1,3,5-trisbromobenzene
Conditions | Yield |
---|---|
With dihydrogen peroxide In tetrahydrofuran for 0.166667h; Heating; | 100% |
Multi-step reaction with 2 steps 1: 92 percent / aq. NaOH / 0.5 h / 0 - 5 °C 2: 2 percent / aq. HI; HBF4 / acetonitrile / 24 h / 60 °C View Scheme | |
Multi-step reaction with 2 steps 1: 92 percent / aq. NaOH / 0.5 h / 0 - 5 °C 2: 13 percent / Et3PhCH2N(+)Cl(-); MeSO3H; Cu / acetonitrile / 1 h / 40 °C View Scheme |
Conditions | Yield |
---|---|
Stage #1: 2,4,6-tribromoaniline With hydrogenchloride; sodium nitrite In water Stage #2: With ethanol In water | 92% |
With sulfuric acid; sodium nitrite In ethanol at 20℃; Reflux; | 90% |
With ethanol; sulfuric acid; benzene Reagens 4: Natriumnitrit; |
(2,4,6-tribromophenyl)triethylsilane
1,3,5-trisbromobenzene
Conditions | Yield |
---|---|
With potassium fluoride In tetrahydrofuran; water for 12h; Heating; | 91% |
Conditions | Yield |
---|---|
With tetrafluoroboric acid; hydrogen iodide In acetonitrile at 60℃; for 24h; | A 2% B 84% |
C10H12Br3N3
A
1,3,5-trisbromobenzene
B
1,3,5-tribromo-2-chloro-benzene
Conditions | Yield |
---|---|
With methanesulfonic acid; N-benzyl-N,N,N-triethylammonium chloride; copper In acetonitrile at 40℃; for 1h; | A 13% B 78% |
2-methoxycarbonylphenylboronic acid
1,3,5-trisbromobenzene
Conditions | Yield |
---|---|
54% |
A
1,3,5-trisbromobenzene
B
2,4,6-tribromobenzenediazohydroxide
Conditions | Yield |
---|---|
With 2,2,2-trifluoroethanol at 34℃; for 24h; Irradiation; Further byproducts given; | A 47% B 8.8% |
With 2,2,2-trifluoroethanol at 34℃; for 24h; Irradiation; Further byproducts given; | A 47% B 8.8% |
With 2,2,2-trifluoroethanol at 34℃; for 24h; Further byproducts given; | A 35.5% B 4.1% |
A
1,3,5-trisbromobenzene
B
2,4,6-tribromobenzenediazohydroxide
Conditions | Yield |
---|---|
With 2,2,2-trifluoroethanol at 34℃; for 24h; Product distribution; influence of magnetic field; | A 47% B 8.8% C n/a |
2,4,6-tribromoaniline
copper(I) cyanide
A
1,3,5-trisbromobenzene
B
1,2,3,5-tetrabromobenzene
C
2,4,6-tribromonitrobenzene
D
2,4,6-tribromobenzonitrile
E
2,4,6-tribromophenol
Conditions | Yield |
---|---|
With tert.-butylnitrite In dimethyl sulfoxide at 60℃; for 1.5h; Product distribution; Mechanism; other anilines; | A 37% B 7% C 4% D 20% E 4% |
2,4,6-tribromoaniline
copper(I) cyanide
A
1,3,5-trisbromobenzene
B
2,4,6-tribromonitrobenzene
C
2,4,6-tribromobenzonitrile
D
2,4,6-tribromophenol
Conditions | Yield |
---|---|
With tert.-butylnitrite In dimethyl sulfoxide at 60℃; for 1.5h; Further byproducts given; | A 37% B 4% C 20% D 4% |
2,4,6-tribromoaniline
A
1,3,5-trisbromobenzene
B
1,2,3,5-tetrabromobenzene
C
2,4,6-tribromonitrobenzene
D
2,4,6-tribromobenzonitrile
Conditions | Yield |
---|---|
With tert.-butylnitrite In dimethyl sulfoxide at 60℃; for 1.5h; Further byproducts given; | A 37% B 7% C 4% D 20% |
2,4,6-tribromoaniline
A
1,3,5-trisbromobenzene
B
2,4,6-tribromonitrobenzene
C
2,4,6-tribromobenzonitrile
D
2,4,6-tribromophenol
Conditions | Yield |
---|---|
With tert.-butylnitrite In dimethyl sulfoxide at 60℃; for 1.5h; Further byproducts given; | A 37% B 4% C 20% D 4% |
1,3,5-trisbromobenzene
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid at 25℃; for 24h; Irradiation; | 34.3% |
1,3,5-trisbromobenzene
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid at 34℃; for 24h; Further byproducts given. Yields of byproduct given; | 25% |
1,3,5-trisbromobenzene
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid at 25℃; for 24h; Irradiation; | 20% |
1,3,5-trisbromobenzene
Conditions | Yield |
---|---|
With nitroxide | 13% |
1,3,5-trisbromobenzene
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid at 25℃; for 24h; Irradiation; | 4.4% |
methanol
A
1,3,5-trisbromobenzene
B
2,4,6-tribromoanisole
C
