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281-23-2

Basic Information
CAS No.: 281-23-2
Name: Adamantane
Article Data: 357
Molecular Structure:
Molecular Structure of 281-23-2 (Adamantane)
Formula: C10H16
Molecular Weight: 136.237
Synonyms: Tricyclo[3.3.1.13,7]decane;tricyclo[3.3.1.1(3,7)]decane;Adamantane (8CI);tricyclo[3.3.1.1~3,7~]decane;Tricyclo(3.3.1.13,7)decane;Tricyclo[3.3.1.13.7]decan-1-amine (Amantadine);
EINECS: 206-001-4
Density: 0.977 g/cm3
Melting Point: 209-212 °C (subl.)(lit.)
Boiling Point: 187.142 °C at 760 mmHg
Flash Point: 48.858 °C
Solubility: Insoluble in water.
Appearance: slightly beige crystals
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 24/25-36-26
PSA: 0.00000
LogP: 2.83260
Synthetic route
768-90-1

1-Adamantyl bromide

281-23-2

adamantane

Conditions
ConditionsYield
With triethylsilane; dilauryl peroxide; 1-dodecylthiol at 70℃; for 1h;100%
With triethylsilane; dilauryl peroxide; 1-dodecylthiol In cyclohexane at 80℃; for 1h;100%
With sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); cPS-SnBu2Cl In 1,2-dimethoxyethane at 80℃; for 0.5h;100%
22110-53-8

1-adamantyl isocyanide

281-23-2

adamantane

Conditions
ConditionsYield
With Perbenzoic acid; diphenylsilane In 1,4-dioxane for 1h; Heating;100%
75480-69-2

1-(phenylseleno)tricyclo<3.3.1.13,7>decane

281-23-2

adamantane

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); 1,1,2,2-tetraphenyldisilane In ethyl acetate for 14h; Reduction; Heating;100%
With Perbenzoic acid; methyl phosphite In 1,4-dioxane for 5h; Heating;41 % Chromat.
79057-62-8

O-(adamantan-1-yl) S-methyl carbonodithioate

281-23-2

adamantane

Conditions
ConditionsYield
With sodium formate; (Bu4N)2S2O8 In N,N-dimethyl-formamide at 75℃; for 0.5h; Barton-McCombie deoxygenation;100%
With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane In toluene at 130℃; for 0.0833333h; Barton-McCombie deoxygenation;77%
With 1-ethyl-piperidine; 2,2'-azobis(isobutyronitrile); hypophosphorous acid In 1,4-dioxane for 1h;100 % Chromat.
With dibutylphosphine oxide; 1,1'-azobis(1-cyanocyclohexanenitrile) In 1,4-dioxane for 8h; Heating;90 % Chromat.
768-95-6

1-adamanthanol

A

281-23-2

adamantane

B

773-32-0

2-(1-adamantyl)propane

Conditions
ConditionsYield
With triisopropylborane; trifluorormethanesulfonic acid In 1,1,2-Trichloro-1,2,2-trifluoroethane 1.) -30 deg C, 30 min 2.) room temp., 6 h;A 99.9%
B 0.1%
768-95-6

1-adamanthanol

281-23-2

adamantane

Conditions
ConditionsYield
With hydrogen; aluminum oxide; nickel at 180℃;99%
With indium(III) chloride; diphenylsilyl chloride In 1,2-dichloro-ethane at 80℃; for 3h;99%
With boron trifluoride diethyl etherate In water for 2h; Inert atmosphere; Reflux;29%
700-57-2

1-adamantanol

281-23-2

adamantane

Conditions
ConditionsYield
With hydrogen; aluminum oxide; nickel at 170℃;99%
Multi-step reaction with 2 steps
1: 81 percent / NaI; HI / 48 h / 90 - 100 °C
2: 35 percent Chromat. / t-BuOK / dimethylsulfoxide / 3 h / Irradiation
View Scheme
Multi-step reaction with 2 steps
1: 81 percent / NaI; HI / 48 h / 90 - 100 °C
2: 20 percent Chromat. / t-BuOK / dimethylsulfoxide / 3 h / Irradiation
View Scheme
2825-83-4

