Conditions | Yield |
---|---|
With dibromoisocyanuric acid In dichloromethane at 20℃; for 24h; Reagent/catalyst; Solvent; Temperature; UV-irradiation; | 100% |
Conditions | Yield |
---|---|
Stage #1: 3,4-dibromoaniline With hydrogenchloride In diethyl ether; water for 0.0833333h; Stage #2: With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Stage #3: With hypophosphorous acid In water at 4 - 25℃; for 72h; | 81% |
Conditions | Yield |
---|---|
With PyHBrCl2; iron(III) chloride In dichloromethane at 20℃; for 2h; | A 19% B 72% |
With lead(IV) acetate; trifluoroacetic acid; potassium bromide at 25℃; for 0.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With bromine; ZnBr2 on silica (100 Angstroem) In hexane at 25℃; for 0.116667h; Yields of byproduct given; |
1,2-dibromobenzene
Conditions | Yield |
---|---|
With tetrabutylammomium bromide In acetonitrile at 60℃; for 0.75h; Substitution; | 53% |
With tetrabutylammomium bromide; copper In acetonitrile at 20℃; for 0.75h; Substitution; | 51% |
1,2-dibromobenzene-4-sulfonic acid
1,2-dibromobenzene
Conditions | Yield |
---|---|
With hydrogen bromide at 250℃; |
Conditions | Yield |
---|---|
With hydrogen bromide at 250 - 260℃; |
Conditions | Yield |
---|---|
With bromine; Nitrogen dioxide In water; trifluoroacetic acid at 20℃; for 0.16h; Product distribution; | |
With bromine | |
With ferrocenium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; bromine; zinc(II) oxide In dichloromethane for 3h; Heating; | |
Multi-step reaction with 2 steps 1: bromine / 1.5 h / 40 °C / Darkness; Inert atmosphere; Green chemistry 2: bromine / dichloromethane / 2 h / 40 °C / Darkness; Inert atmosphere; Green chemistry View Scheme |
bromobenzene
A
bromochlorobenzene
B
para-dichlorobenzene
C
2-bromo-1-chlorobenzene
D
1.4-dibromobenzene
E
chlorobenzene
F
1,2-dibromobenzene
Conditions | Yield |
---|---|
With potassium chloride; cobalt(III) acetate; trifluoroacetic acid at 20℃; for 15h; Product distribution; Mn(CH3COO)3, 600 - 216 h, various conc. of aq. CF3COOH; |
bromobenzene
A
1,3-dibromobenzene
B
1.4-dibromobenzene
C
1,2-dibromobenzene
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. |
Conditions | Yield |
---|---|
With oxygen; potassium bromide; sodium nitrite In water; trifluoroacetic acid at 20℃; for 24h; Product distribution; | |
With hydrogen bromide; oxygen; ruthenium trichloride at 145℃; under 750.075 Torr; for 17h; |
1,2,4-tribromobenzene
A
bromobenzene
B
1,3-dibromobenzene
C
1.4-dibromobenzene
D
benzene
E
1,2-dibromobenzene
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. |
1,2-dibromobenzene
Conditions | Yield |
---|---|
With copper(ll) bromide |
1,2-dibromobenzene
Conditions | Yield |
---|---|
With bromine; acetic acid |
Conditions | Yield |
---|---|
at 200 - 700℃; Quantum yield; |
chlorosulfonic acid
hydrogen bromide
iodine
benzene
1,2-dibromobenzene
1,2-dibromobenzene
Conditions | Yield |
---|---|
man fuehrt in das Perbromid ueber und zersetzt dieses mit Soda; |
1,2-dibromobenzene
Conditions | Yield |
---|---|
With ethyl nitrite; ethanol |
Conditions | Yield |
---|---|
With bromine at 480℃; |
aluminium trichloride
bromobenzene
A
1.4-dibromobenzene
B
1,2-dibromobenzene
Conditions | Yield |
---|---|
at 90℃; |
carbon disulfide
bromobenzene
bromine
aluminium bromide
