrieved 2001.