576-26-1

Basic information

• Product Name: 2,6-Dimethylphenol
• Synonyms: VIC-M-XYLENOL;1,2,6-Xylenol;1,3-Dimethyl-2-hydroxybenzene;1-Hydroxy-2,6-dimethylbenzene;2,6-dimethyl-pheno;ai3-08524;m-2-Xylenol;phenol,2,6-dimethyl-
• CAS NO: 576-26-1
• Molecular Formula: C₈H₁₀O
• Molecular Weight: 122.16
• EINECS: 209-400-1
• Product Categories: Aromatic Phenols;Phenoles and thiophenoles
• Mol File: 576-26-1.mol
• Article Data: 186

Chemical Properties

• Melting Point: 43-45 °C(lit.)
• Boiling Point: 203 °C(lit.)
• Flash Point: 173 °F
• Appearance: Colorless to yellow-brownish/Low Melting Solid
• Density: 1.15
• Vapor Pressure: 0.2 hPa (20 °C)
• Refractive Index: 1.5371
• Storage Temp.: Store at +15°C to +25°C.
• Solubility: 8g/l
• PKA: pK1:10.59 (25°C)
• Explosive Limit: 1.4%(V)
• Water Solubility: 10 g/L (20 ºC)
• Stability: Stable. Very flammable. Incompatible with oxidizing agents, acid chlorides, acid anhydrides, steel, copper, copper alloys, bases
• Merck: 14,10082
• BRN: 1446677
• CAS DataBase Reference: 2,6-Dimethylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Dimethylphenol(576-26-1)
• EPA Substance Registry System: 2,6-Dimethylphenol(576-26-1)

Safety Data

• Hazard Codes: T,N
• Statements: 24/25-34-51/53
• Safety Statements: 26-36/37/39-45-61
• RIDADR: UN 2261 6.1/PG 2
• WGK Germany: 2
• RTECS: ZE6125000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 576-26-1(Hazardous Substances Data)

Usage

Chemical Properties

colourless crystals or white powder. soluble in alcohol, ether, chloroform, benzene and alkali solution, slightly soluble in water.

Occurrence

Reported found in smoked fatty fish, boiled and cooked cured pork, rum, malt whiskey, Japanese whiskey, coffee, katsuobushi (dried bonito) and lamb’s lettuce (Valerianella locusta).

Uses

Similar to other xylenol compounds, 2,6-dimethylphenol is used in the synthesis of anti-oxidant compounds due to the phenol moiety in the structure. In addition, this compound is used as a a reactant in the synthesis of polyphenylene ether polymers.

Preparation

From coal tar oil or coal hydrogenation.Synthesis of 2,6-dimethylphenol: The gas-phase catalytic reaction of phenol and methanol is carried out, and then purified by rectification, and the product purity can reach more than 99%.Selective phenol methylation to 2,6-dimethylphenol in a fluidized bed of iron-chromium mixed oxide catalyst with o–cresol circulationCatalytic synthesis of 2,6-dimethylphenol from methanol and cyclohexanone over titanium oxide-supported vanadium oxide catalysts

Application

2,6-dimethylphenol is generally applied in industry as a monomer in polymerization reaction. For the production of polyphenylene ether resins, polyester and polyether resins.

Aroma threshold values

Detection: 400 ppb

General Description

2,6-dimethylphenol is a colorless to off-white crystalline solid with a sweet tarry odor. Odor threshold concentration: 0.4 mg/L . (NTP, 1992)

Reactivity Profile

2,6-Dimethylphenol is incompatible with bases, acid chlorides, acid anhydrides, and oxidizing agents. Corrodes steel, brass, copper, and copper alloys.

Fire Hazard

2,6-Dimethylphenol is combustible.

Flammability and Explosibility

Nonflammable

Purification Methods

Fractionally distil 2,6-xylenol under nitrogen, crystallise it from *benzene or hexane, and sublime it at 38o/10mm. [Beilstein 6 IV 3122.]

InChI:InChI=1/C8H10O/c1-6-4-3-5-7(2)8(6)9/h3-5,9H,1-2H3

Synthetic route

1-tert-butoxycarbonyloxy-2,6-dimethylbenzene → 2.6-dimethylphenol (576-26-1)

Conditions	Yield
With sodium methylate In methanol; dichloromethane at 20℃; for 3h;	98%
With hydrogenchloride In 1,4-dioxane for 3h; Product distribution; Heating; deprotection;	91%
In 2,2,2-trifluoroethanol at 100℃; for 1h; Microwave irradiation;	96 %Spectr.