A
1.4-dibromobenzene
B
1,2-dibromobenzene
Conditions | Yield |
---|---|
at 55℃; Kinetics; |
bromobenzene
bromine
A
1,3-dibromobenzene
B
1.4-dibromobenzene
C
1,2-dibromobenzene
Conditions | Yield |
---|---|
at 375 - 500℃; |
bromobenzene
bromine
A
1,3-dibromobenzene
B
1.4-dibromobenzene
C
1,2-dibromobenzene
Conditions | Yield |
---|---|
at 55℃; Product distribution; |
bromobenzene
bromine
A
1,3-dibromobenzene
B
1.4-dibromobenzene
C
1,2-dibromobenzene
Conditions | Yield |
---|---|
at 55℃; Product distribution; |
benzene
A
bromobenzene
B
1,3-dibromobenzene
C
1.4-dibromobenzene
D
1,2,3,4,5,6-hexabromocyclohexane
E
1,2-dibromobenzene
Conditions | Yield |
---|---|
With bromine at 55℃; for 16h; Product distribution; Irradiation; temperature; |
Conditions | Yield |
---|---|
With bromine; aluminium at 55℃; | |
With bromine; iron at 55℃; |
biphenyl
benzene
A
bromobenzene
B
2-Bromobiphenyl
C
1,3-dibromobenzene
D
4-bromo-1,1'-biphenyl
E
3-bromobiphenyl
F
1,2-dibromobenzene
Conditions | Yield |
---|---|
With bromine at 50℃; for 20h; Product distribution; Irradiation; other time, reagents ratio; |
Methyl phenyl sulfone
bromine
A
methyl bromide
B
bromobenzene
C
1,2-dibromobenzene
Conditions | Yield |
---|---|
at 250℃; |
2,4,6-trimethylaniline
1,2-dibromobenzene
N1,N2-bis(2,4,6-trimethylphenyl)-1,2-benzenediamine
Conditions | Yield |
---|---|
With ammonium chloride; sodium t-butanolate; palladium diacetate In water; argon; toluene | 100% |
With tri-tert-butylphosphonium tetrafluoroborate; palladium diacetate; sodium t-butanolate In toluene at 60 - 135℃; Inert atmosphere; | 87% |
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; palladium diacetate In toluene for 12h; Heating; | 86% |
5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone
1,2-dibromobenzene
1-(2-bromophenyl)-5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; diethyl ether; hexane at -110℃; for 3.5h; | 100% |
1,2-dibromobenzene
N,N'-diphenyl-o-phenylenediamine
Conditions | Yield |
---|---|
With ammonium chloride; aniline; sodium t-butanolate; palladium diacetate In water; argon; toluene | 100% |
2,5-Dimethylaniline
1,2-dibromobenzene
N,N'-bis(2,5-dimethylphenyl)-o-phenylenediamine
Conditions | Yield |
---|---|
With ammonium chloride; sodium t-butanolate; palladium diacetate In water; argon; toluene | 100% |
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene at 110℃; for 14h; Inert atmosphere; | 100 %Chromat. |
3,5-dimethylaminoaniline
1,2-dibromobenzene
N,N'-di(3,5-dimethylphenyl)benzene-1,2-diamine
Conditions | Yield |
---|---|
With ammonium chloride; sodium t-butanolate; palladium diacetate In water; argon; toluene | 100% |
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene at 110℃; for 14h; Inert atmosphere; | 100 %Chromat. |
2,5-di-tert-butylaniline
1,2-dibromobenzene
B
N,N'-bis(2,5-di-t-butylphenyl)-o-phenylenediamine
Conditions | Yield |
---|---|
With ammonium chloride; sodium t-butanolate; palladium diacetate In water; argon; toluene | A n/a B 100% |
3,4,5-trimethoxyphenylboronic Acid
1,2-dibromobenzene
Conditions | Yield |
---|---|
With palladium diacetate; potassium carbonate In ethanol; N,N-dimethyl acetamide at 20℃; for 3h; Suzuki Coupling; | 100% |
Conditions | Yield |
---|---|
