TRICYCLODECANE
Adamantane
CAS: 281-23-2
Molecular Formula: C10H16
TRICYCLODECANE - Names and Identifiers
| Name | Adamantane |
| Synonyms | Adamantan Adamantane TRICYCLODECANE [6]diadamantane TRICYCLO[3.3.1.1]DECANE tricyclo(3.3.1.13,7)decane TRICYCLO[3.3.1.13,7]DECANE tricyclo[3.3.1.1~3,7~]decane Tricyclo(3,3,1,1,3,7)-decane decahydro-3,5,1,7-[1,2,3,4]butanetetraylnaphthalene 3,5,1,7-[1,2,3,4]butanetetraylnaphthalene,decahydro- |
| CAS | 281-23-2 |
| EINECS | 206-001-4 |
| InChI | InChI=1/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 |
TRICYCLODECANE - Physico-chemical Properties
| Molecular Formula | C10H16 |
| Molar Mass | 136.23 |
| Density | 1,07 g/cm3 |
| Melting Point | 209-212 °C (subl.) (lit.) |
| Boling Point | 185.55°C (rough estimate) |
| Water Solubility | Insoluble in water. |
| Solubility | Insoluble in water |
| Appearance | Colorless crystal |
| Specific Gravity | 1.07 |
| Color | White to beige |
| Merck | 14,149 |
| BRN | 1901173 |
| Storage Condition | Store below +30°C. |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents. |
| Refractive Index | 1.5680 |
| MDL | MFCD00074719 |
| Physical and Chemical Properties | Character: colorless crystals. Melting Point: 209-212 ℃ (sublimation),208 relative density: 1.07(20 ℃) |
| Use | For the synthesis of adamantane derivatives |
TRICYCLODECANE - Risk and Safety
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R50 - Very Toxic to aquatic organisms |
| Safety Description | S24/25 - Avoid contact with skin and eyes. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
| UN IDs | UN 3077 9 / PGIII |
| WGK Germany | 2 |
| RTECS | YK0493000 |
| TSCA | Yes |
| HS Code | 29021990 |
| Hazard Note | Irritant |
TRICYCLODECANE - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| characteristics | (1) very stable to light;(2) good lubrication;(3) extremely lipophilic;(4) basically no odor, is a sublimation;(5) Although the reactivity is not as good as benzene, it is very easy to synthesize its derivatives. |
| Discovery history | In 1932, the Czechs Landa and others discovered adamantane from the petroleum fractionates of the South Moravian oil field. Its structure was confirmed the following year using X-ray technology. Adamantane was first synthesized in 1940 by Vladimir Prelog, a Yugoslav chemist living in Switzerland, through a step-by-step synthesis method. Adamantane was a very precious compound at the time. In 1957, Paul Schleyer, a chemist in Princeton, USA, was trying to use aluminum chloride as a catalyst to heat and convert the internal hydrogenated dicyclopentadiene into the external isomer. The product contains about 10% of adamantane by-products. Schleyer seized this opportunity to improve the yield of adamantane by optimizing the conditions. So just two steps from the cheap petrochemical product cyclopentadiene dimer can be used to make adamantane. Since then, the price of adamantane has fallen like an avalanche and has become a very cheap and easily available compound. Due to the special cage structure of adamantane, it has aroused great interest in the chemical world, which gave rise to the birth of cage compound chemistry. Later, it was discovered that amantadine has antiviral activity, which has received special attention from the pharmaceutical industry. In the current chemistry world, the systematic research around adamantane has formed an independent discipline: adamantane chemistry. 1-adamantyl is a large and stable substituent, which exists in some stable carbene (Persistent carbene). The famous Jacobson (Jacobson) asymmetric Diels-Alder reaction catalyst contains an adamantyl group. |
| Cluster compound | Adamantane is a tricyclic aliphatic hydrocarbon, which is a cluster compound, naturally occurring in petroleum, with a content of about four parts per million. It is a cyclic tetrahedron composed of 10 carbon atoms and 16 hydrogen atoms obtained by the reaction of dicyclopentadiene and hydrogen under the combined action of nickel catalyst and aluminum trichloride catalyst. This is a high symmetry Cage-like compound. Because the spatial arrangement structure of its carbon atoms is the same as the basic unit of the diamond lattice, it is known as adamantane. Adamantane is characterized by high thermal stability, excellent lubricity, great lipophilicity, odorless, and lower reactivity than benzene. The hydrogen on the bridgehead carbon atom (1,3,5,7) has high chemical activity, Substitution reaction can occur to produce many derivatives: 1-Bromoadamantane, 1-nitroadamantane, 1-aminoadamantane hydrochloride and 1-adamantylethylamine hydrochloride (can prevent and treat influenza caused by A2 virus), etc.; can also be oxidized to produce adamantol. It can also be used to make special polymers, especially optical and photosensitive materials; it can also be used in gasoline production, cocatalyst, lubricating oil and pharmaceutical production, and can also be used as agricultural chemicals and daily chemicals. It is a good new organic material. |
