108-38-3

Basic information

• Product Name: 1,3-Dimethylbenzene
• Synonyms: m-Xylene(8CI);1,3-Xylene;3-Methyltoluene;NSC 61769;m-Dimethylbenzene;m-Methyltoluene;m-xylol;M-Xylene;1,3-Dimethylbenzene
• CAS NO: 108-38-3
• Molecular Formula: C₈H₁₀
• Molecular Weight: 106.165
• EINECS: 203-576-3
• Mol File: 108-38-3.mol
• Article Data: 306

Chemical Properties

• Melting Point: -48℃
• Boiling Point: 140.567 °C at 760 mmHg
• Flash Point: 25 °C
• Appearance: Colorless transparent liquid
• Density: 0.87 g/cm³
• Refractive Index: 1.496-1.498
• CAS DataBase Reference: 1,3-Dimethylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dimethylbenzene(108-38-3)
• EPA Substance Registry System: 1,3-Dimethylbenzene(108-38-3)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: R10:; R20/21:; R36/38:
• Safety Statements: S25:
• Hazardous Substances Data: 108-38-3(Hazardous Substances Data)

Usage

General Description

1,3-Dimethylbenzene, also known as meta-xylene, is a colorless liquid hydrocarbon compound with a strong odor. It is commonly found as a component of gasoline and other petroleum products, and is utilized in the production of dyes, resins, and plastics. 1,3-Dimethylbenzene is highly flammable and can pose health hazards if inhaled or ingested, causing irritation to the respiratory system and skin. It is also considered a potential environmental pollutant, as it can contaminate air, water, and soil through industrial and transportation activities. Due to its potential health and environmental risks, 1,3-Dimethylbenzene is closely regulated and its use is subject to strict safety measures and controls.

InChI:InChI=1/C8H10/c1-7-4-3-5-8(2)6-7/h3-6H,1-2H3

Synthetic route

3-(3,5-Dimethyl-phenoxy)-benzo[d]isothiazole 1,1-dioxide (132636-71-6) → m-xylene (108-38-3) + saccharin (81-07-2)

Conditions	Yield
With sodium hypophosphite; palladium on activated charcoal In water; benzene for 2.5h; Heating;	A 100% B n/a

1-chloromethyl-3-methyl-benzene (620-19-9) → m-xylene (108-38-3)

Conditions	Yield
With palladium dichloride In methanol at 40℃; for 1h; Green chemistry; chemoselective reaction;	99%
With Perbenzoic acid; tri-n-butyl-tin hydride In benzene at 90℃; for 12h; Mechanism; in the presence of α-chlorotoluene (competitor), relative reactivity;

3-methylbenzyl alcohol (587-03-1) → m-xylene (108-38-3)

Conditions	Yield
With palladium dichloride In methanol at 40℃; for 18h; Inert atmosphere; Green chemistry; chemoselective reaction;	99%
With 2,4,6-trimethyl-pyridine; 4,4'-dimethoxyphenyl disulfide; iridium(lll) bis[2-(2,4-difluorophenyl)-5-methylpyridine-N,C20]-4,40-di-tert-butyl-2,20-bipyridine hexafluorophosphate; triphenylphosphine In toluene for 24h; Irradiation;	68 %Chromat.

1-methyl-3-methylene-cyclohexane (3101-50-6) → m-xylene (108-38-3)

Conditions	Yield
With n-butyllithium; potassium 2-methylbutan-2-olate Mechanism; 1) r.t., 16 h, 2) reflux, 6 h; further reagent: D2O;	96%

2,6-dimethylbenzene boronic acid (100379-00-8) → m-xylene (108-38-3)

Conditions	Yield
With water at 20℃; for 48h;	96%
With potassium methanolate In methanol at 120℃; for 12h; Catalytic behavior; Solvent; Sealed tube; Green chemistry;	67 %Chromat.

