1191-08-8

Basic information

• Product Name: 1,4-BUTANEDITHIOL
• Synonyms: butane-1,4-dithiol;1,4-DIMERCAPTOBUTANE;1,4-BUTANEDITHIOL;TETRAMETHYLENE DITHIOL;TETRAMETHYLENE DIMERCAPTAN;1,4-BUTANEDITHIOL, TECH., 90%;1 4-BUTANEDITHIOL 97+%;Butan-1,4-dithiol
• CAS NO: 1191-08-8
• Molecular Formula: C₄H₁₀S₂
• Molecular Weight: 122.25
• EINECS: 214-728-3
• Product Categories: Building Blocks;Chemical Synthesis;Contact Printing;Dithiols;Materials Science;Micro/NanoElectronics;Organic Building Blocks;Self Assembly &Self-Assembly Materials;Sulfur Compounds;Thiols;Thiols/Mercaptans
• Mol File: 1191-08-8.mol
• Article Data: 11

Chemical Properties

• Melting Point: -53.9°C
• Boiling Point: 105-106 °C30 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /liquid
• Density: 1.042 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.563mmHg at 25°C
• Refractive Index: n20/D 1.529(lit.)
• PKA: 10.07±0.10(Predicted)
• BRN: 1697080
• CAS DataBase Reference: 1,4-BUTANEDITHIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-BUTANEDITHIOL(1191-08-8)
• EPA Substance Registry System: 1,4-BUTANEDITHIOL(1191-08-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• F: 13
• Hazardous Substances Data: 1191-08-8(Hazardous Substances Data)

Usage

Description

1,4-Butanedithiol, an alkanedithiol, is a clear colorless to pale yellow liquid that serves as a food odorant. It is known for its distinct smell, which is similar to that of its homologs, such as propane-1,3-dithiol and pentane-1,5-dithiol.

Uses

Used in Food Industry:
1,4-Butanedithiol is used as a flavoring agent for its characteristic odor, which is similar to other alkanedithiols. It is employed to enhance the aroma and taste of various food products, providing a unique and pleasant scent.
Used in Chemical Industry:
1,4-Butanedithiol can be utilized as a building block or intermediate in the synthesis of various organic compounds, particularly those requiring dithiol functional groups. Its chemical properties make it a versatile component in the development of new molecules and materials.
Used in Research and Development:
Due to its unique chemical structure and properties, 1,4-Butanedithiol can be used in research and development for studying the effects of dithiol compounds on various chemical reactions and processes. This can lead to the discovery of new applications and uses for this compound in different industries.

Synthesis Reference(s)

The Journal of Organic Chemistry, 20, p. 50, 1955 DOI: 10.1021/jo01119a009

InChI:InChI=1/C4H10S2/c5-3-1-2-4-6/h5-6H,1-4H2

Synthetic route

2,2'-(butane-1,4-diyldi(sulfanediyl))bis[3-(2-aminophenyl)-4-methyl-1,3-thiazol-3-ium] diiodide → 3-methyl-thiazolo[3,2-a]benzimidazolium iodide + 1,4-Butanedithiol (1191-08-8)

Conditions	Yield
With methanol for 12h; Reflux;	A n/a B 90%

poly(tetramethylenedisulfide) → 1,2-dithiane (505-20-4) + 1,4-Butanedithiol (1191-08-8)

Conditions	Yield
With sodium hydroxide; hydrazine hydrate In water at 75℃; for 2h;	A 52% B 18%

1,4-dibromo-butane (110-52-1) → 1,4-Butanedithiol (1191-08-8)

Conditions	Yield
With sodium hydrogensulfide; ethylene glycol unter Einleiten von Schwefelwasserstoff;
With hexamethyldisilathiane; tetrabutyl ammonium fluoride In tetrahydrofuran at -10 - 20℃;	77 % Chromat.

