583-70-0

Basic information

• Product Name: 2,4-Dimethylbromobenzene
• Synonyms: 4-BROMO-M-XYLENE;4-BROMO-1,3-DIMETHYLBENZENE;2,4-DIMETHYLBROMOBENZENE;1-BROMO-2,4-DIMETHYLBENZENE;4-Bromo-1,3-dimethylbenzene~2,4-Dimethylbromobenzene;4-BROMO-M-XYLENE 97%;4-BROMO-M-XYLENE, TECH., 90%;4-Bromo-m-xylene,97%
• CAS NO: 583-70-0
• Molecular Formula: C₈H₉Br
• Molecular Weight: 185.06
• EINECS: 209-517-8
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Halogen toluene;Benzene derivates;Bromine Compounds;Aryl;Building Blocks;C8;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 583-70-0.mol
• Article Data: 45

Chemical Properties

• Melting Point: -17°C
• Boiling Point: 214 °C(lit.)
• Flash Point: 174 °F
• Appearance: Clear colorless/Liquid
• Density: 1.37 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.328mmHg at 25°C
• Refractive Index: n20/D 1.551(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Insoluble in water
• CAS DataBase Reference: 2,4-Dimethylbromobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dimethylbromobenzene(583-70-0)
• EPA Substance Registry System: 2,4-Dimethylbromobenzene(583-70-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 583-70-0(Hazardous Substances Data)

Usage

Chemical Properties

Clear colourless to light yellow liquid

Uses

4-Bromo-m-xylene is synthesized by the bromination of alkylbenzene substrates by N-bromosuccinimide.

General Description

Gold-catalyzed coupling reaction of pyrazine with 1-bromo-2,4-dimethylbenzene has been reported. 1-Bromo-2,4-dimethylbenzene reacts with Mg and DMF, followed by the reaction with I2 and aq.NH3 to afford the corresponding aromatic nitrile.

InChI:InChI=1/C8H9Br/c1-6-3-4-8(9)7(2)5-6/h3-5H,1-2H3

Synthetic route

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%

5-Bromo-6,8-dimethyl-2,3-dihydro-benzo[1,4]dithiine (135033-46-4) → 1-bromo-2,4-dimethylbenzene (583-70-0)

Conditions	Yield
With Ni(Ra)-W2 In acetic acid at 40℃; for 0.833333h;	90%

2,4-dimethyl-benzoic acid (611-01-8) → 1-bromo-2,4-dimethylbenzene (583-70-0)

Conditions	Yield
With potassium phosphate; tetrabuthylammonium tribromide In acetonitrile at 100℃; for 16h;	80%

Methyl fluoride (593-53-3) + para-bromotoluene (106-38-7) → 1-bromo-2,4-dimethylbenzene (583-70-0) + 4-bromo-o-xylene (583-71-1)

Conditions	Yield
With oxygen at 40℃; under 720 Torr; Mechanism; Irradiation;	A 72% B 28%

2,4-dimethylphenyl trifluoromethanesulfonate (87241-52-9) → 1-bromo-2,4-dimethylbenzene (583-70-0)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos; triisobutylaluminum; butanone; potassium bromide In toluene at 100℃; for 20h; Inert atmosphere;	66%

m-xylene (108-38-3) → 1-bromo-2,4-dimethylbenzene (583-70-0) + 1-bromomethyl-3-methyl-benzene (620-13-3)

Conditions	Yield
With sodium bromate; sodium hydrogensulfite In cyclohexane; water at 20℃; for 4h; Bromination;	A 1% B 64%
With sodium bromate; sodium hydrogensulfite In water; acetonitrile at 20℃; for 4h; Bromination;	A 57% B n/a
With N-Bromosuccinimide at 150℃; under 2625.26 Torr; for 0.0666667h; microwave irradiation;	A 1.5 % Chromat. B 56 % Chromat.