3,5-dimethylbenzoic acid (499-06-9) + 5-phenyl-2,4-pentadienoic acid (1552-94-9, 28010-12-0, 28010-13-1, 38446-98-9, 54352-97-5) → m-xylene (108-38-3)

Conditions	Yield
With silver(I) acetate; potassium carbonate In N,N-dimethyl acetamide at 140℃;	94%

hexan-1-amine (111-26-2) + 5-bromo-1,3-xylene (556-96-7) → m-xylene (108-38-3) + N-n-hexyl-3,5-dimethylbenzenamine + Bis-(3,5-dimethyl-phenyl)-hexyl-amine

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); sodium t-butanolate In toluene at 80℃; for 2h; Arylation;	A n/a B 88% C n/a
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene at 80℃; for 3h; Arylation;

1-iodo-2,4-dimethylbenzene (4214-28-2) → m-xylene (108-38-3)

Conditions	Yield
With formaldehyd; palladium diacetate; caesium carbonate In dimethyl sulfoxide at 80℃; for 12h;	85%

ethyl 2-methylbutyrate (7452-79-1) + carbon monoxide (201230-82-2) + 2,6-xylyllithium (63509-96-6) → 1-(2,6-Dimethyl-phenyl)-3-methyl-pentane-1,2-dione (91873-92-6) + m-xylene (108-38-3)

Conditions	Yield
In tetrahydrofuran; Dimethyl ether at -135℃;	A 84% B 13%

2-Bromo-m-xylene (576-22-7) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → m-xylene (108-38-3) + 2-(2,6-bismethylphenyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane

Conditions	Yield
With triethylamine; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 100℃; for 6h;	A n/a B 82%

2,6-dimethylbenzene boronic acid (100379-00-8) + ethyl bromoacetate (105-36-2) → ethyl 2-(2,6-dimethylphenyl)acetate (105337-15-3) + m-xylene (108-38-3)

Conditions	Yield
With potassium fluoride; benzyltriethylammonium bromide; tris-(o-tolyl)phosphine; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran for 24h; Product distribution / selectivity; Reflux;	A 81.9% B n/a

3,5-dimethylphenyl iodide (22445-41-6) + 4-amino-phenol (123-30-8) → 4-(3,5-dimethylphenoxy)aniline (86823-17-8) + m-xylene (108-38-3)

Conditions	Yield
With copper(l) iodide; potassium carbonate; (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane In propyl cyanide at 70℃; for 24h; Inert atmosphere;	A 76% B 14 %Chromat.

acetic acid methyl ester (79-20-9) + carbon monoxide (201230-82-2) + 2,6-xylyllithium (63509-96-6) → 1-(2,6-Dimethyl-phenyl)-propane-1,2-dione (150457-77-5) + m-xylene (108-38-3)

Conditions	Yield
In tetrahydrofuran; diethyl ether; pentane at -135 - 25℃;	A 9% B 73%
In tetrahydrofuran; Dimethyl ether at -135℃;	A 9% B 48%

bis(trimethylaluminum)–1,4-diazabicyclo[2.2.2]octane adduct (137203-34-0) + 3-Iodotoluene (625-95-6) → m-xylene (108-38-3)

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); dicyclohexyl(2',6'-diisopropyl-4'-sulfobiphenyl-2-yl)phosphonium hydrogen sulfate In tetrahydrofuran at 65℃; for 4h; Inert atmosphere; Ionic liquid; chemoselective reaction;	73%

hexane (110-54-3) → o-xylene (95-47-6) + para-xylene (106-42-3) + ethylbenzene (100-41-4) + m-xylene (108-38-3) + toluene (108-88-3) + benzene (71-43-2)

Conditions	Yield
540 degC; treated 16 h; U type zeolite at 450℃; Product distribution;	A n/a B n/a C n/a D n/a E 10.8% F 72.2%
540 degC; treated 16 h; UHS type zeolite at 450℃; Product distribution;	A n/a B n/a C n/a D n/a E 33.3% F 50%

carbon monoxide (201230-82-2) + 3,5-dimethylphenyl iodide (22445-41-6) → 3,5-dimethylbenzaldehyde (5779-95-3) + m-xylene (108-38-3)