2,6-dimethyl-4-tert-butylphenol (879-97-0) → 2.6-dimethylphenol (576-26-1) + isobutene (115-11-7)

Conditions	Yield
aluminum oxide; nickel(II) sulphate In various solvent(s) at 305℃; Product distribution; fixed, quartz powder bed tubular reactor; gaseous phase in N2 flow; varied: temperature 280 to 330 deg C; N2 flow; quartz powder/catalyst ratio; residence time; substrates other alkylated phenols too;	A 97.5% B n/a

2,6-dimethylcyclohexanone (2816-57-1) + 2,6-dimethylcyclohexanol (5337-72-4) → 2.6-dimethylphenol (576-26-1)

Conditions	Yield
	97%

2,6-bis-<(dimethyamino)methyl>phenol (15827-34-6) → 2.6-dimethylphenol (576-26-1)

Conditions	Yield
With hydrogen; nickel-titanium-aluminum In various solvent(s) at 160℃; for 3h;	96.2%
With hydrogen; nickel-titanium-aluminum In various solvent(s) at 160℃; for 3h; Product distribution; Rate constant; Thermodynamic data; other temperatures; other concentrations of title compound;	96.2%

2,6-dimethylcyclohexanone (2816-57-1) → 2.6-dimethylphenol (576-26-1)

Conditions	Yield
With diethyl dibromomalonate at 100℃; for 48h; Dehydrogenation;	96%
at 330 - 335℃; Leiten ueber Palladium/Kohle;

2,6-dimethyl-1-chlorobenzene (6781-98-2) → 2.6-dimethylphenol (576-26-1)

Conditions	Yield
With cesiumhydroxide monohydrate; bis[(trimethylsilyl)methyl](1,5-cyclooctadiene)palladium(II); 2-((di-adamantan-1-yl)phosphaneyl)-1-(2,6-diisopropylphenyl)-1H-imidazole In tetrahydrofuran at 24℃; for 20h; Inert atmosphere;	96%
With potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos In 1,4-dioxane; water at 100℃; for 8h;	94%
With 5-(di-tert-butylphosphino)-1′, 3′, 5′-triphenyl-1′H-[1,4′]bipyrazole; tris-(dibenzylideneacetone)dipalladium(0); cesiumhydroxide monohydrate In tetrahydrofuran at 24℃; Inert atmosphere; Glovebox; Sealed tube;	92%
Stage #1: 2,6-dimethyl-1-chlorobenzene With potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0); 2-((di-adamantan-1-yl)phosphaneyl)-1-(2,6-diisopropylphenyl)-1H-imidazole In 1,4-dioxane; water at 100℃; for 20h; Inert atmosphere; Stage #2: With hydrogenchloride In 1,4-dioxane; water at 20℃; Inert atmosphere;	90%

2,6-dimethylbenzene boronic acid (100379-00-8) → 2.6-dimethylphenol (576-26-1)

Conditions	Yield
With water; caesium carbonate; hydrazine hydrate at 80℃; for 12h;	96%
With water; 3-chloro-benzenecarboperoxoic acid In ethanol at 20℃; for 6h;	94%
With 2,5-dimethylfuran; zinc(II) phthalocyanine; oxygen; citric acid In tetrahydrofuran at 25℃; under 760.051 Torr; for 1.5h; Irradiation; Sealed tube; Schlenk technique;	93%

2,6-dimethylbenzene boronic acid (100379-00-8) + dihydrogen peroxide (7722-84-1) → 2.6-dimethylphenol (576-26-1)

Conditions	Yield
With ammonium bicarbonate In water at 20℃; for 2h; Schlenk technique;	95%

Ni(CH2C(CH3)2C6H5)OC6H3(CH3)2(((CH3)2CH)2P(CH2)2P(CH(CH3)2)2) (438247-33-7) → 2.6-dimethylphenol (576-26-1) + Ni(CH2C(CH3)2C6H4)(((CH3)2CH)2P(CH2)2P(CH(CH3)2)2) (438247-37-1)