2,4-Xylidine (95-68-1) → 1-bromo-2,4-dimethylbenzene (583-70-0)

Conditions	Yield
With hydrogen bromide diazotization;	50%
With hydrogen bromide Diazotization.Behandlung der Diazoniumsalz-Loesung mit CuBr oder mit Kupfer-Pulver;

Methyl fluoride (593-53-3) + 2-methylphenyl bromide (95-46-5) → 2-Bromo-m-xylene (576-22-7) + 4-bromo-m-xylene (553-94-6) + 1-bromo-2,4-dimethylbenzene (583-70-0) + 2,3-dimethylbromobenzene (576-23-8)

Conditions	Yield
With oxygen at 40℃; under 720 Torr; Mechanism; Irradiation;	A n/a B n/a C 13.7% D 32.8%

2,4-dimethylbenzenediazonium tetrafluoroborate → 2,4-dimethylchlorobenzene (95-66-9) + 1-bromo-2,4-dimethylbenzene (583-70-0)

Conditions	Yield
With sodium bromide; sodium chloride In methanol at 21 - 23.5℃; Product distribution; Kinetics; investigations of thermal dediazoniation in various solvents as a function of viscosity; the reaction are diffusion controlled;	A 3.1% B 5.8%

2-Bromo-m-xylene (576-22-7) → 5-bromo-1,3-xylene (556-96-7) + 1-bromo-2,4-dimethylbenzene (583-70-0)

Conditions	Yield
TfOH2+B(OTf)4- In toluene for 18h; Product distribution; Ambient temperature;	A 3.5 % Chromat. B 69.1 % Chromat.

2-Bromo-m-xylene (576-22-7) → 5-bromo-1,3-xylene (556-96-7) + 1-bromo-2,4-dimethylbenzene (583-70-0) + m-xylene (108-38-3)

Conditions	Yield
With hydrogen; oxygen at 40℃; under 760 Torr; Product distribution; Mechanism; Irradiation; effect of further reagents;

3-methylbicyclo<4.1.0>hepta-1,3,5-triene (75366-05-1) → 4-bromo-m-xylene (553-94-6) + 1-bromo-2,4-dimethylbenzene (583-70-0)

Conditions	Yield
With bromine; tri-n-butyl-tin hydride Product distribution; Mechanism; multistep reaction; reaction regioselectivity; a series of reagents;

m-xylene (108-38-3) → 2-Bromo-m-xylene (576-22-7) + 1-bromo-2,4-dimethylbenzene (583-70-0)

Conditions	Yield
With bromine In dichloromethane Product distribution; the reaction was also performed by using 2,6-dimethyl-trimethylsilylbenzene as starting material;
With bromine In dichloromethane
With ferrocenium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; bromine; zinc(II) oxide In dichloromethane at 20℃; for 1.5h;

m-xylene (108-38-3) → 1-bromo-2,4-dimethylbenzene (583-70-0) + 1,5-dibromo-2,4-dimethylbenzene (615-87-2)

Conditions	Yield
With aluminum oxide; bromine for 0.0166667h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

bromine (7726-95-6) + m-xylene (108-38-3) → 1-bromo-2,4-dimethylbenzene (583-70-0)

1.3-dimethyl-benzene-sulfonic acid-(4) → 1-bromo-2,4-dimethylbenzene (583-70-0)

Conditions	Yield
With copper(ll) bromide

<5-bromo-2.4-dimethyl-phenyl>-magnesium bromide → 1-bromo-2,4-dimethylbenzene (583-70-0)

Conditions	Yield
With diethyl ether; water at 0℃;

diazotized 4-amino-m-xylene → 1-bromo-2,4-dimethylbenzene (583-70-0)

Conditions	Yield
With hydrogen bromide; copper(I) bromide

sodium salt of/the/ 6-bromo-m-xylene-disulfonic acid-(2.4) → 1-bromo-2,4-dimethylbenzene (583-70-0)

Conditions	Yield
With hydrogenchloride at 150 - 160℃; im Rohr;

