57124-87-5

Basic information

• Product Name: 2-Methyltetrahydrofuran-3-thiol
• Synonyms: TETRAHYDRO-2-METHYLFURAN-3-THIOL;2-methyltetrahydrofuran-3-thiol,mixedisomers;tetrahydro-2-methyl-3-furanthio;tetrahydro-2-methyl-3-Furanthiol;FEMA 3787;2-METHYL-3-TETRAHYDROFURANTHIOL;2-METHYLTETRAHYDROFURAN-3-THIOL;3-MERCAPTO-2-METHYLTETRAHYDROFURAN
• CAS NO: 57124-87-5
• Molecular Formula: C₅H₁₀OS
• Molecular Weight: 118.2
• EINECS: 260-572-4
• Product Categories: THIOL;API intermediates;thiol Flavor;Alphabetical Listings;Flavors and Fragrances;M-N;Heterocycles;Sulfur & Selenium Compounds
• Mol File: 57124-87-5.mol

Chemical Properties

• Boiling Point: 160-180 °C
• Flash Point: 30 °C
• Appearance: Clear colorless to pale yellow/Liquid
• Density: 1.04 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.01mmHg at 25°C
• Refractive Index: 1.473-1.491
• Storage Temp.: Flammables area
• PKA: 10.13±0.40(Predicted)
• Water Solubility: insoluble
• CAS DataBase Reference: 2-Methyltetrahydrofuran-3-thiol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyltetrahydrofuran-3-thiol(57124-87-5)
• EPA Substance Registry System: 2-Methyltetrahydrofuran-3-thiol(57124-87-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38-10-36/37/38
• Safety Statements: 37/39-26-16-36-24/25-23
• RIDADR: 1993
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 57124-87-5(Hazardous Substances Data)

Usage

Uses

Used in Flavor Industry:
2-Methyltetrahydrofuran-3-thiol is used as a flavor compound for enhancing the meaty aroma in various food products. Its application reason is due to its strong meaty flavor profile, which can significantly improve the taste and aroma of processed meat products and other food items that require a meaty flavor.
Used in Meat Flavorings:
In the meat flavorings industry, 2-Methyltetrahydrofuran-3-thiol is used as a key ingredient to impart a rich, meaty flavor to products. The application reason is its ability to mimic the taste and aroma of cooked meat, making it an essential component in the creation of artificial or imitation meat products, as well as in enhancing the flavor of natural meat products.

Biochem/physiol Actions

Odor at 0.1% PGTaste at 0.1-0.5 ppm

InChI:InChI=1/C5H10OS/c1-4-5(7)2-3-6-4/h4-5,7H,2-3H2,1H3/t4-,5-/m0/s1

Synthetic route

C7H12O2S → 3-mercapto-2-methyltetrahydrofuran (57124-87-5)

Conditions	Yield
With acetic acid at 20℃; for 0.5h;	87%

2-methyl-3-chlorotetrahydrofuran (30672-41-4) + 3-thioacetoxy-2-methyltetrahydrofuran + potassium thioacetate (10387-40-3) → 3-mercapto-2-methyltetrahydrofuran (57124-87-5) + (2S,3S)-2-methyl-tetrahydrofuran-3-thiol

Conditions	Yield
With sodium methylate In N-methyl-acetamide; methanol; water	A 0.72 g (67%) B n/a

5-Hydroxy-2-pentanone (1071-73-4) → 3-mercapto-2-methyltetrahydrofuran (57124-87-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: phosphoric acid / 200 °C 2: piperidine / 1 h / 20 °C 3: acetic acid / 0.5 h / 20 °C View Scheme

4-ethyloctanoyl chloride (16493-81-5) + 3-mercapto-2-methyltetrahydrofuran (57124-87-5) → C15H28O2S (1236109-83-3)

Conditions	Yield
at 70℃; for 4h;	94%

5-bromo-2-furancarboxaldehyde (1899-24-7) + 3-mercapto-2-methyltetrahydrofuran (57124-87-5) → (±)5-((2-methyltetrahydrofuran-3-yl)thio)furan-2-carbaldehyde

Conditions	Yield
With {NiBr2phan2}; zinc; caesium carbonate In water at 45℃; for 24h; Inert atmosphere; Sealed tube;	74%

2-(3-chlorophenyl)-2H-1,2,3-triazole 1-oxide (1454920-50-3) + 3-mercapto-2-methyltetrahydrofuran (57124-87-5) → 2-(3-chlorophenyl)-4-(2-methyltetrahydrofuran-3-ylthio)-2H-1,2,3-triazole

Conditions	Yield
With nickel(II) sulphate; caesium carbonate; N,N`-dimethylethylenediamine In dimethyl sulfoxide at 60℃; for 18h; regioselective reaction;	73%

para-dinitrobenzene (100-25-4) + 3-mercapto-2-methyltetrahydrofuran (57124-87-5) → 2-methyl-3-((4-nitrophenyl)thio)tetrahydrofuran

