105-67-9

Basic information

• Product Name: 2,4-Xylenol
• Synonyms: 2,4-Xylenol(8CI);1-Hydroxy-2,4-dimethylbenzene;2,4-DMP;2,4-Dimethylphenol;4,6-Dimethylphenol;4-Hydroxy-1,3-dimethylbenzene;Phenol,2,4-dimethyl-;m-Xylenol;2,4-Dimethylphenol
• CAS NO: 105-67-9
• Molecular Formula: C₈H₁₀O
• Molecular Weight: 122.1644
• EINECS: 203-321-6
• Mol File: 105-67-9.mol
• Article Data: 107

Chemical Properties

• Melting Point: 21-23℃
• Boiling Point: 210.9 ºC at 760 mmHg
• Flash Point: 85.6 ºC
• Appearance: clear colorless to yellow liquid
• Density: 1.014 g/cm³
• Vapor Pressure: 0.093mmHg at 25°C
• Refractive Index: 1.54
• Water Solubility: 0.5 g/100 mL (25℃)
• CAS DataBase Reference: 2,4-Xylenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Xylenol(105-67-9)
• EPA Substance Registry System: 2,4-Xylenol(105-67-9)

Safety Data

• Hazard Codes: T:Toxic;;
• Statements: R24/25:; R34:; R51/53:
• Safety Statements: S26:; S36/37/39:; S45:; S61:
• RIDADR: 2261
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 105-67-9(Hazardous Substances Data)

Usage

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

Synthetic route

1,3-dimethyl-4-trimethylsilyloxybenzene (16414-81-6) → 2,4-Xylenol (105-67-9)

Conditions	Yield
With methanol; 1,3-disulfonic acid imidazolium hydrogen sulfate at 20℃; for 0.0666667h; Green chemistry;	96%
With Nanoporous Na+-Montmorillonite Perchloric Acid In ethanol at 20℃; for 0.0833333h;	92%
With caro's acid; silica gel In dichloromethane at 20℃; for 0.333333h;	90%
With methanol at 20℃; for 0.116667h;	87%

1-bromo-2,4-dimethylbenzene (583-70-0) → 2,4-Xylenol (105-67-9)

Conditions	Yield
Stage #1: 1-bromo-2,4-dimethylbenzene With copper(l) iodide; cesium hydroxide; 5-bromo-2-(1H-imidazol-2-yl)pyridine In water; dimethyl sulfoxide; tert-butyl alcohol at 120℃; for 36h; Inert atmosphere; Stage #2: With hydrogenchloride In water; dimethyl sulfoxide; tert-butyl alcohol pH=1 - 2; Inert atmosphere;	90%
With cesiumhydroxide monohydrate; t-BuBrettPhos; C44H62NO5PPdS; water In 1,4-dioxane at 20℃; for 18h; Time; Solvent; Inert atmosphere;	71%
With N1,N2-bis(thiophen-2-ylmethyl)oxalamide; caesium carbonate; copper(I) bromide; sodium hydroxide In water; dimethyl sulfoxide at 85℃; for 20h; Reagent/catalyst; Temperature; Glovebox; Schlenk technique; Sealed tube; Inert atmosphere; chemoselective reaction;

m-xylene (108-38-3) → 2,4-Xylenol (105-67-9)

Conditions	Yield
With dihydrogen peroxide; bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate salt In ethanol; water at 20℃; for 0.666667h;	78%
With hydrogen fluoride; oxygen; arsenic(III) trioxide at 120℃; under 55163.1 Torr;
With 1,2,3,4,5-pentafluoro-6-iodosylbenzene; 5,10,15,20-tetra(2',6'-dichlorophenyl)porphyrinatoiron(III) chloride In methanol; dichloromethane; water at 25℃; for 0.05h;

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 %;

methoxybenzene (100-66-3) → 2-methylmethoxybenzene (578-58-5) + 3-methyl-phenol (108-39-4) + toluene (108-88-3) + 2,4-Xylenol (105-67-9) + benzene (71-43-2) + phenol (108-95-2)

Conditions	Yield
With hydrogen In hexane at 340℃; under 3750.38 Torr; for 3h; Reagent/catalyst;

5-hydroxy-2,4-dimethyl-2-cyclohexenone → 2,4-Xylenol (105-67-9)

Conditions	Yield
With toluene-4-sulfonic acid In benzene at 70℃;	99%
With toluene-4-sulfonic acid In benzene at 70℃;	99%

2,4-bis(2,4-dimethylphenoxymethyl)allyloxybenzene (1253261-50-5) → 2,4-Xylenol (105-67-9)

