Conditions | Yield |
---|---|
With sulfuric acid; dihydrogen peroxide; acetic acid; sodium bromide at 20 - 45℃; Temperature; Reagent/catalyst; | 99% |
With tetrabutylammomium bromide; dihydrogen peroxide; vanadia In water; acetonitrile at 5℃; for 1h; Bromination; | 98% |
With tetra-N-butylammonium tribromide In water; acetonitrile at 5℃; | 98% |
Conditions | Yield |
---|---|
With benzyltrimethylammonium tribromide; calcium carbonate In methanol; dichloromethane | 99% |
With dibromamine-T In acetonitrile at 20℃; for 0.166667h; | 85% |
Multi-step reaction with 2 steps 1: bromine / acetic acid; ethanol / 1 h / 0 °C 2: 3-oxo-1,3-dihydroisobenzofuran-1-carbonitrile; lithium tert-butoxide / tetrahydrofuran / 6.5 h / -78 - 25 °C / Inert atmosphere View Scheme |
2-(3,4-methylenedioxyphenyl)-1,3-dithiane
2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one
A
piperonal
B
2,4,6-tribromophenol
Conditions | Yield |
---|---|
With dihydrogen peroxide In water; acetonitrile at 20℃; for 0.25h; | A 98% B 80% |
4-Methanesulfonyloxy-benzenesulfonic acid 2,4,6-tribromo-phenyl ester
2,4,6-tribromophenol
Conditions | Yield |
---|---|
With sodium hydride In N,N,N,N,N,N-hexamethylphosphoric triamide for 2.16667h; Ambient temperature; | 97% |
Conditions | Yield |
---|---|
With benzyltrimethylammonium tribromide; calcium carbonate In methanol; dichloromethane | 96% |
Conditions | Yield |
---|---|
With water; hydrogen bromide; Aliquat 336 at 105℃; for 5h; Catalytic behavior; | 95% |
2,4,6-tribromophenol
Conditions | Yield |
---|---|
With magnesium In tetrahydrofuran; methanol at 20℃; for 5h; | 91% |
Conditions | Yield |
---|---|
With bromine In dichloromethane at 20℃; regioselective reaction; | 90% |
Multi-step reaction with 2 steps 1: dihydrogen peroxide; water / ethanol / 0.02 h / 20 °C / Green chemistry 2: dihydrogen peroxide; hydrogen bromide; water / ethanol / 0.02 h / 20 °C / Green chemistry View Scheme |
4-Methanesulfonyl-benzenesulfonic acid 2,4,6-tribromo-phenyl ester
2,4,6-tribromophenol
Conditions | Yield |
---|---|
With sodium hydride In N,N,N,N,N,N-hexamethylphosphoric triamide for 2.16667h; Ambient temperature; | 89% |
C6H5Br3O
2,4,6-tribromophenol
Conditions | Yield |
---|---|
With oxygen; copper diacetate; trifluoroacetic acid; lithium bromide In acetonitrile at 80℃; under 760.051 Torr; for 10h; Sealed tube; | 89% |
di(p-tolyl) disulfide
para-thiocresol
4-Methanesulfonyloxy-benzenesulfonic acid 2,4,6-tribromo-phenyl ester
A
tris(p-tolylthio)methane
B
2,4,6-tribromophenol
Conditions | Yield |
---|---|
With sodium hydride In N,N,N,N,N,N-hexamethylphosphoric triamide for 2.16667h; Ambient temperature; | A 22% B 87% |
Conditions | Yield |
---|---|
With trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane; hydrogen bromide In water at 20℃; for 1.6h; | 86% |
With trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane; ammonium bromide; acetic acid at 20℃; for 2h; regioselective reaction; | 85% |
Conditions | Yield |
---|---|
With water; hydrogen bromide; dihydrogen peroxide In ethanol at 20℃; for 0.0166667h; Green chemistry; | 84% |
phenol
A
4-bromo-phenol
B
2-hydroxybromobenzene
C
2,4,6-tribromophenol
Conditions | Yield |
---|---|
With pyridine; bromine; silver nitrate In acetonitrile for 2h; Ambient temperature; | A 3% B 82% C 3% |
With N-Bromosuccinimide In acetonitrile at 20℃; for 0.166667h; | A 12 %Chromat. B 7 %Chromat. C 55 %Chromat. |
(2,4,6-tribromo-phenoxy)-acetic acid
