Conditions | Yield |
---|---|
With hydrazine hydrate; C23H40MnNO2P2; potassium tert-butylate In tert-butyl alcohol at 115℃; for 48h; Wolff-Kishner Reduction; Green chemistry; | 99% |
With carbon monoxide; hydrogen; benzene at 190℃; under 176522 Torr; Reagens 4: Octacarbonyldikobalt, Reagens 5: Kobaltcarbonat; | |
With 2,4,6-trimethyl-pyridine; 4,4'-dimethoxyphenyl disulfide; iridium(lll) bis[2-(2,4-difluorophenyl)-5-methylpyridine-N,C20]-4,40-di-tert-butyl-2,20-bipyridine hexafluorophosphate; triphenylphosphine In toluene for 24h; Irradiation; | 74 %Chromat. |
Conditions | Yield |
---|---|
With nickel dichloride In N,N-dimethyl-formamide at 170℃; for 0.0833333h; microwave irradiation; | 99% |
With bis(1,5-cyclooctadiene)nickel (0); potassium phosphate; tetrabutyl-ammonium chloride; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 20℃; for 30h; Inert atmosphere; Glovebox; Sealed tube; Irradiation; | 7 %Chromat. |
Conditions | Yield |
---|---|
With nickel dichloride In N,N-dimethyl-formamide at 170℃; for 0.0833333h; microwave irradiation; | 95% |
With trans-bis(glycinato)copper(II) monohydrate; tetramethlyammonium chloride In ethanol at 100℃; for 10h; Reagent/catalyst; Finkelstein Reaction; Schlenk technique; Inert atmosphere; | 93% |
With CuCl-alumina In various solvent(s) at 150℃; for 12h; | 67% |
With copper(I) oxide; tetramethlyammonium chloride; L-proline In ethanol at 110℃; for 20h; Inert atmosphere; | 98 %Chromat. |
With iron(III) chloride; sodium chloride In acetonitrile for 2h; Kinetics; Irradiation; Green chemistry; regioselective reaction; |
Conditions | Yield |
---|---|
With palladium; triphenylphosphine In tetrahydrofuran at 70℃; for 12h; Catalytic behavior; Negishi Coupling; Inert atmosphere; Green chemistry; | 95% |
Conditions | Yield |
---|---|
With potassium nitrite; potassium chloride; sodium chloride; iron(II) bromide In water at 20 - 80℃; for 6.16667h; Temperature; | 91% |
Stage #1: p-toluidine With para-dodecylbenzenesulfonic acid; sodium nitrite In tetrachloromethane at 20℃; Stage #2: With triethylamine In tetrachloromethane at 70℃; | 45% |
With tert.-butylnitrite; copper dichloride In acetonitrile |
Conditions | Yield |
---|---|
With sodium tetrahydroborate; cetyltributylphosphonium bromide In water; toluene at 18℃; for 0h; Product distribution; | 91% |
With sodium tetrahydroborate; water In methanol at 20℃; for 0.25h; regioselective reaction; | 81% |
With phosphonic Acid; iodine In 1,2-dichloro-ethane at 120℃; for 36h; Inert atmosphere; | 98 %Chromat. |
With dithionite(2-) In aq. phosphate buffer; acetonitrile at 4℃; pH=7; Kinetics; Inert atmosphere; |
para-chlorotoluene
Conditions | Yield |
---|---|
In dimethyl sulfoxide Ambient temperature; | 89% |
Conditions | Yield |
---|---|
With methanol; magnesium Ambient temperature; | 87% |
With sodium tetrahydroborate In various solvent(s) at 70℃; for 2h; | 76% |
With Perbenzoic acid; tri-n-butyl-tin hydride In benzene at 90℃; for 12h; Mechanism; in the presence of α-chlorotoluene (competitor), relative reactivity; |
Conditions | Yield |
---|---|
With di-tert-butyl peroxide; triethyl phosphite In toluene | 87% |
With di-tert-butyl peroxide; triethyl phosphite In acetonitrile at 25℃; for 6h; Irradiation; | 87% |
With hexacarbonyl molybdenum In tetrahydrofuran Heating; | 61% |
dicobalt octacarbonyl In water; benzene at 185 - 190℃; under 46543.3 Torr; | 44% |
4-methylbenzene diazonium
para-chlorotoluene
Conditions | Yield |
---|---|
With tin(II); chloride; copper(II) nitrate In water Ambient temperature; | 80% |
methyl iodide
A
para-chlorotoluene
B
(E)-N-benzylidene-α-methylbenzylamine
C
chlorobenzene
Conditions | Yield |
---|---|
Stage #1: C20H18ClN3 With lithium diisopropyl amide In tetrahydrofuran at 0℃; Stage #2: methyl iodide In tetrahydrofuran | A n/a B 80% C n/a |
Conditions | Yield |
---|---|
With bis(benzonitrile)palladium(II) dichloride; sodium iodide In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; | 78% |
2-(4-chlorophenyl)-1,3-dithiolane
para-chlorotoluene
Conditions | Yield |
---|---|