Conditions	Yield
With potassium phosphate; 18-crown-6 ether In tetrahydrofuran at 20℃; for 3h;	69%

8-oxo-8H-acenaphtho[1,2-b]pyrrole-9-carboxylicacid ethyl ester + 3-mercapto-2-methyltetrahydrofuran (57124-87-5) → ethyl 3-(2-methyltetrahydrofuran-3-ylthio)-8-oxo-8H-acenaphtho[1,2-b]pyrrole-9-carboxylate (1309112-23-9)

Conditions	Yield
In methanol; chloroform at 20℃;	65%

2-(4-methylphenyl)-1,2,3-triazole N-oxide (1431772-07-4) + 3-mercapto-2-methyltetrahydrofuran (57124-87-5) → 4-(2-methyltetrahydrofuran-3-ylthio)-2-p-tolyl-2H-1,2,3-triazole

Conditions	Yield
With nickel(II) sulphate; caesium carbonate; N,N`-dimethylethylenediamine In dimethyl sulfoxide at 60℃; for 12h; regioselective reaction;	63%

Nα-fluoren-9-ylmethoxycarbonyl-L-cysteine (135248-89-4) + 3-mercapto-2-methyltetrahydrofuran (57124-87-5) → Fmoc-Cys(2-methyloxolane-3-thiol)-OH

Conditions	Yield
Stage #1: 3-mercapto-2-methyltetrahydrofuran With N-chloro-succinimide In dichloromethane at -50℃; for 0.25h; Stage #2: Nα-fluoren-9-ylmethoxycarbonyl-L-cysteine In tetrahydrofuran; dichloromethane at -50℃; for 2h;	60.1%

6-amino-4-fluoronicotinonitrile + 3-mercapto-2-methyltetrahydrofuran (57124-87-5) → 6-amino-4-((2-methyltetrahydrofuran-3-yl)thio)nicotinonitrile

Conditions	Yield
Stage #1: 3-mercapto-2-methyltetrahydrofuran With potassium hexamethylsilazane In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: 6-amino-4-fluoronicotinonitrile In tetrahydrofuran at 20℃;	57%

2-chloro-6-methoxy-3-nitropyridine (38533-61-8) + 3-mercapto-2-methyltetrahydrofuran (57124-87-5) → 6-methoxy-2-(2-methyltetrahydrofuran-3-ylsulfanyl)-3-nitropyridine

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;	48%

8-oxo-8H-acenaphthyleno[1,2-b]pyrrole-9-carbonitrile (846038-96-8) + 3-mercapto-2-methyltetrahydrofuran (57124-87-5) → 3-(2-methyltetrahydrofuran-3-ylthio)-8-oxo-8H-acenaphtho[1,2-b]pyrrole-9-carbonitrile (1309112-19-3)

Conditions	Yield
With triethylamine In methanol at 0 - 5℃;	42%

4-chloro-3-iodoquinoline (590371-90-7) + 3-mercapto-2-methyltetrahydrofuran (57124-87-5) → 3-iodo-4-(2-methyltetrahydrofuran-3-ylsulfanyl)quinoline (1268468-59-2)

Conditions	Yield
With caesium carbonate In tetrahydrofuran; 1,4-dioxane at 20 - 90℃;
With caesium carbonate In tetrahydrofuran; 1,4-dioxane at 20 - 90℃; for 4h;

3-mercapto-2-methyltetrahydrofuran (57124-87-5) → (E)-3-[4-(2-methyltetrahydrofuran-3-sulfanyl)quinolin-3-yl]acrylic acid ethyl ester (1310801-64-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: caesium carbonate / tetrahydrofuran; 1,4-dioxane / 4 h / 20 - 90 °C 2: palladium diacetate; potassium acetate; tetrabutyl-ammonium chloride / N,N-dimethyl-formamide / 16 h / 110 °C View Scheme

3-mercapto-2-methyltetrahydrofuran (57124-87-5) → (E)-3-[4-(2-methyltetrahydrofuran-3-sulfonyl)quinolin-3-yl]acrylic acid ethyl ester (1268468-52-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: caesium carbonate / tetrahydrofuran; 1,4-dioxane / 4 h / 20 - 90 °C 2: palladium diacetate; potassium acetate; tetrabutyl-ammonium chloride / N,N-dimethyl-formamide / 16 h / 110 °C 3: acetic acid; peracetic acid / dichloromethane / 0 - 20 °C View Scheme

3-mercapto-2-methyltetrahydrofuran (57124-87-5) → 3-(4-trifluoromethylphenyl)-4-(2-methyltetrahydrofuran-3-ylsulfanyl)quinoline

Conditions	Yield
Multi-step reaction with 2 steps 1: caesium carbonate / tetrahydrofuran; 1,4-dioxane / 4 h / 20 - 90 °C 2: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane / 16 h / 90 °C View Scheme