5,7-Dimethyl-2,3-dihydro-benzo[1,4]dithiine (127634-83-7) → 1-bromo-2,4-dimethylbenzene (583-70-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / Br2 / CHCl3 / 1 h / Ambient temperature 2: 90 percent / Ni(Ra)-W2 / acetic acid / 0.83 h / 40 °C View Scheme

1-bromo-2,4-dimethylbenzene (583-70-0) + 2-chloropropionyl chloride (625-36-5) → 1-(5-bromo-2,4-dimethylphenyl)-3-chloropropan-1-one (84092-78-4)

Conditions	Yield
With aluminium trichloride In carbon disulfide for 0.5h; Friedel-Crafts reaction; Heating;	99%

4-bromoisoquinoline (1532-97-4) + 1-bromo-2,4-dimethylbenzene (583-70-0) → 4-(2,4-dimethylphenyl)isoquinoline (1360592-40-0)

Conditions

Yield

Stage #1: 1-bromo-2,4-dimethylbenzene With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 0.025h; Inert atmosphere; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane at 60℃; for 0.0166667h; Inert atmosphere; Stage #3: 4-bromoisoquinoline With chloro-(2-dicyclohexylphosphino-2,4,6-triisopropyl-1,1-biphenyl)[2-(2-amino-1,1-biphenyl)]palladium(II); potassium hydroxide In tetrahydrofuran; hexane; water at 60℃; for 0.166667h; Suzuki-Miyaura cross-coupling; Inert atmosphere; Sonication;

96%

1-bromo-2,4-dimethylbenzene (583-70-0) + N-tosyl-1,2-oxazetidine → C17H21NO3S

Conditions	Yield
Stage #1: 1-bromo-2,4-dimethylbenzene With tert.-butyl lithium In tetrahydrofuran; pentane at -78 - -40℃; Inert atmosphere; Stage #2: N-tosyl-1,2-oxazetidine With N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; pentane at -60℃; for 1h; Inert atmosphere;	96%

potassium phosphate + 1-bromo-2,4-dimethylbenzene (583-70-0) + bis(di-tert-butyl(3,5-di-(tert-butyl)phenyl)phosphine)dichloropalladium + 2-Methylphenylboronic acid (16419-60-6) → 2’,2,4-trimethylbiphenyl (76708-74-2)

Conditions	Yield
In water; toluene	96%

vinyl sulfonamide (2386-58-5) + 1-bromo-2,4-dimethylbenzene (583-70-0) → (E)-2-(2,4-Dimethyl-phenyl)-ethenesulfonic acid amide (405262-58-0)

Conditions	Yield
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 130℃; for 12h; Heck reaction;	95%

1-bromo-2,4-dimethylbenzene (583-70-0) + phenyl trimethylsiloxane (2996-92-1) → 2,4-dimethyl-1,1'-biphenyl (4433-10-7)

Conditions	Yield
With tetrabutyl ammonium fluoride; palladium(II) acetylacetonate; 3,9-bis(2,4-tBu-PhO)tetraoxa-3,9-diphosphaspiro[5.5]undecane In xylene at 80℃; Hiyama coupling;	95%

1-bromo-2,4-dimethylbenzene (583-70-0) + (1R,2R,4aS,8aS)-2,5,5,8a-tetramethyl-1-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)decahydronaphthalen-2-yl acetate → (1R,2R,4aS,8aS)-1-(2,4-dimethylbenzyl)-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; ruphos In water; tert-butyl alcohol at 100℃; for 18h; Suzuki Coupling; Schlenk technique; Inert atmosphere;	95%

1-bromo-2,4-dimethylbenzene (583-70-0) + phenylboronic acid (98-80-6) → 2,4-dimethyl-1,1'-biphenyl (4433-10-7)