Conditions	Yield
With hydrogen; potassium carbonate In 1,4-dioxane at 120 - 140℃; under 30003 Torr; for 20h; Autoclave;	A 71% B 6%

butanoic acid methyl ester (623-42-7) + carbon monoxide (201230-82-2) + 2,6-xylyllithium (63509-96-6) → 1-(2,6-Dimethyl-phenyl)-pentane-1,2-dione (91887-15-9) + m-xylene (108-38-3)

Conditions	Yield
In tetrahydrofuran; Dimethyl ether at -135℃;	A 66% B 20%

3,5-dimethylphenyl iodide (22445-41-6) + di(cyclohexa-2,5-dien-1-yl)silane → di(cyclohexa-2,5-dien-1-yl)(3,5-dimethylphenyl)silane + m-xylene (108-38-3)

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); diisopropylamine In benzene at 20℃; for 24h; Glovebox; Sealed tube;	A 66% B n/a

2,4-dimethylbenzaldazine (28042-78-6) → 5,7-dimethylphthalazine (78032-06-1) + m-xylene (108-38-3)

Conditions	Yield
With aluminium trichloride; aluminum tri-bromide at 185 - 195℃; for 0.5h;	A 65% B n/a

pyrilium tetrafluoroborate + phenyllithium (591-51-5) → (2Z,4E)-5-phenylpenta-2,4-dienal (121077-51-8) + m-xylene (108-38-3)

Conditions	Yield
In tetrahydrofuran at -78℃; for 4h; Yields of byproduct given;	A 61% B n/a

1-chloro-3,5-dimethylbenzene (556-97-8) + bis(pinacol)diborane (73183-34-3) → 2,2'-(3,5-dimethyl-1,2-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) + m-xylene (108-38-3) + 2-(3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (325142-93-6)

Conditions	Yield
With bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0); potassium methanolate In hexane at 25℃; for 6h; Inert atmosphere; Irradiation;	A 3% B 19 %Chromat. C 61%

n-heptane (142-82-5) → o-xylene (95-47-6) + para-xylene (106-42-3) + ethylbenzene (100-41-4) + m-xylene (108-38-3) + toluene (108-88-3) + benzene (71-43-2)

Conditions	Yield
540 degC; treated 16 h; U type zeolite at 450℃; Product distribution;	A n/a B n/a C n/a D n/a E 58.5% F 6%
540 degC; treated 16 h; UHS type zeolite at 450℃; Product distribution;	A n/a B n/a C n/a D n/a E 42.8% F 8.8%

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%

tert-butyl (2,4-dimethylphenyl)carbonate + bis(pinacol)diborane (73183-34-3) → 2-(2,4-bismethylphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane + m-xylene (108-38-3)

Conditions	Yield
With cesium fluoride; 2-mercaptopyridine sodium salt In acetonitrile at 30 - 35℃; for 36h; Irradiation; Inert atmosphere;	A 57% B 13 %Chromat.

3,5-dimethylcyclohexan-1-ol (5441-52-1) → 3,5-dimethylcyclohexanone (2320-30-1) + m-xylene (108-38-3) + 3,5-Dimethylphenol (108-68-9)

Conditions	Yield
aluminum oxide; nickel at 350℃; Product distribution; effect of temperature on conversion; various temperatures, catalysts various origin and amount;	A 34.5% B 56% C 0.7%

1-methyl-3-methylcyclohexa-2,5-dienecarboxylic acid (31689-43-7) → m-xylene (108-38-3) + (1S,5S)-1,5-Dimethyl-6-oxa-bicyclo[3.2.1]oct-2-en-7-one

Conditions	Yield
With chlorosulfonic acid In dichloromethane at 0℃; for 0.166667h;	A 32% B 53%

1-methyl-3-methylcyclohexa-2,5-dienecarboxylic acid (31689-43-7) → C9H12O2 (643749-27-3) + m-xylene (108-38-3)

Conditions	Yield
With chlorosulfonic acid In dichloromethane at 0℃; for 0.166667h;	A 53% B 32%

