583-71-1

Basic information

• Product Name: 4-Bromo-o-xylene
• Synonyms: 4-bromo-1,2-dimethyl-benzen;4-Bromo-ortho-xylene;4-bromo-o-xylen;o-Xylene, 4-bromo-;4-Bromo-1,2-dimethylbenzene~3,4-Dimethylbromobenzene;4-Bromo-O-Xylene97%;4-Bromo-o-xylene, remainder 3-bromo-o-xylene, 75%;4-BROMO-O-XYLENE / 1-BROMO3,4-DIMETHYLBENZENE
• CAS NO: 583-71-1
• Molecular Formula: C₈H₉Br
• Molecular Weight: 185.06
• EINECS: 209-518-3
• Product Categories: Aromatic Halides (substituted);Halogen toluene;Benzene derivates;Bromine Compounds
• Mol File: 583-71-1.mol
• Article Data: 31

Chemical Properties

• Melting Point: −12-−10 °C
• Boiling Point: 215 °C(lit.)
• Flash Point: 177 °F
• Appearance: Clear colourless to light yellow liquid
• Density: 1.37 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.234mmHg at 25°C
• Refractive Index: n20/D 1.555(lit.)
• Storage Temp.: Store below +30°C.
• Water Solubility: Not miscible in water.
• BRN: 2040354
• CAS DataBase Reference: 4-Bromo-o-xylene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-o-xylene(583-71-1)
• EPA Substance Registry System: 4-Bromo-o-xylene(583-71-1)

Safety Data

• Hazard Codes: Xn,N,Xi
• Statements: 22-36/37/38-50/53
• Safety Statements: 26-60-61-24/25
• RIDADR: UN 1701 6.1/PG 2
• WGK Germany: 3
• RTECS: CY9020400
• F: 19
• TSCA: Yes
• Hazardous Substances Data: 583-71-1(Hazardous Substances Data)

Usage

Chemical Properties

Clear colourless to light yellow liquid

Uses

4-Bromo-o-xylene is used as synthetic organic materials and soluble polyimide resin intermediates.

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

Synthetic route

o-xylene (95-47-6) → 4-bromo-o-xylene (583-71-1)

Conditions	Yield
With K10-montmorillonite clay; bromine In tetrachloromethane for 1.5h; Ambient temperature;	96%
With carbon dioxide; bromine at 40℃; under 187519 Torr; for 2h; Supercritical conditions; Green chemistry;	95%
With tetrabutylammomium bromide; dihydrogen peroxide; vanadia In water; acetonitrile at 5℃; for 1.5h; Bromination;	92%

o-xylene (95-47-6) → 4-bromo-o-xylene (583-71-1) + 2,3-dimethylbromobenzene (576-23-8)

Conditions	Yield
With bromine; acetic acid	A 82% B 18%
With bromine; iodine In dichloromethane at -10 - 20℃; for 7.58333h;	A 75% B 15%
With hydrogenchloride; sodium hypochlorite; sodium bromide In water at 29.85℃; for 8h; Product distribution; Further Variations:; Temperatures;	A 24.6% B 68.5%

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%

3,4-dimethylbenzenesulfonic acid (618-01-9) → 4-bromo-o-xylene (583-71-1)

Conditions	Yield
With copper(ll) bromide

4-amino-o-xylene (95-64-7) → 4-bromo-o-xylene (583-71-1)

Conditions	Yield
With sulfuric acid Diazotization.Behandlung der Diazoniumsalz-Loesung mit CuBr in der Waerme;
(i) (diazotization), aq. HBr, (ii) Cu; Multistep reaction;

o-xylene (95-47-6) → 4-bromo-o-xylene (583-71-1) + 2,3-dimethylbromobenzene (576-23-8) + 2-methylbenzyl bromide (89-92-9) + α,α'-dibromo-o-xylene (91-13-4)

Conditions	Yield
With bromine In water for 0.333333h; Ambient temperature; Irradiation;	A 3 % Chromat. B 2 % Chromat. C 16 % Chromat. D 79 % Chromat.

o-xylene (95-47-6) + bromine (7726-95-6) + iodine (7553-56-2) → 4-bromo-o-xylene (583-71-1)

o-xylene (95-47-6) + bromine (7726-95-6) + iodine (7553-56-2) → 4-bromo-o-xylene (583-71-1) + dibromoxylene (24932-49-8) + 1,2-dibromo-4,5-dimethylbenzene (24932-48-7) + 1,2,3,4-tetrabromo-5,6-dimethylbenzene (2810-69-7)

diazotized 4-amino-o-xylene → 4-bromo-o-xylene (583-71-1)

o-xylene (95-47-6) → 4-bromo-o-xylene (583-71-1) + 2-methylbenzyl bromide (89-92-9)