1,4-bis-acetylsulfanyl-butane (6633-90-5) → 1,4-Butanedithiol (1191-08-8)

Conditions	Yield
With sodium hydrogensulfide; ethanol
With sodium hydroxide In acetone Ambient temperature;

VUF 8334 (2986-37-0) → 1,4-Butanedithiol (1191-08-8)

Conditions	Yield
With potassium hydroxide; water

1,2-dithiane (505-20-4) + 1.3-propanedithiol (109-80-8) → 1,2-dithiolane (557-22-2) + 1,4-Butanedithiol (1191-08-8)

Conditions	Yield
With potassium tert-butylate In dimethylsulfoxide-d6 Equilibrium constant; other solvents;

1,2-dithiane (505-20-4) + benzene-1,2-diethanethiol (112453-80-2) → 1,4-Butanedithiol (1191-08-8) + 5,6,9,10-Tetrahydro-7,8-dithia-benzocyclooctene (128846-12-8)

Conditions	Yield
With deuteriated sodium hydroxide; water-d2 In dimethylsulfoxide-d6 Equilibrium constant; Thermodynamic data; ΔG0;

1,2-dithiane (505-20-4) + triphenylphosphine (603-35-0) → 1,4-Butanedithiol (1191-08-8) + Triphenylphosphine oxide (791-28-6)

Conditions	Yield
With water In ethanol at 26℃; Rate constant; Kinetics; Thermodynamic data; different temperatures, ΔH(excit.), ΔS(excit.);
With water In ethanol at 26℃;

1,2-dithiane (505-20-4) → 1,4-Butanedithiol (1191-08-8)

Conditions	Yield
With phosphate buffer; lipoamide dehydrogenase; oxidized lipoamide; NAD; egg albumin In methanol; water at 30℃; Equilibrium constant;
With DL-dithiothreitol In d(4)-methanol; water-d2 at 25℃; Equilibrium constant; phosphate buffer(0.5 mM, pH 7.0);

1,4-bis-thiocarbamoylsulfanyl-butane (50852-78-3) + alkali → 1,4-Butanedithiol (1191-08-8)

1,4-Diiodobutane (628-21-7) + dithiocarbamidacidic ammonium → 1,4-Butanedithiol (1191-08-8)

Conditions	Yield
With ethanol Erwaermen das Bisdithiourethan mit waessr.Kalilauge;

tetramethylene-bis-dithio carbaminate → 1,4-Butanedithiol (1191-08-8)

Conditions	Yield
With alkali

Butan-1,4-bis-thiuroniumion → 1,4-Butanedithiol (1191-08-8)

Conditions	Yield
With sodium hydroxide In water Reflux; Schlenk technique; Inert atmosphere;	4.5 g

1,4-Butanedithiol (1191-08-8) + zinc (7440-66-6) → Zn(S2C4H8-1,4)

Conditions	Yield
In acetonitrile byproducts: H2; Electrolysis; electrochemical cell with a platinum cathode and a Zn-anode attached to a platinum wire, in presence of Et4NClO4, N2 bubbled slowly through the soln., reaction time: 2.5 h, 10 V; filtered, washed with CH3CN, dried in vac.; elem. anal.;	100%

1,4-Butanedithiol (1191-08-8) → 1,2-dithiane (505-20-4)

Conditions	Yield
Stage #1: 1,4-Butanedithiol With 10-molybdo-2-vanadophosphoric acid In ethanol; water at 70℃; for 0.25h; Stage #2: With potassium permanganate In ethanol; water at 80℃; for 8h;	99%
With benzyltriphenylphosphonium peroxodisulfate In acetonitrile for 1.2h; Heating;	98%
With 1-butyl-4-aza-1-azoniabicyclo[2.2.2]octane dichromate In acetonitrile for 1.2h; Heating;	98%

1,4-Butanedithiol (1191-08-8) + p-chlorphenylisocyanate (104-12-1) → Tetramethylen-1,4-bis(N-4-chlorphenyl-thiolurethan)

Conditions	Yield
N-benzyl-trimethylammonium hydroxide In diethyl ether at 20℃; for 1h;	98%