3,5-dibromo-ortho quinone diazide
D
2,4,6-tribromophenol
Conditions | Yield |
---|---|
bei der Belichtung.Irradiation; |
Conditions | Yield |
---|---|
bei der Belichtung.Irradiation; |
Conditions | Yield |
---|---|
zersetzt sich in Dunkel; |
Conditions | Yield |
---|---|
zersetzt sich in Sonnenlicht.Irradiation; |
Conditions | Yield |
---|---|
With aluminium trichloride |
Conditions | Yield |
---|---|
With aluminium trichloride |
Conditions | Yield |
---|---|
durch Ueberfuehrung in das Diazoniumperbromid und dessen Zersetzung mit Alkohol; |
Conditions | Yield |
---|---|
With potassium hydroxide at 150℃; |
2,4,6-tribromobenzaldehyde
1,3,5-trisbromobenzene
Conditions | Yield |
---|---|
With potassium hydroxide |
2,4,6-tribromo-benzenesulfonic acid
1,3,5-trisbromobenzene
1,3,5-trisbromobenzene
Conditions | Yield |
---|---|
With tri-tert-butyl phosphine; palladium diacetate; caesium carbonate In toluene for 72h; Inert atmosphere; Reflux; | 100% |
Conditions | Yield |
---|---|
Stage #1: methanol; 1,3,5-trisbromobenzene In toluene at 135℃; under 5320.36 Torr; for 0.75h; Stage #2: With triethylamine In toluene at 165℃; under 8360.56 Torr; for 11h; Temperature; | 99.5% |
With sodium methylate; copper(l) chloride In N,N-dimethyl-formamide at 100 - 110℃; for 6h; | 90% |
Stage #1: methanol; 1,3,5-trisbromobenzene In N,N-dimethyl-formamide Stage #2: With copper(l) iodide; sodium methylate |
1,3,5-trisbromobenzene
trimethylsilylacetylene
1,3,5-tris-(1-trimethylsilylethynyl)benzene
Conditions | Yield |
---|---|
Stage #1: 1,3,5-trisbromobenzene With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine at 50℃; for 0.25h; Sonogashira Cross-Coupling; Stage #2: trimethylsilylacetylene at 90℃; for 48h; Sonogashira Cross-Coupling; | 99% |
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 65℃; for 16h; Sonogashira coupling; | 96.4% |
With pyridine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 90℃; for 12h; Inert atmosphere; | 96.6% |
1,3,5-trisbromobenzene
tris((2-phenyl)ethynyl)indium
1,3,5-tris(2-phenylethynyl)benzene
Conditions | Yield |
---|---|
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran Heating; | 99% |
chloro-trimethyl-silane
1,3,5-trisbromobenzene
3,5-Bis-trimethylsilyl-bromobenzene
Conditions | Yield |
---|---|
Stage #1: 1,3,5-trisbromobenzene With n-butyllithium In diethyl ether at -78℃; for 1h; Stage #2: chloro-trimethyl-silane In diethyl ether at -78 - 20℃; Further stages.; | 99% |
Stage #1: 1,3,5-trisbromobenzene With n-butyllithium In diethyl ether; hexane at -80℃; for 0.25h; Inert atmosphere; Stage #2: chloro-trimethyl-silane In diethyl ether; hexane at -80 - 20℃; for 1h; Inert atmosphere; | 98% |
Stage #1: 1,3,5-trisbromobenzene With n-butyllithium In diethyl ether; hexane at -78℃; Stage #2: chloro-trimethyl-silane In diethyl ether; hexane at -78 - 20℃; | 85% |
With hydrogenchloride In diethyl ether; magnesium | 56% |
1,3,5-trisbromobenzene
tert-butyl 1-(4-cyanophenyl)hydrazine-1-carboxylate
Conditions | Yield |
---|---|
With caesium carbonate; palladium diacetate; tri-tert-butyl phosphine In hexane; toluene at 20 - 110℃; for 2.5h; | 99% |
1,3,5-trisbromobenzene
N-(4-benzoyl-phenyl)-hydrazinecarboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
With caesium carbonate; palladium diacetate; tri-tert-butyl phosphine In hexane; toluene at 20 - 110℃; for 3.5h; | 99% |
1,3,5-trisbromobenzene
N-(2-methoxy-phenyl)-hydrazinecarboxylic acid tert-butyl ester
N'-[3,5-bis-(N'-tert-butoxycarbonyl-N'-(2-methoxy-phenyl)-hydrazino)-phenyl]-N-(2-methoxy-phenyl)-hydrazinecarboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
With caesium carbonate; palladium diacetate; tri-tert-butyl phosphine In hexane; toluene at 20 - 110℃; for 2.5h; | 99% |