Conditions	Yield
With N-Bromosuccinimide In water at 150℃; under 2625.26 Torr; for 0.0666667h; Irradiation;	A 11 % Chromat. B 51 % Chromat.

styrene (292638-84-7) + 4-bromo-o-xylene (583-71-1) → (E)-1,2-dimethyl-4-stirylbenzene (28271-18-3, 81228-92-4)

Conditions	Yield
With {1,3-bis[2,6-bis(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene}dichloro(pyridine)palladium; caesium carbonate In neat (no solvent) at 100℃; for 12h; Heck Reaction;	99%

4-bromo-o-xylene (583-71-1) + thiophenol (108-98-5) + 9-methyl-9H-fluorene-9-carbonyl chloride (82102-37-2) → S-phenyl 3,4-dimethylbenzothioate

Conditions

Yield

Stage #1: 4-bromo-o-xylene; thiophenol With bis(benzonitrile)palladium(II) dichloride; sodium acetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene Inert atmosphere; Glovebox; Stage #2: 9-methyl-9H-fluorene-9-carbonyl chloride With N-Methyldicyclohexylamine; bis(dibenzylideneacetone)-palladium(0); tri tert-butylphosphoniumtetrafluoroborate at 120℃; for 18h; Inert atmosphere; Glovebox;

98%

4-bromo-o-xylene (583-71-1) → 4-bromo-1,2-dicyanobenzene (70484-01-4)

Conditions	Yield
With ammonia; oxygen at 359.84℃; Temperature;	97.3%

4-bromo-o-xylene (583-71-1) → 3,4-dimethylphenylmagnesium bromide (89980-68-7)

Conditions	Yield
With iodine In tetrahydrofuran	96.3%
With iodine; magnesium In diethyl ether Inert atmosphere; Reflux;

4-bromo-o-xylene (583-71-1) + sodium methylate (124-41-4) → 3,4-dimethylanisole (4685-47-6)

Conditions	Yield
With copper(I) bromide In methanol at 125 - 130℃; for 4h; Autoclave;	96%

3,4-dimethylbenzaldehyde (5973-71-7) + 4-bromo-o-xylene (583-71-1) → 3,3',4,4'-tetramethylbenzophenone (4659-48-7)

Conditions	Yield
Stage #1: 4-bromo-o-xylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.666667h; Stage #2: 3,4-dimethylbenzaldehyde In tetrahydrofuran; hexane at -78 - 20℃; Stage #3: With iodine; potassium carbonate In tert-butyl alcohol at 90℃; for 8h;	95%

4-bromo-o-xylene (583-71-1) + 3-aminopentane (616-24-0) → N-(1-ethylpropyl)-3,4-dimethyl-benzenamine (56038-89-2)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; caesium carbonate In toluene at 80℃; for 6h; Reagent/catalyst; Buchwald-Hartwig Coupling;	93.7%

4-bromo-o-xylene (583-71-1) → 4-bromo-1,2-bis-bromomethyl-benzene (69189-19-1)

Conditions	Yield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 1h; Heating / reflux;	93%
With bromine; dibenzoyl peroxide at 125 - 130℃; for 2h;	87%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 3h; Reflux;	80.1%

4-bromo-o-xylene (583-71-1) → 3,4,3',4'-Tetramethylbiphenyl (4920-95-0)

Conditions	Yield
With iodine; magnesium; nickel dichloride at 90℃; for 8h; Inert atmosphere;	91%
With [2,2]bipyridinyl; nickel; zinc; triphenylphosphine In N,N-dimethyl-formamide at 90℃; for 24h;	80%
With tetraethylammonium tosylate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide Ambient temperature; electrolysis;	78%

n-butyl formate (592-84-7) + 4-bromo-o-xylene (583-71-1) → butyl 3,4-dimethylbenzoate (1242139-06-5)

Conditions	Yield
With palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; catacxium A In acetonitrile at 140℃; for 16h; Inert atmosphere;	91%

potassium hydrogenfluoride (1279123-63-5) + diisopropylamine borane (55124-35-1) + 4-bromo-o-xylene (583-71-1) → potassium (3,4-dimethylphenyl)trifluoroborate