With C24H12Cu2F9N4O7; tetrabutylammomium bromide; ammonia; caesium carbonate In water at 110 - 140℃; for 16h; | 99% |
With ammonium hydroxide; copper(l) iodide; N,N-dimethylethylenediamine In dimethyl sulfoxide at 130℃; for 18h; Reagent/catalyst; Time; Sealed tube; Inert atmosphere; | 92% |
With ammonium hydroxide In water at 20℃; for 12h; Green chemistry; | 92% |
With ammonia; water; copper(II) sulfate at 180 - 190℃; | |
With [Cu2(2,7-bis(pyridin-2-yl)-l,8-naphthyridine)(OH)(CF3COO)3]; tetrabutylammomium bromide; ammonia; caesium carbonate In water at 120℃; for 16h; Sealed tube; | 100 %Spectr. |
ethyl trifluoroacetate,
1,2-dibromobenzene
1-(2-bromophenyl)-2,2,2-trifluoroethan-1-one
Conditions | Yield |
---|---|
Stage #1: 2,3-dibromobenzene With n-butyllithium Stage #2: ethyl trifluoroacetate, | 99% |
Stage #1: 2,3-dibromobenzene With n-butyllithium at -110℃; Metallation; Stage #2: ethyl trifluoroacetate, Acylation; |
Conditions | Yield |
---|---|
With potassium carbonate; bis(dibenzylideneacetone)-palladium(0); 3-(2,6-diisopropylphenyl)-1-(2-diphenylphosphanylbenzyl)-3H-imidazol-1-ium chloride In N,N-dimethyl acetamide at 120℃; for 16h; Heck reaction; | 99% |
With palladium diacetate; tri-tert-butyl phosphine; sodium acetate In N,N-dimethyl acetamide at 130℃; for 24h; Heck reaction; | 60% |
(2,6-dimethylphenyl)magnesium bromide
1,2-dibromobenzene
4-methylfluorene
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium (0); tri-tert-butyl phosphine In tetrahydrofuran at 20℃; for 20h; | 99% |
palladium diacetate In tetrahydrofuran at 20℃; for 20h; | 99% |
2-Methoxyphenylboronic acid
1,2-dibromobenzene
2’-bromo-2-methoxybiphenyl
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In methanol; toluene for 24h; Suzuki reaction; Reflux; Inert atmosphere; | 99% |
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 50℃; for 4h; Suzuki coupling; | 71% |
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium (0); tri-tert-butyl phosphine In tetrahydrofuran at 20℃; for 20h; | 99% |
palladium diacetate In tetrahydrofuran at 20℃; for 20h; | 99% |
Conditions | Yield |
---|---|
99% | |
With palladium diacetate; sodium t-butanolate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride | |
With palladium diacetate; sodium t-butanolate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride |
Conditions | Yield |
---|---|
With 2-((dicyclohexylphosphino)methyl)-1,3-bis(2,6-diisopropylphenyl)-4,5-dimethyl-1H-imidazol-3-ium iodide; ammonia; palladium diacetate; sodium t-butanolate In 1,4-dioxane at 120℃; under 7500.75 Torr; for 24h; Autoclave; Inert atmosphere; | 99% |
With 2-(di-tert-butylphosphino)-1-mesityl-4,5-diphenyl-1H-imidazole; ammonia; palladium diacetate; sodium t-butanolate In 1,4-dioxane at 120℃; under 7500.75 Torr; for 24h; Autoclave; Inert atmosphere; | > 99 %Chromat. |
9,9-dimethyl-3,6-dimethoxy-9-stannafluorene
1,2-dibromobenzene
2,11-dimethoxytriphenylene
Conditions | Yield |
---|---|
With bis(tri-t-butylphosphine)palladium(0) In tetrahydrofuran at 60℃; for 12h; | 99% |
Conditions | Yield |
---|---|
With 1,2,3,4-tetrahydroquinolin-8-ol; caesium carbonate; copper(I) bromide In N,N-dimethyl-formamide at 130℃; for 48h; Inert atmosphere; chemoselective reaction; | 99% |
N-phenylacetamidine
1,2-dibromobenzene
2-methyl-1-phenyl-1H-benzimidazole
Conditions | Yield |
