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Adamantane

HCID 9238
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
281-23-2
Standard SMILES
C1C2CC3CC1CC(C2)C3
InChIKey
ORILYTVJVMAKLC-UHFFFAOYSA-N
Molecular formula
C10H16
Average molar mass
136.23 g/mol
Monoisotopic mass
136.12520051

Overview

Adamantane is a polycyclic alkane and a member of adamantanes.

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
AdamentanediadamantaneTRICYCLODECANEAadamantaneAdamantane,98%HOMOADAMANTANEAdamantane >
206-001-4Adamantantricyclo[3.3.1.1]decanetricyclo[3.3.1.1~3,7~]decaneMFCD00074719A 0696; NSC 527913tricyclo[3.3.1.13,7]decanAdamantane (purified by sublimation)

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
75.1

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Other Organic Compounds
DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesSchoenflies notation
LogP5.2
Physical DescriptionWhite crystalline powder; [Alfa Aesar MSDS]

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

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H319 (13%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

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.

Hazard information

Regulatory Information · 3 items

Chemical: Tricyclo[3.3.1.13,7]decane

REACH registered substance: Tricyclo[3.3.1.13,7]decane (EC: 206-001-4)

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%)

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
2
tsca
TSCA listed
rtecs
YK0493000
ridadr
UN 3077 9 / PGIII
hs_code
2902199090
risk_code
36/37/38-50
Signal word
Warning
Symbol(GHS)
GHS09

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 · 4 items

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.

Related reactions

75 records
New reaction record
HRID 9743 reaction equation
HRID 9743As reactantuspto-grants-2006_08
HRID 36486 reaction equation
HRID 36486As reactantuspto-grants-1995_05
HRID 73722 reaction equation
HRID 73722As productuspto-grants-2014_09
HRID 103519 reaction equation
HRID 103519As productTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 117819 reaction equation
HRID 117819As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 123999 reaction equation
HRID 123999As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 289661 reaction equation
HRID 289661As reactantTraining data from https://doi.org/10.1039/C8SC04228D (8/10)
HRID 345107 reaction equation
HRID 345107As reactantuspto-grants-1991_10
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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
More actions
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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
2902199090 · 2902199090
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 · Aquatic Chronic 4
REACH Registrations
Active
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

UsesThe diamine as curing agent for epoxy resins [US 3053907 (1962 to du Pont)].

Upstream & downstream products

Upstream raw materials

DicyclopentadieneAluminum chloride1-Adamantanecarboxylic acid2-Ethyladamantane1,1'-DIADAMANTYLp-(1-Adamantyl)toluene1-Iodoadamantane

Downstream products

Butyldi-1-adamantylphosphineRimantadine hydrochloride1-Adamantanol1-BromoadamantaneAmantadine1,3-Adamantanediol5-Hydroxyadamantan-2-one1,3-Dimethyladamantane

Additional notes

Definitionadamantane: A colourless crystallinehydrocarbon C10H16; m.p.269°C. It is found in certain petroleumfractions. The structure containsthree symmetrically fusedcyclohexane rings.