5287-45-6

Basic information

• Product Name: 3-Methyl-2-buten-1-thiol
• Synonyms: PRENYL MERCAPTAN;FEMA 3896;3-METHYLBUT-2-ENE-1-THIOL;3-METHYL-2-BUTENE-1-THIOL;3-METHYL-2-BUTEN-1-THIOL;1-MERCAPTO-3-METHYL-2-BUTENE;Prenylmercaptan1%inTriacetin;methylbutenthiol,3-methyl-2-buten-1-thiol
• CAS NO: 5287-45-6
• Molecular Formula: C₅H₁₀S
• Molecular Weight: 102.2
• Product Categories: Metal Isotopes;thiol Flavor;Sulfur & Selenium Compounds
• Mol File: 5287-45-6.mol

Chemical Properties

• Boiling Point: 127 °C
• Flash Point: 45.7 °C
• Appearance: /
• Density: 0.862 g/cm³
• Vapor Pressure: 14.4mmHg at 25°C
• Refractive Index: 1.468
• Storage Temp.: Freezer
• PKA: 10.18±0.25(Predicted)
• Stability: Readily Oxidized
• CAS DataBase Reference: 3-Methyl-2-buten-1-thiol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-2-buten-1-thiol(5287-45-6)
• EPA Substance Registry System: 3-Methyl-2-buten-1-thiol(5287-45-6)

Safety Data

• RIDADR: UN 3336 3/PG III
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 5287-45-6(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
3-Methyl-2-buten-1-thiol is used as an aroma compound for its ability to enhance and provide a rich, complex scent to various products. Its strong odor makes it an essential component in the creation of artificial coffee flavors and fragrances, where it helps to mimic the natural aroma of coffee beans.
Used in Food Industry:
In the food industry, 3-Methyl-2-buten-1-thiol is used as a flavoring agent to impart a unique taste and aroma to a variety of products. Its characteristic smell and taste make it a popular choice for adding depth and complexity to the flavor profiles of different food items, particularly those with coffee or roasted notes.
Used in Coffee Production:
3-Methyl-2-buten-1-thiol plays a crucial role in the coffee production process, as it is one of the key compounds responsible for the distinct aroma of coffee. It is used to enhance the natural flavors and aromas of coffee beans, making it an important ingredient in the development of coffee products, from instant coffee to specialty blends.
Used in Spice Industry:
The spice industry also utilizes 3-Methyl-2-buten-1-thiol for its potent and distinctive odor. It is employed as a component in the formulation of various spice blends and seasonings, where it adds a unique and rich flavor profile to the final product. This application helps to create a more diverse and interesting range of spices for use in the culinary world.

InChI:InChI=1/C5H10S/c1-5(2)3-4-6/h3,6H,4H2,1-2H3

Synthetic route

thiourea (17356-08-0) + prenyl bromide (870-63-3) → prenyl mercaptan (5287-45-6)

Conditions	Yield
In ethanol at 80℃; for 3h;	83%

3-Methylthiophene (616-44-4) → prenyl mercaptan (5287-45-6)

Conditions	Yield
With methanol; ammonia; sodium

2-methyl-but-2-ene (513-35-9) → prenyl mercaptan (5287-45-6)

Conditions	Yield
With sulfur at 170℃;

dithiocarbamic acid (594-07-0) + prenyl bromide (870-63-3) → prenyl mercaptan (5287-45-6)

Conditions	Yield
With ammonia beim Erwaermen des Reaktionsprodukts mit Alkalilauge;

isoprene (78-79-5) → prenyl mercaptan (5287-45-6)

Conditions	Yield
(i) thiourea, aq. HBr, (ii) aq. TsOH, (iii) aq. NaOH; Multistep reaction;

S-methyl S-<1-(3-methyl-2-butenyl)>dithiocarbonate → prenyl mercaptan (5287-45-6)

Conditions	Yield
With potassium hydroxide In 1,4-dioxane for 2h; Heating;

