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
• Article Data: 2

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

Chemical Properties

Yellow Liquid

Uses

3-Methyl-2-buten-1-thiol is a volatile aroma compound. It is an Important compounds in coffee aroma. It is used to food spice.

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.