108-36-1

Basic information

• Product Name: 1,3-Dibromobenzene
• Synonyms: 1,3-dibromo-benzen;Benzene, m-dibromo-;Benzene,1,3-dibromo-;m-dibromo-benzen;1,3-DIBROMOBENZENE;M-DIBROMOBENZENE;1,3-Dibromobenzene97%;META-DIBROMOBENZENE
• CAS NO: 108-36-1
• Molecular Formula: C₆H₄Br₂
• Molecular Weight: 235.9
• EINECS: 203-574-2
• Product Categories: Benzene derivates;Bromine Compounds;Aryl;C6;Halogenated Hydrocarbons;alkyl bromide
• Mol File: 108-36-1.mol
• Article Data: 26

Chemical Properties

• Melting Point: -7 °C
• Boiling Point: 218-219 °C(lit.)
• Flash Point: 201 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 1.952 g/mL at 25 °C(lit.)
• Vapor Density: 8.16 (vs air)
• Vapor Pressure: 5 mm Hg ( 66 °C)
• Refractive Index: n20/D 1.608(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 0.068g/l
• Water Solubility: insoluble
• BRN: 1904538
• CAS DataBase Reference: 1,3-Dibromobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dibromobenzene(108-36-1)
• EPA Substance Registry System: 1,3-Dibromobenzene(108-36-1)

Safety Data

• Hazard Codes: Xi,C
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• RIDADR: UN 2711
• WGK Germany: 2
• RTECS: CZ1790000
• TSCA: T
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 108-36-1(Hazardous Substances Data)

Usage

Chemical Properties

clear colourless to light yellow liquid

Uses

1,3-Dibromobenzene is used in Suzuki coupling reaction for the preparation of [n]metacyclophanes. It is used to prepare 5-(3-bromo-phenyl)-2,4-di-tert-butoxy-pyrimidine using Pd(0) (PPh3)4 as a reagent. Further, it undergoes solid-supported potassium fluoride-aluminum oxide palladium-catalyzed polyarylation reaction with phenyl boronic acid to get conjugated polyaryls.

Definition

ChEBI: A dibromobenzene carrying bromo groups at positions 1 and 3.

General Description

1,3-Dibromobenzene undergoes solid-supported [KF-Al2O3] palladium-catalyzed polyarylation reaction with phenyl boronic acid under microwave irradiation to yield conjugated polyaryls.

InChI:InChI=1/C6H4Br2/c7-5-2-1-3-6(8)4-5/h1-4H

Synthetic route

2,6-dibromobenzenediazonium o-benzenedisulfonimide → 1,3-dibromobenzene (108-36-1)

Conditions	Yield
With dihydrogen peroxide In tetrahydrofuran for 0.333333h; Heating;	92%
Multi-step reaction with 2 steps 1: 95 percent / aq. NaOH / 0.5 h / 0 - 5 °C 2: 11 percent / aq. HI; HBF4 / acetonitrile / 24 h / 60 °C View Scheme
Multi-step reaction with 2 steps 1: 95 percent / aq. NaOH / 0.5 h / 0 - 5 °C 2: 12 percent / aq. HCl; Cu / acetonitrile / 0.25 h / 20 - 25 °C View Scheme

m-bromobenzoic acid (585-76-2) → 1,3-dibromobenzene (108-36-1)

Conditions	Yield
With bromine; dibromoisocyanuric acid In dichloromethane at 20℃; for 24h; UV-irradiation;	92%

n-butyllithium (109-72-8, 29786-93-4) + (3,5-dibromophenyl)trimethyltin (17197-37-4) → (3,5-dibromophenyl)dimethylbutyltin + 1,3-dibromobenzene (108-36-1) + n-butyltrimethyltin (1527-99-7) + (3-bromophenyl)trimethylstannane (17113-76-7)

Conditions	Yield
In diethyl ether; hexane byproducts: C4H9Br; n-BuLi in hexane adding to an ether soln. of the stannane at -78°C, stirring for 30 min, hydrolyzing with 2 N HCl, org. layer sepg., drying over MgSO4; identified by gas chromy. and chromato-mass spectrometry;	A 1% B 82% C n/a D 13%