3-mercapto-2-methyltetrahydrofuran (57124-87-5) → 3-(4-trifluoromethylphenyl)-4-(2-methyltetrahydrofuran-3-sulfonyl)quinoline (1268468-53-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: caesium carbonate / tetrahydrofuran; 1,4-dioxane / 4 h / 20 - 90 °C 2: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane / 16 h / 90 °C 3: acetic acid; peracetic acid / dichloromethane / 0 - 20 °C View Scheme

3-mercapto-2-methyltetrahydrofuran (57124-87-5) → 6-methoxy-2-(2-methyltetrahydrofuran-3-ylsulfinyl)-3-nitropyridine

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C 2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 °C View Scheme

3-mercapto-2-methyltetrahydrofuran (57124-87-5) → 6-methoxy-2-((2-methyltetrahydrofuran-3-yl)sulfonyl)-3-nitropyridine

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C 2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C View Scheme

(-)-xanthatin (26791-73-1, 30890-35-8, 119478-96-5) + 3-mercapto-2-methyltetrahydrofuran (57124-87-5) → C20H28O4S

Conditions	Yield
Stage #1: (-)-xanthatin With triethylamine In methanol at 0 - 5℃; for 0.166667h; Michael Addition; Stage #2: 3-mercapto-2-methyltetrahydrofuran In methanol at 0 - 5℃; Michael Addition;

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Leu-OH (35661-60-0) + N-α-tert-butoxycarbonyl-S-(3-nitro-2-pyridylthio)-L-cysteine (76880-29-0) + N-Fmoc L-Phe (35661-40-6) + 3-mercapto-2-methyltetrahydrofuran (57124-87-5) → Boc-Cys(2-methyloxolane-3-thiol)-Gly-Phe-Leu-NH2

Conditions	Yield
Stage #1: Fmoc-Leu-OH With ethyl cyanoglyoxylate-2-oxime; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 20℃; Stage #2: With piperidine In N,N-dimethyl-formamide Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; N-α-tert-butoxycarbonyl-S-(3-nitro-2-pyridylthio)-L-cysteine; N-Fmoc L-Phe; 3-mercapto-2-methyltetrahydrofuran Further stages;

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Leu-OH (35661-60-0) + N-α-tert-butoxycarbonyl-S-(3-nitro-2-pyridylthio)-L-cysteine (76880-29-0) + N-Fmoc L-Phe (35661-40-6) + 3-mercapto-2-methyltetrahydrofuran (57124-87-5) → Cys-Gly-Phe-Leu-NH2

Conditions	Yield
Stage #1: Fmoc-Leu-OH With ethyl cyanoglyoxylate-2-oxime; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 20℃; Stage #2: With piperidine In N,N-dimethyl-formamide Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; N-α-tert-butoxycarbonyl-S-(3-nitro-2-pyridylthio)-L-cysteine; N-Fmoc L-Phe; 3-mercapto-2-methyltetrahydrofuran Further stages;

Upstream product

• 30672-41-4 2-methyl-3-chlorotetrahydrofuran 
• 10387-40-3 potassium thioacetate 
• 1071-73-4 5-Hydroxy-2-pentanone 

Relevant articles and documents

Preparation method and application of 2-methyl tetrahydrofuran-3-thiol

The invention discloses a preparation method of 2-methyl tetrahydrofuran-3-thiol. According to the preparation method, 5-hydroxy-2-pentanone is used as a raw material, and the 2-methyl tetrahydrofuran-3-thiol is prepared by carrying out a dispersion reaction. The preparation method has the advantages that when the 5-hydroxy-2-pentanone (I) and phosphoric acid are taken as raw materials for preparing 4,5-dihydro-2-methylfuran (II), less isomer is produced, so that the generation of by-products in a reaction process can be effectively reduced, and the product quality is greatly improved; an intermediate 2-methyltetrahydrofuran-3-thiol acetate (III) is obtained by enabling the 4,5-dihydro-2-methylfuran (II) to react with thioacetic acid, and 2-methyltetrahydrofuran-3-thiol is then prepared, so that the preparation route is short in reaction time.

Certain lower alkyl 4,5-dihydrothiophene-3-thiols

Novel sulphur containing food flavor substances are provided containing an oxygen or sulphur atom in a five or six membered ring structure, one alkyl or hydroxy alkyl substituent at at least either of the carbon atoms adjacent to the hetero atom and having at least one sulphur or oxygen atom attached to another carbon atom of the ring structure.

Certain 3-furyl sulfides

Novel 3-sulfur derivatives of furan including alkyl furan-3-thiols and bis(alkyl-3-furyl) sulfides and di- and tetrahydro derivatives thereof having meaty and/or roasted aromas and flavors; processes for producing such 3-sulfur derivatives; novel flavoring compositions containing such derivatives; and novel food compositions containing such derivatives.