Conditions	Yield
Stage #1: diisopropylamine borane; 4-bromo-o-xylene With magnesium In tetrahydrofuran at 70℃; Stage #2: With methanol In tetrahydrofuran at 0℃; for 1h; Stage #3: potassium hydrogenfluoride In methanol; water at 20℃; for 1h;	91%

hexadecylamine (143-27-1) + 4-bromo-o-xylene (583-71-1) → C24H43N (1416815-95-6)

Conditions	Yield
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In 1,4-dioxane; toluene at 80℃; Schlenk technique; Inert atmosphere;	90%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + carbon monoxide (201230-82-2) + 4-bromo-o-xylene (583-71-1) → 2,5-dioxopyrrolidin-1-yl 3,4-dimethylbenzoate

Conditions	Yield
With N-Methyldicyclohexylamine; [{Pd(cinnamyl)Cl}2]; 9-methyl-9H-fluorene-9-carbonyl chloride; bis(dibenzylideneacetone)-palladium(0); tri tert-butylphosphoniumtetrafluoroborate In 1,4-dioxane; toluene at 95℃; for 16h; Sealed tube; Glovebox; Inert atmosphere;	90%

4-bromo-o-xylene (583-71-1) + dibutylamine (111-92-2) → Dibutyl-(3,4-dimethyl-phenyl)-amine (105336-41-2)

Conditions	Yield
With C43H58ClO2PPd; sodium t-butanolate; ruphos In tetrahydrofuran at 85℃; for 6h; Inert atmosphere;	90%

4-bromo-o-xylene (583-71-1) + N-benzyl-(S)-proline methyl ester (113304-84-0, 127986-89-4) → (S)-(1-benzylpyrrolidin-2-yl)bis(3,4-dimethylphenyl)methanol

Conditions	Yield
Stage #1: 4-bromo-o-xylene With iodine; magnesium In tetrahydrofuran at 65℃; for 1h; Stage #2: N-benzyl-(S)-proline methyl ester In tetrahydrofuran for 1h;	90%

pyrrolidine (123-75-1) + 4-bromo-o-xylene (583-71-1) → 1-(3,4-dimethylphenyl)pyrrolidine

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); potassium tert-butylate In toluene for 2h; Reflux; Inert atmosphere;	90%

chloro-trimethyl-silane (75-77-4) + 4-bromo-o-xylene (583-71-1) → (3,4-dimethylphenyl)-trimethylsilane (17988-43-1)

Conditions	Yield
Stage #1: 4-bromo-o-xylene With magnesium In tetrahydrofuran at 80℃; for 2h; Stage #2: chloro-trimethyl-silane In tetrahydrofuran for 12h; Reflux;	88.3%
Stage #1: 4-bromo-o-xylene With iodine; magnesium In tetrahydrofuran at 50 - 85℃; for 2h; Stage #2: chloro-trimethyl-silane In tetrahydrofuran at -78 - 20℃; for 0.5h; Stage #3: With water In tetrahydrofuran	77%

4-bromo-o-xylene (583-71-1) + phenylboronic acid (98-80-6) → 3,4-dimethylbiphenyl (4433-11-8)

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); tri-tert-butyl phosphine In 1,1,1,2,3,3,3-Heptafluoropropane; ethanol; 1,1,1,3,3-pentafluorobutane at 20℃; for 24h; Suzuki-Miyaura cross-coupling reaction; Inert atmosphere;	87%
With C21H25ClN2Pd; potassium carbonate In toluene at 80℃; for 2h; Suzuki-Miyaura Coupling;	79%
With C55H66N2O2; palladium diacetate; potassium carbonate In methanol; dichloromethane at 30℃; for 0.5h; Suzuki-Miyaura Coupling;

4-bromo-o-xylene (583-71-1) + C19H15N3S (1450729-39-1) → C26H21N3 (1450729-50-6)

Conditions	Yield
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); magnesium; ethylene dibromide In tetrahydrofuran at 20℃; for 2h; Kumada Cross-Coupling; Inert atmosphere;	87%

benzoxazole (273-53-0) + 4-bromo-o-xylene (583-71-1) → 2-(3,4-dimethylphenyl)benzo[d]oxazole (16155-55-8)

Conditions	Yield
With [(SIPr)PdCl(quinoline‐8‐carboxylate)]; sodium t-butanolate In N,N-dimethyl-formamide at 130℃; for 12h; Reagent/catalyst;	87%