2-methyl-but-2-ene (513-35-9) + sulfur → prenyl mercaptan (5287-45-6)

Conditions	Yield
at 170℃; bei laengerer Reaktionsdauer;

prenyl mercaptan (5287-45-6) + 3,3,3-trichloro-1-nitropropene (763-16-6) → (3-methylbut-2-enyl)(1,1,1-trichloro-3-nitropropan-2yl)sulfane

Conditions	Yield
With triethylamine In tert-butyl alcohol at 25 - 30℃; for 6h;	84%

prenyl mercaptan (5287-45-6) + 5,5,5-trichloro-pent-3-en-2-one (1552-26-7) → 5,5,5-trichloro-4-(3-methylbut-2-enylthio)pentan-2-one

Conditions	Yield
With triethylamine In tert-butyl alcohol at 25 - 30℃; for 8h;	82%

prenyl mercaptan (5287-45-6) + 4,4,4-trichloro-crotononitrile (14252-04-1) → 4,4,4-trichloro-3-(3-methylbut-2-enylthio)butanenitrile

Conditions	Yield
With triethylamine In tert-butyl alcohol at 25 - 30℃; for 12h;	81%

prenyl mercaptan (5287-45-6) + 4,4,4-trichloro-1-phenyl-but-2-en-1-one (21100-66-3) → 4,4,4-trichloro-3-(3-methylbut-2-enylthio)-1-phenylbutan-1-one

Conditions	Yield
With triethylamine In tert-butyl alcohol at 25 - 30℃; for 8h;	80%

prenyl mercaptan (5287-45-6) + phenylacetylene (536-74-3) → 3-Isopropyl-4-phenyl-2,3-dihydro-thiophene (112471-59-7)

Conditions	Yield
With triethyl borane In hexane; benzene	77%

prenyl mercaptan (5287-45-6) + C5H5Cl3O2 → methyl 4,4,4-trichloro-3-(3-methylbut-2-enylthio)butanoate

Conditions	Yield
With triethylamine In tert-butyl alcohol at 25 - 30℃; for 8h;	68%

prenyl mercaptan (5287-45-6) + chloroformic acid ethyl ester (541-41-3) → C8H14O2S

Conditions	Yield
With triethylamine In tetrahydrofuran at -1 - 20℃; for 1h; Inert atmosphere;	66%

prenyl mercaptan (5287-45-6) + 3-(ethoxycarbonyl)-4a-acetoxy-4,4a,9,9a-tetrahydro-1,2-oxazino<5,6-b>indole (106040-12-4) → ethyl α-(hydroxyimino)-β-<2-((3-methyl-2-butenyl)thio)indol-3-yl>propanoate (106040-09-9)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 0℃; for 3h;	64%

prenyl mercaptan (5287-45-6) + phenyl isocyanate (103-71-9) → S-(3-methylbut-2-en-1-yl) phenylcarbamothioate

Conditions	Yield
Stage #1: prenyl mercaptan With potassium hydride In tetrahydrofuran at 0 - 20℃; for 0.5h; Glovebox; Stage #2: phenyl isocyanate In tetrahydrofuran for 6h; Glovebox;	44%

prenyl mercaptan (5287-45-6) + β-3,4-epithiocarane (170716-51-5) → 4α-prenylthiocarane-3β-thiol + C30H50S4

Conditions	Yield
With sodium ethanolate for 15h; Ambient temperature;	A 42% B 36%

prenyl mercaptan (5287-45-6) + 1-dodecyne (765-03-7) → 4-Decyl-3-isopropyl-2,3-dihydro-thiophene (112471-58-6)

Conditions	Yield
With triethyl borane In hexane; benzene	35%

prenyl mercaptan (5287-45-6) → (2,4-dinitro-phenyl)-(3-methyl-but-2-enyl)-sulfide (5287-48-9)

prenyl mercaptan (5287-45-6) + benzoyl chloride (98-88-4) → S-(3-methylbut-2-en-1-yl)benzothioate

