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; | 99% |
4-bromo-2-chloroiodobenzene
1-bromo-3-chlorobenzene
Conditions | Yield |
---|---|
With [Ir(2-phenylpyridine)-2-(4,4’-di-tert-butyl-2,2’-bipyridine)]PF6; N-ethyl-N,N-diisopropylamine In acetonitrile at 25℃; for 1.5h; Irradiation; | 92% |
(3-chlorophenyl)(mesityl)iodonium trifluoromethanesulfonate
1-bromo-3-chlorobenzene
Conditions | Yield |
---|---|
With copper(I) bromide In acetonitrile at 80℃; for 2h; | 92% |
1-bromo-3-chlorobenzene
Conditions | Yield |
---|---|
In dimethyl sulfoxide Ambient temperature; | 90% |
Conditions | Yield |
---|---|
With boron tribromide; dimethyl sulfoxide at 80℃; for 1h; | 90% |
1-bromo-3-chlorobenzene
Conditions | Yield |
---|---|
With tetrabutylammomium bromide In acetonitrile at 60℃; for 0.75h; Substitution; | 75% |
With tetrabutylammomium bromide; copper In acetonitrile at 20℃; for 0.75h; Substitution; | 71% |
1-bromo-3-chlorobenzene
Conditions | Yield |
---|---|
With N-benzyl-N,N,N-triethylammonium chloride; copper In acetonitrile at 20℃; Substitution; | 74% |
3-chlorophenylboronic acid
1-bromo-3-chlorobenzene
Conditions | Yield |
---|---|
With N-Bromosuccinimide In acetonitrile at 81℃; for 8h; | 59% |
Conditions | Yield |
---|---|
With bromine trifluoride; bromine at 0 - 10℃; | A 25% B 5% |
2-(3-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
1-bromo-3-chlorobenzene
Conditions | Yield |
---|---|
With copper(ll) bromide In methanol Heating; | 24% |
4-Bromo-2-chloro-benzoic Acid
5-bromo-3-chloro-3',5'-dimethyl-[1,1'-biphenyl]-2-carboxylic acid
A
1-bromo-3-chlorobenzene
B
3-bromo-5-chloro-3',5'-dimethyl-1,1'-biphenyl
Conditions | Yield |
---|---|
With silver carbonate In dimethyl sulfoxide at 120℃; for 4h; | A 18% B 5% |
Conditions | Yield |
---|---|
With thallium chloride at 100℃; durch Chlorieren; |
3-chlorobenzenediazonium
1-bromo-3-chlorobenzene
Conditions | Yield |
---|---|
With tetrachloromethane at 270℃; |
Conditions | Yield |
---|---|
With hydrogen bromide; acetic acid at 5 - 10℃; Einleiten von N2O3 und anschliessendes Erhitzen; | |
Diazotization.Behandlung der Diazoniumsalz-Loesung mit CuBr und HBr; | |
Stage #1: 3-chloro-aniline With hydrogen bromide; sodium nitrite In water at 0 - 5℃; Stage #2: With hydrogen bromide; copper(I) bromide In water |
Conditions | Yield |
---|---|
durch sukzessive Chlorierung, Bromierung, Verseifung und Behandlung mit Aethylnitrit; |
Conditions | Yield |
---|---|
Diazotization.Behandlung der Diazoniumsalz-Loesung mit CuCl; |
1-bromo-2,3-dichlorobenzene
A
1-bromo-3-chlorobenzene
B
1,2-dichloro-benzene
Conditions | Yield |
---|---|
With hexane at 25℃; for 4h; Irradiation; relative rate of dehalogenation, other polyhalobenzenes; |
Conditions | Yield |
---|---|
With tetrafluoroboric acid; N,N-dimethyl-formamide; sodium nitrite 1) water, 0 deg C, 2 h, 2) 40 deg C, 30 min; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With bromobenzene; Cu-HZSM-5 zeolite at 399.9℃; Mechanism; Product distribution; | A 11.6 % Chromat. B 3.2 % Chromat. |
1,3-dibromo-5-chlorobenzene
benzene
A
1-bromo-3-chlorobenzene
B
m-chlorobiphenyl
C
3-bromo-5-chloro-1,1’-biphenyl
Conditions | Yield |
---|---|
at 25℃; for 20h; | A 1.0 % Chromat. B 30.3 % Chromat. C 25.2 % Chromat. D 36.1 % Chromat. |
1,4-dibromo-2-chlorobenzene
benzene
A