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

281-23-2

adamantane

Conditions
ConditionsYield
With tris(trifluoromethanesulfonyloxy)boron In 1,1,2-Trichloro-1,2,2-trifluoroethane at 0 - 20℃; for 0.5h;98%
With tris(trifluoromethanesulfonyloxy)boron In 1,1,2-Trichloro-1,2,2-trifluoroethane at 0 - 20℃; for 0.5h; Product distribution; sonication, other C(4n+6)H(4n+12), (n=1-3), other polycyclic hydrocarbon, other reactants, reaction condition;98%
With aluminium trichloride at 150 - 180℃;
Mechanism; application of the "prinzip of minimal chemical distance";
768-93-4

1-iodoadamantane

281-23-2

adamantane

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); (C6F13CH2CH2)3SnH; sodium cyanoborohydride In tert-butyl alcohol at 90℃; for 3h;98%
With air; tributyl borane; water In benzene at 20℃;97%
With 1,3-bis(2,6-diiopropylphenyl)imidazol-2-ylidene borane In 1,2,3-trifluorobenzene at 140℃; for 12h;97%
768-93-4

1-iodoadamantane

A

281-23-2

adamantane

B

1-adamantanol

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tributyltin chloride; sodium cyanoborohydride; oxygen-18 In tert-butyl alcohol at 60℃; for 16h; Yields of byproduct given;A n/a
B 98%
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    【Chemical Name】Adamantane 【Synonym】Tricyclo[3.3.1.1(3,7)]decane 【CAS No】281-23-2 【Molecular Formula】C10H16 【Molecular Weight】136.26 【Structural Formula】 【Properties】White crystalline powder; Density: 1.07g/cm3(20/20 deg C); Melting Point: 266.00 -

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    Category : Agrochemicals CAS NO : 281-23-2 EC NO : 206-001-4 Molecular Formula : C10H16 Main Specifications : Synonyms : tricyclo(3.3.1.13,7)decane;tricyclo[3.3.1.1~3,7~]decane;

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Chemistry

Molecular Structure:
Molecular Formula: C10H16
Molecular Weight: 136.24
CAS NO: 281-23-2
EINECS: 206-001-4
H bond acceptors: 0
H bond donors: 0
Freely Rotating Bonds: 0
Polar Surface Area: 0 Å2
Index of Refraction: 1.517
Molar Refractivity: 42.22 cm3
Molar Volume: 139.4 cm3
Surface Tension: 34.4 dyne/cm
Density: 0.976 g/cm3
Flash Point: 48.9 °C
Enthalpy of Vaporization: 40.6 kJ/mol
Boiling Point: 187.1 °C at 760 mmHg
Vapour Pressure: 0.881 mmHg at 25°C
Melting Point: 209-212 °C (subl.)(lit.)
Stability: Stable. Combustible. Incompatible with strong oxidizing agents
Appearance: slightly beige crystals
IUPAC Name: Adamantane
Product Categories of Adamantane (CAS NO.281-23-2): Pharmaceutical Intermediates;Adamantane Derivative;Adamantane derivatives;Adamantanes;Alkanes;Cyclic;Organic Building Blocks

Uses

 Adamantane (CAS NO.281-23-2) is used in some dry etching masks. Besises, it is also used in some polymer formulations.
In dye lasers, Adamantane may be used to extend the life of the gain medium.

Production

Production of Adamantane (CAS NO.281-23-2):

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal > 10gm/kg (10000mg/kg)   Toksikologicheskii Vestnik. Vol. (4), Pg. 42, 1999.
mouse LD50 oral > 10gm/kg (10000mg/kg)   Toksikologicheskii Vestnik. Vol. (4), Pg. 42, 1999.
rat LD50 intraperitoneal > 5gm/kg (5000mg/kg)   Toksikologicheskii Vestnik. Vol. (4), Pg. 42, 1999.
rat LD50 oral > 10gm/kg (10000mg/kg)   Toksikologicheskii Vestnik. Vol. (4), Pg. 42, 1999.

Safety Profile

Safety Information about Adamantane (CAS NO.281-23-2):
Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements:  24/25-36-26 
S24/25: Avoid contact with skin and eyes. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36: Wear suitable protective clothing.
WGK Germany:  2
Hazard Note: Irritant
HS Code:  29021990

Specification

The chemical synonyms of Adamantane (CAS NO.281-23-2): Adamantane (8CI) ; Tricyclo(3.3.1.13,7)decane
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam. 
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Avoid ingestion and inhalation.
Storage: Store in a cool, dry place. Store in a tightly closed container.