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Name	Adamantane	EINECS	206-001-4
CAS No.	281-23-2	Density	0.977 g/cm³
PSA	0.00000	LogP	2.83260
Solubility	Insoluble in water.	Melting Point	209-212 °C (subl.)(lit.)
Formula	C₁₀H₁₆	Boiling Point	187.142 °C at 760 mmHg
Molecular Weight	136.237	Flash Point	48.858 °C
Transport Information	N/A	Appearance	slightly beige crystals
Safety	24/25-36-26	Risk Codes	36/37/38
Molecular Structure		Hazard Symbols	Xi
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);	Article Data	357

Adamantane Synthetic route

: 768-90-1
1-Adamantyl bromide

: 281-23-2
adamantane

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

Adamantane Chemical Properties

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

Adamantane 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.

Adamantane Production

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

Adamantane Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	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.

Adamantane Safety Profile

Safety Information about Adamantane (CAS NO.281-23-2):
Hazard Codes: Irritant Xi
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

Adamantane 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.

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