2,4-dimethylchlorobenzene (95-66-9) → 2,2',4,4'-tetramethylbiphenyl (3976-36-1) + m-xylene (108-38-3)

Conditions	Yield
With PEG-400; sodium hydroxide; zinc; palladium on activated charcoal In water at 100℃; for 2h; coupling; reduction;	A 51% B 38 % Chromat.

triethylsilane (617-86-7) + 3,5-dimethylphenyl iodide (22445-41-6) → (3,5-dimethylphenyl)triethylsilane + m-xylene (108-38-3)

Conditions	Yield
With potassium phosphate; bis(tri-t-butylphosphine)palladium(0) In 1-methyl-pyrrolidin-2-one at 20℃; for 60h;	A 51% B 36 % Chromat.

trans-1,2-dichloroethylene (156-60-5) + 3,5-dimethylphenyl boronic acid (172975-69-8) → 1-[(E)-2-chlorovinyl]-3,5-dimethylbenzene + (E)-1,2-bis(3,5-dimethylphenyl)ethene (13863-27-9) + m-xylene (108-38-3)

Conditions	Yield
With cesium fluoride; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis(di-tert-butylphosphino)biphenyl In 1,4-dioxane at 70℃; Suzuki coupling;	A 50% B n/a C n/a

acetic anhydride (108-24-7) + m-xylene (108-38-3) → 2,4-dimethylacetophenone. (89-74-7)

Conditions	Yield
With gallium tri(nonafluorobutane sulfonate); lithium perchlorate In nitromethane at 20℃; for 6h; Acetylation; Friedel-Crafts reaction;	100%
With lithium perchlorate; hafnium tetrakis(trifluoromethanesulfonate) In nitromethane for 6h; Product distribution; Ambient temperature; effect of var. Lewis acid catalysts, LiClO4 and different solvents;	91%
With hafnium(IV) trifluoromethanesulfonate; lithium perchlorate In nitromethane for 6h; Product distribution; Ambient temperature; other aromatic compounds, acylation and alkylation agents, Lewis acids, var. concetration of LiClO4;	91%

benzoyl chloride (98-88-4) + m-xylene (108-38-3) → 2,4-Dimethyl benzophenone (1140-14-3)

Conditions	Yield
With gallium(III) triflate; 1-dodecyloxy-4-(heptadecafluorooctyl)benzene In carbon dioxide at 100℃; under 60004.8 Torr; for 6h;	100%
Hf[N(SO2C8F17)2]4 In various solvent(s) at 120℃; for 3h;	96%
With VNU-1 In nitrobenzene at 120℃; for 0.0833333h; Friedel-Crafts Acylation; Microwave irradiation;	92%

acetic acid (64-19-7) + m-xylene (108-38-3) → 2,4-dimethylacetophenone. (89-74-7)

Conditions	Yield
With trifluoroacetic anhydride; bismuth(lll) trifluoromethanesulfonate at 30℃; for 6h; Product distribution; Further Variations:; Catalysts; Reagents; Temperatures; reaction times; Friedel-Crafts acetylation;	100%
With trifluoromethylsulfonic anhydride at 20℃; for 0.0833333h; Friedel-Crafts acylation;	97%
Stage #1: acetic acid; m-xylene With trifluoroacetic anhydride In dichloromethane at 20℃; for 0.25h; Stage #2: With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 1h;	88%

m-xylene (108-38-3) → 1,3-dimethylcyclohexane (638-04-0, 2207-03-6, 69685-67-2, 69685-68-3, 129939-72-6, 129939-73-7, 591-21-9)

Conditions	Yield
With hydrogen; [(norbornadiene)rhodium(I)chloride]2; phosphinated polydiacetylene In n-heptane at 30℃; under 60800 Torr; for 1.5h;	100%
With 5% Ru/MgO; hydrogen In tetrahydrofuran at 120℃; under 7600.51 Torr; for 2.9h;	100%
With Ti8O8(14+)*6C8H4O4(2-)*4O(2-)*3.3Li(1+)*0.7Co(2+)*0.7C4H8O*0.7H(1-); hydrogen In neat (no solvent) at 120℃; under 37503.8 Torr; for 18h;	100%

