177-15-1

Basic information

• Product Name: Spiro[1,3-oxathiolane-2,1'-cyclohexane]
• Synonyms: 1-Oxa-4-thiaspiro[4.5]decane;Cyclohexanone O,S-ethylenethioacetal;Spiro[1,3-oxathiolane-2,1'-cyclohexane]
• CAS NO: 177-15-1
• Molecular Formula: C₈H₁₄OS
• Molecular Weight: 0
• Mol File: 177-15-1.mol

Chemical Properties

• Boiling Point: 261.6°C at 760 mmHg
• Flash Point: 112°C
• Appearance: /
• Density: 1.09g/cm³
• Vapor Pressure: 0.0186mmHg at 25°C
• Refractive Index: 1.533
• CAS DataBase Reference: Spiro[1,3-oxathiolane-2,1'-cyclohexane](CAS DataBase Reference)
• NIST Chemistry Reference: Spiro[1,3-oxathiolane-2,1'-cyclohexane](177-15-1)
• EPA Substance Registry System: Spiro[1,3-oxathiolane-2,1'-cyclohexane](177-15-1)

Safety Data

• Hazardous Substances Data: 177-15-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
Spiro[1,3-oxathiolane-2,1'-cyclohexane] serves as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs with potential therapeutic applications, contributing to advancements in medicine.
Used in Agrochemical Production:
In the agrochemical industry, Spiro[1,3-oxathiolane-2,1'-cyclohexane] is utilized in the creation of compounds that can enhance crop protection and yield. Its incorporation into agrochemical products aids in the development of more effective and targeted pest control solutions.
Used in Organic Chemistry Research:
As a reagent, Spiro[1,3-oxathiolane-2,1'-cyclohexane] is instrumental in organic chemistry research. It facilitates the formation of various heterocyclic compounds, which are essential in understanding and expanding the knowledge of organic chemistry and its applications.
Used as a Building Block in Organic Synthesis:
Due to its spirocyclic structure, Spiro[1,3-oxathiolane-2,1'-cyclohexane] acts as a fundamental building block in the assembly of more complex organic molecules. This role is crucial for the synthesis of intricate organic compounds that have specific applications in various industries, including materials science and specialty chemicals.

InChI:InChI=1/C8H14OS/c1-2-4-8(5-3-1)9-6-7-10-8/h1-7H2

Upstream product

• 108-94-1 cyclohexanone 
• 104-15-4 toluene-4-sulfonic acid 
• 60-24-2 2-hydroxyethanethiol 
• 71-43-2 benzene 
• 108-93-0 cyclohexanol 
• 177-10-6 1,3-dioxolane-2-spirocyclohexane 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 65225-58-3 2-ethoxy-1,3-oxathiolane 

Downstream Products

• 1666-13-3 diphenyl diselenide 
• 50984-16-2 rac-2-(phenylseleno)cyclohexanone 
• 108-94-1 cyclohexanone 
• 932-92-3 cyclohexyl ethyl ether 
• 127084-51-9 C₂₀H₄₂OSSn 
• 3778-81-2 2-(cyclohexylthio)ethanol 
• 108-93-0 cyclohexanol 
• 53787-05-6 1-[(2-chloroethyl)sulfanyl]cyclohexane 
• 33266-05-6 6-oxospiro 
• 37457-08-2 cyclohexane-1,1-diylbis(phenylsulfane) 
• 110-82-7 cyclohexane 
• 1569-69-3 Cyclohexanethiol 
• 7133-25-7 cyclohexyl ethyl sulfide 
• 10160-79-9 2-cyclohexyloxy-ethanethiol 

Relevant articles and documents

Facile protection of carbonyl compounds as oxathiolanes and transoxathioacetalization of oxyacetals promoted by iron(III) trifluoroacetate or trifluoromethanesulfonate as chemoselective and recyclable catalysts