1,4-Butanedithiol (1191-08-8) + Cyclohexyl isocyanate (3173-53-3) → Tetramethylen-1,4-bis(N-cyclohexyl-thiolurethan) (102732-86-5)

Conditions	Yield
N-benzyl-trimethylammonium hydroxide In diethyl ether at 20℃; for 1h;	97%

1,4-Butanedithiol (1191-08-8) + acrolein (107-02-8) → 4,9-Dithiadodecandial (158199-68-9)

Conditions	Yield
With triethylamine In chloroform for 12h; Ambient temperature;	97%

1,4-Butanedithiol (1191-08-8) + Isopropyl isocyanate (1795-48-8) → Tetramethylen-1,4-bis(N-isopropyl-thiolurethan) (102732-84-3)

Conditions	Yield
N-benzyl-trimethylammonium hydroxide In diethyl ether at 20℃; for 1h;	97%

1,4-Butanedithiol (1191-08-8) + dehydroqinghaosu (101020-89-7) → C34H50O10S2

Conditions	Yield
Stage #1: 1,4-Butanedithiol With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.75h; Stage #2: dehydroqinghaosu In tetrahydrofuran at -78℃; for 5h; Further stages.;	97%

1,4-Butanedithiol (1191-08-8) + 1,3-(dimethylmethylenedioxy)-2-methyl-2-(methylene-p-toluenesulfonyl)propane → 2,11-bis(3,3-dimethyl-2,4-dioxycyclohexanyl)-4,9-dithiadodecane (688310-83-0)

Conditions	Yield
With sodium In ethanol	96%

1,4-Butanedithiol (1191-08-8) + triallyl isocyanurate (1025-15-6) → 1,3,5-tris[3-(4-mercaptobutylsulfanyl)propyl]isocyanurate

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) at 70℃; for 4h;	96%

1,4-Butanedithiol (1191-08-8) + p-Tolylisocyanate (622-58-2) → Tetramethylen-1,4-bis(N-4-tolyl-thiolurethan)

Conditions	Yield
N-benzyl-trimethylammonium hydroxide In diethyl ether at 20℃; for 1h;	95%

1,4-Butanedithiol (1191-08-8) + cyclododecanone (830-13-7) → 13,18,31,36-tetrathiadispiro<11.6.11.6>hexatriacontane (98051-53-7)

Conditions	Yield
With boron trifluoride diethyl etherate; acetic acid for 22h; Ambient temperature;	94%

1,4-Butanedithiol (1191-08-8) + cadmium (7440-43-9) → Cd(S2C4H8-1,4)

Conditions	Yield
In acetonitrile byproducts: H2; Electrolysis; electrochemical cell with a platinum cathode and a Cd-anode attached to a platinum wire, in presence of Et4NClO4, N2 bubbled slowly through the soln., reaction time: 2.5 h, 20 V; filtered, washed with CH3CN, dried in vac.; elem. anal.;	94%

1,4-Butanedithiol (1191-08-8) + 1-isocyanato-3-trifluoromethyl-benzene (329-01-1) → Tetramethylen-1,4-bis(N-3-trifluoromethyl-phenyl-thiolurethan)

Conditions	Yield
N-benzyl-trimethylammonium hydroxide In diethyl ether at 20℃; for 1h;	93%

η6-m-chlorotoluene-η5-cyclopentadienyliron hexafluorophosphate + 1,4-Butanedithiol (1191-08-8) → ((C6H4CH3)Fe(C5H5))2S(CH2)4S(2+)*2PF6(1-)=[((C6H4(CH3))Fe(C5H5))2S(CH2)4S](PF6)2

Conditions	Yield
With potassium carbonate In tetrahydrofuran; N,N-dimethyl-formamide stirring under N2 atmosphere for 16 h at room temperature; filtn. through a sintered glass crucible into a HCl soln., evapn. (reduced pressure), addn. of aq. NH4PF6, filtn., drying (vac.), washing (ether), drying;	93%

1,4-Butanedithiol (1191-08-8) + 1,2-(4’-oxocyclohexano)[60]fullerene (150304-28-2) → C68H14S2