2,4,6-tribromophenol
Conditions | Yield |
---|---|
Stage #1: (2,4,6-tribromo-phenoxy)-acetic acid With triethylamine In N,N-dimethyl-formamide; toluene for 3h; Curtius rearrangement; Heating; Stage #2: With potassium hydroxide In N,N-dimethyl-formamide; toluene at 25℃; for 0.133333h; Stage #3: With potassium hydroxide; glycerol In ethanol; N,N-dimethyl-formamide; toluene for 2h; Heating; Further stages.; | 82% |
Conditions | Yield |
---|---|
With N-Bromosuccinimide; diisopropylamine In dichloromethane for 1h; Ambient temperature; | A 80% B 5.7 % Chromat. |
di-isopropyl azodicarboxylate
2,6-dibromophenol
A
bis(1-methylethyl) 1,2-hydrazinedicarboxylate
B
2,4,6-tribromophenol
Conditions | Yield |
---|---|
With ZrBr4 In dichloromethane at 20℃; for 2h; | A n/a B 79% |
di(p-tolyl) disulfide
para-thiocresol
4-Methanesulfonyl-benzenesulfonic acid 2,4,6-tribromo-phenyl ester
A
tris(p-tolylthio)methane
B
2,4,6-tribromophenol
Conditions | Yield |
---|---|
With sodium hydride In N,N,N,N,N,N-hexamethylphosphoric triamide for 2.16667h; Ambient temperature; | A 4% B 78% |
3,7-dimethyl-2E,6-octadien-1-yl acetate
A
6-bromo-3,7-dimethylocta-2,7-dienyl acetate
B
(E)-6,7-dibromo-3,7-dimethyloct-2-en-1-yl acetate
C
8-bromo-3,7-dimethylocta-2,7-dienyl acetate
D
2,4,6-tribromophenol
Conditions | Yield |
---|---|
With 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one In dichloromethane for 15h; Ambient temperature; Title compound not separated from byproducts; | A n/a B 14% C n/a D 76% |
2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one
A
6-bromo-3,7-dimethylocta-2,7-dienyl acetate
B
(E)-6,7-dibromo-3,7-dimethyloct-2-en-1-yl acetate
C
8-bromo-3,7-dimethylocta-2,7-dienyl acetate
D
2,4,6-tribromophenol
Conditions | Yield |
---|---|
With methyl geranate In dichloromethane for 15h; Ambient temperature; | A n/a B 14% C n/a D 76% |
2,4-dibromophenol
di-isopropyl azodicarboxylate
A
bis(1-methylethyl) 1,2-hydrazinedicarboxylate
B
2,4,6-tribromophenol
Conditions | Yield |
---|---|
With ZrBr4 In dichloromethane at 20℃; for 4h; | A n/a B 75% |
2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one
2,4,6-tribromophenol
Conditions | Yield |
---|---|
With betaine In ethanol at 60℃; for 72h; | 71.4% |
With 3-oxo-1,3-dihydroisobenzofuran-1-carbonitrile; lithium tert-butoxide In tetrahydrofuran at -78 - 25℃; for 6.5h; Inert atmosphere; | 36% |
With ammonium hydroxide; benzene |
Conditions | Yield |
---|---|
With samarium; copper(l) iodide; potassium iodide In tetrahydrofuran at 20℃; Molecular sieve; diastereoselective reaction; | A 70% B n/a |
(2-bromophenyl)boronic acid
2,4,6-tribromophenol
Conditions | Yield |
---|---|
With water; hydrogen bromide; dihydrogen peroxide In ethanol at 20℃; for 0.0166667h; Green chemistry; | 55% |
phenol
A
4-bromo-phenol
B
2,4-dibromophenol
C
2,4,6-tribromophenol
Conditions | Yield |
---|---|
With hydrogenchloride; C20H17N5O4V(1+)*ClO4(1-); dihydrogen peroxide; potassium bromide In water; acetonitrile at 20℃; for 20h; pH=3; | A 5% B 51% C 2% |
With [oxovanadium(V)(pyridine-2,6-dicarboxylate)(benzohydroxamate)]; dihydrogen peroxide; nitric acid; potassium bromide In water; acetonitrile pH=3; Reagent/catalyst; Overall yield = 72 %; | A 11% B 41% C 12% |
With hydrogenchloride; dihydrogen peroxide; potassium bromide In water; acetonitrile at 20℃; for 20h; pH=Ca. 3; | A 13% B 27% C 41% |
Conditions | Yield |
---|---|
With bromine for 4h; Phase-vanishing reaction with phase screen; Neat (no solvent); | A 41% B 46% |
