17689-16-6

Basic information

• Product Name: Thiepan-2-one
• Synonyms: Thiepan-2-one;ε-Thiocaprolactone
• CAS NO: 17689-16-6
• Molecular Formula: C6H10OS
• Molecular Weight: 130.22
• Mol File: 17689-16-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 210.93°C (rough estimate)
• Flash Point: 101.1°C
• Appearance: /
• Density: 1.025 (estimate)
• Vapor Pressure: 0.0455mmHg at 25°C
• Refractive Index: 1.5115 (estimate)
• CAS DataBase Reference: Thiepan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: Thiepan-2-one(17689-16-6)
• EPA Substance Registry System: Thiepan-2-one(17689-16-6)

Safety Data

• Hazardous Substances Data: 17689-16-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 90, p. 3533, 1968 DOI: 10.1021/ja01015a043

InChI:InChI=1/C6H10OS/c7-6-4-2-1-3-5-8-6/h1-5H2

Upstream product

• 4224-70-8 6-bromohexanoic acid 
• 17689-17-7 6-mercaptocaproic acid 
• 22809-37-6 6-bromohexanoyl chloride 

Downstream Products

• 180714-59-4 C₃₈H₄₀N₂O₉S₂ 

Relevant articles and documents

Poly(thioester) by Organocatalytic Ring-Opening Polymerization

Organocatalysts typically used for the ring-opening polymerization (ROP) of cyclic ester monomers are applied to a thiolactone, ε-thiocaprolactone (tCL). In the absence of an H-bond donor, a nucleophilic polymerization mechanism is proposed. Despite the decreased ability of thioesters and thiols (versus esters and alcohols) to H-bond, H-bonding organocatalysts - a thiourea in combination with an H-bond accepting base - are also effective for the ROP of tCL. The increased nucleophilicity of thiols (versus alcohols) is implicated in the increased Mw/Mn of the poly(thiocaprolactone) versus poly(caprolactone), but deleterious transesterification is suppressed in the presence of a thiourea. The thioester monomer, tCL, is shown to be thermodynamically similar to ε-caprolactam but kinetically similar to ε-caprolactone. (Chemical Equation Presented).

Group 14 Metal Assisted Carbon-Sulfur Bond Formation

-