Conditions	Yield
In tetrahydrofuran (N2); stirring a soln. of nickel complex in THF at room temp. for 12 h; evapn., extn. with Et2O, filtration, concn., addn. of petroleum ether, cooling to -30°C; elem. anal.;	A n/a B 94%

potassium 2,6-dimethylphenyltrifluoroborate → 2.6-dimethylphenol (576-26-1)

Conditions	Yield
With Oxone; water In acetone at 20℃; for 0.0333333h;	94%

2-methoxy-1,3-dimethylbenzene (1004-66-6) → 2.6-dimethylphenol (576-26-1)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium In tetrahydrofuran; ethanol at -30℃; for 2h;	93%
With 1,3-dimethyl-2-imidazolidinone; lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at 185℃; for 12h; further reagent: NaN(SiMe3)2;	91%
With lithium; ethylenediamine In tetrahydrofuran at -10℃; for 1h;	83%
With sodium methylate; 1-dodecylthiol In N,N-dimethyl-formamide at 100℃; for 1h;	75%
With boron trichloride; tetra-(n-butyl)ammonium iodide In dichloromethane at -78 - 20℃; for 2h; dealkylation;	70%

2-(2,6-dimethylphenoxy)tetrahydro-2H-pyran (117658-42-1) → 2.6-dimethylphenol (576-26-1)

Conditions	Yield
With boron trifluoride diethyl etherate; sodium cyanoborohydride In tetrahydrofuran for 8h; Ambient temperature;	92%

2,6-dimethylbenzene boronic acid (100379-00-8) + acetonitrile complex of hypofluorous acid → 2.6-dimethylphenol (576-26-1)

Conditions	Yield
In dichloromethane at 20℃;	92%

methanol (67-56-1) + phenol (108-95-2) → 2.6-dimethylphenol (576-26-1) + 2,3,6-trimethylphenol (2416-94-6)

Conditions	Yield
With haggite at 300℃; for 6h; Autoclave; Inert atmosphere;	A 89.1% B 5.6%

2-Bromo-m-xylene (576-22-7) → 2.6-dimethylphenol (576-26-1)

Conditions	Yield
With potassium hydroxide; water; polyaniline-supported palladium In 1,4-dioxane at 100℃; for 12h;	89%
With copper(l) iodide; lithium pipecolinate; tetrabutyl ammonium fluoride; sodium hydroxide In water at 130℃; for 24h;	45%
Multi-step reaction with 3 steps 1.1: tert.-butyl lithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C / Inert atmosphere 2.1: palladium 10% on activated carbon / 0.08 h / 20 °C / Inert atmosphere 3.1: tetrabutyl ammonium fluoride; water; dihydrogen peroxide; potassium hydrogencarbonate / tetrahydrofuran; methanol / 3 h / 20 °C View Scheme

2,6-dimethyliodobenzene (608-28-6) → 2.6-dimethylphenol (576-26-1)

Conditions	Yield
With sodium hydroxide In water; dimethyl sulfoxide at 120℃; for 16h;	89%
Stage #1: 2,6-dimethyliodobenzene With copper(l) iodide; 2-methyl-8-quinolinol; tetra(n-butyl)ammonium hydroxide In water; dimethyl sulfoxide at 100℃; for 10h; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide at 20℃;	88%
With glycolic Acid; copper hydroxide; sodium hydroxide In water; dimethyl sulfoxide at 120℃; for 6h; Inert atmosphere; Schlenk technique;	87%

Diethyl-carbamic acid 2,6-dimethyl-phenyl ester → 2.6-dimethylphenol (576-26-1)

Conditions	Yield
With zirconocene dichloride In tetrahydrofuran at 20℃; Inert atmosphere;	88%

methanol (67-56-1) + phenol (108-95-2) → 2.6-dimethylphenol (576-26-1) + methoxybenzene (100-66-3) + ortho-cresol (95-48-7)

Conditions	Yield
zirconium(IV) oxide at 320℃; under 112509 Torr; for 1.5h; Product distribution; Kinetics; Further Variations:; Catalysts; Pressures; Temperatures;	A 87% B 0.5% C 6%
aluminum oxide at 290℃; under 195.02 - 600.05 Torr; Kinetics; Product distribution; Rate constant;
samarium(III) oxide; tin(IV) oxide at 349.85℃; for 1h; Product distribution; Further Variations:; Catalysts; Alkylation;

4-bromo-2,6-dimethyl-phenol (2374-05-2) → 2.6-dimethylphenol (576-26-1)

