31543-75-6

Basic information

• Product Name: 2,4-DIBROMOTOLUENE
• Synonyms: 1,3-Dibromo-4-methylbenzene;2,4-dibromo-1-methyl-benzen;Benzene, 2,4-dibromo-1-methyl-;Benzene,2,4-dibromo-1-methyl-;2,4-DIBROMOTOLUENE;2,4-Dibromo-1-methylbenzene;1-Methyl-2,4-dibromobenzene;NSC 139877
• CAS NO: 31543-75-6
• Molecular Formula: C₇H₆Br₂
• Molecular Weight: 249.93
• EINECS: 250-689-9
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Halogen toluene;Bromine Compounds
• Mol File: 31543-75-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: -10 °C
• Boiling Point: 243 °C
• Flash Point: 109℃
• Appearance: /Liquid
• Density: 1.85
• Vapor Pressure: 0.0544mmHg at 25°C
• Refractive Index: 1.601
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2,4-DIBROMOTOLUENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DIBROMOTOLUENE(31543-75-6)
• EPA Substance Registry System: 2,4-DIBROMOTOLUENE(31543-75-6)

Safety Data

• Hazard Codes: Xi
• TSCA: Yes
• Hazardous Substances Data: 31543-75-6(Hazardous Substances Data)

Usage

Chemical Properties

light yellow liquid

InChI:InChI=1/C7H6Br2/c1-5-2-3-6(8)4-7(5)9/h2-4H,1H3

Synthetic route

3-bromo-4-methylbenzenediazonium tetrafluoroborate → 2,4-dibromotoluene (31543-75-6)

Conditions	Yield
With dibenzo-18-crown-6; potassium bromide; copper(ll) bromide; 1,10-Phenanthroline; copper(I) bromide In acetonitrile at 20℃; for 0.333333h; Sandmeyer bromination;	97%

3-bromo-4-methylaniline (7745-91-7) → 2,4-dibromotoluene (31543-75-6)

Conditions	Yield
Stage #1: 3-bromo-4-methylaniline With hydrogen bromide; sodium nitrite at 0℃; Stage #2: With hydrogen bromide; copper(I) bromide for 0.666667h; Heating; Further stages.;	90%

toluene (108-88-3) → 2,4-dibromotoluene (31543-75-6)

Conditions	Yield
With bromine fluoride In ethanol; chloroform at -78℃; for 0.333333h;	80%

toluene (108-88-3) → para-bromotoluene (106-38-7) + 2-methylphenyl bromide (95-46-5) + 2,4-dibromotoluene (31543-75-6)

Conditions	Yield
With N-Bromosuccinimide; iron(III) chloride In acetonitrile for 0.333333h;	A 39% B 48% C 6%

para-bromotoluene (106-38-7) → 3,4-dibromotoluene (60956-23-2) + 2,4-dibromotoluene (31543-75-6)

Conditions	Yield
beim Bromieren;

2-methylphenyl bromide (95-46-5) → 1,4-dibromo-2-methylbenzene (615-59-8) + 2,4-dibromotoluene (31543-75-6)

Conditions	Yield
beim Bromieren;

5-bromo-2-methylaniline (39478-78-9) → 2,4-dibromotoluene (31543-75-6)

2,4-dibromo-5-methylaniline (67643-51-0) → 2,4-dibromotoluene (31543-75-6)

Conditions	Yield
With hydrogenchloride; sodium nitrite Behandlung der erhaltenen Diazoniumsalz-Loesung mit wss. H3PO2 unterhalb 5grad;
With sulfuric acid; sodium nitrite Behandlung der erhaltenen Diazoniumsalz-Loesung mit wss. H3PO2 unterhalb 5grad;

para-bromotoluene (106-38-7) + bromine (7726-95-6) + iodine (7553-56-2) → 3,4-dibromotoluene (60956-23-2) + 2,4-dibromotoluene (31543-75-6)

para-bromotoluene (106-38-7) + amalgamated aluminium → 3,4-dibromotoluene (60956-23-2) + 2,4-dibromotoluene (31543-75-6) + 2,4,5-tribromotoluene (3278-88-4)

Conditions	Yield
beim Bromieren;

2.4-dibromo-3-amino-toluene → 2,4-dibromotoluene (31543-75-6)

Conditions	Yield
With ethanol; nitrogen oxides

2-methylphenyl bromide (95-46-5) + bromine (7726-95-6) + iodine (7553-56-2) → 1,4-dibromo-2-methylbenzene (615-59-8) + 2,4-dibromotoluene (31543-75-6)

