Adamantane
Adamantan · Adamentane · TRICYCLO[3.3.1.13,7]DECANE · diadamantane · TRICYCLODECANE · ADAMANTANE · Adamantane,98% · HOMOADAMANTANE
Identifiers & Physical Properties
| CAS No. | 281-23-2 |
|---|---|
| Molecular formula | C10H16 |
| Average molar mass | 136.23 g/mol |
| Monoisotopic mass | 136.12520051 g/mol |
| SMILES | C1C2CC3CC1CC(C2)C3 |
| InChIKey | ORILYTVJVMAKLC-UHFFFAOYSA-N |
| PubChem CID | 9238 |
| ChEMBL | CHEMBL1230831 |
| ChEBI | CHEBI:40519 |
| EC No. | 206-001-4 |
| DTXSID | DTXSID5022017 |
Chemical & Physical Properties
| XLogP | 3.8 |
|---|---|
| Topological polar surface area | 0 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 0 |
| Rotatable bonds | 0 |
| Heavy atoms | 10 |
| Formal charge | 0 |
| Complexity | 75 |
| Physical Description | White crystalline powder[Alfa Aesar MSDS] |
| Kovats Retention Index | 11211117112011491160111311161118112511281136.911671135.31095.2110411141137.61123114414001325136313201339 |
| Melting point | 209-212 °C (subl.) (lit.) |
| Boiling point | 185.55°C (rough estimate) |
| Density | 1,07 g/cm3 |
| Refractive index | 1.5680 |
| Storage conditions | Store below +30°C. |
| Solubility | 0.00021g/l slightly solubleInsoluble in water. |
| Physical state | Crystals or Crystalline Powder |
| Specific gravity | 1.07 |
| Color | White to beige |
| Merck | 14,149 |
| BRN | 1901173 |
| Henry's law constant | 8.0×10-4 mol/(m3Pa) at 25℃, Roon et al. (2005) |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents. |
| InChI | 1S/C10H16/c1-7-2-9-4-8(1)5-10(3-7)6-9/h7-10H,1-6H2/t7-,8+,9-,10+ |
| InChIKey | ORILYTVJVMAKLC-UHFFFAOYSA-N |
| SMILES | C1[C@H]2C[C@H]3C[C@@H]1C[C@@H](C2)C3 |
| LogP (partition coefficient) | 4.240 |
| CAS DataBase Reference | 281-23-2(CAS DataBase Reference) |
| FDA UNII | PJY633525U |
| NIST Chemistry Reference | Adamantane(281-23-2) |
| EPA Substance Registry System | Tricyclo[3.3.1.13,7]decane (281-23-2) |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
| GHS pictogram | GHS09 |
| Signal word | Warning |
| GHS hazard statements | H413 |
| GHS precautionary statements | P273 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Hazard symbols | Xi,N |
| Risk statements (R) | 36/37/38-50 |
| Safety statements (S) | 24/25-36-26-61 |
| UN transport number | UN 3077 9 / PGIII |
| Water hazard class (WGK) | 2 |
| RTECS number | YK0493000 |
| Autoignition temperature | 287 °C |
| Hazard Note | Irritant |
| TSCA inventory status | TSCA listed |
| Customs code | 29021990 |
| Storage class | 11 - Combustible Solids |
| Hazard class | Aquatic Chronic 4 |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | WarningH319 (13%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H400 (94.4%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]P264+P265, P273, P280, P305+P351+P338, P337+P317, P391, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 54 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatory information | Chemical: Tricyclo[3.3.1.13,7]decaneStatus: Active Update: 29-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/20053Tricyclo3.3.1.13,7decane: Does not have an individual approval but may be used under an appropriate group standard |
| Hazards summary | A mild eye irritantCauses abnormal renal function tests in acute inhalation studies of rats[RTECS] May cause irritation[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Eye Irrit. 2 (13%)Aquatic Acute 1 (94.4%) |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Water hazard class (WGK) | 2 |
| TSCA inventory status | TSCA listed |
| RTECS number | YK0493000 |
| UN transport number | UN 3077 9 / PGIII |
| Customs code | 29021990 |
| Risk statements (R) | 36/37/38-50 |
| Signal word | Warning |
| GHS pictogram | GHS09 |
| Hazard symbols | Xi,N |
| hazard_note | Irritant |
| Safety statements (S) | 24/25-36-26-61 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H413 |
| REACH registrations | Active |
| Hazard class | Aquatic Chronic 4 |
| Autoignition temperature | 287 °C |
| GHS precautionary statements | P273 |
Applications & Uses
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.
Uses
synthon for Amantadine, Rimantadine, Somantadine, Tromantadine
Uses
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.
Uses
The diamine as curing agent for epoxy resins [US 3053907 (1962 to du Pont)].