Conditions	Yield
With sodium sulfite In water at 130℃; for 10h; Sealed tube; Microwave irradiation; Green chemistry;	87%

2,6-dimethyl-4-chlorophenol (1123-63-3) → 2.6-dimethylphenol (576-26-1)

Conditions	Yield
In methanol at 21.85℃; Irradiation;	85%
In isopropyl alcohol for 15h; Irradiation; Inert atmosphere;	92 %Chromat.
With dehaloperoxidase; dihydrogen peroxide In ethanol at 4℃; pH=7; Kinetics; aq. phosphate buffer; Enzymatic reaction;

tert-butyl-[2-(2,6-dimethyl-phenoxy)-ethyl]-diphenyl-silane (845786-38-1) → 2.6-dimethylphenol (576-26-1)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 40℃;	83%

diethyl phosphite potassium salt (54058-00-3) + 2,6-dimethylphenyl trifluoromethanesulphonate (86364-02-5) → 2.6-dimethylphenol (576-26-1) + 2,6-dimethylphenyl diethyl phosphate (39604-15-4)

Conditions	Yield
In ammonia at -33℃; for 21h;	A 12% B 82%

3,5-dimethyl-4-hydroxybenzoic acid (4919-37-3) → 2.6-dimethylphenol (576-26-1)

Conditions	Yield
With decarboxylase at 25℃; for 15h; pH=6.5; Enzymatic reaction;	80.3%
With hydrogenchloride at 200℃;

m-xylene (108-38-3) → 2.6-dimethylphenol (576-26-1) + 2,4-Xylenol (105-67-9)

Conditions	Yield
Stage #1: m-xylene With spiro[bicyclo[2.2.1]heptane-2,4′-[1,2]dioxolane]-3′,5′-dione at 40℃; for 84h; Sealed tube; Stage #2: With methylamine In ethanol	A 5% B 78%
Stage #1: m-xylene With phthaloyl peroxide Heating; Stage #2: With water; sodium hydrogencarbonate In methanol at 40℃; Overall yield = 94 %;
With perfluorodecanoic acid; cytochrome P450Bm3 KT2 (A191T/N239H/I259V/A276T/L353I); oxygen; NADPH In dimethyl sulfoxide at 30℃; pH=7.4; Reagent/catalyst; Enzymatic reaction;
With C27H19N3O7OsS; dihydrogen peroxide; acetic acid In dichloromethane at 23℃; for 0.416667h; Inert atmosphere; Overall yield = 95 %;

2,6-dimethylphenyl acetate (876-98-2) → 2.6-dimethylphenol (576-26-1)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In tetrahydrofuran at 20℃;	75%

2,6-dimethylbenzene boronic acid (100379-00-8) → 2.6-dimethylphenol (576-26-1) + 2,6-dimethylaniline (87-62-7)

Conditions	Yield
With ammonium hydroxide; potassium nitrate In water at 20℃; for 2h; Electrochemical reaction; chemoselective reaction;	A n/a B 73%
With ammonium hydroxide; potassium nitrate In water at 20℃; for 4h; Electrochemical reaction; chemoselective reaction;	A 70% B n/a

2.6-dimethylphenol (576-26-1) → 3,3',5,5'-tetramethyldiphenoquinone (4906-22-3)

Conditions	Yield
With phosphovanadomolybdic acid; oxygen under 750.075 Torr;	100%
With Cu2(ophen)2 In methanol at 28℃; for 12h;	100%
With oxygen In chloroform at 50℃; under 3800.26 Torr; for 24h; Catalytic behavior; Reagent/catalyst; Pressure; Solvent; regioselective reaction;	97%

2.6-dimethylphenol (576-26-1) + C25H26ClN2OP (94669-47-3, 94669-48-4, 76085-17-1) → C33H35N2O2P (94669-51-9, 94669-54-2)

Conditions	Yield
With triethylamine at -76℃;	100%

2.6-dimethylphenol (576-26-1) → dichloro(2,6-dimethylphenoxy)phosphine (141793-36-4)

Conditions	Yield
With lithium chloride; phosphorus trichloride In neat (no solvent) Inert atmosphere; Schlenk technique; Reflux;	100%
With phosphorus trichloride for 5h; Heating;	85%
With phosphorus trichloride
With phosphorus trichloride for 5h; Substitution; Heating;