Conditions	Yield
With potassium phosphate; Pd (sulfur-containing palladacycle); tetra(n-tert-butyl)ammonium bromide In N,N-dimethyl-formamide at 20℃; Suzuki cross-coupling;	94%
With potassium phosphate; 1,1'-bis(4-methoxyphenyl)-3,3'-methylene-diimidazoline-2,2'-diylidene-palladium(II)-dibromide In toluene at 40℃; for 4h; Suzuki-Miyaura Coupling; Inert atmosphere;	94%
With potassium carbonate; [1,1'-bis{(S)-4-isopropyloxazolin-2-yl}ferrocene]Pd(II)Cl2 In toluene at 60℃; for 2h; Suzuki cross-coupling reaction;	92%

1-bromo-2,4-dimethylbenzene (583-70-0) + phenylacetylene (536-74-3) → 1-(2,4-dimethylphenyl)-2-phenylacetylene (78594-13-5)

Conditions	Yield
With potassium phosphate; bis(η3-allyl-μ-chloropalladium(II)); N,N,N′,N′-tetra(diphenylphosphinomethyl)-1,2-ethylenediamine In 1,4-dioxane at 105℃; for 20h; Sonogashira coupling; Inert atmosphere;	94%
With [(Pd{(κ2-C,N)-(3-(dimethylaminomethyl)indole)}µ-OAc)2]; potassium carbonate In water; N,N-dimethyl-formamide at 120℃; for 6h; Catalytic behavior; Sonogashira Cross-Coupling;	39%
With copper(l) iodide; diisopropylamine; sodium tetrachloropalladate(II) at 80℃; Sonogashira coupling;

xanth-9-one (90-47-1) + 1-bromo-2,4-dimethylbenzene (583-70-0) → 9-(2,4-dimethylphenyl)-9-hydroxyxanthene (950597-41-8)

Conditions	Yield
Stage #1: 1-bromo-2,4-dimethylbenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: xanth-9-one In tetrahydrofuran; 1,4-dioxane; hexane at 20℃; for 2h; Further stages.;	94%

triphenylaluminum*THF + 1-bromo-2,4-dimethylbenzene (583-70-0) → 2,4-dimethyl-1,1'-biphenyl (4433-10-7)

Conditions	Yield
palladium diacetate; tricyclohexylphosphine In 1,2-dimethoxyethane at 20℃; for 3h;	94%

pyrrolidine (123-75-1) + 1-bromo-2,4-dimethylbenzene (583-70-0) → 1-(2,4-dimethylphenyl)pyrrolidine (81506-12-9)

Conditions	Yield
With Pd2(OAc)3; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 100℃; for 17h;	93%

ortho-nitrobenzoic acid (552-16-9) + 1-bromo-2,4-dimethylbenzene (583-70-0) → 2,4-dimethyl-2'-nitrobiphenyl

Conditions	Yield
Stage #1: ortho-nitrobenzoic acid With copper(II) carbonate In various solvent(s) at 120℃; for 0.5h; Stage #2: 1-bromo-2,4-dimethylbenzene With potassium fluoride; palladium acetylacetonate; iso-propyldiphenylphoshine In various solvent(s) at 120℃; for 24h; Further stages.;	93%
With potassium fluoride; copper(II) carbonate; bis(acetylacetonato)palladium(II); isopropyldiphenylphosphine In 1-methyl-pyrrolidin-2-one at 120℃; for 24h; Product distribution / selectivity; Molecular sieve;	93 %Chromat.

1-bromo-2,4-dimethylbenzene (583-70-0) + 5,13-bis[(tert-butyldimethylsilyl)oxy]-2,2-dimethyl-2-silatricyclo[8.4.0.0^{3,8}]tetradeca-1(10),3,5,7,11,13-hexaen-9-one (1301205-25-3) → C23H22O2Si

