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
• Article Data: 3

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

Chemical Properties

Colorless to light yellow liqui

Occurrence

Reported found in heated pork meat

Uses

2-Methyltetrahydrofuran-3-thiol is a compound used as flavor

General Description

2-Methyl-3-tetrahydrofuranthiol is a sulfur-containing flavor compound mainly used in meat flavorings.

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 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.