2.6-dimethylphenol (576-26-1) + acetyl chloride (75-36-5) → 2,6-dimethylphenyl acetate (876-98-2)

Conditions	Yield
With n-butyllithium In tetrahydrofuran at 0℃;	100%
With tetrabutyl-ammonium chloride; sodium hydroxide In dichloromethane; water at 0℃; for 0.0833333h;	97%
With triethylamine In dichloromethane
With triethylamine In dichloromethane
With pyridine In dichloromethane at 0℃; for 4h;

2.6-dimethylphenol (576-26-1) + ethyl bromoacetate (105-36-2) → ethyl 2-(2,6-dimethylphenoxy)acetate (6279-47-6)

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 24h;	100%
With caesium carbonate In 1,4-dioxane for 48h; Reflux;	93%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	89%

2.6-dimethylphenol (576-26-1) + allyl tosylate (4873-09-0) → 4-allyl-2,6-dimethylphenol (13037-83-7)

Conditions	Yield
[Ir(1,5-cyclooctadiene)(CH3CN)2]PF6 In toluene at 0℃; for 15h;	100%

2.6-dimethylphenol (576-26-1) + bromoacetic acid methyl ester (96-32-2) → methyl 2-(2,6-dimethylphenoxy)acetate (38930-22-2)

Conditions	Yield
With caesium carbonate In acetonitrile at 20℃; for 24h;	100%
In ethyl acetate; N,N-dimethyl-formamide; mineral oil

4-[(6,7-dimethoxy-4-quinolyl)oxy]-2,5-dimethylaniline (286371-46-8) + 2.6-dimethylphenol (576-26-1) + bis(trichloromethyl) carbonate (32315-10-9) + sodium hydrogencarbonate (144-55-8) → 2,6-Dimethylphenyl N-{4-[(6,7-dimethoxy-4-quinolyl)oxy]-2,5-dimethylphenyl}carbamate

Conditions	Yield
With triethylamine In methanol; dichloromethane; chloroform; toluene	100%

2.6-dimethylphenol (576-26-1) + 4-((6,7-dimethoxyquinolin-4-yl)oxy)aniline (190728-25-7) + bis(trichloromethyl) carbonate (32315-10-9) + sodium hydrogencarbonate (144-55-8) → 2,6-Dimethylphenyl N-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}carbamate

Conditions	Yield
With triethylamine In methanol; dichloromethane; chloroform; toluene	100%

2.6-dimethylphenol (576-26-1) + (pentamethylcyclopentadienyl)TaMe(N(2,6-Me2C6H3))(η(1)-N(2,6-Me2C6H3)C(Me)=CMe2) (166903-87-3) → ((CH3)5C5)Ta(CH3)(OC6H3(CH3)2)(NC6H3(CH3)2) (180386-44-1)

Conditions	Yield
In benzene-d6 Ar-atmosphere, sealed NMR tube; 60°C (3 d); not isolated, detd. by NMR spectroscopy;	100%

2.6-dimethylphenol (576-26-1) → 3,10-dihydroxy-3,5,8,10-tetramethyltricyclo[6.2.2.0(2,7)]dodeca-5,11-diene-4,9-dione (5520-77-4)

Conditions	Yield
Stage #1: 2.6-dimethylphenol With (R)-2-(2-iodoxyphenyl)propanoic acid In tetrahydrofuran at -78℃; Inert atmosphere; Stage #2: With trifluoroacetic acid In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;	100%

2.6-dimethylphenol (576-26-1) + C17H20N2O8 → C25H28N2O8

Conditions	Yield
Stage #1: C17H20N2O8 With 2,4,6-triisopropylphenylsulfonyl chloride; phosphorus pentoxide; potassium carbonate In acetonitrile at 60℃; Inert atmosphere; Stage #2: 2.6-dimethylphenol With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 50℃; for 1h; Inert atmosphere;	100%
Stage #1: C17H20N2O8 With 2,4,6-triisopropylphenylsulfonyl chloride; potassium carbonate In acetonitrile at 60℃; for 2.5h; Inert atmosphere; Stage #2: 2.6-dimethylphenol With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 50℃; for 1h;	100%

2.6-dimethylphenol (576-26-1) + 1-Bromotetradecane (112-71-0) → 2-(tetradecyloxy)-1,3-dimethylbenzene (1335029-37-2)