Conditions	Yield
With sodium hydroxide

Diethyl disulfide (110-81-6) + prenyl mercaptan (5287-45-6) → ethyl-(3-methyl-but-2-enyl)-disulfane (10276-12-7)

prenyl mercaptan (5287-45-6) + S-methylsulfenyl O-methyl thiocarbonate (55048-60-7) → methyl-(3-methyl-but-2-enyl)-disulfane (34776-60-8)

prenyl mercaptan (5287-45-6) → bis(3-methyl-2-buten-1-yl)disulfide (24963-39-1)

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide

prenyl mercaptan (5287-45-6) → 3-methyl-2-(3-methyl-but-2-enylsulfanyl)-butane-1-thiol (29178-27-6)

Conditions	Yield
In hexane Irradiation;

prenyl mercaptan (5287-45-6) + Ethyl 2-bromopropionate (535-11-5, 41978-69-2) → α-Carbethoxyethyl 3-Methyl-2-butenylsulfid (61740-72-5)

Conditions	Yield
With sodium ethanolate In ethanol

prenyl mercaptan (5287-45-6) + syn-3-(benzyloxy)-3-phenyl-1-(tributylstannyl)-1-propanol → 1-(benzyloxy)-4,4-dimethyl-1-phenyl-5-hexane-3-thiol

Conditions	Yield
Yield given. Multistep reaction;

prenyl mercaptan (5287-45-6) + chloral (75-87-6) → 3-Methyl-1-(1,2,2,2-tetrachloro-ethylsulfanyl)-but-2-ene (85022-07-7)

prenyl mercaptan (5287-45-6) + acetyl chloride (75-36-5) → ethanethioic acid S-(3-methyl-2-butenyl) ester (33049-93-3)

Conditions	Yield
In pyridine	1.0 g

prenyl mercaptan (5287-45-6) + isopentanoyl chloride (108-12-3) → S-(3-methylbut-2-en-1-yl) 3-methylbutanethioate (75631-91-3)

Conditions	Yield
In pyridine	1.7 g

prenyl mercaptan (5287-45-6) + Chloromethyltrimethylsilane (2344-80-1) → 3-methyl-1-trimethylsilylmethylthio-2-butene (151108-99-5)

Conditions	Yield
With n-butyllithium 1) HMPA, ether, 0 deg C; Yield given. Multistep reaction;

Upstream product

• 616-44-4 3-Methylthiophene 
• 513-35-9 2-methyl-but-2-ene 
• 594-07-0 dithiocarbamic acid 
• 870-63-3 prenyl bromide 
• 78-79-5 isoprene 
• 17356-08-0 thiourea 

Downstream Products

• 5287-48-9 (2,4-dinitro-phenyl)-(3-methyl-but-2-enyl)-sulfide 
• 33049-93-3 ethanethioic acid S-(3-methyl-2-butenyl) ester 
• 112471-59-7 3-Isopropyl-4-phenyl-2,3-dihydro-thiophene 

Relevant articles and documents

Exploiting the Synthetic Potential of Sesquiterpene Cyclases for Generating Unnatural Terpenoids

The substrate flexibility of eight purified sesquiterpene cyclases was evaluated using six new heteroatom-modified farnesyl pyrophosphates, and the formation of six new heteroatom-modified macrocyclic and tricyclic sesquiterpenoids is described. GC-O analysis revealed that tricyclic tetrahydrofuran exhibits an ethereal, peppery, and camphor-like olfactoric scent.

Potassium fluoride on alumina: One-pot synthesis of S-allyl-S-methyldithiocarbonates by tandem condensation-alkylation-sigmatropic rearrangement

Allyl alcohols adsorbed on Al2O3-KF at room temperature reacted wit carbon disulfide and iodomethane and gave S-allyl-S-methyldithiocarbonate. Linalool did not give a rearrangement product. With chrysanthemyl alcohol, opening of the cyclopropane ring was observed.