Conditions	Yield
Stage #1: 1-bromo-2,4-dimethylbenzene With sec.-butyllithium In tetrahydrofuran at -78℃; for 0.333333h; Inert atmosphere; Stage #2: 5,13-bis[(tert-butyldimethylsilyl)oxy]-2,2-dimethyl-2-silatricyclo[8.4.0.0^{3,8}]tetradeca-1(10),3,5,7,11,13-hexaen-9-one In tetrahydrofuran at -78 - 20℃; for 1h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; water for 0.333333h; Inert atmosphere;	93%
Stage #1: 1-bromo-2,4-dimethylbenzene With sec.-butyllithium In tetrahydrofuran at -78℃; for 0.333333h; Inert atmosphere; Stage #2: 5,13-bis[(tert-butyldimethylsilyl)oxy]-2,2-dimethyl-2-silatricyclo[8.4.0.0^{3,8}]tetradeca-1(10),3,5,7,11,13-hexaen-9-one In tetrahydrofuran at -78 - 20℃; for 1h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; water for 0.333333h; Inert atmosphere;	93%

C27H33Al*C4H8O + 1-bromo-2,4-dimethylbenzene (583-70-0) → 2,4-dimethyl-2',4',6'-trimethylbiphenyl

Conditions	Yield
Stage #1: C27H33Al*C4H8O; palladium diacetate; tricyclohexylphosphine In toluene at 100℃; for 1h; Stage #2: 1-bromo-2,4-dimethylbenzene In toluene at 60℃; for 5h; Further stages.;	92%

1-bromo-2,4-dimethylbenzene (583-70-0) + 2-Methylphenylboronic acid (16419-60-6) → 2’,2,4-trimethylbiphenyl (76708-74-2)

Conditions	Yield
With bis(dicyclopentyl(2-methoxyphenyl)phosphine)dichloropalladium(II) In water; toluene at 100℃; for 3h; Cooling;	92%
With caesium carbonate In toluene at 80℃; for 12h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;	82%
With Pd(CN(2,6-(2,6-(i-Pr)2C6H3)2C6H3))2; sodium t-butanolate In isopropyl alcohol at 60℃; for 8h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube;	74%

2,2,2-trifluoroethanol (75-89-8) + 1-bromo-2,4-dimethylbenzene (583-70-0) → 2,4-dimethyl-1-(2,2,2-trifluoroethoxy)benzene

Conditions	Yield
Stage #1: 2,2,2-trifluoroethanol With sodium In 1,4-dioxane Stage #2: 1-bromo-2,4-dimethylbenzene With N,N-dimethyl-formamide; copper(I) bromide In 1,4-dioxane at 110℃; for 6h; Sealed tube;	92%

1-bromo-2,4-dimethylbenzene (583-70-0) + 4-methoxyphenylboronic acid (5720-07-0) → 4′-methoxy-2,4-dimethyl-1,1′-biphenyl (1092060-87-1)

Conditions	Yield
With caesium carbonate In toluene at 80℃; for 12h; Catalytic behavior; Reagent/catalyst; Time; Temperature; Solvent; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;	91%

morpholine (110-91-8) + 1-bromo-2,4-dimethylbenzene (583-70-0) → 4-(2,4-dimethylphenyl)morpholine (31538-14-4)

Conditions	Yield
With sodium t-butanolate; palladium diacetate In 1,4-dioxane at 110℃; for 16h;	90%
With palladium diacetate; di-tert-butylneopentylphosphonium tetrafluoroborate; sodium t-butanolate In toluene at 50℃; for 2h; Hartwig-Buchwald amination;	88%

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;

1-bromo-2,4-dimethylbenzene (583-70-0) + 2-amino-benzenethiol (137-07-5) → 2-(2,4-dimethylphenylsulphanyl)benzeneamine (1019453-85-0)

Conditions	Yield
With copper(l) iodide at 200℃; for 22h; Reagent/catalyst; Inert atmosphere;	89%

acrylic acid n-butyl ester (141-32-2) + 1-bromo-2,4-dimethylbenzene (583-70-0) → (E)-n-butyl 3-(2,4-dimethylphenyl)acrylate

