1,2,3,5-tetrachlorobenzene
A
1,3,5-trichlorobenzene
B
1,2,4-Trichlorobenzene
Conditions | Yield |
---|---|
With radical anion of p,p'-di-tert-butylbiphenyl In tetrahydrofuran at -25℃; Irradiation; | A 2.8% B 97.2% |
1-bromo-3,5-dichlorobenzene
1,3,5-trichlorobenzene
Conditions | Yield |
---|---|
With chlorine; sodium thiosulfate | 97.2% |
Conditions | Yield |
---|---|
With sulfuric acid; hypophosphorous acid; sodium nitrite In water at -5 - 25℃; | 95% |
With tetrafluoroboric acid; N,N-dimethyl-formamide; sodium nitrite In water at 45℃; for 0.25h; Product distribution; or benzene, room temperature, 3 h; | 94% |
Stage #1: 2,4,6-trichloroaniline With sulfuric acid Stage #2: With sodium nitrite In water for 0.75h; Cooling with ice; Stage #3: With sodium hypophosphite hydrate In hexane; water at 20℃; Cooling with ice; | 84% |
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; N-benzyl-N,N,N-triethylammonium chloride; sodium nitrite In tetrachloromethane 1.) 0 deg C, 1.5 h, 2.) r.t., 14 h; | 95% |
1,3-dibromo-5-chlorobenzene
1,3,5-trichlorobenzene
Conditions | Yield |
---|---|
With chlorine; sodium thiosulfate In tetrachloromethane | 91% |
LINDANE
A
1,3,5-trichlorobenzene
B
1,2,4-Trichlorobenzene
C
1,2,3-trichlorobenzene
Conditions | Yield |
---|---|
With ammonia at 25℃; Product distribution; Further Variations:; Reagents; Dehalogenation; | A 5% B 87% C 8% |
at 25℃; pH=8.32; Kinetics; Product distribution; Further Variations:; pH-values; | |
With (5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato)iron(III) chloride; tetrabutylammonium perchlorate In N,N-dimethyl-formamide for 4h; Electrolysis; |
Conditions | Yield |
---|---|
With tetrafluoroboric acid; hydrogen iodide In acetonitrile at 60℃; for 24h; | A 3% B 86% |
1,2,3,5-tetrachlorobenzene
A
1,3,5-trichlorobenzene
B
1,2,4-Trichlorobenzene
C
1,2,3-trichlorobenzene
Conditions | Yield |
---|---|
With radical anion of p,p'-di-tert-butylbiphenyl; triethylamine In tetrahydrofuran at 45℃; Irradiation; | A 18.8% B 75.5% C 5.7% |
With radical anion of p,p'-di-tert-butylbiphenyl; triethylamine In tetrahydrofuran at 45℃; Product distribution; Rate constant; Mechanism; Irradiation; radical anion of naphthalene, different temperatures, without Et3N; | A 18.8% B 75.5% C 5.7% |
With radical anion of p,p'-di-tert-butylbiphenyl In tetrahydrofuran at 45℃; Irradiation; | A 59.2% B 40.5% C 0.3% |
In acetonitrile at 40℃; Product distribution; Mechanism; Quantum yield; Irradiation; in the presence of triethylamine; | A 18.77 % Chromat. B 75.45 % Chromat. C 5.78 % Chromat. |
With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene at 70℃; Rate constant; relative reactivity in dehalogenation; |
A
1,3,5-trichlorobenzene
B
2,2',4,4',6,6'-Hexachlorobiphenyl
C
2,4,6-trichlorobenzenediazohydroxide
D
2,2',4,4',6,6'-Hexachlor-azobenzen
Conditions | Yield |
---|---|
With 2,2,2-trifluoroethanol at 34℃; for 24h; Irradiation; Further byproducts given; | A 51.4% B 12.4% C 1.5% D 15.3% |
A
1,3,5-trichlorobenzene
B
2,2',4,4',6,6'-Hexachlorobiphenyl
C
2,4,6-trichlorobenzenediazohydroxide
D
2,2',4,4',6,6'-Hexachlor-azobenzen
Conditions | Yield |
---|---|
With 2,2,2-trifluoroethanol at 34℃; for 24h; Product distribution; influence of magnetic field; | A 51.4% B 12.4% C 1.5% D 15.3% E n/a |
A
1,3,5-trichlorobenzene
B
2,2',4,4',6,6'-Hexachlorobiphenyl
C
2,2',4,4',6,6'-Hexachlor-azobenzen
Conditions | Yield |
---|---|
With 2,2,2-trifluoroethanol at 34℃; for 24h; Further byproducts given; | A 40.4% B 3.5% C 2.3% |
3-Amino-3-(2,4,6-trichlor-phenylazo)propensaeuremethylester
A
1,3,5-trichlorobenzene
B
2,4,6-trichlorophenylhydrazine hydrochloride
C
2,2',4,4',6,6'-Hexachlor-azobenzen
Conditions | Yield |
---|---|
With hydrogenchloride In methanol for 0.5h; Ambient temperature; | A 37% B 35% C n/a |