2,6-dibromoaniline (608-30-0) → 1,3-dibromobenzene (108-36-1)

Conditions	Yield
Stage #1: 2,6-dibromoaniline With sulfuric acid; sodium nitrite In water at 0 - 5℃; for 3h; Stage #2: With hypophosphorous acid In water at 70 - 80℃; for 3h; Reagent/catalyst; Temperature;	81%
Diazotization.Behandlung der Diazoniumsalz-Loesungen mit H3PO2 bei 5grad;
With tetrahydrofuran; n-Amyl nitrite

3-bromobenzenediazonium o-benzenedisulfonimide → 1,3-dibromobenzene (108-36-1)

Conditions	Yield
With tetrabutylammomium bromide; copper In acetonitrile at 20℃; for 0.75h; Substitution;	80%
With tetrabutylammomium bromide In acetonitrile at 60℃; for 0.75h; Substitution;	78%

C10H13Br2N3 (401631-86-5) → 1,3-dibromobenzene (108-36-1) + 1,3-dibromo-2-iodo-benzene (19821-80-8)

Conditions	Yield
With tetrafluoroboric acid; hydrogen iodide In acetonitrile at 60℃; for 24h;	A 11% B 79%

C10H13Br2N3 (401631-86-5) → 1,3-dibromobenzene (108-36-1) + 1,3-dibromo-2-chlorobenzene (19230-27-4)

Conditions	Yield
With hydrogenchloride; copper In acetonitrile at 20 - 25℃; for 0.25h;	A 12% B 79%

3-bromophenyl trifluoromethanesulfonate (66107-31-1) → 1,3-dibromobenzene (108-36-1)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos; triisobutylaluminum; butanone; potassium bromide In toluene at 100℃; for 24h; Inert atmosphere;	78%

(3-bromophenyl)boronic acid (89598-96-9) → 1,3-dibromobenzene (108-36-1)

Conditions	Yield
With N-Bromosuccinimide In acetonitrile at 81℃; for 8h;	65%

7-(Dibrommethylen)bicyclo<2.2.1>hepta-2,5-dien → 1,3-dibromobenzene (108-36-1) + 6,6-Dibromfulven (41605-39-4) + acetylene (74-86-2)

Conditions	Yield
at 450℃; under 0.0001 Torr; for 4h; Title compound not separated from byproducts;	A n/a B 60% C n/a

isophthalic acid (121-91-5) → 1,3-dibromobenzene (108-36-1)

Conditions	Yield
With Bromotrichloromethane; bromine; dibromoisocyanuric acid at 120℃; for 60h; Time; UV-irradiation;	17%

tetrachloromethane (56-23-5) + N-Bromosuccinimide (128-08-5) + cyclohexene (110-83-8) + dibenzoyl peroxide (94-36-0) → 1,3-dibromobenzene (108-36-1) + 1.4-dibromobenzene (106-37-6)

ethyl nitrite (109-95-5) + 2,4-dibromo-aniline (615-57-6) → 1,3-dibromobenzene (108-36-1)

ethanol (64-17-5) + 3-bromo-benzenediazonium; tribromoide → 1,3-dibromobenzene (108-36-1)

1.4-dibromobenzene (106-37-6) → 1,3-dibromobenzene (108-36-1)

Conditions	Yield
With aluminium trichloride
With aluminium trichloride

3,5-dibromoaniline (626-40-4) → 1,3-dibromobenzene (108-36-1)

Conditions	Yield
With sulfuric acid; sodium nitrite

2,4-dibromo-aniline (615-57-6) → 1,3-dibromobenzene (108-36-1)

Conditions	Yield
With ethyl nitrite
Diazotization.Behandlung der Diazoniumsalz-Loesungen mit H3PO2 bei 5grad;
ueberfuehrung in das Diazoniumnitrat und erhitzen desselben mit Wasser;

2,6-dibromobenzaldehyde (67713-23-9) → 1,3-dibromobenzene (108-36-1)

Conditions	Yield
With potassium hydroxide

Acetanilid (103-84-4) → 1,3-dibromobenzene (108-36-1)