| Amantadine | Amantadine (English: Amantadine alias: amantadine, tricyclodecylamine) can promote the release of dopamine after entering the brain tissue, or delay the metabolism of dopamine To exert an anti-tremor paralysis effect, it is an anti-tremor paralysis drug. The anti-Parkinson's disease mechanism is mainly to promote the synthesis and release of striatal dopamine, reduce the reuptake of dopamine by nerve cells, and have anti-acetylcholine effect, thereby improving the symptoms of Parkinson's disease patients, and has a better effect on limb stiffness. Its effect is generally maintained for no more than 1 year. Do not take this drug for a long time, because it may have side effects on the cardiovascular system. Amantadine is the first antiviral drug used to suppress influenza viruses. The United States approved it as a preventive drug in 1966 when the Asian flu epidemic occurred. In 1976, it was confirmed as a therapeutic drug on the basis of preventive drugs. The efficacy and safety of this drug for adult patients have been widely recognized. However, the therapeutic dose is very close to the dose that produces side effects. It is difficult to determine the dose and administration plan for the elderly and those with chronic cardiopulmonary disease or kidney disease, so it has not been popularized and applied in clinical practice. In Japan, amantadine has been used as a treatment for Parkinson's disease until 1998. It was not approved for the treatment of influenza virus type A infectious diseases. The indications have obvious effects on tremor paralysis. The effect of relieving tremor and rigidity is good, and the effect is fast. It has obvious effects 48 hours after medication, and reaches a peak after 2 weeks. The drug is excreted by the kidney in its original form, and the excretion of acidic urine is accelerated. Anti-Asian influenza A- II virus effect, the protection rate of contact with this type of influenza is about 70%. The antipyretic effect is effective for a variety of inflammation, sepsis, viral pneumonia, etc. If combined with antibiotics, the antipyretic effect is better than antibiotics alone. |
| use | is mainly used for the synthesis of anti-cancer, anti-tumor and other specific drugs. It can also be used to prepare advanced lubricants, photographic photosensitive material surfactants, pesticides, catalysts, etc. The hydrogen on its bridgehead carbon atom (ie 1,3,5,7) is prone to substitution reaction. For example, adamantane reacts with excess bromine to form 1-bromoadantane; reacts with nitrogen dioxide at 175°C to form 1-nitroadamantane; oxidizes with chromium trioxide and acetic acid to form 1-adamantol. Adamantane can also be made by isomerization of tetrahydrodicyclopentadiene in the presence of anhydrous aluminum chloride. Its derivatives can be used as drugs, such as 1-aminoadamantane hydrochloride and 1-adamantylethylamine hydrochloride can prevent and treat influenza caused by A2 virus. Adamantane is used to synthesize adamantane derivatives. Commonly used as pharmaceutical intermediates, can also be used as photosensitive material raw materials; epoxy resin curing agent; intermediates for cosmetics and surfactants, etc. used in the production and synthesis of pharmaceutical intermediates; pesticide intermediates; veterinary drug intermediates; rubber and photosensitive materials; information technology. adamantane is a cyclic tetrahedral hydrocarbon containing 10 carbon atoms and 16 hydrogen atoms. Its basic structure is chair-shaped cyclohexane, which is a highly symmetrical and very stable compound. Adamantane has the following characteristics:(1) very stable to light;(2) good lubrication;(3) extremely lipophilic:(4) basically no odor, is a sublimation;(5) although the reactivity is not as good as benzene, but the synthesis of its derivatives is very easy. A cyclic tetrahedral hydrocarbon containing 10 carbon atoms and 16 hydrogen atoms. Its basic structure is chair-shaped cyclohexane, which is a highly symmetrical and very stable compound. It has very stable light, good lubrication, extremely lipophilic, basically no odor, and is a sublimation; although the reactivity is not as good as benzene, it is very easy to synthesize its derivatives. |
| Production method | Adamantane exists in petroleum with a content of about 4 parts per million. Adamantane can be catalyzed by the hydrogenation of dicyclopentadiene to obtain tetrahydrodicyclopentadiene, and then isomerized in the presence of anhydrous aluminum chloride. The process is as follows: 1. Catalytic hydrogenation Add dicyclopentadiene and nickel catalyst to the autoclave, and replace the air in the kettle with nitrogen. Then start the stirring hydrogen reaction. The pressure in the first half is 0.5-0.7MPa, the pressure in the second half is 1.5-2MPa, the temperature is 120 ℃, and it takes about 12 hours until no hydrogen is absorbed. Let stand for 3-4h, stratify, sample and test, olefin content should be below 2%. 2. Isomerization Add tetrahydrodicyclopentadiene into a dry glass-lined tank, then add anhydrous aluminum trichloride, keep temperature at 35 ℃, stir and dissolve. Add water dropwise within 3 hours, gradually increase the temperature to 75 ℃, cool down to 40 ℃ after 5 hours of reaction, add water to destroy aluminum trichloride, start steam distillation, collect the steamed adamantane, filter dry, and wash with a small amount of acetone to obtain adamantane. |
| spontaneous combustion temperature | 287°C |
Last Update：2024-04-09 20:49:11
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