Basic information
- Standard SMILES
C1C2CC3CC1CC(C2)C3- InChIKey
ORILYTVJVMAKLC-UHFFFAOYSA-N- Molecular formula
- C10H16
- Average molar mass
- 136.23 g/mol
- Monoisotopic mass
- 136.12520051
Names & identifiers
- Preferred name
- Adamantane
- IUPAC
- adamantane
- English name
- Adamantane
- Molecular formula
- C10H16
- Molecular weight
- 136.23
Names & synonyms
ADAMANTANE281-23-2Tricyclo[3.3.1.13,7]decaneTricyclo[3.3.1.1(3,7)]decaneTricyclo(3.3.1.13,7)decanePJY633525UNSC-527913DTXSID5022017CHEBI:40519tricyclo(3.3.1.1(3,7))decaneRefChem:388771DTXCID302017
Show more names
AdamentanediadamantaneTRICYCLODECANEAdamantane,98%HOMOADAMANTANEAdamantane >[6]diadamantane
206-001-4Adamantantricyclo[3.3.1.1~3,7~]decaneMFCD00074719A 0696; NSC 527913tricyclo[3.3.1.13,7]decantricyclo[3.3.1.1]decaneAdamantane; Tricyclo[3.3.1.1(3),7]decane
Database identifiers
- CAS
281-23-2- PubChem CID
- 9238
- DTXSID
DTXSID5022017- ChEMBL
CHEMBL1230831- ChEBI
CHEBI:40519- UNII
- PJY633525U
- EC Number
- 206-001-4
- Nikkaji
- J45.672A
Properties
Computed structural properties
- XLogP
- 3.8
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 0
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 75
Experimental & physicochemical properties
Physical DescriptionWhite crystalline powder; [Alfa Aesar MSDS]
Kovats Retention Index
1121；1117；1120；1120；1149；1160；1160；1149；1113；1116；1117；1118；1120；1116；1113；1117；1120；1125；1120；1128
1136.9；1116；1116；1116；1167；1135.3；1095.2；1095；1104；1114；1137.6；1095；1104；1114；1123；1123；1144
1400；1325；1325；1363；1320；1339；1363；1400；1363
Physicochemical properties
- Melting point
- 209 · 209-212 °C (subl.) (lit.)
- Boiling point
- 185.55 °C · 185.55°C (rough estimate)
- Density
- 1 · 1,07 g/cm3
- refractive index
- 1.568 · 1.5680
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 0.00021 g/l · 0.00021g/l slightly soluble
- form
- Crystals or Crystalline Powder
- Specific Gravity
- 1.07 · 1.07
- color
- White to beige
- Water Solubility
- Insoluble in water.
- Merck
- 14 · 14,149
- BRN
- 1901173 · 1901173
- Henry's Law Constant
- 8 · 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
- 4.24 · 4.240
- CAS DataBase Reference
- 281 · 281-23-2(CAS DataBase Reference)
- FDA UNII
- 633525 U · PJY633525U
- NIST Chemistry Reference
- Adamantane(281-23-2)
- EPA Substance Registry System
- 3.3 · Tricyclo[3.3.1.13,7]decane (281-23-2)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 9 · GHS09
- Signal word
- Warning
- Hazard statements
- 413 · H413
- Precautionary statements
- 273 · P273
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- Xi,N
- Risk Statements
- 36 · 36/37/38-50
- Safety Statements
- 24 · 24/25-36-26-61
- RIDADR
- 3077 · UN 3077 9 / PGIII
- WGK Germany
- 2 · 2
- RTECS
- 493000 · YK0493000
- Autoignition Temperature
- 287 °C · 287 °C
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HS Code
- 29021990 · 29021990
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 · Aquatic Chronic 4
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Warning
H319 (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.
