cis-1,3-Dimethylcyclohexane

• CAS: 638-04-0
• Catalog Number: ACM638040
• Category: Alkanes
• Molecular Weight: 112.21
• Molecular Formula: C₈H₁₆
• Synonyms: Hexahydro-m-xylene, cis-1,3-Dimethylcyclohexane, 1,3-Dimethylcyclohexane,c&t, Cyclohexane, 1,3-dimethyl-, trans-1,3-Dimethylcyclohexane, 1,3-DIMETHYLCYCLOHEXANE, 118389_ALDRICH, MolPort-003-910-912, CID11564, NSC74161, Cyclohexane, 1,3-dimethyl-, cis-, EINECS 209-707-0, EINECS 211-316-5, NSC 74159, Cyclohexane, 1,3-dimethyl-, trans-, 1,3-DIMETHYLCYCLOHEXANE, Cis-trans, ST5409829, D0699, 1,3-Dimethylcyclohexane, mixture of cis and trans, Cyclohexane, 1,3-dimethyl-, cis- (8CI)(9CI)
• IUPAC Name: 1,3-dimethylcyclohexane
• Canonical SMILES: CC1CCCC(C1)C
• InChI Key: SGVUHPSBDNVHKL-UHFFFAOYSA-N
• Boiling Point: 120ºC(lit.)
• Melting Point: -76ºC
• Flash Point: 42 °F
• Density: 0.784 g/mL at 25ºC(lit.)
• EC Number: 211-316-5
• Exact Mass: 112.12500
• Hazard Statements: H225-H304-H315-H336-H410
• H-Bond Acceptor: 0
• H-Bond Donor: 0
• Packing Group: II
• RIDADR: NONH for all modes of transport
• Safety Description: 16-29-33
• Symbol: GHS02

Case Study

Ring-Opening Reaction of 1,3-Dimethylcyclohexane over Iridium Catalysts

Do, Phuong T., et al. Journal of Catalysis, 2006, 238(2), 477-488.

This research explored the ring-opening reaction of 1,3-dimethylcyclohexane (1,3-DMCH) utilizing Ir catalysts mounted on Al2O3, SiO2, and TiO2 supports. Researchers used this cycloalkane molecule as a test reactant to examine potential reaction pathways in diesel and gasoline treatment processes that aim to enhance both cetane number (CN) and octane number. Ring-opening of cycloalkanes can improve CN only when C single bond cleavage occurs at the substituted position.
Key Findings
· The ring opening of 1,3-DMCH over a highly dispersed Ir/Al2O3 catalyst produces three main products: 2-methylheptane (2-MC7), 4-methylheptane (4-MC7), and 2,4-dimethylhexane (2,4-DMC6), which correspond to C-C openings at positions a, b, and c, respectively.
· There is a notable difference in the cleavage ratio of substituted to unsubstituted bonds depending on the support used, with the trend as follows: Ir/Al2O3 ≈ Ir/TiO2 >> Ir/SiO2. Therefore, to enhance the cetane number (CN), titania or alumina supports are preferable, whereas silica is the best choice for achieving a higher octane number.
· Additionally, the propensity for breaking the substituted C-C bonds at position a (inside the methyl groups) and position b (outside) varies with the support as well. The ratio a/b is crucial since there is a substantial difference in CN between the products resulting from these two bond cleavages. Opening at position a yields 2-MC7 (CN = 47), while opening at position b results in 4-MC7 (CN = 40), making a higher a/b ratio favorable. The C-C bond inside the two methyl substituents (a) is preferentially ruptured in comparison with the C-C bonds outside the groups (b).

Custom Q&A

What is the molecular formula of cis-1,3-Dimethylcyclohexane?

The molecular formula of cis-1,3-Dimethylcyclohexane is C8H16.

What is the molecular weight of cis-1,3-Dimethylcyclohexane?

The molecular weight of cis-1,3-Dimethylcyclohexane is 112.21 g/mol.

What is the IUPAC name for cis-1,3-Dimethylcyclohexane?

The IUPAC name for cis-1,3-Dimethylcyclohexane is (1R,3S)-1,3-dimethylcyclohexane.

What is the InChI of cis-1,3-Dimethylcyclohexane?

The InChI of cis-1,3-Dimethylcyclohexane is InChI=1S/C8H16/c1-7-4-3-5-8(2)6-7/h7-8H,3-6H2,1-2H3/t7-,8+.

What is the InChIKey of cis-1,3-Dimethylcyclohexane?

The InChIKey of cis-1,3-Dimethylcyclohexane is SGVUHPSBDNVHKL-OCAPTIKFSA-N.

What is the canonical SMILES of cis-1,3-Dimethylcyclohexane?

The canonical SMILES of cis-1,3-Dimethylcyclohexane is CC1CCCC(C1)C.

How many hydrogen bond donor counts are there in cis-1,3-Dimethylcyclohexane?

There are 0 hydrogen bond donor counts in cis-1,3-Dimethylcyclohexane.

How many hydrogen bond acceptor counts are there in cis-1,3-Dimethylcyclohexane?

There are 0 hydrogen bond acceptor counts in cis-1,3-Dimethylcyclohexane.

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

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

How many defined atom stereocenter counts are there in cis-1,3-Dimethylcyclohexane?

There are 2 defined atom stereocenter counts in cis-1,3-Dimethylcyclohexane.