4-bromo-o-xylene (583-71-1) + zirconocene dichloride → 1,2,3,4,5-Penta(3,4-dimethylphenyl)-1,3-cyclopentadiene

Conditions	Yield
With tri-tert-butyl phosphine; caesium carbonate; palladium diacetate In N,N-dimethyl-formamide at 130℃; for 3h; Arylation;	85%

9H-fluorene (86-73-7) + 4-bromo-o-xylene (583-71-1) → C29H26 (135926-14-6)

Conditions	Yield
With potassium tert-butylate; triphenylphosphine; bis(dibenzylideneacetone)-palladium(0) In toluene at 100℃; for 12h; Catalytic behavior; Schlenk technique; Inert atmosphere; Glovebox;	85%

4-bromo-o-xylene (583-71-1) + diphenylamine (122-39-4) → N,N-diphenyl-3,4-xylidene (173460-10-1)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium 10% on activated carbon; sodium t-butanolate In 1,3,5-trimethyl-benzene for 24h; Inert atmosphere; Reflux;	83%

4-bromo-o-xylene (583-71-1) + 4-(4-ethylcyclohexyl)-2,3-difluorophenylboronic acid (1123312-73-1) → C22H26F2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In water; N,N-dimethyl-formamide for 3h; Inert atmosphere; Reflux;	83%

potassium cyanate (590-28-3) + carbon monoxide (201230-82-2) + 4-bromo-o-xylene (583-71-1) + isopropyl alcohol (67-63-0) → isopropyl 3,4-dimethylbenzoylcarbamate

Conditions	Yield
With dichloro(1,5-cyclooctadiene)palladium(II); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene at 70℃; for 8h;	82%

Di-sec-butylamin (626-23-3) + 4-bromo-o-xylene (583-71-1) → Di-sec-butyl-(3,4-dimethyl-phenyl)-amine (105336-44-5)

Conditions	Yield
With potassium amide for 5h; Heating;	81%

Dichloromethylsilane (75-54-7) + 4-bromo-o-xylene (583-71-1) → bis(3,4-dimethylphenyl)(methyl)silane (1264172-81-7)

Conditions	Yield
Stage #1: 4-bromo-o-xylene With magnesium In tetrahydrofuran Inert atmosphere; Stage #2: Dichloromethylsilane In tetrahydrofuran at 0 - 20℃; for 18h; Inert atmosphere;	81%

4-bromo-o-xylene (583-71-1) + 4-chlorobenzaldehyde (104-88-1) → 1-(3,4-dimethylphenyl)-1-(4-chlorophenyl)methanol (1292631-43-6)

Conditions	Yield
Stage #1: 4-bromo-o-xylene With boric acid tributyl ester; magnesium; lithium chloride In tetrahydrofuran at 25℃; Stage #2: 4-chlorobenzaldehyde In tetrahydrofuran at 25℃; for 1h;	81%

Upstream product

• 95-47-6 o-xylene 
• 593-53-3 Methyl fluoride 
• 106-38-7 para-bromotoluene 
• 7726-95-6 bromine 
• 7553-56-2 iodine 
• 95-64-7 4-amino-o-xylene 
• 618-01-9 3,4-dimethylbenzenesulfonic acid 

Downstream Products

• 24932-49-8 dibromoxylene 
• 24932-48-7 1,2-dibromo-4,5-dimethylbenzene 
• 96843-22-0 1-bromo-2-chloro-4,5-dimethyl-benzene 
• 95-64-7 4-amino-o-xylene 
• 859782-02-8 4-bromo-1,2-bis-diacetoxymethyl-benzene 
• 934-80-5 1,2-dimethyl-4-ethylbenzene 
• 87776-80-5 2-(3,4-dimethylphenyl)-1-ethanol 
• 53600-88-7 2-(3,4-Dimethyl-phenyl)-bicyclo[2.2.1]heptan-2-ol 
• 15089-75-5 2-Brom-4.5-dimethyl-acetophenon 
• 27650-62-0 1-<3,4-Dimethyl-phenyl>-propanol-(2) 
• 105336-36-5 Butyl-(2,3-dimethyl-phenyl)-methyl-amine 
• 105336-37-6 Butyl-(3,4-dimethyl-phenyl)-methyl-amine 
• 105336-44-5 Di-sec-butyl-(3,4-dimethyl-phenyl)-amine 
• 7397-00-4 1-(3,4-dimethylphenyl)-2,2-dimethylpropan-1-one 

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