Conditions	Yield
With potassium phosphate; [1,1'-bis{(S)-4-isopropyloxazolin-2-yl}ferrocene]Pd(II)Cl2 In 1-methyl-pyrrolidin-2-one at 140℃; for 3h; Heck cross-coupling reaction;	88%

norborn-2-ene (498-66-8) + 1-bromo-2,4-dimethylbenzene (583-70-0) → 5,7-dimethyl-1,2,3,4,4a,8b-hexahydro-1,4-cis,exo-methanobiphenylene

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In N,N-dimethyl-formamide at 105℃; for 24h;	87%

AlPhEt2(THF) + 1-bromo-2,4-dimethylbenzene (583-70-0) → 2,4-dimethyl-1,1'-biphenyl (4433-10-7)

Conditions	Yield
Stage #1: AlPhEt2(THF) With palladium diacetate; tricyclohexylphosphine In toluene for 0.166667h; Inert atmosphere; Stage #2: 1-bromo-2,4-dimethylbenzene In toluene at 20℃; for 3h; Inert atmosphere;	87%

1-bromo-2,4-dimethylbenzene (583-70-0) + 2-(perfluoropropyl)aniline → 3-methyl-9-(heptafluoropropyl)acridine

Conditions	Yield
Stage #1: 1-bromo-2,4-dimethylbenzene With magnesium In tetrahydrofuran at 70℃; Inert atmosphere; Stage #2: 2-heptafluoropropylaniline In tetrahydrofuran at -70 - 23℃; Inert atmosphere;	86%

1-bromo-2,4-dimethylbenzene (583-70-0) + butan-1-ol (71-36-3) → 1-butoxy-2,4-dimethylbenzene (31268-68-5)

Conditions	Yield
With palladium diacetate; caesium carbonate; 2-N,N-(dimethylamino)-2'-di-tert-butylphosphino-1,1'-binaphthyl In toluene at 70℃; for 18h;	85%

1-bromo-2,4-dimethylbenzene (583-70-0) + 2,4-Xylidine (95-68-1) → 2,2′4,4′-tetramethyldiphenylamine (19616-28-5)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 10h; Inert atmosphere; Reflux;	85%
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 10h; Inert atmosphere; Reflux;	85%
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 10h; Inert atmosphere; Reflux;	85%

1-bromo-2,4-dimethylbenzene (583-70-0) + 2-methyl-N-[(5-methylfuran-2-yl)methylidene]propane-2-sulfinamide → N-[(2,4-dimethyl phenyl)(5-methylfuran-2-yl)methyl]-2-methylpropane-2-sulfinamide

Conditions	Yield
Stage #1: 1-bromo-2,4-dimethylbenzene With magnesium In tetrahydrofuran at 40℃; Stage #2: 2-methyl-N-[(5-methylfuran-2-yl)methylidene]propane-2-sulfinamide In tetrahydrofuran at 20℃;	85%
Stage #1: 1-bromo-2,4-dimethylbenzene With magnesium In tetrahydrofuran at 40℃; Stage #2: 2-methyl-N-[(5-methylfuran-2-yl)methylidene]propane-2-sulfinamide In tetrahydrofuran at 20℃;	85%
Stage #1: 1-bromo-2,4-dimethylbenzene With magnesium In tetrahydrofuran at 40℃; Stage #2: 2-methyl-N-[(5-methylfuran-2-yl)methylidene]propane-2-sulfinamide In tetrahydrofuran at 20℃;	85%
Stage #1: 1-bromo-2,4-dimethylbenzene With magnesium In tetrahydrofuran at 40℃; Stage #2: 2-methyl-N-[(5-methylfuran-2-yl)methylidene]propane-2-sulfinamide In tetrahydrofuran at 20℃;	85%