With hydrogenchloride In methanol for 0.5h; Product distribution; Mechanism; Ambient temperature; | A 37% B 35% C n/a |
2-methoxyacrylic acid ethyl ester
2,4,6-trichlorobenzoic acid
A
1,3,5-trichlorobenzene
Conditions | Yield |
---|---|
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane; dimethyl sulfoxide at 130℃; for 24h; Solvent; Sealed tube; Inert atmosphere; stereoselective reaction; | A n/a B 24% C 16% D n/a |
1,3,5-trichlorobenzene
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid at 34℃; for 24h; Irradiation; | 13% |
With trifluorormethanesulfonic acid at 34℃; for 24h; | 6.8% |
pyridine
alpha-hexachlorocyclohexane
A
1,3,5-trichlorobenzene
B
1,2,4-Trichlorobenzene
C
1,2,3-trichlorobenzene
quinoline
alpha-hexachlorocyclohexane
A
1,3,5-trichlorobenzene
B
1,2,4-Trichlorobenzene
C
1,2,3-trichlorobenzene
Conditions | Yield |
---|---|
at 105 - 110℃; |
Conditions | Yield |
---|---|
With tetrachloromethane at 290℃; | |
With hydrogenchloride at 260℃; |
ethanol
delta-lindane
A
1,3,5-trichlorobenzene
B
1,2,4-Trichlorobenzene
C
1,2,3-trichlorobenzene
Conditions | Yield |
---|---|
Product distribution; |
ethanol
LINDANE
A
1,3,5-trichlorobenzene
B
1,2,4-Trichlorobenzene
C
1,2,3-trichlorobenzene
Conditions | Yield |
---|---|
Product distribution; |
ethanol
beta-hexachlorocyclohexane
A
1,3,5-trichlorobenzene
B
1,2,4-Trichlorobenzene
C
1,2,3-trichlorobenzene
Conditions | Yield |
---|---|
Product distribution; |
ethanol
alpha-hexachlorocyclohexane
A
1,3,5-trichlorobenzene
B
1,2,4-Trichlorobenzene
C
1,2,3-trichlorobenzene
Conditions | Yield |
---|---|
Product distribution; |
Conditions | Yield |
---|---|
With nitrogen bei Licht- und Waermestrahlung einer 100 Watt-Lampe; |
Conditions | Yield |
---|---|
With sodium ethanolate | |
With sodium methylate In methanol; dimethyl sulfoxide at 50.1℃; Rate constant; |
Conditions | Yield |
---|---|
ueber mehrere Stufen; |
2,4,6-trichlorobenzaldehyde
1,3,5-trichlorobenzene
Conditions | Yield |
---|---|
With potassium hydroxide |
5-chloro-1,3-benzenediamine
1,3,5-trichlorobenzene
Conditions | Yield |
---|---|
diazotiert und mit CuCl+HCl behandelt; |
alpha-hexachlorocyclohexane
A
1,3,5-trichlorobenzene
B
1,2,4-Trichlorobenzene
C
1,2,3-trichlorobenzene
Conditions | Yield |
---|---|
With potassium phosphate; palladium diacetate; DavePhos In toluene at 90℃; Suzuki Coupling; Inert atmosphere; Schlenk technique; | 100% |
With potassium phosphate; palladium bis(dibenzylideneacetone)palladium(0); catacxium A In toluene at 110℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere; Sealed tube; | 94% |
With trans-chloro(9-phenanthrenyl)bis(triphenylphosphine)nickel(II); potassium carbonate; triphenylphosphine In toluene at 110℃; for 18h; Suzuki-Miyaura Coupling; Inert atmosphere; | 91% |
With potassium carbonate In ethanol; water at 90℃; for 36h; Suzuki-Miyaura Coupling; | 21% |
Conditions | Yield |
---|---|
Stage #1: 1,3,5-trichlorobenzene With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere; Stage #2: acetaldehyde In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
Stage #1: 1,3,5-trichlorobenzene With magnesium; ethylene dibromide; lithium chloride In tetrahydrofuran at 25℃; for 0.5h; Stage #2: carbon dioxide In tetrahydrofuran at 25℃; for 1h; Further stages; | 99% |
1,3,5-trichlorobenzene
4-methylphenylboronic acid
1,3,5-tris(4-methyl-phenyl)-benzene
Conditions | Yield |
---|---|
With potassium phosphate; tetrabutylammomium bromide In water at 95℃; for 20h; Suzuki-Miyaura Coupling; | 99% |
With potassium phosphate; palladium bis(dibenzylideneacetone)palladium(0); catacxium A In toluene at 110℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere; Sealed tube; | 90% |
With potassium carbonate In ethanol; water at 90℃; for 24h; Suzuki-Miyaura Coupling; | 12% |