1,4-bis-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzene (5565-36-6) + m-xylene (108-38-3) + bis-[(trifluoroacetoxy)iodo]benzene (2712-78-9) → C14H14I(1+)*C2F3O2(1-) (1417418-28-0)

Conditions	Yield
With air In dichloromethane at 20℃; for 6h; regioselective reaction;	100%

m-xylene (108-38-3) → 3-(chloromethyl)benzyl chloride (626-16-4)

Conditions	Yield
With chlorine; 1-butyl-3-methylimidazolium chloride at 58℃; for 3h; Reagent/catalyst; Temperature; Irradiation; Ionic liquid;	99.18%
With chlorine Sonnenlicht;
With phosphorus pentachloride at 190℃;

1,1-Diphenylmethanol (91-01-0) + m-xylene (108-38-3) → ((2,4-dimethylphenyl)methylene)dibenzene (6944-21-4)

Conditions	Yield
With silica gel supported sodium hydrogen sulfate at 60℃; for 0.5h; Friedel-Crafts type alkylation;	99%
With boron trifluoride diethyl etherate; water at 80℃; for 2h; regioselective reaction;	92%
With phosphorus pentoxide

perfluoro-o-phenylenemercury trimer (18734-63-9) + m-xylene (108-38-3) → perfluoro-ortho-phenylene mercury trimer - meta-xylene (1:1) (649559-07-9)

Conditions	Yield
In further solvent(s) Hg-compound was dissolved by boiling in m-xylene, cooled; slow evapd. in a well-aerated fume hood; elem. anal.;	99%

norborna-2,5-diene(1,2-bis(diphenylphosphino)ethane)rhodium(I) tetrafluoroborate (60430-43-5) + m-xylene (108-38-3) → (C6H5)2PCH2CH2P(C6H5)2RhC6H4(CH3)2(1+)*BF4(1-)=[(C6H5)2PCH2CH2P(C6H5)2RhC6H4(CH3)2]BF4 (188659-74-7)

Conditions	Yield
With H2 In methanol (N2); solution of Rh complex was bubbled with H2 (5 min), concn. of the solution, addn. of 1,3-dimethylbenzene, stirring (12 h, room temp.); removal of the solvent;	99%

[Ir(2,6-bis(di-tert-butylphosphinomethylene)pyridine)(cyclooctene)][PF6] (531490-86-5) + m-xylene (108-38-3) → [Ir(2,6-bis(di-tert-butylphosphinomethylene)pyridine)(H)(m-xylyl)][PF6] (898225-76-8)

Conditions	Yield
In m-xylene under N2 atm. soln. Ir complex in m-xylene was heated at 60°C for1 h; solvent was evapd., residue was washed with pentane and ether and dried in vacuo overnight; elem. anal.;	99%

m-xylene (108-38-3) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-(3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (325142-93-6)

Conditions	Yield
With RhH{κ3-P,O,P-[9,9-dimethyl-4,5-bis-(diisopropylphosphino)xanthene2]}; cyclohexene at 110℃; for 48h; Inert atmosphere; Glovebox;	99%
With IrH2(Bpin){κ3-P,O,P-[9,9-dimethyl-4,5-bis(diisopropylphosphino)xanthene]}; cyclohexene at 110℃; for 18h; Inert atmosphere; Glovebox;	95%
With (N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)CuFp at 25℃; for 48h; Inert atmosphere; Glovebox; UV-irradiation; Sealed tube;	80%

silver tetrafluoroborate (14104-20-2) + bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] (12354-84-6, 12354-85-7) + m-xylene (108-38-3) → [pentamethylcyclopentadienyl*iridium(η6-m-xylene)][BF4]2

Conditions	Yield
Stage #1: silver tetrafluoroborate; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] In acetone at 24℃; for 0.25h; Stage #2: m-xylene With trifluoroacetic acid at 24℃;	99%