---|---|
With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 140℃; for 24h; Molecular sieve; Inert atmosphere; regiospecific reaction; | 99% |
N-cyclohexylbenzimidamide
1,2-dibromobenzene
1-cyclohexyl-2-phenyl-1H-benzo[d]imidazole
Conditions | Yield |
---|---|
With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 140℃; for 24h; Molecular sieve; Inert atmosphere; regiospecific reaction; | 99% |
N-(naphthalen-1-yl)benzimidamide
1,2-dibromobenzene
1-(naphthalen-1-yl)-2-phenyl-1H-benzo[d]imidazole
Conditions | Yield |
---|---|
With 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 140℃; for 24h; Molecular sieve; Inert atmosphere; regiospecific reaction; | 99% |
Conditions | Yield |
---|---|
With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 140℃; for 24h; Molecular sieve; Inert atmosphere; regiospecific reaction; | 99% |
With potassium phosphate; 1,10-Phenanthroline; copper(II) oxide In diethylene glycol dimethyl ether at 140℃; for 24h; Inert atmosphere; regiospecific reaction; | 51% |
(R)-2-methoxy-1-phenylethylamine
1,2-dibromobenzene
(2-bromophenyl)-(R)-2-methoxy-1-phenylethylamine
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 80℃; for 48h; Buchwald-Hartwig amination; | 98% |
Conditions | Yield |
---|---|
With {2,6-bis[(di-1-piperidinylphosphino)amino]phenyl}palladium(II) chloride; potassium carbonate In 1,4-dioxane; water; butan-1-ol at 100℃; for 0.5h; Suzuki-Miyaura reaction; | 98% |
With potassium phosphate; dichloro{bis[1-(dicyclohexylphosphanyl)piperidine]}palladium(II) In toluene at 80℃; for 0.166667h; Suzuki-Miyaura cross-coupling reaction; Air; | 98% |
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In tetrahydrofuran at 20℃; for 6h; Suzuki coupling; | 96% |
4-methylphenylboronic acid
1,2-dibromobenzene
4,4′′-dimethyl-o-terphenyl
Conditions | Yield |
---|---|
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In tetrahydrofuran at 20℃; for 6h; Suzuki coupling; | 98% |
With bis(1,5-cyclooctadiene)nickel (0); potassium phosphate; tricyclohexylphosphine In tetrahydrofuran for 20h; Suzuki Coupling; Inert atmosphere; | 97% |
With potassium carbonate In ethanol; water at 20℃; for 8h; Suzuki-Miyaura coupling; | 85% |
With sodium tetrachloropalladate(II); C22H16O8S2(2-)*2Na(1+); sodium hydroxide In ethanol; water at 100℃; for 8h; Suzuki-Miyaura Coupling; Schlenk technique; | 83% |
With potassium carbonate In methanol at 80℃; for 0.5h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere; |
Conditions | Yield |
---|---|
With t-BuONa; Pd(O2CCH3)2; 1,3-bis(2,6-diisopropylphenyl)imidazolim chloride In toluene mixt. of Fe complex, imidazolium salt, t-BuONa, Pd compd. and C6H4Br2 intoluene was heated at 110°C for 12 h; | 98% |
(3-(tert-butyl)-2-methoxyphenyl)boronic acid
1,2-dibromobenzene
2'-bromo-3-tert-butyl-2-methoxybiphenyl
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); water; potassium carbonate In 1,2-dimethoxyethane at 67℃; for 60h; Suzuki coupling; Inert atmosphere; | 98% |
4-(dimethylamino)-N-phenylbenzimidamide
1,2-dibromobenzene
1-phenyl-2-(4-N,N-dimethylamino-phenyl)-1H-benzo[d]imidazole
Conditions | Yield |
---|---|
With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 140℃; for 24h; Molecular sieve; Inert atmosphere; regiospecific reaction; | 98% |