3-bromoaniline (591-19-5) → 1,3-dibromobenzene (108-36-1)

benzene (71-43-2) → 1,3-dibromobenzene (108-36-1) + 1.4-dibromobenzene (106-37-6)

Conditions	Yield
With aluminium trichloride beim Bromieren;

bromobenzene (108-86-1) → 1,3-dibromobenzene (108-36-1) + 1.4-dibromobenzene (106-37-6) + 1,2-dibromobenzene (583-53-9)

Conditions	Yield
With hypobromous acid In 1,4-dioxane; water at 25℃; Rate constant;	A 1 % Chromat. B 64.3 % Chromat. C 35.7 % Chromat.

1,3-Dichlorobenzene (541-73-1) → 1-bromo-3-chlorobenzene (108-37-2) + 1,3-dibromobenzene (108-36-1)

Conditions	Yield
With bromobenzene; Cu-HZSM-5 zeolite at 399.9℃; Mechanism; Product distribution;	A 11.6 % Chromat. B 3.2 % Chromat.

1,2,3-tribromobenzene (608-21-9) + benzene (71-43-2) → 1,3-dibromobenzene (108-36-1) + 2,6-dibromo-1,1'-biphenyl (59080-32-9) + 2,3-dibromo-biphenyl + 2'-bromo-1,1':3',1'-terphenyl

Conditions	Yield
at 25℃; for 24h; Irradiation;	A 9.5 % Chromat. B 14.0 % Chromat. C 12.0 % Chromat. D 3.3 % Chromat.

1,2,4-tribromobenzene (615-54-3) → bromobenzene (108-86-1) + 1,3-dibromobenzene (108-36-1) + 1.4-dibromobenzene (106-37-6) + benzene (71-43-2) + 1,2-dibromobenzene (583-53-9)

Conditions	Yield
With potassium hydroxide; hydrogen; palladium on activated charcoal In 2,2,4-trimethylpentane at 50℃; for 0.666667h; Product distribution; var. cat.: Raney-Ni, add. of Aliquat 336;	A 18 % Chromat. B 3 % Chromat. C 1 % Chromat. D 42 % Chromat. E 30 % Chromat.

Ethyl hexanoate (123-66-0) + 1,3,5-trisbromobenzene (626-39-1) → 1,3-dibromobenzene (108-36-1) + 1-(3,5-Dibromo-phenyl)-hexan-1-one + 1,1-Bis-(3,5-dibromo-phenyl)-hexan-1-ol + Hexanoic acid 1,1-bis-(3,5-dibromo-phenyl)-hexyl ester

Conditions	Yield
With n-butyllithium 1.) Et2O, -78 deg C, 2.) Et2O, -78 deg C; Multistep reaction;

n-hexanoic anhydride (2051-49-2) + 1,3,5-trisbromobenzene (626-39-1) → 1,3-dibromobenzene (108-36-1) + 1-(3,5-Dibromo-phenyl)-hexan-1-one + 1,1-Bis-(3,5-dibromo-phenyl)-hexan-1-ol + Hexanoic acid 1,1-bis-(3,5-dibromo-phenyl)-hexyl ester

Conditions	Yield
With n-butyllithium 1.) Et2O, -78 deg C, 2.) Et2O, -78 deg C; Multistep reaction;

1,3,5-trisbromobenzene (626-39-1) → 1,3-dibromobenzene (108-36-1)

Conditions	Yield
With n-butyllithium 1.) Et2O, -78 deg C, 2.) Et2O, -78 deg C; Multistep reaction;
With hydrocarbon substituted imidazolidine at 20℃;
With 1,3-bis(1,1-dimethylethyl)imidazolidin-2-ylidene In 1,4-dioxane at 120℃; for 4h;
With 1,2,3,4-tetrakis(carbazol-9-yl)-5,6-dicyanobenzene; triethylamine In 1-methyl-pyrrolidin-2-one at 20℃; for 1.33333h; Inert atmosphere; Irradiation;	98 %Chromat.

