576-23-8

Basic information

• Product Name: 2,3-Dimethylbromobenzene
• Synonyms: 2，3-Dimethylbenzene bromide;2,3-DIMETHYLBROMOBENZENE;3-BROMO-O-XYLENE;3-BROMO-1,2-DIMETHYLBENZENE;3-Bromo-1，2-xylene;3-Bromo-ortho-xylene;3-Bromo-1,2-dimethylbenzene~2,3-Dimethylbromobenzene;3-Bromo-o-xylene,99%
• CAS NO: 576-23-8
• Molecular Formula: C₈H₉Br
• Molecular Weight: 185.06
• EINECS: 209-398-2
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Halogen toluene;Benzene derivates;Bromine Compounds
• Mol File: 576-23-8.mol
• Article Data: 17

Chemical Properties

• Melting Point: -20.49°C (estimate)
• Boiling Point: 214 °C(lit.)
• Flash Point: 177 °F
• Appearance: Clear colorless/Liquid
• Density: 1.365 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.27mmHg at 25°C
• Refractive Index: n20/D 1.560(lit.)
• Storage Temp.: Store below +30°C.
• Water Solubility: Not miscible or difficult to mix in water.
• BRN: 2077312
• CAS DataBase Reference: 2,3-Dimethylbromobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dimethylbromobenzene(576-23-8)
• EPA Substance Registry System: 2,3-Dimethylbromobenzene(576-23-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-24/25
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 576-23-8(Hazardous Substances Data)

Usage

Chemical Properties

Clear colourless to light yellow liquid

Uses

3-Bromo-o-xylene is an important raw material and intermediate used in organic synthesis, pharmaceuticals and agrochemicals.

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

Synthetic route

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%

2,3-Dimethylaniline (87-59-2) → 2,3-dimethylbromobenzene (576-23-8)

Conditions	Yield
With nitrogen(II) oxide; copper(ll) bromide In acetonitrile at -78 - 25℃;	73%
With hydrogen bromide diazotization;	40%
With hydrogen bromide Diazotization.Erwaermen der Diazoniumsalz-Loesung mit Kupfer-Pulver;

2,3-Dimethylphenol (526-75-0) → 2,3-dimethylbromobenzene (576-23-8)

Conditions	Yield
With bromine; triphenylphosphine In acetonitrile	60%
With bromine; triphenylphosphine In acetonitrile at 25℃; for 48h;	41.1%

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%

4-bromo-2,3-dimethylaniline (22364-25-6) → 2,3-dimethylbromobenzene (576-23-8)

Conditions	Yield
With hydrogen bromide; sodium nitrite anschliessend Behandeln mit Natriumhypophosphit und wss. Bromwasserstoffsaeure;

2-methyl-1H-cyclopropabenzene (75366-04-0) → 2-Bromo-m-xylene (576-22-7) + 2,3-dimethylbromobenzene (576-23-8)

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

biphenyl (92-52-4) + 3-bromo-5-tert-butyl-o-xylene (61024-97-3) → 2,3-dimethylbromobenzene (576-23-8)

Conditions	Yield
With aluminium trichloride In tetrachloromethane; nitromethane

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.

3-bromo-1.2-dimethyl-benzene-sulfonic acid-(4) → 2,3-dimethylbromobenzene (576-23-8)

Conditions	Yield
With steam; sulfuric acid

6-bromo-1.2-dimethyl-benzene-sulfonic acid-(4) → 2,3-dimethylbromobenzene (576-23-8)

Conditions	Yield
With steam; sulfuric acid

sodium salt of/the/ 3-bromo-1.2-dimethyl-benzenesulfonic acid-(4) → 2,3-dimethylbromobenzene (576-23-8)

Conditions	Yield
With sulfuric acid Destillieren mit ueberhitztem Wasserdampf;

sodium salt of/the/ 6-bromo-1.2-dimethyl-benzenesulfonic acid-(4) → 2,3-dimethylbromobenzene (576-23-8)

Conditions	Yield
With sulfuric acid Destillieren mit ueberhitztem Wasserdampf;

4-t-butyl-o-xylene (7397-06-0) → 2,3-dimethylbromobenzene (576-23-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: Fe, Br2 / CCl4 2: AlCl3 / CCl4; nitromethane View Scheme

2,3-dimethylbromobenzene (576-23-8) → 1-bromo-2,3-bis(bromomethyl)benzene (127168-82-5)

Conditions	Yield
With N-Bromosuccinimide In tetrachloromethane Irradiation;	100%
With N-Bromosuccinimide; Perbenzoic acid In tetrachloromethane for 0.5h; Heating; Irradiation;	94.1%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 0.5h; Heating;	88%

2,3-dimethylbromobenzene (576-23-8) + chloroacetone (78-95-5) → 2-(2,3-dimethylphenyl)-2-methyloxirane (42432-45-1)