P,P-diphenyl-N-(8-aminoquinoline)phosphonamide + m-xylene (108-38-3) → P-[2-(3-methylbenzyl)phenyl]-P-phenyl-N-(8-aminoquinoline)phosphonamide

Conditions	Yield
With dihydrogen peroxide at 100℃; for 24h; Schlenk technique; Inert atmosphere; Green chemistry;	99%

m-xylene (108-38-3) → 1,4-dihydroxy-2,6-dimethylbenzene (654-42-2)

Conditions	Yield
With 2-Ethylhexanoic acid; [Fe(CF3SO3)2((S,S)-N,N’-bis(2-pyridylmethyl)-2,2’-bipyrrolidine)]; dihydrogen peroxide In acetonitrile at 0℃; for 2.5h;	99%

m-xylene (108-38-3) → tetrachloromethane (56-23-5) + hexachlorobenzene (118-74-1)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); chlorine; aluminum oxide; molybdenum(VI) oxide at 380 - 400℃; for 0.00277778h;	A 95.15% B 98.06%

m-xylene (108-38-3) + p-toluenesulfonyl chloride (98-59-9) → 2,4-dimethyl-1-[(4-methylphenyl)sulfonyl]benzene (13249-97-3)

Conditions	Yield
With tin(II) trifluoromethanesulfonate at 120℃; for 8h; Friedel-Crafts sulfonylation;	98%
With [BTBA]Cl-FeCl3 at 60℃; for 0.0166667h; Friedel-Crafts sulfonylation;	97%
With peroxodisulfate ion; zirconium(IV) oxide at 150℃; for 0.5h; Friedel-Crafts reaction;	89%

m-xylene (108-38-3) → 1-bromo-2,4-dimethylbenzene (583-70-0)

Conditions	Yield
With sulfuric acid; dihydrogen peroxide; sodium bromide In water at 49.84℃;	98%
With N-Bromosuccinimide In acetonitrile at 0 - 20℃; Inert atmosphere;	98%
With N-Bromosuccinimide In 1,2-dichloro-ethane at 60℃; for 10h; Sealed tube;	97%

m-xylene (108-38-3) + benzoic acid (65-85-0) → 2,4-Dimethyl benzophenone (1140-14-3)

Conditions	Yield
With trifluoroacetic anhydride; bismuth(lll) trifluoromethanesulfonate at 30℃; for 12h; Friedel-Crafts acetylation;	98%
With pyridin-2-yl trifluoromethanesulfonate; trifluoroacetic acid for 5h; Heating;	95%
With trifluoromethylsulfonic anhydride In nitromethane at 20℃; for 0.0833333h; Friedel-Crafts acylation;	90%

m-xylene (108-38-3) + 2-iodo-4-nitro-1(3)H-imidazole (13369-81-8) → 4(5)-Nitro-2-(2,4-dimethylphenyl)imidazole

Conditions	Yield
In acetonitrile for 4h; Irradiation;	98%

m-xylene (108-38-3) + bis(pinacol)diborane (73183-34-3) → 2-(3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (325142-93-6)

Conditions	Yield
Stage #1: bis(pinacol)diborane With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tert-butyl methyl ether Inert atmosphere; Stage #2: m-xylene In tert-butyl methyl ether at 80℃; for 6h; Inert atmosphere;	98%
With 6Zr(4+)*4O(2-)*4HO(1-)*4C18H12O4(2-)*2C16H10N2O4(2-)*C8H12*Ir(1+)*CH3O(1-) In tetrahydrofuran; n-heptane at 115℃; for 16h; Catalytic behavior; Reagent/catalyst; Temperature; Glovebox; Schlenk technique; Inert atmosphere;	97%
With Ir(1+)*C8H12*CH3O(1-)*6C12H6N2O4(2-)*4Zr(4+)*4HO(1-)*4O(2-) In neat (no solvent) at 100℃; for 7h; Time; Reagent/catalyst; Glovebox; Inert atmosphere; Sealed tube;	94%

m-xylene (108-38-3) → benzene-1,3-dicarbonitrile (626-17-5) + 3-cyanobenzamide (3441-01-8) + 3-Methylbenzonitrile (620-22-4)

