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

Chemical Properties

clear colorless to pale yellow liquid

Synthesis Reference(s)

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

General Description

1,4-Butanedithiol, an alkanedithiol, is a food odorant. Its odor threshold is similar to its other homologs (propane-1,3-dithiol and pentane-1,5-dithiol).

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

Downstream Products

• 15394-33-9 methyl 4-(methylsulfanyl)butyl sulfide 
• 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 
• 90828-06-1 3,6-Dimethyl-10-phenyl-5,10-dihydro-1H-benzo[g]pteridine-2,4-dione 
• 380305-97-5 C₆₀H₆₆S₂Se 
• 191341-60-3 cis-[Pd(butane-1,4-dithiolate)(1,3-bis(diphenylphosphino)propane)] 
• 191341-55-6 cis-[Pt(butane-1,4-dithiolate)(1,3-bis(diphenylphosphino)propane)] 
• 191341-52-3 cis-[Pt(butane-1,4-dithiolate)(1,4-bis(diphenylphosphino)butane)] 
• 191341-58-9 cis-[Pd(butane-1,4-dithiolate)(1,4-bis(diphenylphosphino)butane)] 
• 1198800-07-5 2,2'-[butane-1,4-diylbis(thio)]bis[3,5,6-tris(aziridin-1-yl)benzo-1,4-quinone] 
• 104143-58-0 2,2-diphenyl-1,3-dithiepane 

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