118-72-9

Basic information

• Product Name: 2,6-DIMETHYLTHIOPHENOL
• Synonyms: 2,6-DIMETHYLBENZENETHIOL;2,6-DIMETHYLTHIOPHENOL;FEMA 3666;2,6-dimethyl-benzenethio;Benzenethiol, 2,6-dimethyl-;2,6-Thioxylenol ;2 6-DIMETHYLTHIOPHENOL 95+%;2,6-Dimethylbenzolthiol
• CAS NO: 118-72-9
• Molecular Formula: C₈H₁₀S
• Molecular Weight: 138.23
• EINECS: 204-272-3
• Product Categories: Bioactive Small Molecules;Building Blocks;Cell Biology;Chemical Synthesis;DIG-DY;Organic Building Blocks;Sulfur Compounds;Thiols/Mercaptans
• Mol File: 118-72-9.mol
• Article Data: 8

Chemical Properties

• Melting Point: -30°C (estimate)
• Boiling Point: 122 °C50 mm Hg
• Flash Point: 186 °F
• Appearance: clear colorless to light yellow liquid
• Density: 1.038 g/mL at 25 °C
• Vapor Pressure: 0.187mmHg at 25°C
• Refractive Index: n20/D 1.575
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 7.03±0.50(Predicted)
• Sensitive: Moisture Sensitive
• BRN: 1099405
• CAS DataBase Reference: 2,6-DIMETHYLTHIOPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DIMETHYLTHIOPHENOL(118-72-9)
• EPA Substance Registry System: 2,6-DIMETHYLTHIOPHENOL(118-72-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-36-7/9
• RIDADR: UN 3334
• WGK Germany: 2
• TSCA: T
• HazardClass: IRRITANT, STENCH
• Hazardous Substances Data: 118-72-9(Hazardous Substances Data)

Usage

Description

2,6-Dimethylbenzenethiol, also known as 2,6-dimethyl thiophenol or 2,6-xylenethiol, the molecular formula is C8H10S, which belongs to the class of organic compounds known as thiophenols. Thiophenols are compounds containing a thiophenol ring, which a phenol derivative obtained by replacing the oxygen atom from the hydroxyl group (attached to the benzene) by a sulfur atom. 2,6-Dimethylbenzenethiol is a very weakly acidic compound (based on its pKa). 2,6-Dimethylbenzenethiol is a meaty, metallic, and phenolic tasting compound. 2,6-Dimethylbenzenethiol is found in animal foods. It is present in boiled beef. It is a flavouring ingredient. 2,6-Dimethylbenzenethiol was used in the synthesis of (2,6-Me2C6H3S)2Pb by reacting with Pb(OAc)2.

Chemical Properties

Different sources of media describe the Chemical Properties of 118-72-9 differently. You can refer to the following data:
1. clear colorless to light yellow liquid
2. 2,6-Dimethylthiophenol has a strong odor.

Occurrence

Reported found in boiled beef

Uses

2,6-Dimethylbenzenethiol was used in the synthesis of (2,6-Me2C6H3S)2Pb by reacting with Pb(OAc)2.

Taste threshold values

Meaty, vegetative and nutty with a slight sulfuraceous nuance.

InChI:InChI=1/C8H10S/c1-6-4-3-5-7(2)8(6)9/h3-5,9H,1-2H3/p-1

Synthetic route

benzyl (2,6-dimethylphenyl) sulfide → 2,6-dimethylbenzene-1-thiol (118-72-9)

Conditions	Yield
With bis(cyclopentadienyl)titanium dichloride; dibutylmagnesium In n-heptane; diethylene glycol dimethyl ether at 0℃; for 1h;	96%

bis(2,6-dimethylphenyl)disulfide (2905-17-1) → 2,6-dimethylbenzene-1-thiol (118-72-9)

Conditions	Yield
With indium; ammonium chloride In ethanol for 1h; Reduction; Heating;	94%
With magnesium In methanol for 0.583333h; Ambient temperature;	90%
With sodium tetrahydroborate; zirconium(IV) chloride In tetrahydrofuran at 35℃; for 0.333333h; Reduction;	80%

2,6-dimethyliodobenzene (608-28-6) → 2,6-dimethylbenzene-1-thiol (118-72-9)

Conditions	Yield
With copper(l) iodide; thiourea; L-proline; sodium t-butanolate In dimethyl sulfoxide at 90℃; for 24h; Inert atmosphere;	83%
Multi-step reaction with 2 steps 1: copper(l) iodide; tetra(n-butyl)ammonium hydroxide; sulfur / water / 24 h / 40 °C / Inert atmosphere; Sealed tube 2: hydrogenchloride; zinc / water / Inert atmosphere; Cooling with ice View Scheme

potassium ethyl xanthogenate (140-89-6) + 2,6-Dimethylphenyl diazonium chloride (85518-80-5) → 2,6-dimethylbenzene-1-thiol (118-72-9)

