6-Thiabicyclo[3.2.1]octane

Base Information

• Chemical Name: 6-Thiabicyclo[3.2.1]octane
• CAS No.: 279-91-4
• Molecular Formula: C7H12S
• Molecular Weight: 128.23500
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID90339851
• Nikkaji Number: J100.362C
• Mol file: 279-91-4.mol

Synonyms:6-Thiabicyclo[3.2.1]octane;279-91-4;SCHEMBL10080648;DTXSID90339851

Chemical Property of 6-Thiabicyclo[3.2.1]octane

Chemical Property:

• PSA: 25.30000
• LogP: 2.29200
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 128.06597156
• Heavy Atom Count: 8
• Complexity: 90.4

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2CC(C1)SC2
• General Description: 6-Thiabicyclo[3.2.1]octane is a bicyclic sulfur-containing compound synthesized via reduction of its brominated derivative, endo-4-bromo-6-thiabicyclo[3.2.1]octane, using triphenyltin hydride. It exhibits structural rigidity and steric hindrance due to the sulfur bridge, which contributes to its low reactivity in common elimination, displacement, and solvolytic reactions. The compound serves as a precursor for further derivatives, such as 6-thiabicyclo[3.2.1]oct-3-ene, highlighting its utility in the synthesis of functionalized sulfur heterocycles.

Technology Process of 6-Thiabicyclo[3.2.1]octane

There total 3 articles about 6-Thiabicyclo[3.2.1]octane 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:

4-(hydroxymethyl)cyclohexan-1-ol (33893-85-5) → 6-Thiabicyclo<3.2.1>octan (279-91-4)

Guidance literature:

With hydrogen bromide; Erwaermen des jeweiligen Reaktionsprodukts mit Natriumsulfid in wss. Aethanol;

DOI:10.1021/jo01363a015

Reference yield:

3-(hydroxymethyl)cyclohexan-1-ol (76140-18-6) → 6-Thiabicyclo<3.2.1>octan (279-91-4)

Guidance literature:

With hydrogen bromide; Erwaermen des jeweiligen Reaktionsprodukts mit Natriumsulfid in wss. Aethanol;

DOI:10.1021/jo01363a015

Reference yield:

→ 6-Thiabicyclo<3.2.1>octan (279-91-4)

Guidance literature:

endo-4-Brom-6-thiabicyclo<3.2.1>octan 5, Red.;

DOI:10.1021/jo00805a031

upstream raw materials:

4-(hydroxymethyl)cyclohexan-1-ol

3-(hydroxymethyl)cyclohexan-1-ol

Refernces

Synthesis of endo-4-bromo-6-thiabicyclo[3.2.1]octane and 6-thiabicyclo[3.2.1]oct-3-ene

10.1021/jo00805a031

The study investigates the synthesis and properties of certain cyclic and bicyclic sulfur compounds. Key chemicals involved include 3-cyclohexenylmethyl p-bromobenzenesulfonate (1), which serves as a starting material. Through a series of reactions, it is converted to 3-cyclohexenylmethyl thioacetate (2). The critical step involves bromination of 2 to yield 3,4-dibromocyclohexenylmethyl thioacetate (3), which upon further reaction with potassium hydroxide in methanol, leads to the formation of endo-4-bromo-6-thiabicyclo[3.2.1]octane (5). Compound 5 is then used to synthesize other derivatives like 6-thiabicyclo[3.2.1]octane (6) via reduction with triphenyltin hydride and azobisisobutyronitrile, and 6-thiabicyclo[3.2.1]oct-3-ene (4) through dehydrobromination with potassium hydroxide in ethylene glycol. The study also examines the dipole moment of 5 and explores its reactivity, noting its unreactiveness in common elimination, displacement, and solvolytic reactions, likely due to steric hindrance from the proximity of sulfur to the bromide.