Conditions	Yield
With ammonia; oxygen; B0.5CrK0.02Mo0086Na0009P0.007V at 350 - 420℃; under 1500.15 Torr; Gas phase; Heating / reflux;	A 98% B n/a C n/a

(3S)-3-methoxycarbonyl-3-trifluoroacetylaminopropanoyl chloride (64881-40-9) + m-xylene (108-38-3) → methyl 4-(2,4-dimethylphenyl)-4-oxo-2-(2,2,2-trifluoroacetamido)butanoate (1088806-53-4)

Conditions	Yield
With trifluorormethanesulfonic acid at 0℃; for 1h; Friedel Crafts acylation; Neat (no solvent);	98%

m-xylene (108-38-3) + (R)-N-trifluoroacetylaspartic acid-4-chloride-1-methyl ester (161553-08-8) → methyl 4-(2,4-dimethylphenyl)-4-oxo-2-(2,2,2-trifluoroacetamido)butanoate (1088806-55-6)

Conditions	Yield
With trifluorormethanesulfonic acid at 0℃; for 1h; Friedel Crafts acylation; Neat (no solvent);	98%

2-chlorobenzalacetone (91574-67-3, 91574-68-4, 20766-37-4) + m-xylene (108-38-3) → C18H17ClO

Conditions	Yield
With di-tert-butyl peroxide; [copper(II)(trifluoroacetylacetonate)2]; salicylic acid at 120℃; for 24h; Inert atmosphere; regioselective reaction;	98%

m-xylene (108-38-3) + methyl 2-(2-chlorophenyl)-2-diazoacetate (264882-00-0) → methyl 2-(2-chlorophenyl)-2-(2,4-dimethylphenyl)acetate

Conditions	Yield
With (triphenylphosphine)gold(I) chloride; silver trifluoromethanesulfonate at 20℃; for 0.0666667h; Schlenk technique;	98%
With MCM-41-PPh2-AuOTf at 20℃; for 0.1h; Schlenk technique; Inert atmosphere; regioselective reaction;	87%

tertiary butyl chloride (507-20-0) + m-xylene (108-38-3) → 5-tert-Butyl-m-xylene (98-19-1)

Conditions	Yield
With 4-Chloropyridine; nickel(II) oxide; aluminum (III) chloride; barium titanate; 4-trifluoromethylpyridine; copper(II) sulfate In ethanol at 25℃; for 0.0666667h; Temperature;	97.7%
With aluminum (III) chloride In dichloromethane at 20℃; for 1.5h;	70%
montmorillonite doped with TiCl4 for 0.333333h; Heating;	60%

phthalic anhydride (85-44-9) + m-xylene (108-38-3) → 2-(2,4-dimethylbenzoyl)benzoic acid (2346-63-6)

Conditions	Yield
Stage #1: phthalic anhydride; m-xylene With aluminum (III) chloride at 55℃; for 5h; cooling with salt-ice; Stage #2: With hydrogenchloride In water; m-xylene cooling with ice;	97%
With aluminum (III) chloride at 60℃; for 0.416667h; Catalytic behavior; Reagent/catalyst; Time; Concentration; Friedel-Crafts Acylation; Ionic liquid; Irradiation;	85%
With aluminium trichloride

Upstream product

• 2947-60-6 3-methylbenzyl cyanide 
• 78-92-2 iso-butanol 
• 112-80-1 cis-Octadecenoic acid 
• 60-33-3 linoleic acid 
• 463-40-1 (9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid 
• 6983-79-5 methyl hydrogen all-trans-6,6'-diapocarotene-6,6'-dioate 
• 67-66-3 chloroform 
• 38461-17-5 3,5-dimethylenecyclohexene 
• 6192-52-5 p-toluenesulfonic acid monohydrate 
• 5026-76-6 6-methylhept-1-ene 
• 638-04-0 1,3-dimethylcyclohexane 
• 3073-66-3 1,1,3-trimethylcyclohexane 
• 106-42-3 para-xylene 
• 2808-77-7 2,4-dimethylcyclohexene 