1,3,5-trisbromobenzene (626-39-1) + ethyl acetate (141-78-6) → 1,3-dibromobenzene (108-36-1) + 3,5-dibromoacetophenone (14401-73-1) + 1,1-Bis-(3,5-dibromo-phenyl)-ethanol + Acetic acid 1,1-bis-(3,5-dibromo-phenyl)-ethyl ester

Conditions	Yield
With n-butyllithium 1.) Et2O, -78 deg C, 2.) Et2O, -78 deg C; Yield given. Multistep reaction;
With n-butyllithium 1.) Et2O, -78 deg C, 2.) Et2O, -78 deg C; Multistep reaction;

1,3,5-trisbromobenzene (626-39-1) + Hexanoyl chloride (142-61-0) → 1,3-dibromobenzene (108-36-1) + 1-(3,5-Dibromo-phenyl)-hexan-1-one + 1,1-Bis-(3,5-dibromo-phenyl)-hexan-1-ol + Hexanoic acid 1,1-bis-(3,5-dibromo-phenyl)-hexyl ester

Conditions	Yield
With n-butyllithium 1.) Et2O, -78 deg C, 2.) Et2O, -78 deg C; Multistep reaction;

1H-imidazole (288-32-4) + 1,3-dibromobenzene (108-36-1) → 1,3-bis(1H-imidazol-1-yl)benzene (69506-91-8)

Conditions	Yield
With 1-sulfanyl-2-(dimethylaminomethyl)-3-Me3Si-benzene-Cu(I); potassium carbonate In 1-methyl-pyrrolidin-2-one at 160℃; for 16h;	100%
With copper(l) iodide; potassium carbonate In dimethyl sulfoxide at 150℃; for 48h;	99%
With copper(l) iodide; dimethylaminoacetic acid; potassium carbonate In dimethyl sulfoxide at 110℃; for 48h; Inert atmosphere;	93%

1,3-dibromobenzene (108-36-1) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,2-dioxaborolane (196212-27-8)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide at 90℃; for 48h; Inert atmosphere; Schlenk technique;	100%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 80℃; for 16h; Inert atmosphere; Schlenk technique;	96%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 80℃; for 24h; Suzuki-Miyaura Coupling;	93%

1,3-dibromobenzene (108-36-1) + m-Anisidine (536-90-3) → N,N'-bis(3-methoxyphenyl)-1,3-benzenediamine (202127-21-7)

Conditions	Yield
With sodium t-butanolate; palladium diacetate; bis(diphenylphosphinyl)ferrocene In toluene at 100 - 110℃; for 12h;	100%
With [(π-cinnamyl)Pd(tBuXPhos)]OTf In water at 45℃; for 36h;	91%

1,3-dibromobenzene (108-36-1) + 3-(t-butyl)-4-methoxyphenyl boronic acid (196960-96-0) → 1,3-bis(3-tert-butyl-4-methoxyphenyl)benzene (1202392-73-1)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); barium hydroxide monohydrate In ISOPROPYLAMIDE; water at 80℃; for 48h; Suzuki-Miyaura double cross-coupling; Inert atmosphere;	100%

(1R,5S)-3-benzyl-3-azabicyclo[3.2.1]octan-8-one + 1,3-dibromobenzene (108-36-1) + methyl iodide (74-88-4) → 3-benzyl-8-(3-bromo-phenyl)-8-methoxy-3-aza-bicyclo[3.2.1]octane (778582-06-2)

Conditions	Yield
Stage #1: 1,3-dibromobenzene With n-butyllithium In hexanes; diethyl ether at -78℃; for 1h; Stage #2: (1R,5S)-3-benzyl-3-azabicyclo[3.2.1]octan-8-one In hexanes; diethyl ether at -78℃; for 0.75h; Stage #3: methyl iodide In tetrahydrofuran at 20℃; for 60h;	100%

(1R,5S)-3-benzyl-3-azabicyclo[3.2.1]octan-8-one + 1,3-dibromobenzene (108-36-1) → 3-benzyl-8-(3-bromo-phenyl)-8-hydroxy-3-aza-bicyclo[3.2.1]octane (778581-93-4)

Conditions	Yield
Stage #1: 1,3-dibromobenzene With n-butyllithium In hexanes; diethyl ether at -78℃; for 1.33333h; Stage #2: (1R,5S)-3-benzyl-3-azabicyclo[3.2.1]octan-8-one In hexanes; diethyl ether at -78 - 20℃; Stage #3: With ammonium chloride In water at 20℃; for 18h;	100%