Conditions	Yield
Stage #1: 2,3-dimethylbromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: chloroacetone In tetrahydrofuran; hexane; toluene at -78 - 20℃; for 1.33333h; Product distribution / selectivity;	100%
Stage #1: 2,3-dimethylbromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: chloroacetone In tetrahydrofuran; hexane; toluene at -78 - 20℃; Product distribution / selectivity;	100%

2,3-dimethylbromobenzene (576-23-8) + morpholine[1-(triphenylmethyl)-1H-imidazol-4-yl]methanone → 4-<(2,3-dimethylphenyl)carbonyl>-1-(triphenylmethyl)imidazole (176721-02-1)

Conditions	Yield
Stage #1: 2,3-dimethylbromobenzene With iodine; magnesium In tetrahydrofuran at 65 - 70℃; for 1h; Stage #2: morpholine[1-(triphenylmethyl)-1H-imidazol-4-yl]methanone In tetrahydrofuran at 0 - 40℃; for 1h;	100%

norborn-2-ene (498-66-8) + 2,3-dimethylbromobenzene (576-23-8) → 5,6-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;	96%

2,3-dimethylbromobenzene (576-23-8) + phenylboronic acid (98-80-6) → 2,3-dimethyl-1,1'-biphenyl (3864-18-4)

Conditions	Yield
With potassium carbonate; PdCl2[diethyl(o-ethylphenyl)phosphane]2 In N,N-dimethyl-formamide at 150℃; for 0.5h; Suzuki-Miyaura coupling reaction; microwave irradiation;	96%
With C21H25ClN2Pd; potassium carbonate In toluene at 80℃; for 2h; Suzuki-Miyaura Coupling;	82%
With caesium carbonate; cis-dibromobis[3-(2-propenyl)benzothiazolin-2-ylidene]Pd(II) In N,N-dimethyl-formamide at 100℃; for 19h; Suzuki-Miyaura coupling;	80 % Chromat.
With potassium phosphate; C17H14O*C108H156N3O6P9*3Pd In tetrahydrofuran at 79.84℃; for 24h; Suzuki coupling; Inert atmosphere;	99 %Spectr.

2,3-dimethylbromobenzene (576-23-8) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2,3-dimethylbenzaldehyde (5779-93-1)

Conditions	Yield
Stage #1: 2,3-dimethylbromobenzene With magnesium In tetrahydrofuran for 1h; Inert atmosphere; Reflux; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 20℃; for 2h; Concentration; Temperature;	96%

2,3-dimethylbromobenzene (576-23-8) + 1-(1-triphenylmethyl-1H-imidazol-4-yl)-1-ethanone (116795-55-2) → 4-<1-(2,3-dimethylphenyl)-1-hydroxyethyl>-1-(triphenylmethyl)imidazole (176721-03-2)

Conditions	Yield
Stage #1: 2,3-dimethylbromobenzene With magnesium In tetrahydrofuran for 1h; Reflux; Stage #2: 1-(1-triphenylmethyl-1H-imidazol-4-yl)-1-ethanone In tetrahydrofuran at 20℃; for 2h; Time;	89.7%

2,3-dimethylbromobenzene (576-23-8) + (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-(2,3-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;	89%

methyl 3-(4-ethynylphenyl)propanoate (1068471-18-0) + 2,3-dimethylbromobenzene (576-23-8) → methyl 3-(4-((2,3-dimethylphenyl)ethynyl)phenyl)propanoate (1082059-34-4)

Conditions	Yield
With copper(l) iodide; sodium tetrachloropalladate(II); 2-[bis(1,1-dimethylethyl)phosphino]-1-phenyl-1H-indole In 2,3-dimethyl-2,3-diaminobutane at 80℃; Sonogashira coupling; Inert atmosphere;	86%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 50℃; Sonogashira coupling; Inert atmosphere;	14%

2,3-dimethylbromobenzene (576-23-8) + 4(5)formylimidazole (3034-50-2) → (2,3-dimethylphenyl)(1H-imidazol-4-yl)methanol

Conditions	Yield
Stage #1: 2,3-dimethylbromobenzene With iodine; magnesium In tetrahydrofuran for 1h; Reflux; Stage #2: 4(5)formylimidazole at 50℃; for 4h;	86%

carbon dioxide (124-38-9) + 2,3-dimethylbromobenzene (576-23-8) → 2,3-dimethylbenzoic acid (603-79-2)

Conditions	Yield
Stage #1: 2,3-dimethylbromobenzene With tert.-butyl lithium In diethyl ether Stage #2: carbon dioxide	84%
(i) Mg, (ii) /BRN= 1900390/; Multistep reaction;

2,3-dimethylbromobenzene (576-23-8) + phenyllithium (591-51-5) → 2,3-dimethyl-1,1'-biphenyl (3864-18-4)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In tetrahydrofuran; toluene at 20℃; for 1h; Schlenk technique; Inert atmosphere;	84%

2,3-dimethylbromobenzene (576-23-8) + 2,3-dimethylphenylmagnesium bromide (134640-85-0) → 2,2′,3,3′-tetramethylbiphenyl (7495-46-7)