Conditions	Yield
With sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 20℃;	89%

2,4-bis(2,4-bis(2,4-dimethylphenoxymethyl)phenoxymethyl)allyloxybenzene (1253261-52-7) → 2,4-Xylenol (105-67-9)

Conditions	Yield
With sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 20℃;	93%

2,4-dimethyl(allyloxy)benzene (93981-82-9) → 2,4-Xylenol (105-67-9)

Conditions	Yield
With sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 20℃; for 0.5h;	93%

4-hydroxy-3-methyl-benzaldehyde (15174-69-3) → 2,4-Xylenol (105-67-9)

Conditions	Yield
With formic acid In water at 130℃; for 6h; Green chemistry;
With hydrogen In ethanol at 170℃; under 7500.75 Torr; for 22h; Autoclave;

2,4-bis(2,4-bis(2,4-dimethylphenoxymethyl)phenoxymethyl)allyloxybenzene (1253261-52-7) → C59H64O7 (1253261-58-3) + 2,4-Xylenol (105-67-9)

Conditions	Yield
With sodium tetrahydroborate; palladium on carbon In tetrahydrofuran at 20℃;	A n/a B 80%

C28H44O2P2 → 2,4-Xylenol (105-67-9)

Conditions	Yield
With chlorobis(ethylene)rhodium(I) dimer; hydrogen In 1,4-dioxane at 150℃; under 2585.81 Torr;	77%

2,4-bis(2,4-dimethylphenoxymethyl)allyloxybenzene (1253261-50-5) → C27H32O3 (1253261-56-1) + 2,4-Xylenol (105-67-9)

Conditions	Yield
With sodium tetrahydroborate; palladium on carbon In tetrahydrofuran at 20℃;	A n/a B 70%

methanol (67-56-1) + phenol (108-95-2) → p-cresol (106-44-5) + 2.6-dimethylphenol (576-26-1) + 3-methyl-phenol (108-39-4) + methoxybenzene (100-66-3) + ortho-cresol (95-48-7) + 2,4-Xylenol (105-67-9)

Conditions	Yield
With zeolite HBEA at 199.84℃; under 759.826 Torr; for 4h; Catalytic behavior; Reagent/catalyst; Inert atmosphere;

2,4-dimethyl(allyloxy)benzene (93981-82-9) → 2,4-dimethylpropoxybenzene (1253261-54-9) + 2,4-Xylenol (105-67-9)

Conditions	Yield
With sodium tetrahydroborate; palladium on carbon In tetrahydrofuran at 20℃; for 48h;	A n/a B 54%

2,4-dimethylphenyl benzylsulfonate → 2,4-Xylenol (105-67-9)

Conditions	Yield
With 4,4'-di-tert-butylbiphenyl; lithium In tetrahydrofuran at -50℃; for 0.8h;	73%

sodium[tetrakis(2,4-dimethylphenyloxy)borate] → 2,4-Xylenol (105-67-9)

Conditions	Yield
Stage #1: sodium[tetrakis(2,4-dimethylphenyloxy)borate] In tetrahydrofuran at 20℃; Electrolysis; Stage #2: With citric acid In tetrahydrofuran; water for 0.0833333h;	99%

methylmagnesium bromide (75-16-1) + 2,4-dichlorophenol (120-83-2) → 2-methyl-4-chlorophenol (1570-64-5) + 2,4-Xylenol (105-67-9)

Conditions	Yield
With Ni(1,2-bis(diphenylphosphanyl)-benzene)Cl2 In toluene at 0 - 75℃; Inert atmosphere; regioselective reaction;	A 50% B 7%

1-iodo-2,4-dimethylbenzene (4214-28-2) → 2,4-Xylenol (105-67-9)

Conditions	Yield
Stage #1: 1-iodo-2,4-dimethylbenzene 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℃;	91%

nanocrystalline cellulose → 3-methyl-cyclopentanone (1757-42-2, 6195-92-2) + p-cresol (106-44-5) + ortho-cresol (95-48-7) + cyclopentanone (120-92-3) + 2,4-Xylenol (105-67-9) + 3,5-Dimethylphenol (108-68-9) + phenol (108-95-2)

Conditions	Yield
With water at 550℃; under 165492 Torr; Supercritical conditions; Flow reactor;

nanocrystalline cellulose → 2-Methylcyclopentanone (1120-72-5) + 3-methyl-cyclopentanone (1757-42-2, 6195-92-2) + p-cresol (106-44-5) + Mesitol (527-60-6) + propionic acid (802294-64-0) + cyclopentanone (120-92-3) + 2,4-Xylenol (105-67-9) + phenol (108-95-2)

