1-Adamantanol

Base Information

• Chemical Name: 1-Adamantanol
• CAS No.: 768-95-6
• Molecular Formula: C10H16O
• Molecular Weight: 152.236
• Hs Code.: 29061900
• European Community (EC) Number: 212-202-8
• NSC Number: 108837,91633
• UNII: P9J0B0C8ZB
• DSSTox Substance ID: DTXSID10227620
• Nikkaji Number: J3.324C
• Wikidata: Q72436615
• Metabolomics Workbench ID: 126406
• ChEMBL ID: CHEMBL2041310
• Mol file: 768-95-6.mol

Synonyms:1-adamantanol

Chemical Property of 1-Adamantanol

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder or needles
• Vapor Pressure: 0.00466mmHg at 25°C
• Melting Point: 247 °C (subl.)(lit.)
• Refractive Index: 1.58
• Boiling Point: 245.8 °C at 760 mmHg
• PKA: 15.38±0.20(Predicted)
• Flash Point: 101.131 °C
• PSA: 20.23000
• Density: 1.16 g/cm³
• LogP: 1.94750
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• Water Solubility.: Soluble in ethanol , methanol, and diethyl ether. Partly miscible in water.
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 152.120115130
• Heavy Atom Count: 11
• Complexity: 144

Purity/Quality:

99% ^*data from raw suppliers

1-Adamantanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C2CC3CC1CC(C2)(C3)O
• 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. 1-Adamantanol was used in the preparation of 1,3-adamantanediol. It is used in the manufacture of synthetic adamantane derivatives and adapalene.

Technology Process of 1-Adamantanol

There total 314 articles about 1-Adamantanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

acetonitrile (75-05-8,26809-02-9) + trans-N,N'-bis(1-adamantyl)diazene (24325-56-2) → 1,1'-Biadamantane (3732-31-8) + 1-adamanthanol (768-95-6) + N-(1-adamantyl)acetamide (880-52-4) + 1-acetyladamantane (1660-04-4)

Guidance literature:

With thianthrenium perchlorate; Further byproducts given; Ambient temperature;

DOI:10.1021/ja00294a066

Reference yield: 70.0%

1,3,5-triphenylverdazyl (2154-65-6) + acetonitrile (75-05-8,26809-02-9) → 1-adamanthanol (768-95-6) + N-(1-adamantyl)acetamide (880-52-4) + 2,4,6-triphenyl-1--1,2,3,4-tetrahydro-1,2,4,5-tetrazine (85963-93-5) + 1,3,5-triphenyl-6-(2,4,6-triphenyl-1,2,3,4-tetrahydro-1,2,3,5-tetrazinyl)-5,6-dihydro-1,2,3,5-tetrazinium iodide (89257-39-6)

Guidance literature:

With 1-iodoadamantane; at 50 ℃; for 960h; Further byproducts given; sealed tube;

Reference yield: 70.0%

1-iodoadamantane (768-93-4) + acetonitrile (75-05-8,26809-02-9) → 1-adamanthanol (768-95-6) + N-(1-adamantyl)acetamide (880-52-4) + 2,4,6-triphenyl-1--1,2,3,4-tetrahydro-1,2,4,5-tetrazine (85963-93-5) + 1,3,5-triphenyl-6-(2,4,6-triphenyl-1,2,3,4-tetrahydro-1,2,3,5-tetrazinyl)-5,6-dihydro-1,2,3,5-tetrazinium iodide (89257-39-6)

Guidance literature:

With 2,4,6-triphenylverdazyl radical; at 50 ℃; for 960h; Further byproducts given; sealed tube;

upstream raw materials:

1-Adamantyl bromide

pyridine

adamantane

methanol

Downstream raw materials:

1-Adamantanecarboxylic acid

1-chloroadamantane

N-(1-adamantyl)acetamide

1-adamantyl chloroformate

Refernces

Fluorodecarboxylation, rearrangement and cyclisation: the influence of structure and environment on the reactions of carboxylic acids with xenon difluoride

10.1016/j.tetlet.2009.02.090

The study investigates the reactions of various carboxylic acids with xenon difluoride (XeF2) in different reaction environments, specifically in CH2Cl2/Pyrex and CH2Cl2/PTFE. The researchers found that Pyrex acts as an effective heterogeneous catalyst, promoting electrophilic reactions that lead to rearrangement, cyclisation, and cationic products. In contrast, reactions in PTFE primarily result in fluorodecarboxylation, likely via a single electron transfer (SET) mechanism. The study examines six structurally diverse carboxylic acids and shows that the products vary significantly depending on the reaction environment. For instance, in Pyrex, the reaction of 1-adamantanecarboxylic acid with XeF2 yields 1-adamantanol, while in PTFE, it produces 1-fluoroadamantane. The study highlights the profound influence of the reaction vessel material on the mechanism and products of these reactions, providing insights into the formation of intermediate fluoroxenon esters and their subsequent transformations.

1-(4-Nitrophenoxycarbonyl)-7-pyridin-4-yl indolizine: A new versatile fluorescent building block. Application to the synthesis of a series of fluorescent β-cyclodextrins

10.1016/j.tet.2005.02.063

The research focuses on the synthesis and application of a new type of fluorescent building block, 1-(4-nitrophenoxycarbonyl)-7-pyridin-4-yl indolizine, and its derivatives (1a–d). These compounds incorporate a pyridinoindolizine unit and two potentially reactive sites, making them versatile for further structural modifications. The synthesis involves a 1,3-dipolar cycloaddition reaction using bipyridinium ylides and an activated dipolarophile. The newly synthesized building blocks were then reacted with mono-6-amino-6-deoxy-β-cyclodextrin to produce fluorescent water-soluble hosts (2a–d) in good yields. The sensor properties of these hosts were tested in the presence of 1-adamantanol, showing changes in fluorescence emission. Key chemicals involved in this research include bipyridine, various substituted bromoacetophenones, triethylamine, 4-nitrophenylpropiolate, and β-cyclodextrin. The study highlights the potential of these new fluorescent building blocks for applications in biological and supramolecular recognition fields.