1-Adamantanol

• CAS: 768-95-6
• Catalog Number: ACM768956-2
• Category: Main Products
• Molecular Weight: 152.23
• Molecular Formula: C10H16O
• Synonyms: Tricyclo[3.3.1.1(3,7)]decan-1-ol
• IUPAC Name: adamantan-1-ol
• SMILES: C1C2CC3CC1CC(C2)(C3)O
• InChI Key: VLLNJDMHDJRNFK-UHFFFAOYSA-N
• Boiling Point: 245.8ºC at 760 mmHg
• Melting Point: 240ºC
• Flash Point: 240ºC
• Density: 1.16 g/cm³
• Appearance: White crystal
• Active Content: 95%
• EC Number: 212-202-8
• Exact Mass: 152.12000
• Hazard Statements: Xi
• Physical State: Solid
• Safety Description: S24/25
• Stability: Stable under normal temperatures and pressures.
• WGK Germany: 3

Case Study

1-Adamantanol as a Substrate for Regioselective Microbial Hydroxylation to 1,3-Adamantanediol

Mitsukura, Koichi, et al. Journal of bioscience and bioengineering 109.6 (2010): 550-553.

Hydroxylated adamantane derivatives, particularly 1,3-adamantanediol (1,3-ad(OH)2), are valuable functional materials for photoresist layers and other advanced applications. This study investigated the microbial hydroxylation of 1-adamantanol (1-adOH) using soil isolate Streptomyces sp. SA8.
Strain SA8 was selected from 540 screened microorganisms based on its high hydroxylation activity toward 1-adOH. The reaction products were purified and identified by NMR and mass spectrometry as 1,3-ad(OH)2 and 1,4-ad(OH)2. Optimization of culture conditions and the use of detergents significantly enhanced productivity.
Key Results:
· In culture broth with 6.2 g/L 1-adOH and 1% Tween 20, Streptomyces sp. SA8 produced 5.9 g/L 1,3-ad(OH)2 after 120 h at 25 °C, corresponding to 85% conversion with a 85:15 selectivity ratio for 1,3- over 1,4-ad(OH)2-substantially higher regioselectivity than previously reported for Absidia strains (60:40).
· Using resting cells with glycerol as an energy source, 2.3 g/L 1,3-ad(OH)2 was produced from 3.0 g/L 1-adOH (69% conversion) after 96 h, achieving higher volumetric productivity (0.80 g/L·g dry cell /weight/h) than the culture broth system.
· Induction studies showed that 1-adOH itself (0.3% w/v) was the most effective inducer of hydroxylation activity, with Tween 20 further enhancing enzyme formation.
· The hydroxylation system also accepted 2-adamantanol and 2-methyl-2-adamantanol as substrates, yielding meso-2,4-ad(OH)2 and other diols.

1-Adamantanol as a Substrate for Copper-Catalyzed Alkenylation with Isopropanol

Gallyamova, Leysan, et al. "CuBr2-Catalyzed Alkenylation of 1-adamantanol with Isopro-panol." (2022).

Adamantane derivatives are valuable framework compounds with diverse applications in medicine and materials science. Selective introduction of unsaturated side chains into the adamantane skeleton remains challenging. This study reports the copper-catalyzed alkenylation of 1-adamantanol with isopropanol. Using catalytic copper(II) bromide, the reaction proceeds via in situ dehydration of isopropanol to propene, followed by electrophilic addition to the adamantyl cation generated from 1-adamantanol.
Key Results:
· Under optimized conditions ([CuBr2]:[1-AdOH]:[i-PrOH] = 10:100:1000, 220 °C, 4 h), (1E)-prop-1-en-1-yladamantane was obtained in 88% isolated yield, with adamantane (12%) as the only byproduct.
· The reaction exhibits high stereoselectivity for the E-isomer, consistent with DFT calculations (B3LYP/6-31G(d)) showing the E-isomer to be 5.0 kcal/mol more stable than the Z-isomer.
· A plausible mechanism involves: (1) dehydration of isopropanol to propene, (2) generation of 1-adamantyl cation from 1-adamantanol, and (3) electrophilic addition to form the alkenylated product. Adamantane formation likely results from intermolecular hydride transfer.
· The method provides a convenient one-step route to alkenyladamantanes using inexpensive copper catalyst and readily available alcohols, avoiding the need for preformed olefins or strong acids.

1-Adamantanol as a Model Substrate for Flow Friedel-Crafts Alkylation Using a Solid Acid Catalyst

Kasakado, Takayoshi, et al. Journal of the Chinese Chemical Society 67.12 (2020): 2253-2257.

1-Aryladamantanes are valuable framework compounds with applications in materials science and medicinal chemistry. This study evaluated 1-adamantanol as a model substrate for flow Friedel-Crafts alkylation using hydroxy-substituted sulfonic acid-functionalized silica (HO-SAS) as an immobilized acid catalyst. A stainless-steel packed-bed reactor containing HO-SAS was employed in a continuous flow setup, enabling rapid reaction optimization and prolonged operation without catalyst deactivation.
Key Results:
· Under optimized flow conditions (120 °C, 5 min residence time), 1-adamantanol reacted with toluene to give 1-tolyladamantane in 82% yield with high para-selectivity (o/m/p = 0/10/90)-significantly faster than the batch reaction (2 h, 70% yield).
· The flow system demonstrated excellent catalyst durability: over 2.5 h continuous operation, five consecutive fractions maintained 92-97% product yield, attributed to continuous removal of water byproduct from the catalyst bed.
· Substrate scope evaluation showed that 1-adamantanol reacted efficiently with various arenes: anisole gave 75% yield of 1-(methoxyphenyl)adamantane (o/m/p = 32/0/68), o-xylene afforded 93% yield of 1-(3,4-xylyl)adamantane, while benzene showed modest reactivity (30% yield of 1-phenyladamantane).
· The high efficiency in flow (catalyst/substrate ratio = 3.7) enabled by the packed-bed configuration allows for extremely short residence times compared to batch processing.

Custom Q&A

What is the IUPAC name of the product 1-Adamantanol?

The IUPAC name of the product 1-Adamantanol is adamantan-1-ol.

What is the molecular formula of 1-Adamantanol?

The molecular formula of 1-Adamantanol is C10H16O.

What is the boiling point of 1-Adamantanol?

The boiling point of 1-Adamantanol is 245.8°C at 760 mmHg.

What is the melting point of 1-Adamantanol?

The melting point of 1-Adamantanol is 240°C.

What is the purity of 1-Adamantanol?

The purity of 1-Adamantanol is 99%+.

What is the density of 1-Adamantanol?

The density of 1-Adamantanol is 1.16 g/cm³.

What is the appearance of 1-Adamantanol?

The appearance of 1-Adamantanol is white crystal.

What are some typical applications of 1-Adamantanol?

Some typical applications of 1-Adamantanol include its use as an emulsifying agent, dispersing agent, lubricant, and intermediate in organic synthesis.

What percentage of actives does 1-Adamantanol contain?

1-Adamantanol contains 95% actives.

What is the CAS number of 1-Adamantanol?

The CAS number of 1-Adamantanol is 768-95-6.