Conditions	Yield
With water Erwaermen des Reaktionsprodukts mit aethanol. KOH;
With water Erwaermen des Reaktionsprodukts mit LiAlH4 in Aether;

2,6-dimethylaniline (87-62-7) → 2,6-dimethylbenzene-1-thiol (118-72-9)

Conditions	Yield
(i) aq. NaNO2, aq. HCl, (ii) potassium ethylxanthate, (iii) KOEt, EtOH; Multistep reaction;
(i) NaNO2, aq. HCl, (ii) aq. EtOCS2K; Multistep reaction;
Multi-step reaction with 3 steps 1: (i) NaNO2, aq. H2SO4, (ii) /BRN= 3596974/, H2O 2: (i) aq. NaOH, EtOH, (ii) Br2 3: LiAlH4 / diethyl ether View Scheme

Bis-<2,6-dimethyl-phenyl>-dithiolcarbonat (109404-65-1) → 2,6-dimethylbenzene-1-thiol (118-72-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) aq. NaOH, EtOH, (ii) Br2 2: LiAlH4 / diethyl ether View Scheme

2,6-dimethylbenzene-1-thiol (118-72-9) + N,N’-di(2,6-diisopropylphenyl)-1,6,9,13-tetrabromoterrylene-3,4:11,12-tetracarboxdiimide (464885-23-2) → N,N'-bis(2,6-diisopropylphenyl)-1,6,9,14-tetra(2,6-dimethylthiophenoxy)-terrylene-3,4:11,12-tetracarboximide (919488-85-0)

Conditions	Yield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 40℃; for 4h;	100%

2,6-dimethylbenzene-1-thiol (118-72-9) + C45H62O7Si2 → C49H62O5SSi2

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at -78℃; for 2h;	100%

2,6-dimethylbenzene-1-thiol (118-72-9) + benzenesufonyl hydrazide (80-17-1) → S-(2,6-dimethylphenyl) benzenesulfonothioate

Conditions	Yield
With tert.-butylhydroperoxide; sodium iodide In acetonitrile at 25℃; for 12h;	100%
With tert.-butylhydroperoxide; sodium iodide In acetonitrile at 20℃; for 12h;	99%

2,6-dimethylbenzene-1-thiol (118-72-9) → bis(2,6-dimethylphenyl)disulfide (2905-17-1)

Conditions	Yield
With oxygen; SiO2-Cl In dichloromethane at 0℃; for 0.166667h;	99%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In chloroform at 25℃; for 0.0833333h;	99%
With aluminum oxide In neat (no solvent) for 0.5h; Milling; chemoselective reaction;	95%

2,6-dimethylbenzene-1-thiol (118-72-9) + (E)-1-iodo-1-octene (42599-17-7) → (E)-(2,6-dimethylphenyl)(oct-1-enyl)sulfane

Conditions	Yield
With potassium phosphate; (1,10-phenanthroline)bis(triphenylphosphine)copper(I) nitrate In toluene at 110℃; for 4h;	99%

2,6-dimethylbenzene-1-thiol (118-72-9) + cyclohexenone (930-68-7) → (S)-3-(2,6-dimethylphenylthio)-cyclohexanone (177336-50-4)

Conditions	Yield
With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methyl)urea In toluene at 20℃; for 10h; Michael addition; optical yield given as %ee; enantioselective reaction;	99%

2,6-dimethylbenzene-1-thiol (118-72-9) + α-bromopropionyl bromide (563-76-8) → S-2,6-dimethylphenyl α-bromothiopropionate (1247748-11-3)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.5h;	99%
Stage #1: 2,6-dimethylbenzene-1-thiol; α-bromopropionyl bromide With pyridine In dichloromethane at 0℃; Inert atmosphere; Stage #2: With dmap In dichloromethane at 0 - 20℃; Inert atmosphere;	63%

2,6-dimethylbenzene-1-thiol (118-72-9) + chlorobenzene (108-90-7) → 2,6-dimethylphenyl phenyl sulfide (54088-93-6)

Conditions	Yield
With tetrakis(tri-p-tolylphosphite)nickel(0); potassium tert-butylate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; zinc In toluene at 110℃; for 16h; Sealed tube; Inert atmosphere;	99%

2,6-dimethylbenzene-1-thiol (118-72-9) + methoxybenzene (100-66-3) → (2,6-dimethylphenyl)(4-methoxyphenyl)sulfane

Conditions	Yield
With tert-butylammonium hexafluorophosphate(V) In 1,2-dichloro-ethane for 4.5h; Electrolysis; Inert atmosphere; Sealed tube; regioselective reaction;	99%