Conditions | Yield |
---|---|
Stage #1: n-decyl glycolate With sodium methylate at 120℃; Stage #2: 1,3,5-trichlorobenzene at 160℃; | 98.9% |
Conditions | Yield |
---|---|
With nitric acid In sulfuric acid at 25 - 120℃; Product distribution; | 98.5% |
Stage #1: 1,3,5-trichlorobenzene With nitric acid at 40℃; for 0.25h; Stage #2: With sulfuric acid at 40 - 80℃; for 1.5h; | 96% |
With sulfuric acid; nitric acid | 61% |
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 80 - 90℃; Concentration; Reagent/catalyst; Solvent; Temperature; Time; | 98% |
In N,N,N,N,N,N-hexamethylphosphoric triamide at 120℃; for 1h; | 78% |
In methanol; dimethyl sulfoxide at 50.1℃; Rate constant; | |
With methanol at 180℃; |
1,3,5-trichlorobenzene
trichlorofluoromethane
1,3,5-trichloro-2-(trifluoromethyl)benzene
Conditions | Yield |
---|---|
With aluminium trichloride Ambient temperature; | 98% |
With aluminium trichloride 1a) 4 h, r.t., 1b) 4 h, -10 deg C; | 98% |
1,3,5-trichlorobenzene
1,3,5-trichloro-2,4,6-triiodo-benzene
Conditions | Yield |
---|---|
With sulfuric acid; iodine; periodic acid at 20℃; Inert atmosphere; | 98% |
With sulfuric acid; iodine; periodic acid at 20℃; | 98% |
With sulfuric acid; periodic acid | 96% |
Conditions | Yield |
---|---|
With triethylamine In toluene for 8h; Solvent; Time; Reflux; | 96.5% |
1,3,5-trichlorobenzene
α-chlorobis(pentachlorophenyl)methane
Bis-(2,4,6-trichlorophenyl)-methane
Conditions | Yield |
---|---|
With aluminium trichloride at 85℃; for 2.5h; | 96% |
1,3,5-trichlorobenzene
N,N-dimethyl-formamide
2,4,6-trichlorobenzaldehyde
Conditions | Yield |
---|---|
Stage #1: 1,3,5-trichlorobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78℃; for 1.5h; | 96% |
Stage #1: 1,3,5-trichlorobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78℃; for 1.5h; Inert atmosphere; | 95% |
Stage #1: 1,3,5-trichlorobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78℃; for 1.5h; | 95% |
Conditions | Yield |
---|---|
In N,N,N,N,N,N-hexamethylphosphoric triamide at 100℃; for 1h; | 95% |
In N,N-dimethyl acetamide at 100℃; for 24h; |
1,3,5-trichlorobenzene
bis(pinacol)diborane
1,3,5-tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene
Conditions | Yield |
---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); lithium chloride In toluene at 100℃; for 15h; | 95% |
1,3,5-trichlorobenzene
9H-carbazole
1,3,5-tris(9H-carbazol-9-yl)benzene
Conditions | Yield |
---|---|
With di-tert-butyl(2,2-diphenyl-1-methyl-1-cyclopropyl)phosphine; bis(η3-allyl-μ-chloropalladium(II)); methylmagnesium chloride In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene at 5℃; Buchwald-Hartwig Coupling; Inert atmosphere; Reflux; | 94.6% |
With di-tert-butyl(2,2-diphenyl-1-methyl-1-cyclopropyl)phosphine; bis(η3-allyl-μ-chloropalladium(II)); sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 3h; Inert atmosphere; | 67% |
1,3,5-trichlorobenzene
4-methoxyphenylboronic acid
1,3,5-tris(4-methoxyphenyl)benzene
Conditions | Yield |
---|---|
With potassium phosphate; palladium bis(dibenzylideneacetone)palladium(0); catacxium A In toluene at 110℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere; Sealed tube; | 94% |
With 1,3-bis(2,6-diisopropylphenyl)-1,3,2-diazaphospholidine-2-oxide; potassium phosphate; chloro(1-naphthyl)bis(triphenylphosphine)nickel(II) In toluene at 110℃; for 18h; Suzuki Coupling; Schlenk technique; Inert atmosphere; | 67% |
1,3,5-trichlorobenzene
2,4,6-trichlorobenzaldehyde
Conditions | Yield |
---|---|
Stage #1: 1,3,5-trichlorobenzene With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 2,4,6-trichlorobenzaldehyde In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; | 94% |
Stage #1: 1,3,5-trichlorobenzene With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 2,4,6-trichlorobenzaldehyde In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
