1-Adamantanol

1-Adamantanol Basic information
Outline Uses
Product Name:1-Adamantanol
Synonyms:TRICYCLO[3.3.1.1(3,7)]DECAN-1-OL;TRICYCLO[3.3.1.1]DECAN-1-OL;1-HYDROXYDIAMANTANE;1-HYDROXYADAMANTANE;1-AD-OH;1-ADA-OH;1-ADAMANTANOL;1-Adamantol
CAS:768-95-6
MF:C10H16O
MW:152.23
EINECS:212-202-8
Product Categories:Alcohols;Building Blocks;C9 to C10;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;Pharmaceutical Raw Materials;Adamantane Derivative;FINE Chemical & INTERMEDIATES;Adamantane derivatives;Adamantanes;K00001
Mol File:768-95-6.mol
1-Adamantanol Structure
1-Adamantanol Chemical Properties
Melting point 247 °C (subl.) (lit.)
Boiling point 214.73°C (rough estimate)
density 0.8544 (rough estimate)
refractive index 1.4880 (estimate)
Fp 240°C
storage temp. Sealed in dry,Room Temperature
solubility Chloroform (Sparingly), Methanol (Slightly)
pka15.38±0.20(Predicted)
form Crystalline Powder or Needles
color White to off-white
Water Solubility Soluble in ethanol , methanol, and diethyl ether. Partly miscible in water.
Sublimation 240 ºC
BRN 1903952
InChIKeyVLLNJDMHDJRNFK-UHFFFAOYSA-N
CAS DataBase Reference768-95-6(CAS DataBase Reference)
NIST Chemistry Reference1-Adamantanol(768-95-6)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 22-24/25-36-26
WGK Germany 3
RTECS AU4980000
Hazard Note Irritant
HS Code 29061900
MSDS Information
ProviderLanguage
1-Hydroxyadamantane English
ACROS English
SigmaAldrich English
ALFA English
1-Adamantanol Usage And Synthesis
Outline1-adamantanol is also known as 1-hydroxide adamantane, 1-tricyclo [3.3.1.1 (3.7)] decyl alcohol. At room temperature, it is white crystalline powder with the melting point higher than 240 ℃. It is soluble in organic solvents and insoluble in water with sublimation property. It can be used for the manufacture of synthetic adamantane derivatives and adapalene. It can react with vinylidene chloride to generate 1-adamantane acetic acid. 1-adamantyl acetate can further undergo bromination and hydrolyzed into 3-hydroxy-1-adamantyl acetate which can further react with vinylidene chloride to give 1, 3-adamantane di-acetic acid.
1-adamantanol can have Friedel-Crafts alkylation reaction acetanilide in the 98% sulfuric acid medium at room temperature for direct synthesis of 1, 3-bis (4-acetylamino-phenyl) adamantane which can undergo alkaline hydrolysis for synthesis of 1, 3 bis (4-aniline) adamantane. The synthetic route has many advantages including relative high reaction yield and easy purification, etc., therefore greatly facilitating the synthesis of 1, 3-diaryl adamantane derivatives.
The above information is edited by the Chemicalbook of Dai Xiongfeng.

Uses1-adamantanol can be used as the intermediate for synthesis of adamantanes derivatives. For example, it can be used for the manufacture of synthetic adamantane derivatives and adapalene. It can react with vinylidene chloride to give 1-adamantane acetic acid.
Chemical Propertieswhite to off-white crystalline powder or needles
Uses1-Adamantanol was used in the preparation of 1,3-adamantanediol. It is used in the manufacture of synthetic adamantane derivatives and adapalene.
Synthesis Reference(s)Synthetic Communications, 19, p. 2061, 1989 DOI: 10.1080/00397918908052598
Tetrahedron Letters, 28, p. 1941, 1987 DOI: 10.1016/S0040-4039(00)96015-5
Purification MethodsIf 2-adamantanol is a suspected impurity, then dissolve the substance (10g) in acetone (100mL) and add Jones's reagent [CrO3 (10.3g) in H2O (30mL)], then conc H2SO4 (8.7mL) is added dropwise (turns green in colour) until excess reagent is present (slight red colour). Stir overnight, decant the acetone solution from the Cr salts and adamantan-2-one, dry (Na2SO4) and evaporate to dryness. The residue (ca 7g) is chromatographed through Al2O3 (250g) and washed with 50% *benzene/pet ether (b 40-60o), then 100% Et2O (to remove any adamantan-2-one present) and the 1-adamantanol is then eluted with 5% MeOH in Et2O. The eluate is evaporated, and the residue is recrystallised from pet ether (b 30-60o) at -70o, m 287.2-288.5o. It also crystallises from MeOH and can be sublimed in vacuo. It has characteristic IR, max 3640, 1114, 1086, 982 and 930cm-1. [Schleyer & Nicholas J Am Chem Soc 83 182 1961.] [Beilstein 6 IV 391.] Alternatively, if free from the 2-isomer, dissolve it in tetrahydrofuran, dilute with H2O to precipitate the alcohol. Collect, dry and sublime it in a vacuum at 130o. [Stetter et al. Chem Ber 92 1629 1959.]
4-CHLOROADAMANTAN-1-OL FMOC-ASP(O-1-ADA)-OH AURORA 109 1-Adamantanol Adamantane 2-Adamantanol, 98+%,2-Adamantanol, 98+%,2-ADAMANTANOL,2-ADAMANTANOL AKOS BC-1011 1-(3-(Dimethylamino)propoxy)adamantane ethyl iodide 1,4-Adamantandiol 5-Hydroxyadamantan-2-one AURORA 5535 AKOS BB-8750 AKOS BC-0967 AKOS BB-9596 AKOS BC-1178 1-ADAMANTYL 2-CHLOROACETATE 1-ADAMANTYLOXYCARBONYL FLUORIDE AKOS BC-0527

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