With tetra-N-butylammonium tribromide In water; tert-butyl alcohol at 23℃; for 72h; pH=1; | A 13 %Spectr. B 86 %Spectr. |
5-bromo-2-geranyl-1,4-benzenediol
A
1,3,5-tribromo-2-methoxymethoxybenzene
C
2,4,6-tribromophenol
Conditions | Yield |
---|---|
A 16% B 35% C 42% |
Conditions | Yield |
---|---|
With dibromamine-T In acetonitrile at 20℃; | A 40% B 10% |
With bromine In water; tert-butyl alcohol at 23℃; for 72h; pH=1; | A 8 %Spectr. B 88 %Spectr. |
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-tribromophenol
4-diisopropylsilanyl-benzoic acid 2,4,6-tribromo-phenyl ester
Conditions | Yield |
---|---|
With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride In pyridine at 20℃; for 0.5h; | 100% |
Conditions | Yield |
---|---|
With tribenzylamine In benzene for 0.166667h; | 99.8% |
1,3,5-trichloro-2,4,6-triazine
2,4,6-tribromophenol
phenol
2,4,6-tris(2,4,6-tribromophenoxy)-1,3,5-triazine
Conditions | Yield |
---|---|
With sodium hydroxide; hydrogen bromide; bromine; hydrazine In water; acetone | 99% |
tert.-butylhydroperoxide
tri(p-tolyl)antimony
2,4,6-tribromophenol
benzene
Conditions | Yield |
---|---|
Stage #1: tert.-butylhydroperoxide; tri(p-tolyl)antimony; 2,4,6-tribromophenol In diethyl ether at 20℃; for 24h; Stage #2: benzene In n-heptane | 99% |
2,4,6-tribromophenol
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 18h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
Stage #1: 2-chloro-ethanol With tetrachlorosilane In 1,4-dioxane at 0 - 50℃; for 2h; Inert atmosphere; Stage #2: 2,4,6-tribromophenol In 1,4-dioxane at 80℃; for 5h; Stage #3: 2-chloro-ethanol In 1,4-dioxane at 25 - 50℃; for 4.5h; Solvent; Temperature; | 98.8% |
Conditions | Yield |
---|---|
Stage #1: 2,3-Dichloro-1-propanol With tetrachlorosilane In diethylene glycol dimethyl ether at 8 - 35℃; for 2h; Inert atmosphere; Stage #2: 2,4,6-tribromophenol In diethylene glycol dimethyl ether at 90℃; for 4h; Inert atmosphere; Stage #3: 2,3-Dichloro-1-propanol In diethylene glycol dimethyl ether at 50 - 95℃; for 5h; Temperature; Solvent; Inert atmosphere; | 98.6% |
4-bromophenyl butyl ether
2,4,6-tribromophenol
1,3,5-tribromo-2-phenoxybutoxybenzene
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 17h; | 98.5% |
1-Bromooctadecane
2,4,6-tribromophenol
1,3,5-tribromo-2-octadecyloxybenzene
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 17h; | 98.5% |
Conditions | Yield |
---|---|
In diethyl ether; water aq. H2O2 was added to mixt. of SbPh3 and ligand in ether, allowed to stand for 12 h; solvent was evapd., washed with benzene, dried; | 98% |
1,3,5-trichloro-2,4,6-triazine
2,4,6-tribromophenol
2,4,6-tris(2,4,6-tribromophenoxy)-1,3,5-triazine
Conditions | Yield |
---|---|
With magnesium silicate; sodium hydroxide; sodium sulfite; trimethylamine In dichloromethane; water at 3 - 30℃; Product distribution / selectivity; Reflux; | 98% |
Stage #1: 2,4,6-tribromophenol With potassium carbonate In acetone for 1.5h; Heating / reflux; Stage #2: 1,3,5-trichloro-2,4,6-triazine In acetone at 25℃; for 3.25h; Heating / reflux; |
ethyl 5-bromovalerate
2,4,6-tribromophenol
ethyl 5-(2,4,6-tribromophenoxy)pentanoate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 24h; | 98% |
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 12h; Inert atmosphere; | 88% |
Conditions | Yield |
---|---|
