Outline Uses
ChemicalBook > CAS DataBase List > 1-Adamantanol

1-Adamantanol

Outline Uses
Product Name
1-Adamantanol
CAS No.
768-95-6
Chemical Name
1-Adamantanol
Synonyms
ADAMANTANOL;ADAMANTAN-1-OL;1-Adamantol;1-Admantanol;(3s,5s,7s)-adamantan-1-ol;1-AD-OH;1-HYDROXYADAMANTANE;1-ADA-OH;damantol-(1);1-Adamatanol
CBNumber
CB2135047
Molecular Formula
C10H16O
Formula Weight
152.23
MOL File
768-95-6.mol
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1-Adamantanol Property

Melting point:
247 °C (subl.) (lit.)
Boiling point:
214.73°C (rough estimate)
Density 
0.8544 (rough estimate)
refractive index 
1.4880 (estimate)
Flash point:
240°C
storage temp. 
Sealed in dry,Room Temperature
solubility 
Chloroform (Sparingly), Methanol (Slightly)
form 
Crystalline Powder or Needles
pka
15.38±0.20(Predicted)
color 
White to off-white
Water Solubility 
Soluble in ethanol , methanol, and diethyl ether. Partly miscible in water.
Sublimation 
240 ºC
BRN 
1903952
InChIKey
VLLNJDMHDJRNFK-UHFFFAOYSA-N
CAS DataBase Reference
768-95-6(CAS DataBase Reference)
NIST Chemistry Reference
1-Adamantanol(768-95-6)
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
130346
Product name
1-Adamantanol
Purity
ReagentPlus , 99%
Packaging
5g
Price
$36.4
Updated
2024/03/01
Sigma-Aldrich
Product number
130346
Product name
1-Adamantanol
Purity
ReagentPlus , 99%
Packaging
25g
Price
$83.7
Updated
2024/03/01
TCI Chemical
Product number
A0939
Product name
1-Adamantanol
Purity
>98.0%(GC)
Packaging
25g
Price
$86
Updated
2024/03/01
TCI Chemical
Product number
A0939
Product name
1-Adamantanol
Purity
>98.0%(GC)
Packaging
250g
Price
$429
Updated
2024/03/01
Alfa Aesar
Product number
A10209
Product name
1-Adamantanol, 99%
Packaging
10g
Price
$33.65
Updated
2024/03/01
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1-Adamantanol Chemical Properties,Usage,Production

Outline

1-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.

Uses

1-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.

Description

1-Adamantanol is a cyclic molecule with a hydroxyl group. It is produced by the oxidation of 2-methyl-2-adamantanol. 1-Adamantanol has been shown to be an effective substrate for bioremediation in wastewater treatment plants and can be used as a precursor to produce trifluoroacetic acid.

Chemical Properties

white to off-white crystalline powder or needles

Uses

1-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 Methods

If 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.]

1-Adamantanol Preparation Products And Raw materials

Raw materials

Adamantane N-Hydroxyphthalimide Cobalt acetate N,N-Dimethylformamide Sodium thiosulfate Oxygen Hydrochloric acid Government regulation Acetic acid Methanol

Preparation Products

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View Lastest Price from 1-Adamantanol manufacturers

hebei hongtan Biotechnology Co., Ltd
Product
1-Adamantanol 768-95-6
Price
US $30.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
2000kg
Release date
2024-03-25
WUHAN FORTUNA CHEMICAL CO., LTD
Product
1-Adamantanol 768-95-6
Price
US $0.00/KG
Min. Order
1KG
Purity
98%min
Supply Ability
30tons/month
Release date
2023-02-02
Hebei Weibang Biotechnology Co., Ltd
Product
1-Adamantanol 768-95-6
Price
US $30.00-10.00/KG
Min. Order
50KG
Purity
99%
Supply Ability
500000kg
Release date
2024-10-29

768-95-6, 1-AdamantanolRelated Search:

Adamantane Amantadine Altrenogest 3-AMINO-1-ADAMANTANOL,1-AMINO-3-ADAMANTANOL,3-AMINO-1-ADAMANTANOL,1-AMINO-3-ADAMANTANOL,3-Amino-1-adamantanol Hydrate,3-Amino-1-adamantanol Hydrate 2-Pyrrolidinecarbonitrile,1-acetyl-,(2S)-(9CI) Dichloroacetyl chloride Vildagliptin Impurity 25 Vildagliptin Impurity 6 Vildagliptin IMpurity 2 (Mixture of DiastereoMers) N-acetic acid-1-aMino-3-adaMantanol Vildagliptin Impurity 19 1,3,5,7-tetrahydroxyadamantane L-Proline, 4-chloro-, trans- 2-Pyrrolidinecarboxamide,1-(hydroxyacetyl)-,(S)-(9CI) Vildagliptin Carboxylic Acid Vildagliptin iMpurity A-F Cyanuric acid cis-cyclo(Pro-Pro)

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  • HYDROXY ADAMANTANE (1-ADAMANTANOL)
  • 768-95-6
  • C9 to C30
  • Alcohols
  • Building Blocks
  • Oxygen Compounds
  • Organic Building Blocks
  • Adamantanes
  • Alcohols
  • Building Blocks
  • C9 to C10
  • Chemical Synthesis
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  • Oxygen Compounds
  • FINE Chemical & INTERMEDIATES
  • Adamantane derivatives