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, is an organic compound with the molecular formula C8H10S. It belongs to the class of thiophenols, which are phenol derivatives where the oxygen atom from the hydroxyl group (attached to the benzene) is replaced by a sulfur atom. 2,6-DIMETHYLTHIOPHENOL is characterized by its meaty, metallic, and phenolic taste, as well as its strong odor. It is a very weakly acidic compound, and it appears as a clear colorless to light yellow liquid.

Uses

Used in Flavor Industry:
2,6-Dimethylbenzenethiol is used as a flavoring ingredient for its meaty, vegetative, and nutty taste with a slight sulfuraceous nuance. It is commonly found in animal foods, particularly in boiled beef, where it contributes to the overall flavor profile.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2,6-dimethylbenzenethiol is used in the synthesis of (2,6-Me2C6H3S)2Pb by reacting with Pb(OAc)2. This application highlights its utility in the preparation of various organometallic compounds.

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

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

Downstream Products

• 2905-17-1 bis(2,6-dimethylphenyl)disulfide 
• 91638-71-0 2,6-dimethyl-4-tert-butylbenzenethiol 
• 21557-49-3 [2,5-Dichloro-4-(2,6-dimethyl-phenylsulfanylthiocarbonylamino)-phenyl]-dithiocarbamic acid 2,6-dimethyl-phenyl ester 
• 55545-16-9 2-(2,6-dimethyl-phenylsulfanyl)-4,5-dihydro-thiazole 
• 4163-79-5 (2,6-dimethylphenyl)(methyl)sulfane 
• 100058-48-8 Ethylxanthogensaeure-(2,6-dimethyl-phenylester) 
• 16463-11-9 2,6-dimethylphenyl 2-methyl-2-propyl sulfide 
• 141079-83-6 (R)-3-(2,6-Dimethyl-phenylsulfanyl)-butyric acid 
• 158870-93-0 (S)-3-<(2,6-dimethylphenyl)thio>-1,2-propanediol 
• 92286-70-9 2-(2,6-dimethylphenylthio)ethylamine 
• 72462-92-1 γ-(2,6-Dimethylphenylthio)-buttersaeureethylester 
• 32133-94-1 2,6-Dimethylphenylmercaptoessigsaeure 
• 163524-43-4 1-[(2,6-dimethylphenyl)sulfanyl]-2-(trimethylsilyl)ethane 

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