2-methylphenyl bromide (95-46-5) + bromine (7726-95-6) + amalgamated aluminium → 1,4-dibromo-2-methylbenzene (615-59-8) + 2,4-dibromotoluene (31543-75-6)

ethanol (64-17-5) + 2,4-dibromo-5-methylaniline (67643-51-0) + nitrogen oxides → 2,4-dibromotoluene (31543-75-6)

Conditions	Yield
nachfolgendes Kochen;

Ni(mes)(o-tol)(PMe2Ph)2 → 2,4,6-trimethylphenyl bromide (576-83-0) + 2,4-dibromotoluene (31543-75-6) + 2,2',4,6-tetramethylbiphenyl (89970-02-5) + 3-bromo-2,2',4,6-tetramethyl-1,1'-biphenyl

Conditions	Yield
With bromine In diethyl ether for 0.5h; Ambient temperature; Yield given. Further byproducts given;

2-bromo-4-nitrotoluene (7745-93-9) → 2,4-dibromotoluene (31543-75-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: SnBr2 2.1: NaNO2 2.2: CuBr View Scheme

Phenetole (103-73-1) → para-bromotoluene (106-38-7) + 2-methylphenyl bromide (95-46-5) + 2,4-dibromotoluene (31543-75-6) + benzyl bromide (100-39-0)

Conditions	Yield
With hydrogenchloride; dihydrogen peroxide; hexaammonium heptamolybdate tetrahydrate In water at 20 - 25℃; for 22h;

toluene (108-88-3) → 3,3'-dimethyl-biphenyl (612-75-9) + 2-Bromo-5-fluorotoluene (452-63-1) + 2-methylphenyl bromide (95-46-5) + 2,4-dibromotoluene (31543-75-6)

Conditions	Yield
With 2BrF4H(1-)*Ba(2+) In 1,1,2-Trichloro-1,2,2-trifluoroethane at 45℃; for 5h;	A 17 %Chromat. B 9 %Chromat. C 14 %Chromat. D 24 %Chromat.

2,4-dibromotoluene (31543-75-6) → 2,4-dibromo-1-(bromomethyl)benzene (64382-92-9)

Conditions	Yield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 1h; Heating;	85%
beim Bromieren;
durch Bromieren;

carbon dioxide (124-38-9) + 2,4-dibromotoluene (31543-75-6) → 4-methyl isophthalic acid (3347-99-7)

Conditions	Yield
Stage #1: carbon dioxide With o-phenylenebis(diphenylphosphine); copper(II) acetate monohydrate In 1,4-dioxane at 65℃; for 0.416667h; Schlenk technique; Stage #2: 2,4-dibromotoluene With palladium diacetate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane; toluene at 100℃; for 16h; Schlenk technique;	62%

NH-pyrazole (288-13-1) + 2,4-dibromotoluene (31543-75-6) → 1-(3-bromo-4-methylphenyl)pyrazole

Conditions	Yield
With copper(l) iodide; L-valine; potassium carbonate In dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere; Sealed tube;	53%

2,4-dibromotoluene (31543-75-6) + (diphenylmethylsilyl)dimesitylborane (440361-72-8) → (3-bromo-4-methylphenyl)dimesitylborane + C20H19BrSi

Conditions	Yield
Stage #1: (diphenylmethylsilyl)dimesitylborane With sodium t-butanolate In 1,4-dioxane; hexane at 50℃; for 0.0833333h; Inert atmosphere; Stage #2: 2,4-dibromotoluene In 1,4-dioxane; hexane at 50℃; for 24h; Inert atmosphere;	A 29% B n/a

2,4-dibromotoluene (31543-75-6) → para-bromotoluene (106-38-7)

Conditions	Yield
With diethyl ether; magnesium Behandlung der gebildeten Grignard-Verbindung mit Wasser;

2,4-dibromotoluene (31543-75-6) → 2,4,5-tribromotoluene (3278-88-4)

Conditions	Yield
With aluminium amalgam beim Bromieren;

2,4-dibromotoluene (31543-75-6) → 2,4-dibromobenzoic acid (611-00-7)

Conditions	Yield
With nitric acid

2,4-dibromotoluene (31543-75-6) → 1,5-dibromo-2-methyl-4-nitrobenzene (860753-33-9)

Conditions	Yield
With nitric acid

2,4-dibromotoluene (31543-75-6) → 2,4-dibromo-3,5-dinitro-toluene (857001-30-0)