Conditions	Yield
With titanium tetrachloride In tetrahydrofuran; 1,2-dichloro-benzene at 20℃; for 0.5h;	93%

1,4-Butanedithiol (1191-08-8) + triphenylindium (3958-47-2) → phenyl(butyl-1,4-dithiol)indane (119754-82-4)

Conditions	Yield
In toluene byproducts: C6H6; Thiol added dropwise to refluxing soln. of InPh3, molar ratio 1/1, N2-atmosphere, stirred at room temp. for 1 h, pptn.; ppt. washed with hexane, dried in vacuum, elem. anal.;	91.3%

1,4-Butanedithiol (1191-08-8) + para-fluorophenyl isocyanate (1195-45-5) → Tetramethylen-1,4-bis(N-4-fluorphenyl-thiolurethan)

Conditions	Yield
N-benzyl-trimethylammonium hydroxide In diethyl ether at 20℃; for 1h;	91%

1,4-Butanedithiol (1191-08-8) + C25H31NO3 → C29H39NO2S2

Conditions	Yield
With hydrogen bromide; trimethyl orthoformate In toluene at 110℃; for 6h;	90.15%

1,4-Butanedithiol (1191-08-8) + dimethyl(methylthio)sulfonium tetrafluoroborate (5799-67-7) → 1,2-dithiane (505-20-4)

Conditions	Yield
In dichloromethane at 0 - 5℃;	90%

carbon disulfide (75-15-0) + 1,4-Butanedithiol (1191-08-8) + bromoacetic acid methyl ester (96-32-2) → methoxycarbonylmethyl 4-(methoxycarbonylmethylthio)butyl trithiocarbonate + 1,4-butanediyl bis(methoxycarbonylmethyl trithiocarbonate)

Conditions	Yield
With sodium hydroxide; Aliquat 336 In water at 20℃; for 5h;	A 6% B 90%
With sodium hydroxide; Aliquat 336 In water at 20℃; for 5h;	A 8% B 90%

iodobenzene (591-50-4) + 1,4-Butanedithiol (1191-08-8) → 1,4-bis-phenylsulfanyl-butane (5330-89-2)

Conditions	Yield
With potassium hydroxide; copper(II) oxide In dimethyl sulfoxide at 80℃; for 5h;	90%

indium (7440-74-6) + 1,4-Butanedithiol (1191-08-8) → (1,4-SC4H8SH)indium(I)

Conditions	Yield
In acetonitrile byproducts: H2; Electrochem. Process; N2 atmosphere; electrochemical reaction of indium and org. compd. in MeCN (indium anode, supporting electrolyte (Et4N)ClO4, 2 h, 20 V 20 mA, room temp.); collecting, washing (MeCN), drying (vac.); elem anal.;	90%

1,4-Butanedithiol (1191-08-8) + N,N-bis(methoxymethyl)-N-(m-methoxyphenyl)amine (1443365-06-7) → 3-(m-methoxyphenyl)-1,5,3-dithiazonane

Conditions	Yield
Stage #1: N,N-bis(methoxymethyl)-N-(m-methoxyphenyl)amine In ethanol; ethyl acetate at 20℃; for 0.5h; Inert atmosphere; Stage #2: 1,4-Butanedithiol In ethanol; ethyl acetate at 20℃; for 5h; Inert atmosphere;	90%

1,4-Butanedithiol (1191-08-8) + N,N-bis(methoxymethyl)-N-phenylamine (13657-44-8) → 3-phenyl-1,5,3-dithiazonane

Conditions	Yield
Stage #1: N,N-bis(methoxymethyl)-N-phenylamine In ethyl acetate at 20℃; for 0.5h; Inert atmosphere; Stage #2: 1,4-Butanedithiol In ethyl acetate at 20℃; for 5h; Reagent/catalyst; Inert atmosphere;	89%

1,4-Butanedithiol (1191-08-8) + N,N-bis(methoxymethyl)-N-(p-chlorophenyl)amine (1451094-78-2) → 3-(p-chlorphenyl)-1,5,3-dithiazonane