With palladium diacetate; caesium carbonate; tri tert-butylphosphoniumtetrafluoroborate In toluene for 2h; Heating; | 99% |
1,3,5-trisbromobenzene
1-tert-butoxycarbonyl-1-(4-phenylphenyl)hydrazine
Conditions | Yield |
---|---|
With caesium carbonate; palladium diacetate; tri-tert-butyl phosphine In hexane; toluene at 20 - 110℃; for 3.5h; | 99% |
1,3,5-trisbromobenzene
Conditions | Yield |
---|---|
With caesium carbonate; palladium diacetate; tri-tert-butyl phosphine In hexane; toluene at 20 - 110℃; for 2.5h; | 99% |
1,3,5-trisbromobenzene
3-methoxyphenylboronic acid
3,3''-dimethoxy-5'-(3-methoxyphenyl)-1,1':3',1''-terphenyl
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 80℃; for 48h; | 99% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 48h; Suzuki coupling; Inert atmosphere; Reflux; |
1,3,5-trisbromobenzene
2-amino-5-methylbenzoic acid methyl ester
1,3,5-tris(2-carbomethoxy-4-methylphenylamino)benzene
Conditions | Yield |
---|---|
With tri-tert-butyl phosphine; palladium diacetate; caesium carbonate In toluene for 72h; Inert atmosphere; Reflux; | 99% |
1,3,5-trisbromobenzene
Conditions | Yield |
---|---|
With tri-tert-butyl phosphine; palladium diacetate; caesium carbonate In toluene for 72h; Inert atmosphere; Reflux; | 99% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 90℃; for 12h; | 98% |
In N,N-dimethyl-formamide at 80℃; for 8h; | 70% |
In N,N-dimethyl-formamide at 80℃; for 28h; Inert atmosphere; | 48.9% |
In pyridine; methanol at 115℃; Rate constant; Product distribution; | |
In N,N-dimethyl-formamide at 90℃; for 0.25h; |
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 potassium tert-butylate In 5,5-dimethyl-1,3-cyclohexadiene at 130℃; for 7h; Buchwald-Hartwig coupling reaction; | 86% |
With potassium tert-butylate In 5,5-dimethyl-1,3-cyclohexadiene at 130℃; for 7h; Reagent/catalyst; Buchwald-Hartwig Coupling; Glovebox; | 86% |
Conditions | Yield |
---|---|
With sodium t-butanolate; tris(dibenzylideneacetone)dipalladium (0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 100℃; for 24h; | 98% |
1,3,5-trisbromobenzene
C9H15ClMg
Conditions | Yield |
---|---|
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane at 20℃; for 48h; Grignard reaction; | 98% |
Conditions | Yield |
---|---|
With methanol; Methyl formate; copper(l) chloride at 115℃; for 2h; Autoclave; Green chemistry; | 98% |
With copper(I) chloride In N,N-dimethyl-formamide at 130℃; for 6h; | 91% |
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 1h; Suzuki-Miyaura reaction; | 98% |
With sodium carbonate; palladium diacetate In water; N,N-dimethyl-formamide at 60℃; for 12h; Suzuki; | 97% |
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); tri-tert-butyl phosphine In 1,1,1,2,3,3,3-Heptafluoropropane; ethanol; 1,1,1,3,3-pentafluorobutane at 20℃; for 24h; Inert atmosphere; | 96% |
1,3,5-trisbromobenzene
N-phenyl-hydrazine carboxylic acid tert-butyl ester
N'-[3,5-bis-(N'-tert-butoxycarbonyl-N'-phenyl-hydrazino)-phenyl]-N-phenylhydrazinecarboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
With caesium carbonate; palladium diacetate; tri-tert-butyl phosphine In hexane; toluene at 20 - 110℃; for 2.5h; | 98% |
With palladium diacetate; caesium carbonate; tri tert-butylphosphoniumtetrafluoroborate In toluene for 2h; Heating; | 98% |
1,3,5-trisbromobenzene
tert-butyl 1-p-tolylhydrazinecarboxylate
Conditions | Yield |
---|---|
With caesium carbonate; palladium diacetate; tri-tert-butyl phosphine In hexane; toluene at 20 - 110℃; for 2.5h; | 98% |
1,3,5-trisbromobenzene
1,1-dimethyl-1,3-dihydrobenzo[c][1,2]oxasilole
(3,5-dibromophenyl)[2-(hydroxymethyl)phenyl]dimethylsilane
Conditions | Yield |
---|---|
Stage #1: 1,3,5-trisbromobenzene With n-butyllithium In diethyl ether; hexane at -78℃; for 2.5h; Stage #2: 1,1-dimethyl-1,3-dihydrobenzo[c][1,2]oxasilole In diethyl ether; hexane at -78 - 20℃; | 98% |