1-bromo-3-chlorobenzene
B
4-bromo-1,1'-biphenyl
C
4-bromo-3-chloro-1,1'-biphenyl
D
2-chloro-4-bromobiphenyl
Conditions | Yield |
---|---|
at 25℃; for 20h; | A 2.7 % Chromat. B 8.2 % Chromat. C 4.3 % Chromat. D 17.1 % Chromat. |
Conditions | Yield |
---|---|
With Bromotrichloromethane; cyclohexane In 1,2-dichloro-ethane at 65℃; for 24h; Product distribution; Mechanism; |
Conditions | Yield |
---|---|
at 475℃; |
1-bromo-3-chlorobenzene
Conditions | Yield |
---|---|
With bromine; acetic acid |
1-bromo-3-chlorobenzene
Conditions | Yield |
---|---|
With hydrogen bromide Behandlung mit CuBr; |
1-bromo-3-chlorobenzene
Conditions | Yield |
---|---|
With sodium carbonate |
1-bromo-3-chlorobenzene
Conditions | Yield |
---|---|
With tetrachloromethane; bromine |
Conditions | Yield |
---|---|
With bromine at 475℃; |
Conditions | Yield |
---|---|
Stage #1: 1-bromo-3-chlorobenzene With lithium diisopropyl amide In tetrahydrofuran at -78℃; Stage #2: carbon dioxide In tetrahydrofuran at -78 - 20℃; for 2h; | 100% |
With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -75℃; for 2h; | 94% |
Stage #1: 1-bromo-3-chlorobenzene With n-butyllithium; diisopropylamine In tetrahydrofuran; hexanes at -78℃; for 2h; Stage #2: carbon dioxide In tetrahydrofuran; hexanes for 0.25h; Stage #3: With hydrogenchloride In tetrahydrofuran; hexanes; water Product distribution / selectivity; | 85% |
Stage #1: 1-bromo-3-chlorobenzene With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 1.5h; Stage #2: carbon dioxide In tetrahydrofuran; hexane at -78℃; for 0.333333h; Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane | |
Stage #1: 1-bromo-3-chlorobenzene With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -75℃; for 4h; Inert atmosphere; Stage #2: carbon dioxide In tetrahydrofuran at -70 - 20℃; for 5.5h; Inert atmosphere; |
1-bromo-3-chlorobenzene
acrylic acid n-butyl ester
3-chloro-trans-cinnamic acid n-butyl ester
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 5h; Heck reaction; | 100% |
With tetrabutylammonium acetate; palladium diacetate at 100℃; for 0.5h; Heck reaction; Air atmosphere; Ionic liquid; chemoselective reaction; |
1-bromo-3-chlorobenzene
1-t-Butoxycarbonylpiperazine
tert-butyl 4-(3-chlorophenyl)piperazine-1-carboxylate
Conditions | Yield |
---|---|
Stage #1: 1-bromo-3-chlorobenzene; 1-t-Butoxycarbonylpiperazine With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In xylene at 50℃; Stage #2: With macroporous polymer-supported isocyanate In xylene at 50℃; for 24h; | 100% |
With sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 100℃; | 83% |
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; XPhos In 1,4-dioxane at 95℃; for 2h; Inert atmosphere; | 61.2% |
With bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; DavePhos | |
With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene for 16h; Inert atmosphere; Heating; | 1.5 g |
Conditions | Yield |
---|---|
With potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos In 1,4-dioxane; water at 100℃; for 1h; | 99% |
Multi-step reaction with 2 steps 1: copper dichloride; potassium carbonate / 20 h / 130 °C / Inert atmosphere; Schlenk technique 2: potassium hydroxide / dimethyl sulfoxide / 3 h / 100 °C / Schlenk technique View Scheme | |