Upstream product

• 108-38-3 m-xylene 
• 95-68-1 2,4-Xylidine 
• 576-22-7 2-Bromo-m-xylene 
• 135033-46-4 5-Bromo-6,8-dimethyl-2,3-dihydro-benzo[1,4]dithiine 
• 7726-95-6 bromine 
• 611-01-8 2,4-dimethyl-benzoic acid 
• 87241-52-9 2,4-dimethylphenyl trifluoromethanesulfonate 
• 75366-05-1 3-methylbicyclo<4.1.0>hepta-1,3,5-triene 
• 593-53-3 Methyl fluoride 
• 95-46-5 2-methylphenyl bromide 
• 106-38-7 para-bromotoluene 
• 127634-83-7 5,7-Dimethyl-2,3-dihydro-benzo[1,4]dithiine 

Downstream Products

• 874-41-9 1-ethyl-2,4-dimethyl-benzene 
• 76890-08-9 2-(2,4-dimethyl-phenyl)-quinoline 
• 76890-13-6 2-methyl-11H-indeno<1,2-b>quinoline 
• 116432-91-8 1-(4-Chloro-phenylsulfanyl)-2,4-dimethyl-benzene 
• 22744-31-6 2,4-Dimethyl-2',4',6'-tri-tert.butyl-benzophenon 
• 81506-12-9 N-(2,4-dimethylphenyl)pyrrolidine 
• 95-63-6 1,2,4-Trimethylbenzene 
• 119571-23-2 tris-(2,4-dimethyl-phenyl)-stibine 
• 405262-58-0 (E)-2-(2,4-Dimethyl-phenyl)-ethenesulfonic acid amide 
• 58983-20-3 diethyl 2,4-dimethylphenylphosphonate 
• 78594-13-5 1-(2,4-dimethylphenyl)-2-phenylacetylene 
• 95-68-1 2,4-Xylidine 
• 141763-00-0 4-bromo-6-methylsulfonyl-m-xylene 
• 1237-53-2 2-chloro-4,6-bis(2',4'-dimethylphenyl)-1,3,5-triazine 

Relevant articles and documents

Chemistry of ethanediyl S,S-acetals 6-an example of vicarious nucleophilic substitution of hydrogen in 1,4-benzodithians

1,4-Benzodithians, when treated with bromine in anhydrous chloroform, undergo very fast monobromination at the aromatic ring. By the use of quantum mechanical semiempirical calculations, the reaction is shown to proceed most likely via a vicarious nucleophilic substitution of hydrogen.

Molecular tweezers based on trivalent phosphine, preparation method of molecular tweezers, metal-molecular tweezers catalyst, and preparation method and application of metal-molecular tweezers catalyst

The invention relates to the technical field of inorganic-metal organic crossing and relates to the technical field of molecular tweezers, in particular to molecular tweezers based on trivalent phosphine, a preparation method of the molecular tweezers, a metal-molecular tweezer catalyst, a preparation method of the metal-molecular tweezer catalyst and an application of the metal-molecular tweezercatalyst, the molecular tweezer based on trivalent phosphine is named as P-MV-PCN-521-R, and R is any one of benzoic acid, p-nitrobenzoic acid, formic acid, p-methylbenzoic acid and dichloroacetic acid. The molecular tweezers based on the trivalent phosphine have distance adjustability. The trivalent phosphine-based metal-molecular tweezer catalyst provided by the invention has a high crystallinesurface area and a high specific surface area. The trivalent phosphine-based metal-molecular tweezer catalyst has good chemical stability and thermal stability, and is a primary condition for applyingthe trivalent phosphine-based metal-molecular tweezer catalyst to the actual field. The trivalent phosphine-based metal-molecular tweezer catalyst with adjustable distance provided by the invention has good selectivity for bromination of aromatic compounds.

Regioselective Halogenation of Arenes and Heterocycles in Hexafluoroisopropanol

Regioselective halogenation of arenes and heterocycles with N-halosuccinimides in fluorinated alcohols is disclosed. Under mild condition reactions, a wide diversity of halogenated arenes are obtained in good yields with high regioselectivity. Additionally, the versatility of the method is demonstrated by the development of one-pot sequential halogenation and halogenation-Suzuki cross-coupling reactions.