Stage #1: 1,3-Dichloro-2-propanol With tetrachlorosilane In 1,1,2,2-tetrachloroethane at 8 - 35℃; for 2h; Inert atmosphere; Stage #2: 2,4,6-tribromophenol In 1,1,2,2-tetrachloroethane at 85℃; for 4.5h; Inert atmosphere; Stage #3: 1,3-Dichloro-2-propanol In 1,1,2,2-tetrachloroethane at 50 - 90℃; for 5.5h; Solvent; Temperature; Inert atmosphere; | 98% |
1-methyl-1H-imidazole
1,3,5-trichloro-2,4,6-triazine
2,4,6-tribromophenol
2,4,6-tris(2,4,6-tribromophenoxy)-1,3,5-triazine
Conditions | Yield |
---|---|
Stage #1: 1-methyl-1H-imidazole; 2,4,6-tribromophenol In chlorobenzene at 40℃; for 2h; Stage #2: 1,3,5-trichloro-2,4,6-triazine In chlorobenzene at 20 - 25℃; for 4h; Temperature; | 98% |
Conditions | Yield |
---|---|
Stage #1: 2-bromoethanol With tetrachlorosilane In diethylene glycol dimethyl ether at 0 - 20℃; for 2h; Inert atmosphere; Stage #2: 2,4,6-tribromophenol In diethylene glycol dimethyl ether at 60℃; for 5h; Stage #3: 2-bromoethanol In diethylene glycol dimethyl ether at 25 - 45℃; for 5.5h; Solvent; Temperature; | 97.3% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide Heating; | 97.1% |
Conditions | Yield |
---|---|
With sodium In methanol for 7h; Heating; | 97% |
4-methoxyphenylboronic acid
2,4,6-tribromophenol
2,4,6-tris(4-methoxyphenyl)phenol
Conditions | Yield |
---|---|
With sodium carbonate; palladium diacetate In water; N,N-dimethyl-formamide at 60℃; for 12h; Suzuki; | 97% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 27℃; | 97% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h; | 97% |
With sodium hydride In mineral oil at 80℃; |
Conditions | Yield |
---|---|
With pyrographite In dichloromethane at 20℃; for 1.5h; Acetylation; | 96% |
With lanthanum(III) nitrate at 20℃; for 0.3h; | 95% |
With sodium acetate | |
With sodium hydroxide | |
With sulfuric acid; acetic acid |
Conditions | Yield |
---|---|
With sodium carbonate; palladium diacetate In water; N,N-dimethyl-formamide at 60℃; for 12h; Suzuki; | 96% |
With potassium fluoride; palladium diacetate for 0.166667h; Suzuki coupling reaction; microwave irradiation; | 76% |
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 6h; Suzuki-Miyaura coupling reaction; Inert atmosphere; | 62% |
With C28H40Br4N4Pd2; potassium carbonate In water; acetone at 20℃; for 24h; Suzuki Coupling; | 50% |
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate at 100℃; for 0.5h; Suzuki-Miyaura Coupling; Microwave irradiation; Inert atmosphere; |
Conditions | Yield |
---|---|
With cesium fluoride In acetonitrile for 5h; Heating; | 96% |
Conditions | Yield |
---|---|
With ammonia In chloroform at 55℃; for 2h; Temperature; Concentration; Solvent; Reagent/catalyst; Inert atmosphere; Sealed tube; | 95.3% |
mononitrophenyl carbonate
2,4,6-tribromophenol
bis(2,4,6-tribromophenyl) carbonate
Conditions | Yield |
---|---|
dmap In dichloromethane at 25℃; for 8h; | 95% |
2,4,6-TRIBROMOPHENOL (118-79-6) can be used as antiseptic & germicide (eg, in pharmaceutical prepns). It is also used for producing disinfectant and preservative drug bismuth tribromophenate.
2,4,6-TRIBROMOPHENOL (118-79-6) is used also as an flame retardant in epoxy, polyurethane, plastics, paper, textiles and others; as well as an intermediate for the production of other commercial flame retardants and fire extinguishing media. It can be used as an antiseptic agent.
1. | orl-rat LD50:2 g/kg | 85JCAE Prehled Prumyslove Toxikologie; Organicke Latky Marhold, J.,Prague, Czechoslovakia.: Avicenum,1986,524. |
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