Hazard information
Regulatory Information
Chemical: Tricyclo[3.3.1.13,7]decane
Status: Active Update: 29-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/20053
Tricyclo3.3.1.13,7decane: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryA mild eye irritant; Causes abnormal renal function tests in acute inhalation studies of rats; [RTECS] May cause irritation; [Alfa Aesar MSDS]
Hazard Classes and CategoriesEye Irrit. 2 (13%)；Aquatic Acute 1 (94.4%)
Regulatory information
Regulatory Information
Chemical: Tricyclo[3.3.1.13,7]decane
Status: Active Update: 29-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/20053
Tricyclo3.3.1.13,7decane: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- YK0493000
- ridadr
- UN 3077 9 / PGIII
- hs_code
- 29021990
- risk_code
- 36/37/38-50
- Signal word
- Warning
- Symbol(GHS)
- GHS09
- hazard_code
- Xi,N
- hazard_note
- Irritant
- safety_code
- 24/25-36-26-61
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H413
- REACH Registrations
- Active
- Hazard Classifications
- Aquatic Chronic 4
- Autoignition Temperature
- 287 °C
- Precautionary statements
- P273
Chemistry & industry
Uses & manufacturing
UsesThe diamine compound: used as a curing agent for epoxy resins; [Merck Index]
General Manufacturing InformationTricyclo[3.3.1.13,7]decane: ACTIVE
Applications
UsesAdamantane 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.
Usessynthon for Amantadine, Rimantadine, Somantadine, Tromantadine
UsesAdamantane 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.
UsesThe diamine as curing agent for epoxy resins [US 3053907 (1962 to du Pont)].
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海犇特化工有限公司13761726461 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
爱斯特（成都）生物制药股份有限公司+86-28-85122536 85324413 · [email protected]
北京安司莫森技术有限公司010-82954736 13391601435 · [email protected]
科瑞迪化学400-821-5857 021-64326257 · [email protected]
Syntechem Co.,Ltd[email protected]
Ark Pharm, Inc.847-367-3680 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
阿法埃莎（中国）化学有限公司400-6106006 · [email protected]
安耐吉化学&3A（安徽泽升科技股份有限公司）400-0056266 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
嘉兴市艾森化工有限公司0573-85285100 18627885956 · [email protected]
上海泰坦科技股份有限公司400-6009262 15618770481 · [email protected]
玛雅试剂+86 (573) 82222445 (0)18006601000 452520369 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
湖南汇百侍生物科技有限公司0731-85526065 13308475853 · [email protected]
上海源叶生物科技有限公司13636370518 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
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北京伊诺凯科技有限公司400-810-7969 010-59572699 · [email protected]
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TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
上海贤鼎生物科技有限公司4009209199 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
上海睿升化工科技有限公司+86-021-50935922
Cato Research Chemicals Inc.020-81960175 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
上海笛柏生物科技有限公司400-008-9730,021-54359730 400-008-9730 · [email protected]
日照力德士化工有限公司010-51268198 · [email protected]
郑州阿尔法化工有限公司0371-53732842 15981811963 · [email protected]
郑州鸿晟医药科技有限公司0371-0371-13526885213 15637198702 · [email protected]
美岚实业（上海）有限公司021-58958189 · [email protected]
上海石洋化工有限公司021-56795766 · [email protected]
上海爱蝶实业有限公司021-58957966 18930537195 · [email protected]
四川省维克奇生物科技有限公司028-81700200 18116577057 · [email protected]
成都零六生物科技有限公司400-1166-196 13458535857 · [email protected]
广拓化学（上海）有限公司021-60899189-8001 18918189673 · [email protected]
雷丁试剂0510-85629785 18013409632 · [email protected]
湖南华腾制药有限公司400-8592883 · [email protected]
上海创赛科技有限公司400-6087598 15021221957 · [email protected]
上海馨远医药科技有限公司021-24206007 13764915196 · [email protected]
潍坊鲁泽新材料有限公司0536-7971999 13583611556 · [email protected]
Additional notes
Definitionadamantane: A colourless crystallinehydrocarbon C10H16; m.p.269°C. It is found in certain petroleumfractions. The structure containsthree symmetrically fusedcyclohexane rings.
Related reactions
75 records
Linked notes
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