Conditions	Yield
With water at 500℃; under 165492 Torr; Supercritical conditions; Flow reactor;

...Expand

(2,4-dimethyl-phenyl)-methallyl ether (127797-62-0) → 2,4-Xylenol (105-67-9) + 2,3-dihydro-2,2,5,7-tetramethylbenzofuran

Conditions	Yield
With hexacarbonyl molybdenum In toluene at 115℃; for 55h; Yields of byproduct given;	A n/a B 60%

2,4-dimethylphenyl trifluoromethanesulfonate (87241-52-9) → m-xylene (108-38-3) + 2,4-Xylenol (105-67-9)

Conditions	Yield
With lithium; nickel dichloride In tetrahydrofuran at 20℃; Reduction;	A 58% B 15%

2,4-dimethylanisole (6738-23-4) → 2,4-Xylenol (105-67-9)

Conditions	Yield
With lithium; ethylenediamine In tetrahydrofuran at -10℃; for 5h;	34%
With boron tribromide In dichloromethane at 0℃; for 2h;

sodium[tetrakis(2,4-dimethylphenyloxy)borate] → 2,2'-dihydroxy-3,3',5,5'-tetramethylbiphenyl (26567-10-2) + 2,4-Xylenol (105-67-9)

Conditions	Yield
Stage #1: sodium[tetrakis(2,4-dimethylphenyloxy)borate] In N,N-dimethyl-formamide at 20℃; Electrolysis; Stage #2: With citric acid In water; N,N-dimethyl-formamide for 0.0833333h;	A 2% B 65%
Stage #1: sodium[tetrakis(2,4-dimethylphenyloxy)borate] In acetonitrile at 40℃; Electrolysis; Stage #2: With citric acid In water; acetonitrile for 0.0833333h;	A 63 % Chromat. B 28 % Chromat.

(E)-1-(4,4-dimethylpent-2-enyloxy)-2,4-dimethylbenzene (1260760-32-4) → (E)-2-(4,4-dimethylpent-2-enyl)-4,6-dimethylphenol (1260760-80-2) + 2,4-Xylenol (105-67-9)

Conditions	Yield
With triphenylphosphine gold (I) chloride; silver trifluoromethanesulfonate In 1,2-dichloro-ethane at 20℃; for 65h; Claisen type rearrangement; Inert atmosphere;	A 56% B 31%

nanocrystalline cellulose → 2-Methylcyclopentanone (1120-72-5) + 3-methyl-cyclopentanone (1757-42-2, 6195-92-2) + p-cresol (106-44-5) + n-hexan-3-one (589-38-8) + ortho-cresol (95-48-7) + cyclopentanone (120-92-3) + 2,4-Xylenol (105-67-9) + 3,5-Dimethylphenol (108-68-9) + phenol (108-95-2)

Conditions	Yield
With water at 525℃; under 165492 Torr; Supercritical conditions; Flow reactor;

...Expand

2-[2.4]xylyl-propanol-(2) (83208-06-4) → 2,4-Xylenol (105-67-9)

Conditions	Yield
With sodium perborate; boron trifluoride diethyl etherate In tetrahydrofuran 1.) 0 deg C, 30 min; 2.) 50 deg C, 1 h;	73%

benzenesulfonic acid (98-11-3) → 2,4-Xylenol (105-67-9)

Conditions	Yield
With toluene-4-sulfonic acid

vanillin (121-33-5) → 2-Methoxy-4-methylphenol (93-51-6) + 2-methoxy-phenol (90-05-1) + 2,4-Xylenol (105-67-9)

Conditions	Yield
With hydrogen In decalin at 120℃; under 15001.5 Torr; for 2h;

2,4-Xylenol (105-67-9) + methyl iodide (74-88-4) → 2,4-dimethylanisole (6738-23-4)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 5h; Methylation;	100%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Cooling with ice;	85%
With potassium carbonate In water; N,N-dimethyl-formamide at 20℃; Cooling with ice;	85%

bromoacetic acid methyl ester (96-32-2) + 2,4-Xylenol (105-67-9) → (2,4-Dimethyl-phenoxy)-acetic acid methyl ester (95450-79-6)

Conditions	Yield
With potassium carbonate In butanone for 5.5h; Heating;	100%

indan-1,2,3-trione hydrate (485-47-2) + 2,4-Xylenol (105-67-9) → 2-Hydroxy-2-(2-hydroxy-3,5-dimethyl-phenyl)-indan-1,3-dione (71321-32-9)