1,3-dibromobenzene (108-36-1) + 5-{4,4,5,5-tetramethyl-1,3,2-(2-dioxaborolanyl)}-2-{(E)-2-phenyl-2-diphenylborylethenyl}pyridine (1160604-94-3) → 1,3-bis[5-{(E)-2-(2-phenyl-2-diphenyl-borylethenyl)pyridyl}]benzene (1160604-69-2)

Conditions	Yield
With sodium hydroxide; bis(tri-t-butylphosphine)palladium(0) In tetrahydrofuran; water at 60℃; for 12h; Inert atmosphere;	100%

1,3-dibromobenzene (108-36-1) + C22H39BO3Si (1254941-69-9) → C38H58O2Si2 (1254941-70-2)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In tetrahydrofuran; water at 65℃; for 12h; Suzuki-Miyaura coupling;	100%

1,3-dibromobenzene (108-36-1) + 3-methoxyphenylboronic acid (10365-98-7) → 3,3''-dimethoxy-1,1':3',1''-terphenyl (171820-21-6)

Conditions	Yield
With potassium carbonate In ethanol at 80℃; for 36h; Suzuki-Miyaura Coupling; Inert atmosphere;	100%

1,3-dibromobenzene (108-36-1) → m-phenylenediamine (108-45-2)

Conditions	Yield
With C24H12Cu2F9N4O7; tetrabutylammomium bromide; ammonia; caesium carbonate In water at 110 - 140℃; for 16h;	99%
With {(o-C6H4(NCHC6H4O)2)cobalt(II)}2; ammonia at 150℃; under 1500.15 Torr; for 10h; Autoclave; Inert atmosphere; Large scale;	73%
With ammonia; water; copper(II) sulfate at 175 - 180℃;

1,3-dibromobenzene (108-36-1) + 4-trimethylstannyl-pyridine (59020-06-3) → 1,3-bis(4-pyridyl)benzene (170165-79-4)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; lithium chloride In toluene at 110℃;	99%

1,3-dibromobenzene (108-36-1) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → m-bromobenzoic aldehyde (3132-99-8)

Conditions	Yield
Stage #1: 1,3-dibromobenzene With tri-n-butyllithium magnesate complex In toluene at 0℃; for 1.5h; Stage #2: N,N-dimethyl-formamide In toluene at 0℃; for 0.5h; Stage #3: With citric acid at 20℃;	99%
Stage #1: 1,3-dibromobenzene With n-butyllithium; isopropylmagnesium chloride In tetrahydrofuran; hexane at 0 - 5℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 0℃; for 1h; Further stages.;	90%
Stage #1: 1,3-dibromobenzene With n-butyllithium In tetrahydrofuran at -78℃; for 0.583333h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78 - 20℃; for 1.5h;	63.21%

pyrrolidine (123-75-1) + 1,3-dibromobenzene (108-36-1) → 1-(3-bromophenyl)-pyrrolidine (219928-13-9)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 80℃; for 4.5h; Sealed tube;	99%
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 80℃; for 4.5h; Sealed tube;	99%
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 80℃; for 4.5h;	78%

n-butyllithium (109-72-8, 29786-93-4) + chloro-trimethyl-silane (75-77-4) + 1,3-dibromobenzene (108-36-1) → (3-bromophenyl)trimethylsilane (17878-47-6)

Conditions	Yield
In water	99%

1,3-dibromobenzene (108-36-1) + N-methylaniline (100-61-8) → N1,N3-dimethyl-N1,N3-diphenylbenzene-1,3-diamine (308123-55-9)

Conditions	Yield
With (6-Dipp)PdCl2-SPhos; sodium t-butanolate In neat (no solvent) at 110℃; for 24h; Buchwald-Hartwig Coupling;	99%
With potassium hexamethylsilazane In 1,4-dioxane at 100℃; for 1h; metal-free Buchwald-Hartwig amination; Inert atmosphere;	96 %Chromat.