Conditions	Yield
With sulfuric acid; nitric acid

2,4-dibromotoluene (31543-75-6) + copper(II) cyanide → 2,4-dicyanotoluene (1943-88-0)

diethyl ether (60-29-7) + 2,4-dibromotoluene (31543-75-6) + magnesium → para-bromotoluene (106-38-7)

Conditions	Yield
Behandlung mit Eis und wss. HCl;

tetrachloromethane (56-23-5) + 2,4-dibromotoluene (31543-75-6) + bromine (7726-95-6) + amalgamated aluminium → 2,4,5-tribromotoluene (3278-88-4) + 2,4,6-tribromotoluene (6320-40-7)

diethyl ether (60-29-7) + 2,4-dibromotoluene (31543-75-6) + magnesium → 5-bromo-2-methylbenzoic acid (79669-49-1)

Conditions	Yield
Behandlung mit CO2;

2,4-dibromotoluene (31543-75-6) + nitric acid (7697-37-2) → 2,4-dibromobenzoic acid (611-00-7)

2,4-dibromotoluene (31543-75-6) + nitric acid (7697-37-2) → 1,5-dibromo-2-methyl-4-nitrobenzene (860753-33-9) + 2,4-dibromo-3,5-dinitro-toluene (857001-30-0)

Upstream product

• 95-46-5 2-methylphenyl bromide 
• 39478-78-9 5-bromo-2-methylaniline 
• 67643-51-0 2,4-dibromo-5-methylaniline 
• 108-88-3 toluene 
• 106-38-7 para-bromotoluene 
• 7726-95-6 bromine 
• 7553-56-2 iodine 
• 64-17-5 ethanol 
• 103-73-1 Phenetole 
• 7745-93-9 2-bromo-4-nitrotoluene 
• 7745-91-7 3-bromo-4-methylaniline 

Downstream Products

• 79669-49-1 5-bromo-2-methylbenzoic acid 
• 611-00-7 2,4-dibromobenzoic acid 
• 860753-33-9 1,5-dibromo-2-methyl-4-nitrobenzene 
• 857001-30-0 2,4-dibromo-3,5-dinitro-toluene 
• 3347-99-7 4-methyl isophthalic acid 
• 24162-63-8 2,4-dibromostyrene 
• 1184179-43-8 C₇H₄Br₄ 
• 1285505-91-0 C₁₀H₈Br₂O₂ 
• 1285505-89-6 C₁₂H₁₂Br₂O₂ 
• 1285505-86-3 N-[(E)-3-(2,4-dibromo-phenyl)-2-methyl-acryloyl]-guanidine 
• 40180-69-6 1,1'-(4-Methyl-1,3-benzoldiyl)bisethanon 
• 87976-23-6 2,4,5-tribromo-benzoic acid 
• 67643-51-0 2,4-dibromo-5-methylaniline 
• 36789-29-4 N-(2,4-dibromo-5-methylphenyl)acetamide 

Relevant articles and documents

The first syntheses of 3-bromofascaplysin, 10-bromofascaplysin and 3,10-dibromofascaplysin-marine alkaloids from Fascaplysinopsis reticulata and Didemnum sp. by application of a simple and effective approach to the pyrido[1,2-a:3,4-b′]diindole system

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PROCESS FOR THE PREPARATION OF 4-BROMOPHENYL DERIVATIVES

Disclosed is a process for the preparation of a mixture of 4-bromophenyl derivatives (compound of formula (2)) and 2,4-dibromophenyl derivatives (compound of formula (3)) comprising the steps of [1] reacting in a two-phase (liquid-liquid) system a bromide containing source with a phenyl derivative (formula (1)) in the presence of an excess of an oxidizing agent, an acid, and optionally a catalyst selected from vanadium pentoxide and ammonium heptamolybdate forming 4-bromo- (compound of formula (2)) and 2,4-dibromo derivatives (compound of formula (3)) and as intermediate product the 2-bromo derivative (compound of formula (4)) which reacts in step [2] to the 2,4-dibromo derivative (formula (3)) according to the following reaction scheme 2 wherein R1 is hydroxy; C1-C5alkoxy; or -NR2R3; and R2 and R3 independently from each other are hydrogen; or C1-C5alkyl.

Halogenation of Aromatic Compounds by N-chloro-, N-bromo-, and N-iodosuccinimide

An efficient and mild method for the halogenation of aromatic compounds using N-chloro-, N-bromo-, and N-iodosuccinimide in the presence of NH 4NO3 or FeCl3 in acetonitrile was developed.