Conditions	Yield
In acetic acid for 0.5h; Heating;	100%

morpholine (110-91-8) + formaldehyd (50-00-0) + 2,4-Xylenol (105-67-9) → 2,4-dimethyl-6-morpholin-4-ylmethyl-phenol (97032-14-9)

Conditions	Yield
With aluminum oxide Mannich type reaction, aminomethylation; Irradiation; microwave;	100%

2,4-Xylenol (105-67-9) → tris(2,4-dimethylphenoxy)borone (20340-62-9)

Conditions	Yield
With boric acid In toluene for 12h; Heating;	100%

benzyl bromide (100-39-0) + 2,4-Xylenol (105-67-9) → 1-(benzyloxy)-2,4-dimethylbenzene (19578-72-4)

Conditions	Yield
With potassium carbonate In acetone for 12h; Reflux; Sealed tube;	100%
With potassium phosphate; tetrabutylammomium bromide In water at 20℃; for 2h; Sealed tube; Green chemistry;	99%

formaldehyd (50-00-0) + dimethyl amine (124-40-3) + 2,4-Xylenol (105-67-9) → 2-(N,N-dimethylaminomethyl)-4,6-dimethylophenol (52777-93-2)

Conditions	Yield
In ethanol for 48h; Inert atmosphere; Schlenk technique; Reflux;	99%
In water at 0 - 100℃; for 2.5h; Mannich Aminomethylation;	78%

acetic anhydride (108-24-7) + 2,4-Xylenol (105-67-9) → 2,4-dimethylphenyl acetate (877-53-2)

Conditions	Yield
With 4-(dimethylamino)pyridine hydrochloride In toluene at 60℃; for 8h;	99%
With rice husk ash at 80℃; for 0.2h; Green chemistry;	97%
With Cu(2+)*Zr(4+)*2PO4(3-) = CuZr(PO4)2 at 60℃; for 0.333333h;	95%

Cinnamoyl chloride (102-92-1) + 2,4-Xylenol (105-67-9) → 2,4-dimethylphenyl trans-cinnamate (99430-00-9)

Conditions	Yield
With pyridine In benzene for 1h; Heating;	99%
With magnesium In benzene for 2h; Heating;	69%

4-(2,6-di-tert-butyl-4-methylphenoxy)-2,6-di-tert-butyl-4-methyl-2,5-cyclohexadien-1-one (2179-51-3) + 2,4-Xylenol (105-67-9) → 1,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)ethane (1516-94-5) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + 2,6-di-tert-butyl-4-(3,5-dimethyl-2-hydroxyphenyl)-4-methylcyclohexa-2,5-dien-1-one (131544-07-5) + 3,5-di-tert-butyl-4-hydroxybenzyl 2,4-dimethylphenyl ether (131544-12-2)

Conditions	Yield
In triethylamine	A 3.9% B 99% C 54% D 17%

dimethyl acetylenedicarboxylate (762-42-5) + 2,4-Xylenol (105-67-9) → C14H16O5

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In dichloromethane at 20℃; for 0.166667h;	99%

methanesulfonyl chloride (124-63-0) + 2,4-Xylenol (105-67-9) → 2,4-dimethylphenyl methanesulfonate (723755-74-6)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 1h;	99%
With triethylamine In dichloromethane

bis(2,4,6-trimethylphenyl)iodonium triflate (139139-80-3) + 2,4-Xylenol (105-67-9) → 2,4-dimethylphenyl(2,4,6-trimethylphenyl) ether (1268694-21-8)

Conditions	Yield
Stage #1: 2,4-Xylenol With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.25h; Stage #2: bis(2,4,6-trimethylphenyl)iodonium triflate In tetrahydrofuran at 40℃; for 0.25h;	99%
Stage #1: 2,4-Xylenol With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.25h; Stage #2: bis(2,4,6-trimethylphenyl)iodonium triflate In tetrahydrofuran at 40℃; for 0.25h;	99%

titanium(IV) isopropylate (546-68-9) + 2,4-Xylenol (105-67-9) → [(2,4-dimethylphenoxy)2Ti(isopropoxy)2] (1394844-93-9)

Conditions	Yield
In cyclohexane at 20℃; Inert atmosphere; Schlenk technique;	99%

2-Picolinic acid (98-98-6) + 2,4-Xylenol (105-67-9) → 2,4-dimethylphenyl picolinate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;	99%