2,6-dimethylbenzene-1-thiol (118-72-9) + 2-chloro-benzaldehyde (89-98-5) → 2-((2,6-dimethylphenyl)thio)benzaldehyde (540774-00-3)

Conditions	Yield
With sodium carbonate In N,N,N,N,N,N-hexamethylphosphoric triamide at 100℃; for 5h;	98%

2,6-dimethylbenzene-1-thiol (118-72-9) + (S)-(-)-β-methyl-β-propiolactone (65058-82-4) → (R)-3-(2,6-Dimethyl-phenylsulfanyl)-butyric acid (141079-83-6)

Conditions	Yield
With sodium hydroxide In water; isopropyl alcohol 1.) 0 deg C, 10 min, 2.) rt, 2 h;	97%

2,6-dimethylbenzene-1-thiol (118-72-9) + cis-di-tert-butyl 1-tosylaziridine-2,3-dicarboxylate (1292810-19-5) → di-tert-butyl 2-(2,6-dimethylphenylthio)-3-(4-methylphenylsulfonamido)succinate (1292810-12-8)

Conditions	Yield
Stage #1: cis-di-tert-butyl 1-tosylaziridine-2,3-dicarboxylate With (1R,2R)-2-(tert-butyldiphenylsilyloxy)-N-(dipyrrolidin-1-ylmethylene)-2,3-dihydro-1H-inden-1-amine In di-isopropyl ether at -50℃; for 0.5h; Inert atmosphere; Stage #2: 2,6-dimethylbenzene-1-thiol In di-isopropyl ether at -50℃; for 48h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	97%

2,6-dimethylbenzene-1-thiol (118-72-9) + ortho-methylphenyl iodide (615-37-2) → (2,6-dimethylphenyl)(o-tolyl)sulfane (38630-01-2)

Conditions	Yield
With sodium hydroxide; copper(l) iodide; tetrabutylammomium bromide In toluene for 22h; Ullmann coupling; Heating;	96%

2,6-dimethylbenzene-1-thiol (118-72-9) + trans-1-bromomethyl-2-iodocyclopropane → 1-(trans-2-iodocyclopropylmethylsulfanyl)-2,6-dimethylbenzene

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide for 3h;	96%

2,6-dimethylbenzene-1-thiol (118-72-9) + 1-Chloro-4-iodobenzene (637-87-6) → (4-chlorophenyl)(2,6-dimethylphenyl)sulfide

Conditions	Yield
With sodium hydroxide; copper(l) iodide; tetrabutylammomium bromide In toluene for 22h; Ullmann coupling; Heating;	96%

2,6-dimethylbenzene-1-thiol (118-72-9) + (2E)-5-phenyl-2-pentanophenone (134273-12-4) → (S)-3-(2,6-dimethylphenylthio)-1,5-diphenylpentan-1-one

Conditions	Yield
With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methyl)urea In toluene at 20℃; for 12h; Michael addition; optical yield given as %ee; enantioselective reaction;	96%

2,6-dimethylbenzene-1-thiol (118-72-9) + C40H39BrO7 (1401236-92-7) → C44H39BrO5S (1401236-98-3)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at -78 - -55℃; for 3.5h;	96%

2,6-dimethylbenzene-1-thiol (118-72-9) + methacrylic acid methyl ester (80-62-6) → methyl 3-((2,6-dimethylphenyl)thio)-2-hydroxy-2-methylpropanoate

Conditions	Yield
Stage #1: 2,6-dimethylbenzene-1-thiol; methacrylic acid methyl ester In 1,2-dichloro-ethane; acetonitrile at 20℃; for 6h; Stage #2: With triphenylphosphine In 1,2-dichloro-ethane; acetonitrile for 2h;	96%
With oxygen; copper diacetate; benzoic acid In 1,2-dichloro-ethane at 50℃; for 3h;	68%

2,6-dimethylbenzene-1-thiol (118-72-9) + trimethanolato(pentamethylcyclopentadienyl)titanium(IV) → pentamethylcyclopentadienyl-2,6-dimethylphenylthiodimethoxytitanium

Conditions	Yield
In toluene at 20℃; Inert atmosphere;	96%

2,6-dimethylbenzene-1-thiol (118-72-9) + iodobenzene (591-50-4) → 2,6-dimethylphenyl phenyl sulfide (54088-93-6)

Conditions	Yield
With copper(l) iodide; 2.9-dimethyl-1,10-phenanthroline; sodium t-butanolate In toluene at 110℃; for 24h;	95%
With tetra(n-butyl)ammonium hydroxide In water at 50℃; for 24h; Inert atmosphere; Sealed tube; chemoselective reaction;	93%
With copper(l) iodide; sodium t-butanolate In acetonitrile at 0℃; for 8h; Sealed tube; Irradiation; Inert atmosphere;	72%