Oxathioacetalization of carbonyl compounds and transoxathioacetalization of O,O-acetals/ketals are reported under nearly neutral conditions promoted by iron(III) trifluoroacetate [Fe(CF3CO2)3] or trifluoromethanesulfonate

Ytterbium(III) triflate-catalyzed conversion of carbonyl compounds into 1,3-oxathiolanes in ionic liquids

The reaction of carbonyl compounds with 2-mercapto-ethanol to prepare 1,3-oxathiolanes has been successfully carried out in ionic liquids using ytterbium(III) triflate as a catalyst. Yields of the products are high and the catalyst can be easily recovered

Introducing catalytic activity in helical nanostructures: Microwave assisted oxathioacetalisation catalysed by Al-containing helical mesoporous silicas

Al-containing helical mesoporous silicas have been synthesized and characterised by different techniques, showing outstanding activities (comparable to those obtained with sulfuric acid) in the oxathioacetalization of cyclohexane. The Royal Society of Che

Facile protection of carbonyl compounds as oxathiolanes and thioacetals promoted by PEG1000-based dicationic acidic ionic liquid as chemoselective and recyclable catalyst

Efficient oxathioacetalization and thioacetalization of carbonyl compounds have been achieved in high yields employing PEG1000-based dicationic acidic ionic liquid as a catalyst. The PEG ionic liquid and toluene have the advantages of both homo

Tantalum(V) chloride-silica gel: An efficient catalyst for conversion of carbonyl compounds to 1,3-oxathiolanes

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Ceric ammonium nitrate as a convenient catalyst for protection of carbonyl compounds as 1,3-oxathianes

A mild and efficient method for the protection of carbonyl compounds as 1,3-oxathianes has been established by the catalytic use of ceric ammonium nitrate at ambient temperature. While different types of aryl and alkyl ketones and aldehydes were protected

Synthesis and Carbon-13 Nuclear Magnetic Resonance Spectroscopy of 5,6-Dihydro-2-methyl-1,4-oxathiin, trans-Tetrahydro-1,4-benzoxathiin, 1,4-Tetrahydro-benzoxathiin, the 4-Oxides, 4,4-Dioxides and Related Acyclic Compounds

The results of a 13C NMR spectral investigation involving 5,6-dihydro-1,4-oxathiins, 1,4-tetrahydrobenzoxathiin, trans-tetrahydro-1,4-benzoxathiin, and the corresponding sulfoxides and sulfones are reported.An interpretation involving a dipolar structure with (2p -> 2p)? conjugation as opposed to (2p -> 3d)? interactions with the vinyloxy sulfides seems consistent with trends in the 13C NMR shifts.For the sulfoxides and sulfones, the substituent-induced chemical shift (SCS) effects at the β vinylic carbons (βSO and βSO2 effects) are considerably less than those at sp3 carbons.The γSO and γSO2 values at the sp2γ carbons indicate deshielding, in contrast to the shielding at the sp3 carbons.

Blue LED-Promoted Oxathiacetalization of Aldehydes and Ketones

In synthetic chemistry, the protection of aldehydes and ketones is crucial during multistep synthesis of complex molecules. Organic chemists have paid substantial attention to the synthesis of 1,3-oxathiolanes and 1,3-oxathianes because of their considera

Silica-gel supported sulfamic acid (SA/SiO2) as an efficient and reusable catalyst for conversion of ketones into oxathioacetals and dithioacetals

A simple and efficient method for the conversion of carbonyl compounds to oxathioacetals and dithioacetals using SA/SiO2 as an acid catalyst has been achieved. SA/SiO2 is easily recovered from the reaction mixture and can be reused at least 15 times without loss of catalytic activity.

An efficient method for the oxathioacetalization of carbonyl compounds using N-bromosaccharin as a catalyst

A mild and highly chemoselective method for the preparation of oxathiolane from aliphatic and aromatic aldehydes and ketones with 2-mercaptoethanol in the presence of catalytic amount of N-bromosaccharin at room temperature is reported.