1-iodo-butane (542-69-8) + carbon monoxide (201230-82-2) + 2,4-Xylenol (105-67-9) → C13H18O2 (723757-89-9)

Conditions	Yield
With rhodium(III) chloride; 1,3-bis-(diphenylphosphino)propane; sodium carbonate; sodium bromide In 1,4-dioxane at 120℃; under 750.075 Torr; for 24h; Inert atmosphere; chemoselective reaction;	99%

2,4-Xylenol (105-67-9) → 2-bromo-4,6-dimethylphenol (15191-36-3)

Conditions	Yield
With trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane; hydrogen bromide In water at 20℃; for 1.4h;	98%
With trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane; ammonium bromide; acetic acid at 20℃; for 2h; regioselective reaction;	98%
With benzyltriphenylphosphonium tribromide; calcium carbonate In methanol; dichloromethane at 20℃; for 0.5h;	94%

acetic acid (64-19-7) + 2,4-Xylenol (105-67-9) → 3,5-dimethyl-2-hydroxyacetophenone (1198-66-9)

Conditions	Yield
With boron trifluoride diethyl etherate for 0.0333333h; microwave irradiation;	98%
With iron(III) chloride for 0.0166667h; Friedel Crafts acylation; Microwave irradiation; regioselective reaction;	60%
With boron trifluoride diethyl etherate

formaldehyd (50-00-0) + N,N,N',N'-tetraethyldiethylenetriamine (123-12-6) + 2,4-Xylenol (105-67-9) → 2,4-dimethyl-6-bis(2-(diethylamino)-ethyl)aminomethyl phenol (620598-29-0)

Conditions	Yield
Stage #1: formaldehyd; N,N,N',N'-tetraethyldiethylenetriamine at 80℃; for 2h; Stage #2: 2,4-Xylenol In methanol for 24h; Heating;	98%
Stage #1: formaldehyd; N,N,N',N'-tetraethyldiethylenetriamine at 80℃; for 1h; Stage #2: 2,4-Xylenol In methanol for 24h; Heating;	70%

acetyl chloride (75-36-5) + 2,4-Xylenol (105-67-9) → 2,4-dimethylphenyl acetate (877-53-2)

Conditions	Yield
With pyridine In dichloromethane; water	98%
With Fe/SWCNTs at 20℃; for 0.2h;	95%
With pyridine In dichloromethane at 0 - 20℃; for 5h;

formaldehyd (50-00-0) + butyl 3-mercaptopropionate (16215-21-7) + 2,4-Xylenol (105-67-9) → butyl 3-(2-hydroxy-3,5-dimethylbenzylsulfanyl)propionate (1192176-12-7)

Conditions	Yield
With dimethyl amine In ethanol; N,N-dimethyl-formamide for 2h; Inert atmosphere; Reflux;	98%
With dimethyl amine In ethanol; N,N-dimethyl-formamide for 2h; Reflux; Inert atmosphere;

1-Phenyl-2-propyn-1-ol (4187-87-5) + 2,4-Xylenol (105-67-9) → 2,4-dimethyl-6-(1-phenylprop-2-ynyl)phenol (1214890-86-4)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; Inert atmosphere;	98%

2,4-Xylenol (105-67-9) + 4-(2-oxoimidazolidin-1-yl)benzene-1-sulfonyl chloride → 2,4-dimethylphenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonate (1311945-66-0)

Conditions	Yield
With triethylamine In dichloromethane at 25℃; for 24h; Inert atmosphere;	98%

4-chlorobenzaldehyde (104-88-1) + 2,4-Xylenol (105-67-9) → 6,6'-((4-chlorophenyl)methylene)bis(2,4-dimethylphenol)

Conditions	Yield
With sulfonated reduced graphene oxide nanosheets In water for 0.1h; Catalytic behavior; Microwave irradiation;	98%
With sulfonatedreduced graphene oxide nanosheet In neat (no solvent) at 100℃; for 0.5h; Catalytic behavior; Green chemistry;	90%
With toluene-4-sulfonic acid In neat (no solvent) at 100℃; for 0.833333h;	81%

4-bromo-benzaldehyde (1122-91-4) + 2,4-Xylenol (105-67-9) → 6,6'-((4-bromophenyl)methylene)bis(2,4-dimethylphenol)

Conditions	Yield
With sulfonated reduced graphene oxide nanosheets In water for 0.0833333h; Catalytic behavior; Microwave irradiation;	98%
With sulfonatedreduced graphene oxide nanosheet In neat (no solvent) at 100℃; for 0.333333h; Catalytic behavior; Green chemistry;	95%