2,6-dimethylbenzene-1-thiol (118-72-9) + ethyl acrylate (140-88-5) → 3-(2,6-dimethylphenylsulfanyl)propionic acid ethyl ester (850175-21-2)

Conditions	Yield
With sodium hydride In dichloromethane; mineral oil at 50℃;	95%
With potassium carbonate In dichloromethane at 20℃; for 18h;	87%

2,6-dimethylbenzene-1-thiol (118-72-9) + 2-chloro-ethanol (107-07-3) → 2-(2,6-dimethyl phenylthio) 1-hydroxyethane

Conditions	Yield
With sodium hydroxide In water	95%

2,6-dimethylbenzene-1-thiol (118-72-9) + 4-tolyl iodide (624-31-7) → (2,6-dimethylphenyl)(p-tolyl)sulfane

Conditions	Yield
With sodium hydroxide; copper(l) iodide; tetrabutylammomium bromide In toluene for 22h; Ullmann coupling; Heating;	95%

2,6-dimethylbenzene-1-thiol (118-72-9) + carbonylgold(I) chloride (50960-82-2) → gold (7440-57-5, 457905-15-6)

Conditions	Yield
With CO In dichloromethane byproducts: HCl, (SC6H3Me2-2,6)2; 1 atm CO, -65°C;	95%

2,6-dimethylbenzene-1-thiol (118-72-9) + 3-iodobenzonitrile (69113-59-3) → 3-(2,6-dimethylphenylthio)benzonitrile (1270110-52-5)

Conditions	Yield
With copper on iron; potassium carbonate In N,N-dimethyl acetamide at 100℃; for 8h;	95%

2,6-dimethylbenzene-1-thiol (118-72-9) + 1,3-diethyl-2-bromobenzene (65232-57-7) → (2,6-diethylphenyl)(2,6-dimethylphenyl)sulfane

Conditions	Yield
With Pd-PEPPSI-(2,6-(3-pentyl)pentylphenyl-2H-imidazol-2-ylidene)Cl-o-picoline; potassium tert-butylate; lithium isopropoxide In toluene at 23℃; for 24h; Glovebox; Inert atmosphere;	95%

2,6-dimethylbenzene-1-thiol (118-72-9) + (3-bromo-4-methoxyphenyl)-phenylmethanone (116413-49-1) → C22H20O2S (1427470-15-2)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine In toluene for 3h; Inert atmosphere; Reflux;	95%

2,6-dimethylbenzene-1-thiol (118-72-9) + 9-bora-bicyclo[3.3.1]nonane (280-64-8) → C16H23BS

Conditions	Yield
With triethylamine In [D3]acetonitrile at 60℃; for 24h; Inert atmosphere;	95%

2,6-dimethylbenzene-1-thiol (118-72-9) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → C14H21BO2S

Conditions	Yield
With triethylamine In [D3]acetonitrile at 120℃; for 96h; Inert atmosphere;	95%
With C8H12BN In chloroform-d1 at 80℃; for 24h; Glovebox; Schlenk technique; Inert atmosphere;

Upstream product

• 608-28-6 2,6-dimethyliodobenzene 
• 109404-65-1 Bis-<2,6-dimethyl-phenyl>-dithiolcarbonat 
• 87-62-7 2,6-dimethylaniline 
• 2905-17-1 bis(2,6-dimethylphenyl)disulfide 
• 140-89-6 potassium ethyl xanthogenate 
• 85518-80-5 2,6-Dimethylphenyl diazonium chloride 

Downstream Products

• 16463-11-9 2,6-dimethylphenyl 2-methyl-2-propyl sulfide 
• 158870-93-0 (S)-3-<(2,6-dimethylphenyl)thio>-1,2-propanediol 
• 2905-17-1 bis(2,6-dimethylphenyl)disulfide 
• 470480-41-2 [Ru(2,6-dimethylthiophenol)4(MeCN)] 
• 166193-53-9 [(CH₃)2Ga(SC₆H₃(CH₃)2)]4 
• 185690-76-0 2,6-Me₂C₆H₃SCo(dimethylglyoximate^(1-))2(pyridine) 
• 868257-98-1 Ru(1-5-η5-cyclooctadienyl)(SC6H3Me2-2,6)(PMe3)2 
• 104216-45-7 3-(2,6-dimethylphenylsulfanyl)-propanoic acid 
• 21128-60-9 allyl 2,6-dimethylbenzene sulfide 
• 32228-19-6 (E)-(2,6-dimethylphenyl)(styryl)sulfane 
• 38630-01-2 (2,6-dimethylphenyl)(o-tolyl)sulfane 
• 163524-43-4 1-[(2,6-dimethylphenyl)sulfanyl]-2-(trimethylsilyl)ethane 
• 32133-94-1 2,6-Dimethylphenylmercaptoessigsaeure 

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