Conditions	Yield
With potassium carbonate In acetonitrile for 48h; Williamson synthesis; Inert atmosphere; Reflux;	99.3%
Stage #1: 2.6-dimethylphenol With sodium hydroxide In ethanol at 25℃; for 2h; Stage #2: 1-Bromotetradecane In ethanol; N,N-dimethyl-formamide at 60℃; for 6h;	79%

2.6-dimethylphenol (576-26-1) → di(2,6-xylyl)phosphorochloridate (81639-99-8)

Conditions	Yield
With hydrogenchloride; trichlorophosphate; magnesium chloride In 5,5-dimethyl-1,3-cyclohexadiene	99.2%
With magnesium chloride; trichlorophosphate at 150℃; for 4h;	92%
With trichlorophosphate	53%

2.6-dimethylphenol (576-26-1) → 4-bromo-2,6-dimethyl-phenol (2374-05-2)

Conditions	Yield
With benzyltrimethylammonium tribromide In methanol; dichloromethane	99%
With phosphotungstic acid; N-bromosaccharin In acetonitrile at 0℃; regioselective reaction;	98%
With 2,4,4,6-tetrabromo-3-n-pentadecylcyclohexa-2,5-dienone In cyclohexane at 20℃; for 24h;	96%

2.6-dimethylphenol (576-26-1) → 2,6-dimethyl-4-nitro phenol (2423-71-4)

Conditions	Yield
With tetrabutylammonium chromate; sodium nitrite In dichloromethane for 23h; Reflux; chemoselective reaction;	99%
With trichloroisocyanuric acid; bismuth subnitrate/charcoal In dichloromethane at 20℃; for 2h; regioselective reaction;	85%
With silica-acetate; dinitrogen tetraoxide In dichloromethane at 20℃; for 0.0833333h;	83%

2.6-dimethylphenol (576-26-1) → 3,3',5,5'-tetramethyl-4,4'-dihydroxybiphenyl (2417-04-1)

Conditions	Yield
Stage #1: 2.6-dimethylphenol With oxygen In tert-butyl alcohol at 70℃; under 760.051 Torr; for 18h; Green chemistry; Stage #2: With hydrogen In tert-butyl alcohol at 50℃; under 760.051 Torr; for 4h; Catalytic behavior; Temperature; Solvent; Time; Green chemistry;	99%
With CuCl(OH)*TMEDA In dichloromethane at 20℃; for 5h;	93%
Stage #1: 2.6-dimethylphenol In dichloromethane at 20℃; for 5h; Stage #2: With sodium dithionite In ethanol for 2h; Heating;	93%

2.6-dimethylphenol (576-26-1) + acetic anhydride (108-24-7) → 2,6-dimethylphenyl acetate (876-98-2)

Conditions	Yield
With silver trifluoromethanesulfonate at 60℃; for 0.15h; neat (no solvent);	99%
With 4-(N,N-dimethylamino)pyridine based 1,3,5,7-tetraphenyladamantane polymer In neat (no solvent) at 25℃; for 1.5h; Schlenk technique;	98%
With sulfuric acid at 0 - 20℃; for 1h;	94%

2.6-dimethylphenol (576-26-1) + trifluoromethylsulfonic anhydride (358-23-6) → 2,6-dimethylphenyl trifluoromethanesulphonate (86364-02-5)

Conditions	Yield
With triethylamine In chloroform at 20℃; for 25.5h;	99%
With 2,4,6-trimethyl-pyridine In dichloromethane	93%
With triethylamine In dichloromethane at -78 - 20℃; for 14h; Inert atmosphere;	90%

2.6-dimethylphenol (576-26-1) + carbonic acid dimethyl ester (616-38-6) → 2-methoxy-1,3-dimethylbenzene (1004-66-6)

Conditions	Yield
With dimanganese decacarbonyl at 180℃; for 1h; Reagent/catalyst;	99%
With N-butyl-4-methylpyridinium bromide at 170℃; for 2h; Inert atmosphere; Ionic liquid; Green chemistry; chemoselective reaction;	70%
N,N,N',N'-tetrabutyl-N''-methylguanidine at 180℃; for 4.5h;	91 % Chromat.