Conditions	Yield
Stage #1: N,N-bis(methoxymethyl)-N-(p-chlorophenyl)amine In ethyl acetate at 20℃; for 0.5h; Inert atmosphere; Stage #2: 1,4-Butanedithiol In ethyl acetate at 20℃; for 5h; Inert atmosphere;	89%

calcium carbide + 1,4-Butanedithiol (1191-08-8) → 1,4-bis(vinylthio)-n-butane (36648-04-1)

Conditions	Yield
With water; potassium hydroxide In N,N-dimethyl-formamide at 100℃; for 3h; Sealed tube;	89%

1,4-Butanedithiol (1191-08-8) + N,N-bis(methoxymethyl)-N-(m-bromophenyl)amine → 3-(m-bromphenyl)-1,5,3-dithiazonane

Conditions	Yield
Stage #1: N,N-bis(methoxymethyl)-N-(m-bromophenyl)amine In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: 1,4-Butanedithiol In dichloromethane at 20℃; for 5h; Inert atmosphere;	88%

carbon disulfide (75-15-0) + 1,4-Butanedithiol (1191-08-8) + ethyl iodide (75-03-6) → ethyl 4-(ethylthio)butyl trithiocarbonate + 1,4-butanediyl bis(ethyl trithiocarbonate)

Conditions	Yield
With sodium hydroxide; Aliquat 336 In water at 20℃; for 5h;	A 12% B 87%

1,4-Butanedithiol (1191-08-8) + woollins’ reagent (122039-27-4) → 2-phenyl-1,3,2-dithiaphosphepane-2-selenide

Conditions	Yield
In toluene at 130℃; for 6h; Schlenk technique; Inert atmosphere;	87%

Upstream product

• 110-52-1 1,4-dibromo-butane 
• 6633-90-5 1,4-bis-acetylsulfanyl-butane 
• 2986-37-0 VUF 8334 
• 505-20-4 1,2-dithiane 
• 109-80-8 1.3-propanedithiol 
• 112453-80-2 benzene-1,2-diethanethiol 
• 603-35-0 triphenylphosphine 
• 50852-78-3 1,4-bis-thiocarbamoylsulfanyl-butane 
• 628-21-7 1,4-Diiodobutane 

Downstream Products

• 15394-33-9 methyl 4-(methylsulfanyl)butyl sulfide 
• 101788-14-1 1,4-Bis-(benzylsulfonyl)-butan 
• 18282-76-3 1,4-bis(benzylsulfanyl)butane 
• 54738-37-3 2-(4-[1,3]dithiepan-2-yl-styryl)-5-nitro-1-vinyl-1H-imidazole 
• 505-20-4 1,2-dithiane 
• 109-80-8 1.3-propanedithiol 
• 91-20-3 naphthalene 
• 613-81-0 bis(2-naphthyl)sulfide 
• 111220-29-2 1,4-bis(naphthalen-2-ylthio)butane 
• 607-53-4 bis(1-naphthyl)sulfide 
• 111220-27-0 C₂₄H₂₂S₂ 
• 113307-72-5 1-phenylthio-7,12-dithiaspiro<5.6>dodecane 
• 82313-72-2 15-Hydroxy-15-phenyl-2,7-dithia<1.8>paracyclophan 
• 82313-55-1 15-Phenyl-2,7-dithia<1.8>paracyclophan 

Relevant articles and documents

3-(2-aminophenyl)-4-methyl-1,3-thiazole-2(3H)-thione as an ecofriendly sulphur transfer agent to prepare alkanethiols in high yield and high purity

A new process is described for preparing very pure linear alkanethiols and linear α,ω-alkanedithiols using a sequential alkylation of the title compound, followed by a ring closure to quantitatively give the corresponding 3-methyl[1,3]thiazolo[3,2-a]-[3,1

A general and mild synthesis of thioesters and thiols from halides

The conversion of a wide variety of halides to thioesters by reaction with potassium thiocetate under mild conditions is described, and the generality of the method is demonstrated.