Downstream Products

• 6597-59-7 2-(2,4-dimethylphenyl)ethanol 
• 62343-67-3 β-(3,5-Dimethylphenyl)ethyl alcohol 
• 94143-65-4 1,2-bis(2,4-dimethylphenyl)ethane 
• 56290-42-7 1-(2,4-dimethyl-phenyl)-butane-1,3-dione 
• 20116-65-8 dimethyl 4-methylphthalate 
• 21483-46-5 dimethyl 3-methylbenzene-1,2-dicarboxylate 
• 50919-64-7 dimethyl 3,5-dimethylphthalate 
• 4168-10-9 2-(3-methylbenzyl)succinic anhydride 
• 132972-06-6 β-(2,4-dimethyl)benzoyl acrylic acid 
• 15880-03-2 4-(2,4-dimethylphenyl)-4-oxobutanoic acid 
• 110514-97-1 1,3,5,7-tetramethyl-naphtho[2,3-c]furan-4,9-quinone 
• 102749-19-9 3,4-Bis-(2,4-dimethyl-benzoyl)-2,5-dimethyl-furan 
• 102545-90-4 N-[2-(2,4-dimethyl-benzoyl)-phenyl]-phthalimide 
• 35031-55-1 1-(2,4-dimethyl-phenyl)-propan-1-one 

Relevant articles and documents

Rational Design of Zinc/Zeolite Catalyst: Selective Formation of p-Xylene from Methanol to Aromatics Reaction

The production of p-xylene from the methanol to aromatics (MTA) reaction is challenging. The catalytic stability, which is inversely proportional to the particle size of the zeolite, is not always compatible with p-xylene selectivity, which is inversely proportional to the external acid sites. In this study, based on a nano-sized zeolite, we designed hollow triple-shelled Zn/MFI single crystals using the ultra-dilute liquid-phase growth technique. The obtained composites possessed one ZSM-5 layer (≈30 nm) in the middle and two silicalite-1 layers (≈20 nm) epitaxially grown on two sides of ZSM-5, which exhibited a considerably long lifetime (100 % methanol conversion >40 h) as well as an enhanced shape selectivity of p-xylene (>35 %) with a p-xylene/xylene ratio of ≈90 %. Importantly, using this sandwich-like zeolite structure, we directly imaged the Zn species in the micropores of only the ZSM-5 layer and further determined the specific structure and anchor location of the Zn species.

Photochemical and electrochemical C-N borylation of arylhydrazines

The C-N borylation of arylhydrazine hydrochlorides with bis(pinacolato)diboron was achieved under photochemical and electrochemical conditions, respectively. This novel and scalable transformation provides two efficient and mild transition-metal-free synt

Metal-Free Heterogeneous Semiconductor for Visible-Light Photocatalytic Decarboxylation of Carboxylic Acids

A suitable protocol for the photocatalytic decarboxylation of carboxylic acids was developed with metal-free ceramic boron carbon nitrides (BCN). With visible light irradiation, BCN oxidize carboxylic acids to give carbon-centered radicals, which were trapped by hydrogen atom donors or employed in the construction of the carbon-carbon bond. In this system, both (hetero)aromatic and aliphatic acids proceed the decarboxylation smoothly, and C-H, C-D, and C-C bonds are formed in moderate to high yields (35 examples, yield up to 93%). Control experiments support a radical process, and isotopic experiments show that methanol is employed as the hydrogen atom donor. Recycle tests and gram-scale reaction elucidate the practicability of the heterogeneous ceramic BCN photoredox system. It provides an alternative to homogeneous catalysts in the valuable carbon radical intermediates formation. Moreover, the metal-free system is also applicable to late-stage functionalization of anti-inflammatory drugs, such as naproxen and ibuprofen, which enrich the chemical toolbox.