2,4-Xylenol (105-67-9) + teroxirone (2451-62-9) → metaxalone (1665-48-1)

Conditions	Yield
With potassium hydroxide; 4-methyl-2-pentanone at 0 - 120℃; for 3 - 4h;	97%

1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) + 2,4-Xylenol (105-67-9) → 1,3-dimethyl-4-trimethylsilyloxybenzene (16414-81-6)

Conditions	Yield
With 1,3-disulfonic acid imidazolium hydrogen sulfate In neat (no solvent) at 20℃; for 0.0166667h; Green chemistry;	97%
With poly(4-vinylpyridine) In acetonitrile at 20℃; for 0.333333h;	97%
With 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate at 20℃; for 0.0166667h; Neat (no solvent);	96%

benzoic acid anhydride (93-97-0) + 2,4-Xylenol (105-67-9) → 2,4-dimethylphenyl benzoate (76048-43-6)

Conditions	Yield
With 4-(dimethylamino)pyridine hydrochloride In toluene at 60℃; for 10h;	97%

Upstream product

• 1198-37-4 2,4-dimethylquinoline 
• 35523-91-2 2,4-dimethylphenyl azide 
• 1879-09-0 2,4-dimethyl-6-tert-butylphenol 
• 6738-23-4 2,4-dimethylanisole 
• 628-13-7 pyridine hydrochloride 
• 20484-31-5 2-diethylaminomethyl-4-methylphenol 
• 70853-94-0 N-(2,4-dimethylphenyl)hydroxylamine 
• 15499-90-8 N,N',N''-tris(ethoxycarbonyl)-hexahydro-1,3,5-triazine 
• 108-38-3 m-xylene 
• 67-56-1 methanol 
• 106-44-5 p-cresol 
• 7205-91-6 phenylthiomethyl chloride 
• 2432-14-6 3,5-dibromo-4-hydroxytoluene 
• 917-54-4 methyllithium 

Downstream Products

• 34857-09-5 4-(2-hydroxy-3,5-dimethyl-phenyl)-4-oxo-cis-crotonic acid 
• 34857-10-8 4-(2-hydroxy-3,5-dimethyl-phenyl)-4-oxo-trans-crotonic acid 
• 883310-86-9 maleic acid mono-(2,4-dimethyl-phenyl ester) 
• 7356-03-8 4-(2-Hydroxy-3,5-dimethylphenyl)-4-oxobutanoic Acid 
• 22421-91-6 2,4-Dimethylphenyl Hydrogen Succinate 
• 108971-56-8 2-[N-(2-hydroxy-ethyl)-anilinomethyl]-4,6-dimethyl-phenol 
• 102471-03-4 3,5-bis-(2-hydroxy-3,5-dimethyl-benzyl)-tetrahydro-[1,3,5]oxadiazin-4-one 
• 6538-35-8 6,6'-methylenebis(2,4-dimethylphenol) 
• 57914-22-4 tris-(2-hydroxy-3,5-dimethylbenzyl)amine 
• 27179-97-1 4,6,4',6'-tetramethyl-2,2'-(2-aza-propanediyl)-di-phenol 
• 24623-61-8 3,5-dimethylsalicylaldehyde 
• 3761-23-7 1-(2,4-dimethylphenoxy)-2,4-dinitrobenzene 
• 93406-68-9 N-(2-hydroxy-3,5-dimethyl-benzhydryl)-acetamide 
• 32094-31-8 6,6'-((phenyl)methylene)bis(2,4-dimethylphenol) 

Related news

Further improvements in the 2,4-Xylenol (cas 105-67-9) spectrophotometric method for nitrate08/19/2019

Improvements are described for the 2,4-xylenol spectrophotometric method for nitrate that reduce the elapsed and working time. Diluted (22 + 3) sulfuric acid is added quickly to the sample solution while the flask is immersed in tap water. 2,4-xylenol solution is added, the 6-nitro-2,4-xylenol f...detailed

Characterisation of a degradative plasmid in Pseudomonas putida that controls the expression of 2,4-Xylenol (cas 105-67-9) degradative genes08/17/2019

Pseudomonas putida strain NCIB9866 (RA4000) carries an 85-kb plasmid, pRA4000, can utilize p-cresol and 2,4-xylenol, and is resistant to inorganic mercuric ions. The loss of this phenotype from a pRA4000-cured derivative, combined with DNA analysis and conjugation studies, showed that pRA4000 en...detailed

