13678-68-7

Basic information

• Product Name: Furfuryl thioacetate
• Synonyms: Ethanethioic acid S-(2-furanylmethyl) ester;FEMA 3162;FURFURYL THIOACETATE;S-FURFURYL ACETOTHIOATE;S-FURFURYL THIOACETATE;THIOACETIC ACID S-FURFURYL ESTER;Acetic acid, thio-, S-furfuryl ester;Ethanethioicacid,S-(2-furanylmethyl)ester(9CI)
• CAS NO: 13678-68-7
• Molecular Formula: C₇H₈O₂S
• Molecular Weight: 156.2
• EINECS: 237-173-9
• Product Categories: thioester Flavor;Building Blocks;Furans;Heterocyclic Building Blocks;Alphabetical Listings;E-F;Flavors and Fragrances
• Mol File: 13678-68-7.mol

Chemical Properties

• Boiling Point: 90-92 °C12 mm Hg(lit.)
• Flash Point: 199 °F
• Appearance: Dark brown/Liquid
• Density: 1.171 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.203mmHg at 25°C
• Refractive Index: n20/D 1.526(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Furfuryl thioacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Furfuryl thioacetate(13678-68-7)
• EPA Substance Registry System: Furfuryl thioacetate(13678-68-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-24/25
• RIDADR: UN 3334
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 9
• Hazardous Substances Data: 13678-68-7(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 13678-68-7 differently. You can refer to the following data:
1. dark brown liquid
2. Furfuryl thioacetate has a burnt, roasted odor.

Occurrence

Reported found as a constituent in coffee

Uses

Different sources of media describe the Uses of 13678-68-7 differently. You can refer to the following data:
1. 2-Furfurylthiol Acetate is a sulfur-substituted furan derivative used as flavouring agent. 2-Furfurylthiol Acetate is a precursor to furfurylmercaptan which is very prone to oxidation to the disulfide. We will provide a detailed procedure for the preparation of the thiol from the thioacetate with spectral data upon request.
2. S-Furfuryl thioacetate (S-2-furfuryl thioacetate) has been used in lipase (from Candida rugosa) mediated synthesis of 2-furfurylthiol.
3. Furfuryl thioacetate is a sulfur-substituted furan derivative used as flavouring agent. e. We will provide a detailed procedure for the preparation of the thiol from the thioacetate with spectral data upon request.

Taste threshold values

Taste characteristics at 1 ppm: roasted, alliaceous, garlic, coffee, meaty, savory and sulfureous.

General Description

Furfuryl thioacetate is a sulfur-containing flavor compound mainly found in coffee.

InChI:InChI=1/C7H8O2S/c1-6(8)10-5-7-3-2-4-9-7/h2-4H,5H2,1H3

Upstream product

• 98-02-2 2-thiolomethyl-furan 
• 64-19-7 acetic acid 
• 4437-20-1 furfuryl disulfide 
• 108-24-7 acetic anhydride 

Downstream Products

• 98-02-2 2-thiolomethyl-furan 

Relevant articles and documents

Air-Tolerant Direct Thiol Esterification with Carboxylic Acids Using Hydrosilane via Simple Inorganic Base Catalysis

Direct thioesterification of carboxylic acids with thiols using nontoxic activation agents is highly desirable. Herein, an efficient and practical protocol using safe and inexpensive industrial waste polymethylhydrosiloxane as the activation agent and K3PO4 with 18-crown-6 as a catalyst is described. Various functional groups on carboxylic acid and thiol substituents can be tolerated by the present system to afford thioesters in yields of 19-100%.

4-Imidazol-1-yl-butane-1-sulfonic acid ionic liquid: Synthesis, structural analysis, physical properties and catalytic application as dual solvent-catalyst

4-Imidazol-1-yl-butane-1-sulfonic acid (ImBu-SO3H) has been successfully synthetized and fully characterized by FT-IR and high-resolution NMR spectroscopy (1H, 13C). The “plausible” alternative structures of ImBu-SO3H were discussed on the basis of its NMR data. The ionic liquid showed interesting dual solvent-catalyst property, which was studied experimentally for the acetylation of a variety of functionalized alcohols, phenols, thiols, amines and α-tocopherol (α-CTP) as the most active form of vitamin E with acetic anhydride and which provided good yields within a short reaction time. ImBu-SO3H was successfully recycled by product extraction with an average recovered yield of 82% for 5 subsequent runs. The catalytic activity of the recycled ImBu-SO3H showed almost no loss even after five consecutive runs.

Poly(N-vinylimidazole) as an efficient catalyst for acetylation of alcohols, phenols, thiols and amines under solvent-free conditions

Poly(N-vinylimidazole) is able to promote instantaneous quantitative acetylation of a variety of functionalized alcohols, phenols, thiols and amines with acetic anhydride at room temperature under solvent-free conditions. This new method consistently has excellent yields and the catalyst can be reused and recovered several times. Furthermore, the reaction can even be carried out on a larger scale. The Royal Society of Chemistry.

A succinimide-N-sulfonic acid catalyst for acetylation reactions in absence of a solvent

A small amount of succinimide-N-sulfonic acid efficiently catalyzed the acetylation of a variety alcohols, phenols, thiols, amines and aldehydes with acetic anhydride at room temperature under solvent free conditions. This catalyst has the advantages of excellent yields and short reaction times and the reaction can be carried out on a large scale, which makes it potentially useful for industrial applications.

Magnesium bistrifluoromethanesulfonimide as a new and efficient acylation catalyst

Magnesium bistrifluoromethanesulfonimide catalyzed the acetylation of phenols, alcohols, and thiols under solvent-free conditions at room temperature and in short times. Electron-deficient and sterically hindered phenols provided excellent yields. The catalyst was found to be general for acylation with other anhydrides, such as propionic, isobutyric, pivalic, chloroacetic, and benzoic anhydrides. The rate of acylation was influenced by the electronic and steric factors associated with the anhydride. The reaction with less electrophilic anhydrides (e.g., chloroacetic and benzoic anhydrides) required higher temperature (～80 °C). Chemoselective acetylation, pivalation, and benzoylation took place with acid-sensitive alcohols without any competitive dehydration/rearrangement.

A preparative scale reduction of alkyl disulfides with tributyl phosphine and water

A series of alkyl disulfides has been shown to be reduced by tributyl phosphine at room temperature. The resulting thiols were then acylated in the same pot and isolated in good yields. This sequence is convenient and is a practical option for the preparation of gram quantities of thiol or thioester from the corresponding disulfide.