4740-00-5

Basic information

• Product Name: 3-Methylthiolane
• Synonyms: Tetrahydro-3-methylthiophene;3-METHYLTETRAHYDROTHIOPHENE;3-Methylthiolane
• CAS NO: 4740-00-5
• Molecular Formula: C₅H₁₀S
• Molecular Weight: 102.2
• Mol File: 4740-00-5.mol
• Article Data: 2

Chemical Properties

• Melting Point: -81.16°C
• Boiling Point: 138.34°C
• Flash Point: 28.1 °C
• Appearance: /liquid
• Density: 0.959
• Vapor Pressure: 10.9mmHg at 25°C
• Refractive Index: 1.4902
• CAS DataBase Reference: 3-Methylthiolane(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methylthiolane(4740-00-5)
• EPA Substance Registry System: 3-Methylthiolane(4740-00-5)

Safety Data

• Hazardous Substances Data: 4740-00-5(Hazardous Substances Data)

Usage

General Description

3-Methylthiolane is an organic sulfur compound with the formula C4H7S. It is also known as 2,3-dihydrothiophene. It is a colorless liquid that is commonly used as a flavor substance in the food industry due to its strong roasted aroma and has also been used in the tobacco industry. It is insoluble in water but is miscible with organic solvents. 3-Methylthiolane, due to its sulfur content, is considered to have critical potential in contributing to the 'meaty' flavor of cooked foods. However, handling and usage of this compound must be done with caution as it can cause eye and skin irritation upon contact.

InChI:InChI=1/C5H10S/c1-5-2-3-6-4-5/h5H,2-4H2,1H3

Upstream product

• 314056-82-1 1-phenylselenyl-2-thia-5-hexene 

Downstream Products

• 111082-40-7 1-(2,5-Dihydroxy-phenyl)-3-methyl-tetrahydro-thiophenium; chloride 
• 28335-08-2 1-(2,5-dihydroxyphenyl)thiolanium chloride monohydrate 
• 872-93-5 3-methylsulfolane 

Relevant articles and documents

The regiochemistry of cyclization of α-sulfenyl-, α-sulfinyl-, and α-sulfonyl-5-hexenyl radicals: Procedures leading to regioselective syntheses of cyclic sulfones and sulfoxides

A study of the cyclization of α-sulfenyl-, α-sulfinyl-, and α-sulfonyl-5-hexenyl and 5-methyl-5-hexenyl radicals reveals a unique contrast in the mode of ring closure of the radicals. In the case of the 5-hexenyl radicals, the sulfinyl-substituted species displays unexpected regioselectivity relative to its analogues. Thus, while the α-S- and α-SO2-5-hexenyl radicals give measurable and increasing quantities of 6-endo product, the α-sulfinyl species cyclizes with high selectivity (95.5:4.5) via a 5-exo mode. By contrast, ring closure of the 5-methyl-5-hexenyl radicals is found to give substantially the 6-endo product in all cases. It is the α-sulfonyl-5-methyl-5-hexenyl radical that now exhibits high regioselectivity (97.5:2.5) for 6-endo closure: an illustration of the synthetic value of this observation is the independent synthesis of the model cyclohexyl sulfone 61 in high yield. It is found that ring closure under the conditions employed occurs irreversibly in all cases.