Hydropyrolysis of 2,4-Xylenol (cas 105-67-9) under pressure08/16/2019

The hydrocracking of 2,4-xylenol, chosen as a model compound for the hydropyrolysis of phenolic fractions was studied as a function of the following parameters: temperature, pressure, residence time and hydrogen partial pressure so as to determine the yield of light aromatic hydrocarbons (B T X)...detailed

Equilibrium properties: paper with an experimental partVapor-liquid equilibria in the binary systems formed by para-cresol and 2,4-Xylenol (cas 105-67-9) with tetralin at 101.1 and 26.6 kPa☆08/15/2019

Isobaric vapor-liquid equilibria of para-cresol(1) + tetralin(2) and 2,4-xylenol(1) + tetralin(2) binary mixtures, measured at 101.1 kPa and 26.6 kPa, are reported. Activity coefficients are evaluated and correlated by Wilson equation.detailed

Selective determination of 2,4-Xylenol (cas 105-67-9) by gas chromatography/supersonic jet/resonance-enhanced multiphoton ionization/time-of-flight mass spectrometry08/13/2019

Gas chromatography/supersonic jet/resonance-enhanced multiphoton ionization/time-of-flight mass spectrometry (GC/SSJ/REMPI/TOF-MS) was employed for isomer-selective determination of 2,4-xylenol in river and seawater samples. The sample containing 2,4-xylenol was measured using argon, rather than...detailed

Relevant articles and documents

Sodium perborate: A convenient reagent for benzylic hydroperoxide rearrangement

Sodium perborate in boron trifluoride etherate has been found to be an effective reagent for the hydroperoxide rearrangement of electron rich and highly substituted benzylic tertiary alcohols to phenols in good yields.

Photochemical reactions of oxygen atoms with toluene, m-xylene, p-xylene, and mesitylene: An infrared matrix isolation investigation

The photochemical reactions of oxygen atoms with methylated benzenes (toluene, m-xylene, p-xylene, and mesitylene) were investigated in solid argon matrices at 12 K with UV light of λ ≥ 280 nm, producing ketene functionalities. The toluene/O atom reaction

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.

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Evaluation of acute toxicity and genotoxicity of liquid products from pyrolysis of Eucalyptus grandis wood

Slow pyrolysis of Eucalyptus grandis wood was performed in an oven laboratory, and smoke was trapped and condensed to yield liquid products. Polycyclic aromatic hydrocarbons (PAHs) and phenolic fractions were isolated from the former liquid products using adsorption column chromatography (ACC) and identified by GC/MS. Concentrations of PAH and phenolic fractions in total pyrolysis liquids were respectively 48.9 μg/g and 8.59% (w/w). Acute toxicity of total samples of pyrolysis liquids and the phenolic fraction was evaluated by means of two bioassays, namely, 24-h immobilization bioassay with Daphnia magna and Microtox(TM) bioassays, the latter employing the luminescent bacteria Photobacterium phosphoreum. Total pyrolysis liquids and the PAH fraction were evaluated for genotoxicity by the Microtox(TM) bioassay conducted using rehydrated freeze-dried dark mutant of the luminescent bacteria Vibrio fisheri strain M169. Total pyrolysis liquids and the phenolic fraction, respectively, in concentrations of 170 and 68 mg/L were able to immobilize 50% (EC50) of the D. magna population following 24-h exposure. Concentrations of 19 and 6 mg/L, respectively, for total pyrolysis liquids and phenolic fraction were the effective concentrations that resulted in a 50% (EC50) reduction in light produced by bacteria in the Microtox(TM) bioassay. Accordingly, the Microtox(TM) bioassay was more sensitive to toxic effects of both kind of samples than the D. magna bioassay, particularly for the phenolic fraction. Regarding to the genotoxicity evaluation, the results achieved by Microtox(TM) bioassay showed that total pyrolysis liquids had no genotoxic effects with and without exogenous metabolic activation using rat liver homogenate (S9). However, the PAH fraction showed toxic effects with rat liver activation and had a dose-response number (DRN) equal to 1.6, being in this way suspected genotoxic. The lowest detected concentration (LDC) of the PAH fraction able to cause genotoxic effects was 375 μg/L.

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Phenylthioalkylation-Desulphurisation for the C-Alkylation of Phenols

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Efficient Transformation of Anisole into Methylated Phenols over High-Silica HY Zeolites under Mild Conditions

Transformation of anisole (methoxybenzene), a typical component of bio-oil, into phenol and methylated phenols was studied over HY zeolites with framework Si/Al ratios of 5, 15, 25, and 35. It was demonstrated that the amounts of Bronsted acid and Lewis acid sites, the ratio of Lewis acid and Bronsted acid sites, and the textural properties of the zeolites were all crucial parameters that influenced the catalytic performance. The Bronsted acid and Lewis acid sites of the zeolites catalyzed the reaction cooperatively and efficiently promoted the transmethylation. The hierarchical channel system with fully open micropore-mesopore connectivity was favorable to reduce the amount of coke generated.