1,3-dibromobenzene (108-36-1) + 4-methoxy-3-methylbenzonitrile (53078-71-0) → (3-bromophenyl)(4-methoxy-3-methylphenyl)methanimine (1260433-04-2)

Conditions	Yield
Stage #1: 1,3-dibromobenzene With n-butyllithium In diethyl ether at -78℃; for 0.5h; Stage #2: 4-methoxy-3-methylbenzonitrile In diethyl ether at -78 - 20℃; for 2h; Stage #3: With ammonium acetate	99%

1,3-dibromobenzene (108-36-1) + (4-(benzyloxy)-3-methoxyphenyl)boronic acid (243990-53-6) → 4,4''-bis(benzyloxy)-3,3''-dimethoxy-1,1':3',1''-terphenyl

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In N,N-dimethyl-formamide at 60℃; Suzuki Coupling; Inert atmosphere;	99%

1,3-dibromobenzene (108-36-1) → 1,5-dibromo-2,4-diiodobenzene (96843-23-1)

Conditions	Yield
With sulfuric acid; iodine at 125 - 135℃; for 48h; Inert atmosphere;	98.6%
With sulfuric acid; iodine at 125 - 135℃; for 6h;	70%
With sulfuric acid; iodine at 130℃; for 6h; Inert atmosphere; Schlenk technique;	60%

morpholine (110-91-8) + 1,3-dibromobenzene (108-36-1) → 4-(3-morpholinophenyl)morpholine (51100-94-8)

Conditions	Yield
With sodium t-butanolate; tris(dibenzylideneacetone)dipalladium (0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 100℃; for 24h;	98%
With C30H25BrN3PPdS; potassium carbonate In iso-butanol at 100℃; for 24h; Buchwald-Hartwig Coupling; Inert atmosphere;	77.3%
With potassium hexamethylsilazane In 1,4-dioxane at 100℃; for 0.5h; metal-free Buchwald-Hartwig amination; Inert atmosphere;	86 %Chromat.

1,3-dibromobenzene (108-36-1) + 4-methoxyphenylboronic acid (5720-07-0) → 4,4’’-dimethoxy-1,1′:3′,1’’-terphenyl (1568-74-7)

Conditions	Yield
With potassium carbonate In ethanol; water at 20℃; for 4h; Suzuki-Miyaura Coupling;	98%
With potassium phosphate; C17H15N4O3S(1-)*Na(1+); palladium dichloride In water at 100℃; for 6h; Suzuki-Miyaura Coupling; Inert atmosphere; Green chemistry;	92%
With sodium carbonate; palladium diacetate In water; N,N-dimethyl-formamide at 60℃; for 12h; Suzuki;	90%

1,3-dibromobenzene (108-36-1) + 4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid (195730-31-5) → 1,3-bis(benzocyclobuten-4-yl)benzene

Conditions	Yield
With borax; tetrabutylammomium bromide; palladium dichloride In ethanol at 20℃; for 3h; Suzuki coupling;	98%

1,3-dibromobenzene (108-36-1) + bis(pinacol)diborane (73183-34-3) → 2-(3,5-dibromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (408492-26-2)

Conditions	Yield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; cyclopentyl methyl ether; 1,1'-di(pyridin-2-yl)-1,1',3,3'-tetrahydro-2,2'-bibenzo[d][1,3,2]diazaborole at 100℃; for 16h; Schlenk technique; Inert atmosphere;	98%
Stage #1: bis(pinacol)diborane With C24H28ClIrN2O In n-heptane; isopropyl alcohol at 75℃; for 1h; Sealed tube; Inert atmosphere; Stage #2: 1,3-dibromobenzene In n-heptane; isopropyl alcohol Sealed tube; Inert atmosphere;	98%
With 4,4'-di-tert-butyl-2,2'-bipyridine; [Ir(COD)(OMe)]2 In tetrahydrofuran at 80℃; for 16h;

1,3-dibromobenzene (108-36-1) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 3-bromobenzoate (69038-74-0)