Multi-step reaction with 2 steps 1: fac-tris(2-phenylpyridinato-N,C2')iridium(III); tributyl-amine; water / acetonitrile / 36 h / 25 °C / Schlenk technique; Inert atmosphere; Sealed tube; Irradiation 2: air / 16 h / 25 °C / Inert atmosphere View Scheme | |
With copper(l) iodide; C20H20N4O4; caesium carbonate; Benzaldoxime In dimethyl sulfoxide at 80℃; for 18h; Inert atmosphere; Glovebox; |
Conditions | Yield |
---|---|
With copper(I) bromide In methanol; sodium methylate | 99% |
1-bromo-3-chlorobenzene
di-tert-butyl dicarbonate
3-chlorobenzoic acid tert-butyl ester
Conditions | Yield |
---|---|
Stage #1: 1-bromo-3-chlorobenzene With n-butyllithium; butyl magnesium bromide In tetrahydrofuran; hexane; toluene at -10℃; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; hexane; toluene at -10℃; Stage #3: With citric acid In tetrahydrofuran; hexane; toluene Further stages.; | 99% |
Stage #1: 1-bromo-3-chlorobenzene With n-butyllithium; butyl magnesium bromide In tetrahydrofuran; hexane; toluene at -10℃; for 1h; Inert atmosphere; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; hexane; toluene at -10℃; for 2h; Inert atmosphere; | 99% |
Stage #1: 1-bromo-3-chlorobenzene With n-hexyllithium In 2-methyltetrahydrofuran; hexane at 0℃; for 0.000194444h; Flow reactor; Stage #2: di-tert-butyl dicarbonate In 2-methyltetrahydrofuran; hexane at 0℃; for 0.00475h; Flow reactor; | 50% |
1-bromo-3-chlorobenzene
carbon monoxide
aniline
3-chloro-N-phenylbenzamide
Conditions | Yield |
---|---|
With palladium diacetate; sodium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 80℃; under 760.051 Torr; for 15h; | 99% |
Conditions | Yield |
---|---|
With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 80℃; | 99% |
1-bromo-3-chlorobenzene
carbon monoxide
benzylamine
N-benzyl-(3-chloro)benzamide
Conditions | Yield |
---|---|
With triethylamine In toluene at 70℃; under 760.051 Torr; for 7h; Catalytic behavior; | 99% |
Conditions | Yield |
---|---|
Stage #1: 9H-carbazole With methylmagnesium chloride In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene at 5 - 20℃; for 0.166667h; Inert atmosphere; Stage #2: 1-bromo-3-chlorobenzene With PdCl(π-allyl)(cyclohexyl-(1-methyl-2,2-diphenylcyclopropylphophine)) In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene at 108 - 112℃; for 2h; Inert atmosphere; | 99% |
Stage #1: 9H-carbazole With methylmagnesium chloride In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene at 5 - 20℃; for 0.333333h; Inert atmosphere; Stage #2: 1-bromo-3-chlorobenzene With di-tert-butyl(2,2-diphenyl-1-methyl-1-cyclopropyl)phosphine; bis(η3-allyl-μ-chloropalladium(II)) In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene at 110℃; for 1h; | 98.5% |
With bis(di-tert-butyl(2-butenyl)phosphine)dichloropalladium; sodium t-butanolate In o-xylene at 135℃; for 9h; Reagent/catalyst; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In 1,2-dimethoxyethane at 35℃; for 4h; ultrasonic acceleration of reduction; | A 98% B n/a |
Conditions | Yield |
---|---|
With 3,5-di-tert-butyl-2-hydroxybenzaldehyde; potassium carbonate; palladium dichloride In ethanol; water at 20℃; for 2h; Suzuki-Miyaura Coupling; | 98% |
With (BeDABCO)2Pd2Cl6; potassium carbonate In ethanol at 20℃; for 0.0166667h; Suzuki-Miyaura Coupling; | 97% |