With ammonium sulfate; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; ammonia; sodium t-butanolate; tert-butyl XPhos In 1,4-dioxane at 100℃; for 24h; Reagent/catalyst; Sealed tube; Inert atmosphere; | 93% |
With lithium amide; ammonia at -50℃; | |
With ammonia |
Conditions | Yield |
---|---|
With potassium hydroxide; (Tricyclohexyl-n-dodecyl)phosphonium bromide In toluene at 50℃; for 3h; | A n/a B 93% |
1,3,5-trichlorobenzene
n-decyl magnesium bromide
1,3,5-tridecylbenzene
Conditions | Yield |
---|---|
1,2-bis(diphenylphosphino)ethane nickel(II) chloride In diethyl ether 1.) 18 h, 0 deg C to room temperature, 2.) 2 h, reflux; | 93% |
Conditions | Yield |
---|---|
With Pd-PEPPSI-IPrAn; potassium tert-butylate In toluene at 80℃; for 24h; Suzuki coupling; Inert atmosphere; | 93% |
1,3,5-trichlorobenzene
4-(4-nitrophenoxy)phenol
Conditions | Yield |
---|---|
Stage #1: 4-(4-nitrophenoxy)phenol With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere; Stage #2: 1,3,5-trichlorobenzene In N,N-dimethyl-formamide at 150℃; for 12h; Inert atmosphere; | 92.8% |
chloro-trimethyl-silane
1,3,5-trichlorobenzene
(2,4,6-trichlorophenyl)trimethylsilane
Conditions | Yield |
---|---|
Stage #1: 1,3,5-trichlorobenzene With sec.-butyllithium In tetrahydrofuran; cyclohexane at -100℃; for 2h; Stage #2: chloro-trimethyl-silane In tetrahydrofuran; cyclohexane | 92% |
Stage #1: 1,3,5-trichlorobenzene With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -75℃; Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at -75℃; | 72% |
1,3,5-trichlorobenzene
chloroform
α,α,α',α',α'',α'',2,4,6-nonachloromesitylene
Conditions | Yield |
---|---|
With aluminum (III) chloride at 125℃; for 72h; Friedel Crafts alkylation; pressure tube; | 91% |
With aluminum (III) chloride at 125℃; for 72h; Autoclave; | 73% |
With aluminium trichloride at 100℃; for 18h; | 64% |
With aluminum (III) chloride for 67h; Friedel-Crafts Alkylation; Sealed tube; Heating; | 32% |
With aluminum (III) chloride at 125℃; for 72h; |
Conditions | Yield |
---|---|
Stage #1: 1,3,5-trichlorobenzene With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -75℃; for 2h; Stage #2: With iodine In tetrahydrofuran; hexane at -75℃; | 91% |
1,3,5-trichlorobenzene
para-methylphenylmagnesium bromide
1,3,5-tris(4-methyl-phenyl)-benzene
Conditions | Yield |
---|---|
With 1-[2-(diphenylphosphino)phenyl]ethanol; bis(acetylacetonate)nickel(II) In diethyl ether at 20℃; for 2h; | 91% |
Stage #1: 1,3,5-trichlorobenzene; para-methylphenylmagnesium bromide; 1-[2-(diphenylphosphino)phenyl]ethanol; bis(acetylacetonate)nickel(II) In diethyl ether for 2h; Stage #2: With methanol In diethyl ether Product distribution / selectivity; | 91% |
1. | dlt-oin-oin-par 10 ppm | EVETBX Environmental Entomology. 2 (1973),1029. | ||
2. | dlt-oin-oin-skn 10 ppm | EVETBX Environmental Entomology. 2 (1973),1029. | ||
3. | mnt-mus-ipr 425 mg/kg/24H | MUTAEX Mutagenesis. 2 (1987),111. | ||
4. | orl-rat LD50:800 mg/kg | 48RKAL Industrial and Environmental Xenobiotics: Metabolism and Pharmacokinetics of Organic Chemicals and Metals, Proceedings of an International Conference, Prague ,Gut, I., et al.,Berlin, Fed. Rep, Ger..: Springer-Verlag,1981,389. | ||
5. | orl-mus LD50:3350 mg/kg | NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) UCRL-13701 . | ||
6. | ipr-mus LD50:2260 mg/kg | MUTAEX Mutagenesis. 2 (1987),111. |
(1)It must be separated from strong oxidants and keep in a well-ventilated room.
(2)When spilled,sweep it into containers; if appropriate, moisten first to prevent dusting. Carefully collect remainder, then remove to safe place. Do NOT let this chemical enter the environment.
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