1-Adamantanemethanol

Base Information

• Chemical Name: 1-Adamantanemethanol
• CAS No.: 770-71-8
• Molecular Formula: C11H18O
• Molecular Weight: 166.263
• Hs Code.: 29061900
• European Community (EC) Number: 212-225-3
• DSSTox Substance ID: DTXSID20227818
• Nikkaji Number: J79.946G
• Wikidata: Q72436597
• Mol file: 770-71-8.mol

Synonyms:Tricyclo(3.3.1.13,7)dec-1-ylmethanol;1-Hydroxymethyl-adamantane;1-Adamantane Methanol;

Chemical Property of 1-Adamantanemethanol

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0.00148mmHg at 25°C
• Melting Point: 115- 118 °C
• Refractive Index: 1.545
• Boiling Point: 263.1 °C at 760 mmHg
• Flash Point: 123.4 °C
• PSA: 20.23000
• Density: 1.088 g/cm³
• LogP: 2.19510
• Storage Temp.: Store below +30°C.
• Water Solubility.: Insoluble in water. Solubility in methanol (almost transparency).
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 166.135765193
• Heavy Atom Count: 12
• Complexity: 156

Purity/Quality:

99% ^*data from raw suppliers

1-Adamantanemethanol ^*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)CO
• Description: 1-Adamantanemethanol acts as guest molecule and forms β-cyclodextrin complexes. It reacts with 3,4,5,6-tetrafluorophthalonitrile to yield 3,4,5,6-tetra-(1-adamantylmethoxy)phthalonitrile.
• Uses: 1-Adamantanemethanol was used in the synthesis of axially disubstituted silicon(IV) phthalocyanines. It is used as a reagent in the synthesis of adamantane and noradamantane based histone deacetylase (HDAC) inhibitors for the treatment of cancer. It is also used as a reagent in the synthesis of (1-adamantyl)methyl glycidyl ether, a versatile building block for living polymerization. References Gopalan, B., et al.: Bioorg. Med. Chem. Lett., 23, 2532 (2013); Suzuki, T., et al.: J. Med. Chem., 55, 9562 (2012); Moers, C., et al.: Macromol. Rapid Comm., 35, 1075 (2014) 1-Adamantanemethanol was used in the synthesis of axially disubstituted silicon(IV) phthalocyanines.

Technology Process of 1-Adamantanemethanol

There total 50 articles about 1-Adamantanemethanol 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: 99.0%

methyl adamantane-1-carboxylate (711-01-3) → 1-adamantanemethanol (770-71-8)

Guidance literature:

With Li⁽¹⁺⁾*C₁₂H₂₈AlO₃^(1-); In tetrahydrofuran; hexane; for 0.5h; Ambient temperature;

DOI:10.1021/jo00184a010

Reference yield: 99.0%

carbon monoxide (201230-82-2) + 1-iodoadamantane (768-93-4) → 1-adamantanemethanol (770-71-8)

Guidance literature:

carbon monoxide; 1-iodoadamantane; With diethoxymethylane; [CuCl(IPr^Me)]; lithium methanolate; In tetrahydrofuran; at 60 ℃; for 16h; under 2280.15 Torr; Sealed tube;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; diethyl ether; at 20 ℃; for 2h;

DOI:10.1002/anie.201801814

Reference yield: 98.0%

1-Adamantanecarboxylic acid (828-51-3) → 1-adamantanemethanol (770-71-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; Reflux;

DOI:10.1002/ejoc.201500691

upstream raw materials:

ethyl 1-adamantanecarboxylate

2-adamantan-1-yl-2-ethoxy-oxazolidine-4,5-dione

1-Adamantanecarboxylic acid

1-Adamantanecarbonyl chloride

Downstream raw materials:

Homoadamantane-3-carboxylic acid

Homoadamantane-1-carboxylic acid

[4-(Tetrahydro-pyran-2-yloxy)-phenyl]-acetic acid adamantan-1-ylmethyl ester

1-(bromomethyl)adamantane

Refernces

• 1、 Saito, Susumu,Wen, Ke,Yoshioka, Shota. "Development of effective bidentate diphosphine ligands of ruthenium catalysts toward practical hydrogenation of carboxylic acids". . p. 1510 - 1524. Retrieved 2021/06/18.
• 2、 Caiger, Lewis,Constantin, Timothée,Douglas, James J.,Juliá, Fabio,Leonori, Daniele,Sheikh, Nadeem S.,Sinton, Conar. "Radical hydroxymethylation of alkyl iodides using formaldehyde as a C1 synthon". . p. 10448 - 10454. Retrieved 2021/08/20.