2.6-dimethylphenol (576-26-1) + 3-(4-Chlorophenyl)-2H-1,2,4-triazin-5-one + trifluoroacetic anhydride (407-25-0) → 3-(4-Chloro-phenyl)-6-(4-hydroxy-3,5-dimethyl-phenyl)-1-(2,2,2-trifluoro-acetyl)-1,6-dihydro-2H-[1,2,4]triazin-5-one

Conditions	Yield
for 0.5h; Ambient temperature;	99%

2.6-dimethylphenol (576-26-1) + di-tert-butyl dicarbonate (24424-99-5) → 1-tert-butoxycarbonyloxy-2,6-dimethylbenzene

Conditions	Yield
With dmap In dichloromethane at 20℃;	99%
With dmap In hexane for 0.05h; Product distribution; protection of var. hindered phenols; var. time;	98%
With dmap In hexane for 0.0833333h;	98%

2.6-dimethylphenol (576-26-1) + phthalimidesulfenyl chloride (54974-07-1) → N-(3,5-Dimethyl-4-hydroxyphenylthio)phthalimide (233600-07-2)

Conditions	Yield
In chloroform at 20℃; Substitution;	99%

2.6-dimethylphenol (576-26-1) + 1,1'-carbonyldiimidazole (530-62-1) → 2,6-dimethylphenyl 1H-imidazole-1-carboxylate

Conditions	Yield
In dichloromethane for 24h; Heating;	99%
In dichloromethane for 5h; Heating;	91%

Schwartz's reagent + 2.6-dimethylphenol (576-26-1) → bis(η5-cyclopentadienyl)chloro(2,6-dimethylphenoxy)zirconium(IV)

Conditions	Yield
In benzene byproducts: H2; React. of starting materials in benzene (anhydrous conditions, dry Ar) provides gas evolution. Stirring of mixt.; Removal of solvent by trap-to-trap distn., filtn., elem. anal.;	99%

2.6-dimethylphenol (576-26-1) + {Co(Al(O-i-Pr)4)2} → {Co(Al(O-i-Pr)2(2,6-Me2C6H3O)2)2}

Conditions	Yield
In benzene byproducts: isopropanol; anhyd. conditions; Co(Al(OC3H7)4)2 : 2,6-dimethylphenol = 1 : 4; refluxed (2 h); fractionated isopropanol; solvent removed (reduced pressure); elem.anal.;	99%

2.6-dimethylphenol (576-26-1) + trimethylaluminium dimer → [Me2Al(2,6-dimethylphenoxide)]2

Conditions	Yield
In hexane byproducts: CH4; dry N2-atmosphere; slight excess of Al2Me6; evapn.; elem. anal.;	99%

(E)-1,3-bis(4-bromophenyl)prop-2-en-1-ol + 2.6-dimethylphenol (576-26-1) → (E)-4-(1,3-bis(4-bromophenyl)allyl)-2,6-dimethylphenol (1044744-31-1)

Conditions	Yield
With gold(III) chloride In dichloromethane at 20℃; for 15h; Friedel Crafts alkylation; Molecular sieve; Inert atmosphere; regioselective reaction;	99%

2.6-dimethylphenol (576-26-1) + 4-(1-hydroxy-1,3-diphenylprop-2-ynyl)benzonitrile (1192167-42-2) → 4-(6-hydroxy-5,7-dimethyl-1,3-diphenyl-1H-inden-1-yl)benzonitrile (1192167-48-8)

Conditions	Yield
With ytterbium(III) triflate In nitromethane at 80℃; Inert atmosphere; regioselective reaction;	99%

2.6-dimethylphenol (576-26-1) + p-nitrobenzanilide (3393-96-2) → (4‐hydroxy‐3,5‐dimethylphenyl)(phenyl)methanone (5336-56-1)

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane at 50℃; for 3h; Friedel Crafts acylation; Inert atmosphere;	99%

Upstream product

• 2816-57-1 2,6-dimethylcyclohexanone 
• 824-42-0 2-methoxy-3-methylbenzaldehyde 
• 23802-11-1 2-(dimethylamino-methyl)-6-methyl-phenol 
• 111-87-5 octanol 
• 67-56-1 methanol 
• 108-95-2 phenol 
• 123-75-1 pyrrolidine 
• 876-98-2 2,6-dimethylphenyl acetate 
• 127-18-4 1,1,2,2-tetrachloroethylene 
• 40790-56-5 2,6-dimethyl-2-cyclohexen-1-one 
• 95-47-6 o-xylene 
• 526-73-8 1,2,3-trimethylbenzene 
• 108-94-1 cyclohexanone 
• 103576-49-4 4,5-dimethyl-4-hexen-1-in-3-one 