Conditions	Yield
Stage #1: 1,3-dibromobenzene With n-butyllithium; butyl magnesium bromide In tetrahydrofuran; hexane; toluene at -5℃; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; hexane; toluene at -5℃; Stage #3: With citric acid In tetrahydrofuran; hexane; toluene Further stages.;	98%
Stage #1: 1,3-dibromobenzene With n-butyllithium; butyl magnesium bromide In tetrahydrofuran; hexane; toluene at -5℃; for 1h; Inert atmosphere; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; hexane; toluene at -5℃; for 2h; Inert atmosphere;	98%

1,3-dibromobenzene (108-36-1) + 4-(difluoromethoxy)-3,5-dimethylbenzonitrile (1260433-19-9) → (3-bromophenyl)(4-(difluoromethoxy)-3,5-dimethylphenyl)methanimine (1260433-20-2)

Conditions	Yield
Stage #1: 1,3-dibromobenzene With n-butyllithium In diethyl ether at -78℃; for 0.5h; Inert atmosphere; Stage #2: 4-(difluoromethoxy)-3,5-dimethylbenzonitrile In tetrahydrofuran; diethyl ether at 0 - 20℃; for 2h; Stage #3: With ammonium acetate In tetrahydrofuran; methanol; diethyl ether	98%

1,3-dibromobenzene (108-36-1) + 2-Methoxyphenylboronic acid (5720-06-9) → 3'-bromo-2-methoxybiphenyl (337535-26-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In methanol; toluene for 24h; Suzuki reaction; Reflux; Inert atmosphere;	98%
Stage #1: 1,3-dibromobenzene; 2-Methoxyphenylboronic acid With sodium carbonate In ethanol; toluene for 0.5h; Sealed tube; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In ethanol; toluene at 80℃; Inert atmosphere;	57.76%
Stage #1: 1,3-dibromobenzene; 2-Methoxyphenylboronic acid With sodium carbonate In ethanol; toluene for 0.5h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In ethanol; toluene at 80℃; Sealed tube; Inert atmosphere;	57.76%

1,3-dibromobenzene (108-36-1) + diphenyl diselenide (1666-13-3) → 3,5-dibromophenyl phenyl selenide (1393715-73-5)

Conditions	Yield
Stage #1: 1,3-dibromobenzene With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; bis(pinacol)diborane; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 80℃; for 24h; Inert atmosphere; Stage #2: diphenyl diselenide With [2,2]bipyridinyl; copper(l) chloride In water; dimethyl sulfoxide at 80℃; for 24h; Inert atmosphere; regioselective reaction;	98%

1,3-dibromobenzene (108-36-1) + N-methyl-4-(trifluoromethyl)-2-pyridinamine → 1,3-bis(N-methyl-N′-(4-trifluoromethylpyridin-2-yl)amino)benzene

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene at 130℃; for 24h; Inert atmosphere; Sealed tube;	98%

4,4'-(hexafluoroisopropylidene)diphenol (1478-61-1) + 1,3-dibromobenzene (108-36-1) → polymer, hydroxyl-terminated; monomer(s): bisphenol A6F; 1,3-dibromobenzene

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In N,N-dimethyl-formamide; toluene at 135 - 145℃; Ullmann reaction;	97%

1,3-dibromobenzene (108-36-1) → 2,4-dibromonitrobenzene (51686-78-3)

Conditions	Yield
With sulfuric acid; nitric acid at 0 - 20℃; for 1.5h;	97%
With sulfuric acid; nitric acid In dichloromethane at 0 - 20℃; for 0.5h;	95%
With sulfuric acid; nitric acid at 20℃; for 5h;	90%

1,3-dibromobenzene (108-36-1) + 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-henicosafluorododec-1-ene (30389-25-4) → C30H8F42

Conditions	Yield
With tetrabutylammomium bromide; sodium acetate; palladium diacetate In tetrahydrofuran; N,N-dimethyl-formamide at 120℃; for 84h;	97%

Upstream product

• 56-23-5 tetrachloromethane 
• 128-08-5 N-Bromosuccinimide 
• 110-83-8 cyclohexene 
• 94-36-0 dibenzoyl peroxide 
• 109-95-5 ethyl nitrite 
• 615-57-6 2,4-dibromo-aniline 
• 64-17-5 ethanol 
• 106-37-6 1.4-dibromobenzene 
• 626-40-4 3,5-dibromoaniline 
• 608-30-0 2,6-dibromoaniline 
• 67713-23-9 2,6-dibromobenzaldehyde 
• 103-84-4 Acetanilid 
• 591-19-5 m-Bromoaniline 
• 71-43-2 benzene 

