1,3-Dimethyladamantane

• CAS: 702-79-4
• Catalog Number: ACM702794
• Category: Alkanes
• Molecular Weight: 164.29
• Molecular Formula: C12H20
• Description: 1,3-Dimethyladamantane is a dimethylated adamantane derivative. Memantine impurity A.
• Synonyms: 1,3-Dimethyladamantane;1,3-dimethyl-adamantane;1,3-Me2-adamantane;Adamantane,1,3-dimethyl
• Melting Point: -30ºC
• Flash Point: 52ºC
• Density: 0.886
• Appearance: Clear colorless liquid
• EC Number: 211-870-8
• Hazard Codes: F
• Hazard Statements: H226
• HS Code: 2902199090
• LogP: 3.61280
• Refractive Index: 1.477-1.479
• RIDADR: UN 1993 3/PG 3
• Stability: Stable. Incompatible with strong oxidizing agents. Flammable.
• Storage Conditions: Keep away from sources of ignition. Store in a cool, dry place. Store in a tightly closed container.
• Symbol: GHS02
• WGK Germany: 3

Case Study

Study on the Thermal Stability and Decomposition Kinetics of 1,3-Dimethyladamantane

Qin, Xiaomei, et al. Energy & fuels, 2014, 28(10), 6210-6220.

The ring geometry of adamantane derivatives creates distinctive cage-like structures which allow them to store energy. A complete assessment of 1,3-dimethyladamantane's potential as a high-energy-density hydrocarbon fuel required investigation of its thermal stability across different conditions.
Key Findings
· In a batch reactor from 693 K to 743 K the thermal decomposition rate constants of 1,3-DMA increased from 4.00 × 10^-7 s^-1 to 35.19 × 10^-7 s^-1 with Arrhenius parameters A = 2.39 × 10⁷ s^-1 and E_a = 183 kJ·mol^-1. The rate constants measured for 1,3-DMA were significantly reduced when compared to those of traditional fuels including decalin, propylcyclohexane, butylcyclohexane, and n-dodecane which shows that 1,3-DMA has better thermal stability.
· Further experiments in a flowing reactor (873-973 K, 0.1-5.0 MPa) demonstrated that 1,3-DMA conversion and gaseous product yields rose significantly with temperature or pressure, while residence time primarily governed decomposition depth. Methane and hydrogen, formed via demethylation and dehydrogenation, dominated gaseous products.
· Liquid residues contained toluene and xylene as major aromatic compounds, identified through GC-MS, HPLC, and NMR. Based on compositional analysis, a proposed decomposition mechanism involving isomerization, hydrogen transfer, β-scission, and dehydrogenation accounts for the observed product distribution.

Selectivity of Biomimetic Oxidation of 1,3-Dimethyladamantane in a Gif-Type System

Vasil'eva, V. V., et al. Kinetics and catalysis, 2006, 47, 610-623.

The study studied how the composition of the heterogeneous catalytic system made from Fe2SO4·7H2O, picolinic acid (pyridine-2-carboxylic acid), pyridine and system preparation procedures impacts the selectivity during oxidation of 1,3-dimethyladamantane (1,3-DMA) with aqueous hydrogen peroxide solution in aqueous acetonitrile solvent at room temperature under ambient pressure.
1,3-DMA was selected as the substrate due to its structural inclusion of all C-H bond types (primary, secondary, tertiary). Compared to adamantane, 1,3-DMA offers three distinct methylene groups, exists as a liquid under ambient conditions (simplifying handling), and exhibits superior solubility in acetonitrile.
Key Findings
Under optimized catalytic conditions, oxidation product yields increased dramatically from initial values below 1% to over 10%. Three distinct mechanisms were identified: radical, ion-molecule, and radical-cation pathways. The radical mechanism generated a non-selective mixture of products from tertiary and secondary C-H bonds. In contrast, the ion-molecule pathway targeted secondary bonds, while the radical-cation mechanism exclusively oxidized tertiary bonds. Notably, under Gif-type conditions, the selectivity for tertiary alcohol formation matched that of biological oxidation systems.

Custom Q&A

What is the molecular formula of 1,3-Dimethyladamantane?

The molecular formula of 1,3-Dimethyladamantane is C12H20.

When was the PubChem CID for 1,3-Dimethyladamantane created?

The PubChem CID for 1,3-Dimethyladamantane was created on 2005-03-27.

What is the molecular weight of 1,3-Dimethyladamantane?

The molecular weight of 1,3-Dimethyladamantane is 164.29 g/mol.

What is the IUPAC Name of 1,3-Dimethyladamantane?

The IUPAC Name of 1,3-Dimethyladamantane is 1,3-dimethyladamantane.

What is the InChIKey of 1,3-Dimethyladamantane?

The InChIKey of 1,3-Dimethyladamantane is CWNOIUTVJRWADX-UHFFFAOYSA-N.

How many hydrogen bond donor count does 1,3-Dimethyladamantane have?

1,3-Dimethyladamantane has 0 hydrogen bond donor counts.

What is the XLogP3-AA value of 1,3-Dimethyladamantane?

The XLogP3-AA value of 1,3-Dimethyladamantane is 4.6.

How many rotatable bond counts does 1,3-Dimethyladamantane have?

1,3-Dimethyladamantane has 0 rotatable bond counts.

What is the topological polar surface area of 1,3-Dimethyladamantane?

The topological polar surface area of 1,3-Dimethyladamantane is 0Ų.

How many covalently-bonded unit counts does 1,3-Dimethyladamantane have?

1,3-Dimethyladamantane has 1 covalently-bonded unit count.