bis(pinacol)diborane
1,2-dibromobenzene
2-(3,4-dibromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
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 80℃; for 16h; Schlenk technique; Inert atmosphere; | 98% |
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1-(4,4'-di-tert-butyl-[2,2'-bipyridin]-6-yl)-2-(dimethyl(phenyl)silyl)-2,3-dihydro-1H-benzo[d][1,3,2]diazaborole Inert atmosphere; Schlenk technique; Sealed tube; | 97% |
With (1,5-cyclooctadiene)(methoxy)iridium(l) dimer; 4,4'-ditert-butyl-2,2'-bipyridine In tetrahydrofuran at 80℃; for 18h; Inert atmosphere; regioselective reaction; | |
Stage #1: bis(pinacol)diborane With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran for 0.0333333h; Inert atmosphere; Sonication; Stage #2: 2,3-dibromobenzene In tetrahydrofuran at 80℃; for 24h; Inert atmosphere; | |
With (1,5-cyclooctadiene)(methoxy)iridium(l) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 80℃; for 24h; Inert atmosphere; |
N'-(1-(2-aminophenyl)ethylidene)-4-methylbenzenesulfonohydrazide
1,2-dibromobenzene
9-methyl-acridine
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); lithium tert-butoxide; ruphos In 1,4-dioxane; water at 110℃; for 12h; Reagent/catalyst; Temperature; Microwave irradiation; Inert atmosphere; | 98% |
1,2-Dibromobenzene is an organic compound with the formula C6H4Br2, and its systematic name is the same with the product name. With the CAS registry number 583-53-9, it is also named as o-Dibromobenzene. It belongs to the product categories of Aromatic Hydrocarbons (substituted) & Derivatives; Organics; Benzene derivates; Miscellaneous; Bromine Compounds; Aryl; C6; Halogenated Hydrocarbons. Its EINECS number is 209-507-3. In addition, the molecular weight is 235.90. This chemical is used in organic synthesis.
Physical properties of 1,2-Dibromobenzene are: (1)ACD/LogP: 3.628; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.63; (4)ACD/LogD (pH 7.4): 3.63; (5)ACD/BCF (pH 5.5): 336.99; (6)ACD/BCF (pH 7.4): 336.99; (7)ACD/KOC (pH 5.5): 2243.20; (8)ACD/KOC (pH 7.4): 2243.20; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.599; (13)Molar Refractivity: 41.633 cm3; (14)Molar Volume: 121.803 cm3; (15)Polarizability: 16.505×10-24cm3; (16)Surface Tension: 41.02 dyne/cm; (17)Density: 1.937 g/cm3; (18)Flash Point: 95.5 °C; (19)Enthalpy of Vaporization: 44.316 kJ/mol; (20)Boiling Point: 225.421 °C at 760 mmHg; (21)Vapour Pressure: 0.13 mmHg at 25°C.
Preparation : this chemical can be prepared by bromobenzene at the temperature of 20 °C. This reaction will need reagents PyHBrCl2, FeCl3 and solvent CH2Cl2 with the reaction time of 2 hours. The yield is about 72%.
Uses of 1,2-Dibromobenzene: it can be used to produce 3-(2-Bromophenylthio)-4H-[1]benzopyran-4-on by heating. It will need reagent Cu with the reaction time of 30 min. The yield is about 54%.
When you are using this chemical, please be cautious about it as the following:
This chemcial is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing, gloves and eye/face protection.
You can still convert the following datas into molecular structure:
(1)SMILES: Brc1ccccc1Br
(2)Std. InChI: InChI=1S/C6H4Br2/c7-5-3-1-2-4-6(5)8/h1-4H
(3)Std. InChIKey: WQONPSCCEXUXTQ-UHFFFAOYSA-N
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