Downstream Products

• 108-86-1 bromobenzene 
• 25032-74-0 3,3'-dibromobenzophenone 
• 24239-82-5 1,5-dibromo-2,4-dinitrobenzene 
• 13402-32-9 1,3-dibromo-2-nitrobenzene 
• 51686-78-3 2,4-dibromonitrobenzene 
• 861601-98-1 1,3-dibromo-2,4-dinitro-benzene 
• 92-52-4 biphenyl 
• 92-06-8 1,3-diphenylbenzene 
• 68142-19-8 [1,1';3',1'';3'',1''';3''',1'''';3'''',1''''';3''''',1'''''';3'''''',1''''''';3''''''',1'''''''']Noniphenyl 
• 68142-20-1 m-deciphenyl 
• 120856-97-5 m-undeciphenyl 
• 121143-76-8 m-tredeciphenyl 
• 121143-74-6 m-quatuordeciphenyl 
• 68142-21-2 m-quindeciphenyl 

Related news

The disposition and metabolism of 1,3-Dibromobenzene (cas 108-36-1) in the rat08/19/2019

The distribution, excretion and metabolism of 1,3-dibromobenzene following a single i.p. administration to rats 100 or 300 mg/kg was investigated using radiotracer [3H] and GC-MS technique.After 72 hours about 74 to 90% were excreted in urine. The highest radioactivity was observed in the liver,...detailed

Relevant articles and documents

-

-

Nature's hydrides: rapid reduction of halocarbons by folate model compounds

Halocarbons R-X are reduced to hydrocarbons R-H by folate model compounds under biomimetic conditions. The reactions correspond to a halide-hydride exchange with the methylenetetrahydrofolate (MTHF) models acting as hydride donors. The MTHF models are also functional equivalents of dehalohydrogenases but, unlike these enzymes, do not require a metal cofactor. The reactions suggest that halocarbons have the potential to act as endocrinological disruptors of biochemical pathways involving MTHF. As a case in point, we observe the rapid reaction of the MTHF models with the inhalation anaesthetic halothane. The ready synthetic accessibility of the MTHF models as well as their dehalogenation activity in the presence of air and moisture allow for the remediation of toxic, halogenated hydrocarbons.

Base-catalyzed aryl halide isomerization enables the 4-selective substitution of 3-bromopyridines

The base-catalyzed isomerization of simple aryl halides is presented and utilized to achieve the 4-selective etherification, hydroxylation and amination of 3-bromopyridines. Mechanistic studies support isomerization of 3-bromopyridines to 4-bromopyridines proceedsviapyridyne intermediates and that 4-substitution selectivity is driven by a facile aromatic substitution reaction. Useful features of a tandem aryl halide isomerization/selective interception approach to aromatic functionalization are demonstrated. Example benefits include the use of readily available and stable 3-bromopyridines in place of less available and stable 4-halogenated congeners and the ability to converge mixtures of 3- and 5-bromopyridines to a single 4-substituted product.

Preparation method of M-dibromobenzene

The invention provides a preparation method of m-dibromobenzene. The preparation method comprises the following steps: (1) adding a strong acid into 2,4-dibromoaniline or 2,6-dibromoaniline, then adding a sodium nitrite aqueous solution to performing diazotization reaction on the 2,4-dibromoaniline or 2,6-dibromoaniline at low temperature and acid conditions, and preparing diazo dibromoaniline salt aqueous solution after the reaction is completed; (2) adding a reducing agent into the diazo dibromoaniline salt aqueous solution prepared in the step (1), and enabling the system to react fully toprepare an m-dibromobenzene-containing mixed liquid; (3) standing to layer the mixed liquid prepared in the step (2), then separating an inorganic phase from an organic phase, and distilling the organic phase to obtain the m-dibromobenzene. The method is simple in process steps; the obtained product is low in production cost.