Adamantane-1,4-diol

Base Information

• Chemical Name: Adamantane-1,4-diol
• CAS No.: 20098-16-2
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.236
• Hs Code.: 2906199090
• DSSTox Substance ID: DTXSID50401245
• Metabolomics Workbench ID: 57051
• Wikidata: Q27121274
• Mol file: 20098-16-2.mol

Synonyms:adamantane-1,4-diol;20098-16-2;1,4-ADAMANTANDIOL;1,4-Adamantanediol;1,4-dihydroxyadamantane;Tricyclo[3.3.1.13,7]decane-1,4-diol;1,4(a)-Dihydroxyadamantane;Oprea1_146509;SCHEMBL1772242;CHEBI:48583;DTXSID50401245;AUKWRHADVIQZRJ-UHATZWDWSA-N;AUKWRHADVIQZRJ-UHFFFAOYSA-N;AKOS003607725;SB84857;BS-42515;FT-0720332;A814238;Q27121274

Chemical Property of Adamantane-1,4-diol

Chemical Property:

• Melting Point: 327-331 °C
• Boiling Point: 319.0±10.0 °C(Predicted)
• PKA: 14.59±0.40(Predicted)
• PSA: 40.46000
• Density: 1.312±0.06 g/cm3(Predicted)
• LogP: 0.91830
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 168.115029749
• Heavy Atom Count: 12
• Complexity: 198

Purity/Quality:

98%,99%, ^*data from raw suppliers

Adamantane-1,4-diol 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2CC3CC(C2)(CC1C3O)O

Technology Process of Adamantane-1,4-diol

There total 12 articles about Adamantane-1,4-diol 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: 93.0%

chemantane (20098-14-0) → 1,4-dihydroxyadamantane (73346-81-3,73346-82-4,20098-16-2)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 20 ℃; for 4h;

DOI:10.1023/A:1020989123733

Reference yield: 80.0%

1,4-diacetoxyadamantane (68193-15-7,68224-91-9) → 1,4-dihydroxyadamantane (73346-81-3,73346-82-4,20098-16-2)

Guidance literature:

With potassium hydroxide; ethanol;

DOI:10.1021/jo00253a033

Reference yield: 24.0%

adamantane (281-23-2) → 1-adamanthanol (768-95-6) + 1,3-adamantandiol (5001-18-3) + 2-hydroxytricyclo<3.3.1.13,7>decane (700-57-2) + tricyclo<3.3.1.13,7>decane-1-4ax-diol (20098-16-2,73346-81-3,73346-82-4)

Guidance literature:

With Absidia glauca (IMI₂₃₉₆₉₃); In N,N-dimethyl-formamide; at 23 ℃; for 260h; Product distribution; var. fungi of the genus Absidia and times;

upstream raw materials:

1,4-diacetoxyadamantane

4-Nitro-benzenesulfonic acid (1R,2S,3S,5S)-5-hydroxy-adamantan-2-yl ester

1-adamantanol

chemantane

Downstream raw materials:

C₆H₁₅N*C₂₃H₂₇O₆P

Refernces

• 1、 Fukunishi, Koushi,Kohno, Atsuya,Kojo, Shosuke. "Photoacetylation of 2-Substituted Adamantanes. Stereochemistry and Substituent Effects". . p. 4369 - 4374. Retrieved 1988.
• 2、 Zefirova, Olga N.,Raguzin, Ivan S.,Gogol, Vladimir V.,Nurieva, Evgeniya V.,Belenikin, Maxim S.. "Phosphates of bridgehead alcohols as putative inositol monophosphatase inhibitors: Molecular design and synthetic approach". body text. p. 242 - 244. Retrieved 2012/07/14.
• 3、 -. "POSITIVE RESIST COMPOSITION AND PATTERNING PROCESS". . . Retrieved 2010/04/23.