Conditions	Yield
triphenylphosphine; nickel dibromide In tetrahydrofuran Heating;	83%

2,3-dimethylbromobenzene (576-23-8) + crotonaldehyde (123-73-9) → (3-(2,3-xylyl)-2-butenal)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In N,N-dimethyl-formamide; toluene at 100℃; for 18h; Product distribution / selectivity;	83%

2,3-dimethylbromobenzene (576-23-8) + isopropyllithium (1888-75-1) → 2,3-dimethylcumene (22539-65-7)

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0) In toluene at 20℃; for 1h;	83%

2,3-dimethylbromobenzene (576-23-8) + 2-(N,N-diethylcarboxamido)-4-methoxy-3-trimethylsilylphenylboronic acid (666829-97-6) → N,N-diethyl-4-methoxy-3-trimethylsilyl-2′,3′-dimethylbiphenyl-2-carboxamide

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; ethanol; water at 100℃; for 16h; Suzuki-Miyaura Coupling;	83%

2,3-dimethylbromobenzene (576-23-8) + 2-(Nonafluorobutyl)aniline (106877-28-5) → 4-methyl-9-(perfluoropropyl)acridine

Conditions	Yield
Stage #1: 2,3-dimethylbromobenzene With magnesium In tetrahydrofuran at 70℃; Stage #2: 2-(Nonafluorobutyl)aniline In tetrahydrofuran at -70 - 23℃; for 13h; Inert atmosphere; Stage #3: With water; oxygen In tetrahydrofuran	81%

bromobenzene (108-86-1) + 2,3-dimethylbromobenzene (576-23-8) → 2,3-dimethyl-1,1'-biphenyl (3864-18-4)

Conditions	Yield
Stage #1: 2,3-dimethylbromobenzene With iodine; magnesium In tetrahydrofuran at 22℃; for 0.5h; Inert atmosphere; Stage #2: bromobenzene With nickel dichloride In tetrahydrofuran at 66℃; for 3h; Inert atmosphere;	80%

2,3-dimethylbromobenzene (576-23-8) + 1H-imidazole-4-carbonitrile (57090-88-7) → 4-(2,3-dimethylbenzoyl)-1H-imidazole

Conditions	Yield
Stage #1: 2,3-dimethylbromobenzene With magnesium; ethylene dibromide In tetrahydrofuran at 40 - 65℃; for 1h; Stage #2: 1H-imidazole-4-carbonitrile With isopropylmagnesium chloride In tetrahydrofuran at -5 - 0℃; for 2h; Stage #3: With sulfuric acid In tetrahydrofuran; water at 30℃; for 3h;	80%

1-phenylmethyl-4-piperidone (3612-20-2) + 2,3-dimethylbromobenzene (576-23-8) → 1-benzyl-4-(2,3-dimethylphenyl)piperidin-4-ol (1370256-31-7)

Conditions	Yield
Stage #1: 2,3-dimethylbromobenzene With iodine; magnesium In tetrahydrofuran Grignard reaction; Inert atmosphere; Reflux; Stage #2: 1-phenylmethyl-4-piperidone In tetrahydrofuran at 20℃; for 3h; Grignard reaction; Inert atmosphere; Cooling with ice;	79%
With iodine; magnesium In tetrahydrofuran at 0 - 70℃; for 1.5h; Inert atmosphere;

Upstream product

• 593-53-3 Methyl fluoride 
• 95-46-5 2-methylphenyl bromide 
• 95-47-6 o-xylene 
• 92-52-4 biphenyl 
• 61024-97-3 3-bromo-5-tert-butyl-o-xylene 
• 7397-06-0 4-t-butyl-o-xylene 
• 75366-04-0 2-methyl-1H-cyclopropabenzene 
• 526-75-0 2,3-Dimethylphenol 
• 87-59-2 2,3-Dimethylaniline 
• 22364-25-6 4-bromo-2,3-dimethylaniline 

Downstream Products

• 100367-11-1 1,8-bis(2,3-dimethylphenyl)anthracene 
• 183158-34-1 2,3-dimethylphenylboronic acid 
• 80245-28-9 1,2-dimethyl-3-(trifluoromethyl)benzene 
• 72596-34-0 diethyl (2,3-dimethylphenyl)phosphonate 
• 95-65-8 3,4-Dimethylphenol 
• 526-75-0 2,3-Dimethylphenol 
• 212190-11-9 3-(2,3-Dimethylphenyloxy)-anisole 
• 923590-78-7 2-benzyl-4-bromoisoindoline 
• 923590-80-1 2-benzyl-4-vinylisoindoline 
• 923590-81-2 4-vinylisoindoline 
• 923590-92-5 2-benzyl-4-bromoisoindoline hydrochloride 
• 22539-65-7 2,3-dimethylcumene 

Relevant articles and documents

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A NOVEL ROUTE FOR PREPARATION OF L,3:2,4-BIS-(3,4- D IM ETH YLB ENZYLIDENE)SO RB ITO L

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