Downstream Products

• 42900-97-0 1-<(4-Hydroxy-3,5-dimethyl-phenyl)-methyl>-piperidin 
• 112896-07-8 4,4-bis-(4-hydroxy-3,5-dimethyl-phenyl)-1-methyl-piperidine 
• 29237-05-6 4-(4,4'-dihydroxy-3,5,3',5'-tetramethyl-benzhydrylidene)-2,6-dimethyl-cyclohexa-2,5-dienone 
• 3689-45-0 3,3-bis(4-hydroxy-3,5-dimethylphenyl)isobenzofuran-1(3H)-one 
• 5384-21-4 bis(4-hydroxy-3,5-dimethylphenyl)methane 
• 60211-21-4 4,2',6'-trimethyl-2,4'-methanediyl-di-phenol 
• 4397-14-2 4-(hydroxymethyl)-2,6-dimethylphenol 
• 108975-44-6 4-{[N-(2-hydroxy-ethyl)-anilino]-methyl}-2,6-dimethyl-phenol 
• 2786-80-3 4-hydroxy-3,5-dimethoxyazobenzene 
• 1778-65-0 2,6-Dimethyl-4-(4-nitro-phenylazo)-phenol 
• 43109-10-0 2,6-dimethyl-4-[(E)-(2,4-dinitrophenyl)diazenyl]phenol 
• 116130-99-5 (3-bromo-phenyl)-bis-(4-hydroxy-3,5-dimethyl-phenyl)-methane 
• 41388-85-6 (2,6-dimethyl-phenyl)-(1-methyl-allyl)-ether 
• 25751-81-9 2-(4-hydroxy-3,5-dimethyl-phenyl)-ethene-1,1,2-tricarbonitrile 

Relevant articles and documents

Impact of oxygen vacancies in Ni supported mixed oxide catalysts on anisole hydrodeoxygenation

The hydrodeoxygenation (HDO) activity of anisole has been investigated over Ni catalysts on mixed metal oxide supports containing Nb–Zr and Ti–Zr in 1:1 and 1:4 ratios. XRD patterns indicate the incorporation of Ti (or Nb) into the ZrO2 framewo

A mild and practical method for deprotection of aryl methyl/benzyl/allyl ethers with HPPh2andtBuOK

A general method for the demethylation, debenzylation, and deallylation of aryl ethers using HPPh2andtBuOK is reported. The reaction features mild and metal-free reaction conditions, broad substrate scope, good functional group compatibility, and high chemical selectivity towards aryl ethers over aliphatic structures. Notably, this approach is competent to selectively deprotect the allyl or benzyl group, making it a general and practical method in organic synthesis.

Application of two morphologies of Mn2O3for efficient catalyticortho-methylation of 4-chlorophenol

Vapor phaseortho-methylation of 4-chlorophenol with methanol was studied over Mn2O3catalyst with two kinds of morphologies. Here, Mn2O3was prepared by a precipitation and hydrothermal method, and showed the morphology of nanoparticles and nanowires, respectively. XRD characterization and BET results showed that, with the increase of calcination temperature, Mn2O3had a higher crystallinity and a smaller specific surface area. N2adsorption/desorption and TPD measurements indicated that Mn2O3nanowires possessed larger external surface areas and more abundant acid and base sites. Simultaneously, in the fixed bed reactor, methanol was used as the methylation reagent for theortho-methylation reaction of 4-chlorophenol. XRD, XPS, TG-MS and other characterizations made it clear that methanol reduced 4-chlorophenol and its methide, which were the main side-reactions. And Mn3+was reduced to Mn2+under the reaction conditions. Changing the carrier gas N2to a H2/Ar mixture further verified that the hydrogen generated by the decomposition of methanol was not the reason for dechlorination of 4-chlorophenol compounds. Here we summarized the progress of 4-chlorophenol methylation based on the methylation of phenol. Also, we proposed a mechanism of the 4-chlorophenol dechlorination effect which was similar to the Meerwein-Ponndorf-Verley-type (MPV) reaction. The crystal phase and carbon deposition were investigated in different reaction periods by XRD and TG-DTA. The reaction conditions for the two kinds of morphologies of the Mn2O3catalyst such as calcination temperature, reaction temperature, phenol-methanol ratio and reaction space velocity were optimized.