A new mild deprotecting method for O-benzylsulfonyl phenols and alcohols based on a DTBB-catalyzed lithiation

A variety of alcohols and phenols, protected as the corresponding benzylsulfonic esters, were efficiently deprotected by selective reductive cleavage of the sulfur-oxygen bond, using an excess of lithium sand and a catalytic amount (5 mol%) of 4,4′-di-tert-butylbiphenyl (DTBB) as electron carrier, in THF at 0° C. This deprotection system was also efficient at -50 °C and was compatible with a wide range of other functional groups. Georg Thieme Verlag Stuttgart.

Acid-Catalyzed Dehydration of Substituted Dienediols

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ipso-Attack in the Hydroxylation of o- and p-Xylene using bis(trimethylsilyl) Peroxide and Aluminium Chloride

Electrophilic hydroxylation of o- and p-xylene using a range of peroxides, including the title compound, in the presence of Lewis acids results in the formation of mixtures of phenols including those derived by ipso-attack followed by rearrangement; ipso-attack by the hydroxyl radical leads to dealkylation.

Improved oxidation of aromatic and aliphatic hydrocarbons using rate enhancing variants of P450Bm3 in combination with decoy molecules

Enzyme performance can be improved using decoy molecules or engineered variants to accelerate the activity without affecting selectivity. Here we combine a rate accelerator variant of cytochrome P450Bm3 with decoy molecules to enhance the oxidation activity of a range of small organic molecules. This combined approach offers superior biocatalytic efficiency without modifying the product distribution.

Comparison of cresol transformation on USHY and HZSM-5

In the commercial synthesis of cresols, the most common processes include the alkylation of phenol with methanol. The cresol (methylphenol) transformation on zeolite USHY was studied and compared with HZSM-5 with different pore size, structure, and different acidity in a flow reactor at 380°C and 0.1 bar. The cresol turnover numbers for USHY were pretty similar, whereas on HZSM-5, the cresols reactivities followed the sequence p- ≥ m- > o-cresol. The cresols reacted over the zeolites mainly through two parallel reactions, isomerization and disproportionation, whose relative importance depends on the catalysts characteristics (pore structure and acidity), on the reacting cresol itself, and on the reaction conditions (temperature, total pressure, reactant partial pressure, etc). The USHY selectivity toward the monomolecular isomerization reaction was by far lower than that of HZSM-5, due to its size/shape selectivity. On USHY and HZSM-5 catalysts, the o-cresol showed higher disproportionation selectivity than the other two cresol isomers, this proportionation occurring via diphenylmethane intermediates. The cresol isomerization selectivity was limited by product desorption even on a large pore zeolite like USHY. The cresol isomer composition at high conversions on USHY was 44, 42, and 14% for o-, m-, and p-cresol, respectively. Xylenols underwent a rapid isomerization once formed.

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Palladium-catalyzed hydroxylation of aryl and heteroaryl halides enabled by the use of a palladacycle precatalyst

A method for the hydroxylation of aryl and heteroaryl halides, promoted by a catalyst based on a biarylphosphine ligand tBuBrettPhos (L5) and its corresponding palladium precatalyst (1), is described. The reactions allow the cross-coupling of both potassium and cesium hydroxides with (hetero)aryl halides to afford a variety of phenols and hydroxylated heteroarenes in high to excellent yield.

REARRANGEMENT OF DIMETHYLPHENYLACYLATES USING ZEOLITES

The present invention relates to a Fries rearrangement of specific dimethylphenylacylates to form the desired respective hydroxyaryl ketones having two methyl groups bound to the aromatic ring. It has been found that the process is surprisingly very specific in view of the number and position of the methyl group(s) bound to the aromatic ring.

Isotruxene-based porous polymers as efficient and recyclable photocatalysts for visible-light induced metal-free oxidative organic transformations

Two new isotruxene-based porous polymers were prepared and demonstrated to be highly efficient, metal-free heterogeneous photocatalysts for oxidative transformations using air as the mild oxidant under visible-light irradiation. Both catalysts show excellent recyclability. In addition, the reactions can be performed in water, further indicating the greenness of this method. This journal is