With potassium phosphate; tetraphosphine N,N,N′,N′-tetra(diphenylphosphinomethyl)-pyridine-2,6-diamine; palladium dichloride In o-xylene at 90℃; for 2h; Concentration; Time; Temperature; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; | 97% |
Conditions | Yield |
---|---|
With copper In water at 100℃; for 12h; Ullmann reaction; | 98% |
Conditions | Yield |
---|---|
With 2C13H19N2(1+)*Cl6Pd2(2+); cesium fluoride In N,N-dimethyl-formamide at 120℃; for 0.0166667h; Stille Cross Coupling; Microwave irradiation; | 98% |
With [Pd{C6H2-(CH2CH2NH2)-(OMe)2-3,4}Br(PPh3)]; potassium carbonate In N,N-dimethyl-formamide at 90℃; for 0.0333333h; Stille coupling; Microwave irradiation; chemoselective reaction; | 92% |
With [Pd{C6H4(CH2N(CH2Ph)2)}(μ-Br)]2; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 0.0666667h; Stille coupling; Microwave irradiation; chemoselective reaction; | 90% |
With dmap; palladium dichloride for 0.333333h; Stille Cross Coupling; Microwave irradiation; | 61% |
Conditions | Yield |
---|---|
With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 120℃; for 48h; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 2.9-dimethyl-1,10-phenanthroline In 1,4-dioxane at 100℃; for 24h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Sealed tube; regioselective reaction; | 98% |
styrene
1-bromo-3-chlorobenzene
benzonitrile
6-chloro-2,4-diphenylquinoline
Conditions | Yield |
---|---|
With N-n-butyl-N-methylpiperidine bis(trifluoromethanesulfonyl)imide salt; acetylferrocene; H2SiEt2 at 60℃; for 8h; Reagent/catalyst; | 97.9% |
1-bromo-3-chlorobenzene
ethyl trifluoroacetate,
1-(3-chlorophenyl)-2,2,2-trifluoroethanone
Conditions | Yield |
---|---|
Stage #1: 1-bromo-3-chlorobenzene With n-butyllithium In tetrahydrofuran at -78 - -50℃; for 1h; Stage #2: ethyl trifluoroacetate, In tetrahydrofuran at -78 - 20℃; Reagent/catalyst; Solvent; Temperature; | 97.3% |
Stage #1: 1-bromo-3-chlorobenzene With magnesium In diethyl ether Inert atmosphere; Stage #2: ethyl trifluoroacetate, In diethyl ether at -78 - -50℃; for 3.5h; Inert atmosphere; |
methanol
1-bromo-3-chlorobenzene
carbon monoxide
methyl 3-chlorobenzoate
Conditions | Yield |
---|---|
With benzophenone; sodium methylate; cobalt(II) acetate at 40℃; under 750.075 Torr; for 15h; Irradiation; | 97% |
With sodium methylate; C2H5OOCCH2Co(CO)4 In diethyl ether at 25 - 35℃; | 78% |
Conditions | Yield |
---|---|
With potassium carbonate In methanol; water at 45℃; for 6h; Catalytic behavior; Heck Reaction; Green chemistry; stereoselective reaction; | 97% |
With CF3O3S(1-)*C52H46NO2P2Pd(1+); potassium carbonate In 1-methyl-pyrrolidin-2-one at 130℃; for 0.1h; Heck cross-coupling reaction; In air; Microwave irradiation; chemoselective reaction; | 96% |
With triethylamine In N,N-dimethyl-formamide for 0.233333h; Sonication; | 95% |
Conditions | Yield |
---|---|
With propyl methanoate; lithium chloride; copper(I) bromide In propan-1-ol at 110℃; for 4h; Sealed tube; | 97% |
Conditions | Yield |
---|---|
Stage #1: 1-bromo-3-chlorobenzene With n-butyllithium In tetrahydrofuran; hexane at -30℃; Inert atmosphere; Flow reactor; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -30℃; Inert atmosphere; Flow reactor; | 97% |