1,3,5-trisbromobenzene
bis(pinacol)diborane
1,3,5-tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene
Conditions | Yield |
---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 90℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere; | 98% |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 90℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere; | 98% |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 90℃; for 24h; Inert atmosphere; | 96% |
1,3,5-trisbromobenzene
di-p-tolylamine
N1,N1,N3,N3,N5,N5-hexakis(4-methylphenyl)-1,3,5-benzenetriamine
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 60℃; for 7h; Inert atmosphere; Schlenk technique; | 98% |
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 60℃; for 7h; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With (6-Dipp)PdCl2-SPhos; sodium t-butanolate In neat (no solvent) at 110℃; for 24h; Buchwald-Hartwig Coupling; | 98% |
1,3,5-trisbromobenzene
deuterated 1,3,5-tribromobenzene
Conditions | Yield |
---|---|
With water-d2; silver(l) oxide; 2-(dicyclohexylphosphino)-2'-methylbiphenyl In toluene at 60 - 80℃; Reagent/catalyst; | 97.1% |
With water-d2; potassium carbonate; silver carbonate; cyclohexyldiphenylphosphine In toluene at 120℃; for 12h; | 90% |
Conditions | Yield |
---|---|
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran Heating; | 97% |
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran for 6h; Heating; | 97% |
1,3,5-trisbromobenzene
4-methoxyphenylboronic acid
1,3,5-tris(4-methoxyphenyl)benzene
Conditions | Yield |
---|---|
With sodium carbonate; palladium diacetate In water; N,N-dimethyl-formamide at 60℃; for 12h; Suzuki; | 97% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane for 48h; Suzuki Coupling; Inert atmosphere; Reflux; | 95% |
With potassium carbonate In ethanol; water at 20℃; for 0.333333h; Suzuki-Miyaura Coupling; Green chemistry; | 95% |
1,3,5-trisbromobenzene
di-tert-butyl dicarbonate
tert-butyl 3,5-dibromobenzoate
Conditions | Yield |
---|---|
Stage #1: 1,3,5-trisbromobenzene 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.; | 97% |
Stage #1: 1,3,5-trisbromobenzene 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; Temperature; Inert atmosphere; | 97% |
Molecule structure of 1,3,5-Tribromobenzene (CAS NO.626-39-1):
IUPAC Name: 1,3,5-Tribromobenzene
Molecular Formula: C6H3Br3
Molecular Weight: 314.80002 g/mol
Density: 2.281 g/cm3
Melting Point: 117-121 °C(lit.)
Boiling Point: 269.4 °C at 760 mmHg
Flash Point: 115.5 °C
Formula Weight: 314.8 g/mol
Index of Refraction: 1.633
Molar Refractivity: 49.32 cm3
Molar Volume: 137.9 cm3
Surface Tension: 45.6 dyne/cm
Enthalpy of Vaporization: 48.71 kJ/mol
Vapour Pressure: 0.012 mmHg at 25 °C
XLogP3: 4.5
Exact Mass: 313.776441
MonoIsotopic Mass: 311.778488
Canonical SMILES: C1=C(C=C(C=C1Br)Br)Br
InChI: InChI=1S/C6H3Br3/c7-4-1-5(8)3-6(9)2-4/h1-3H
InChIKey: YWDUZLFWHVQCHY-UHFFFAOYSA-N
EINECS: 210-947-3
Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Organics;Benzene derivates;Aryl;C6;Halogenated Hydrocarbons
1,3,5-Tribromobenzene (626-39-1) is used as a fundamental raw material for organic synthesis.
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 22-24/25-37/39-26
S22:Do not breathe dust.
S24/25:Avoid contact with skin and eyes.
S37/39:Wear suitable gloves and eye/face protection.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3
RTECS: DC1957200
HS Code: 29036990
PURITY: 98.5% min
WATER: 0.2% max
1,3,5-Tribromobenzene (CAS NO.626-39-1) is also named as AI3-15483 ; NSC 62439 ; Benzene, 1,3,5-tribromo- . 1,3,5-Tribromobenzene (CAS NO.626-39-1) is Light yellow brown powder. It is insoluble in water, soluble in hot ethanol, glacial acetic acid.
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