Stage #1: 1-bromo-3-chlorobenzene With isopropylmagnesium chloride; lithium chloride; 3-butyl-1-methylimidazolium acetate In tetrahydrofuran at 5 - 10℃; for 3h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran at 0℃; for 4h; Inert atmosphere; Stage #3: With hydrogenchloride In water at 5℃; for 0.5h; Inert atmosphere; | 66.43 g |
1-bromo-3-chlorobenzene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water for 20h; Inert atmosphere; Reflux; | 97% |
Conditions | Yield |
---|---|
With [Pd{C6H4(CH2N(CH2Ph)2)}(μ-Br)]2; potassium carbonate In 1-methyl-pyrrolidin-2-one at 130℃; for 5h; Microwave irradiation; chemoselective reaction; | 96% |
With [Pd{C6H2(CH2CH2NH2)-(OMe)2-2,3}(μ-Br)]2; potassium carbonate In 1-methyl-pyrrolidin-2-one at 120℃; for 0.0666667h; Microwave irradiation; | 96% |
With [Pd(C6H4CH2NH2-κ2-CN)PPh3MOBPPY]OTf; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 0.0333333h; Microwave irradiation; chemoselective reaction; | 92% |
1-bromo-3-chlorobenzene
Pentafluorobenzene
3'-chloro-2,3,4,5,6-pentafluoro-1,1'-biphenyl
Conditions | Yield |
---|---|
With di-tert-butyl(methyl)phosphonium tetrafluoroborate salt; potassium carbonate; palladium diacetate In N,N-dimethyl acetamide at 120℃; | 96% |
Conditions | Yield |
---|---|
With palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; Tri(p-tolyl)phosphine In tetrahydrofuran at 80℃; for 6h; Sonogashira Cross-Coupling; Inert atmosphere; Schlenk technique; | 96% |
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at 90℃; for 72h; Sonogashira Coupling; | 94% |
The Benzene,1-bromo-3-chloro-, with CAS registry number 108-37-2, belongs to the following product categories: (1)Aromatic Halides (substituted); (2)Bromine Compounds; (3)Chlorine Compounds; (4)Aryl; (5)C6; (6)Halogenated Hydrocarbons. It has the systematic name of 1-bromo-3-chlorobenzene. This chemical is a kind of clear colourless to light yellow liquid. The main use of this chemical is for organic synthesis.
Physical properties of Benzene,1-bromo-3-chloro-: (1)ACD/LogP: 3.54; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.54; (4)ACD/LogD (pH 7.4): 3.54; (5)ACD/BCF (pH 5.5): 286.19; (6)ACD/BCF (pH 7.4): 286.19; (7)ACD/KOC (pH 5.5): 1995.61; (8)ACD/KOC (pH 7.4): 1995.61; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: Å2; (13)Index of Refraction: 1.574; (14)Molar Refractivity: 38.83 cm3; (15)Molar Volume: 117.5 cm3; (16)Polarizability: 15.39×10-24cm3; (17)Surface Tension: 38.9 dyne/cm; (18)Enthalpy of Vaporization: 41.33 kJ/mol; (19)Vapour Pressure: 0.609 mmHg at 25°C.
Uses of p-Chloropropiophenone: it can be used to produce 2-bromo-6-chloro-benzoic acid. This reaction will need reagents 2,2,6,6-tetramethylpiperidine, butyllithium and solvents tetrahydrofuran, hexane. The reaction time is 2 hour(s) with reaction temperature of -75 ℃ ℃. The yield is about 94%.
When you are using this chemical, please be cautious about it as the following:
The Benzene,1-bromo-3-chloro- irritates to eyes, respiratory system and skin. This chemical is harmful by inhalation and harmful if swallowed. When use it, wear suitable protective clothing, gloves and eye/face protection. If contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: Clc1cc(Br)ccc1
(2)InChI: InChI=1/C6H4BrCl/c7-5-2-1-3-6(8)4-5/h1-4H
(3)InChIKey: JRGGUPZKKTVKOV-UHFFFAOYAS
(4)Std. InChI: InChI=1S/C6H4BrCl/c7-5-2-1-3-6(8)4-5/h1-4H
(5)Std. InChIKey: JRGGUPZKKTVKOV-UHFFFAOYSA-N
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