With sodium tetrahydroborate; nickel(II) chloride hexahydrate In tetrahydrofuran; methanol at 20℃; for 0.5h; | 78% |
para-chlorotoluene
Conditions | Yield |
---|---|
With potassium hydroxide In 2,2'-[1,2-ethanediylbis(oxy)]bisethanol at 140℃; for 4h; Wolff-Kishner Reduction; | 76% |
4-methylbenzenediazonium tetrafluoroborate
A
p-fluorotoluene
B
para-chlorotoluene
Conditions | Yield |
---|---|
With 1,2-dichloro-ethane Heating; | A 74% B 26 % Chromat. |
Conditions | Yield |
---|---|
With [Au(1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene)(O2CAd)] In toluene at 140℃; for 20h; | 74% |
Conditions | Yield |
---|---|
With iron(III) chloride In ethanol at 50 - 80℃; for 14h; Temperature; Inert atmosphere; | A 26.8% B 72.3% |
Conditions | Yield |
---|---|
With chlorine; natural kaolinitic clay In tetrachloromethane for 2h; Heating; | A 72% B 23% |
With aluminum (III) chloride; chlorine at 50℃; for 6h; Temperature; Inert atmosphere; | A 71.3% B 27.8% |
With hydrogenchloride; 1-(n-butyl)-3-methylimidazolium triflate at 100℃; for 96h; | A 38% B 60% |
1-Chloro-4-(chloromethyl)benzene
A
para-chlorotoluene
B
1,2-bis(4-chlorophenyl)ethane
Conditions | Yield |
---|---|
With nickel In 1,2-dimethoxyethane at 70℃; for 0.5h; | A 20% B 72% |
With magnesium at 600℃; | A 6% B 37% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine)palladium dichloride In benzene at 85℃; for 3h; | A 5% B 70% |
para-chlorotoluene
Conditions | Yield |
---|---|
With N-benzyl-N,N,N-triethylammonium chloride; copper In acetonitrile at 20℃; for 0.75h; Substitution; | 68% |
Conditions | Yield |
---|---|
With 2-pentanol; ReOCl3(SMe2)(OPPh3) for 17h; Green chemistry; chemoselective reaction; | 66% |
With polymethylhydrosiloxane; iron(III) chloride hexahydrate In 1,2-dichloro-ethane at 120℃; for 1h; Microwave irradiation; | 62% |
With hydrazine hydrate; diethylene glycol Erhitzen des mit Kaliumhydroxid versetzten Reaktionsgemisches; | |
With acid; copper cathode bei der elektrolytischen Reduktion; | |
Multi-step reaction with 2 steps 1: acetic acid / ethanol / Reflux 2: potassium hydroxide / 2,2'-[1,2-ethanediylbis(oxy)]bisethanol / 4 h / 140 °C View Scheme |
1,1-Bis-(4-chlorobenzyl)-1,4-dihydronaphthalene
A
para-chlorotoluene
B
1-(4-chlorobenzyl)naphthalene
Conditions | Yield |
---|---|
at 150℃; for 17h; | A 50% B 66% |
at 150℃; for 17h; Mechanism; other dihydroaromatic compounds as substrates; | A 50% B 66% |
para-chlorotoluene
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane In toluene at 110℃; for 0.5h; Temperature; Inert atmosphere; Microwave irradiation; regioselective reaction; | 66% |
perfluoroheptanoic acid
toluene
A
para-chlorotoluene
B
2,2,3,3,4,4,5,5,6,6,7,7,7-Tridecafluoro-heptanoic acid p-tolyl ester
Conditions | Yield |
---|---|
With lead(IV) acetate; lithium chloride | A 65% B 21% |
toluene
A
para-chlorotoluene
B
2,2,3,3,4,4,5,5,6,6,7,7,7-Tridecafluoro-heptanoic acid p-tolyl ester
Conditions | Yield |
---|---|
With lead(IV) acetate; C6F13COOH; lithium chloride | A 65% B 21% |
toluene
A
para-chlorotoluene
B
2-methylchlorobenzene
C
2,4-dichlorotoluene
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hypochlorite In water at 20℃; Product distribution; Further Variations:; Temperatures; molar quantity of reagents; Chlorination; oxidative chlorination; | A 29% B 63% C 3.5% |
With oxone; potassium chloride In acetonitrile at 20℃; for 24h; Product distribution; Further Variations:; Reagents ratio; | |
With sulfuric acid; [BMIM]Cl; chlorine at 70℃; for 8h; |
1-bromo-4-methoxy-benzene
n-heptan1ol
4-Chlorostyrene oxide
A
para-chlorotoluene
B
n-heptyl 4-methoxybenzoate
C
methoxybenzene
Conditions | Yield |
---|---|
With 5%-palladium/activated carbon; sodium fluoride In 1,4-dioxane at 150℃; for 6h; | A 20 %Chromat. B 60% C 9 %Chromat. |
2-methylenesuccinic acid
p-methylbenzenediazonium chloride
A
para-chlorotoluene
B
C12H13ClO4
Conditions | Yield |
---|---|
With copper(II) choride dihydrate In [(2)H6]acetone; water at 25℃; for 2.5h; Meerwein Arylation; | A n/a B 56% |
Trichloroethylene
p-methylbenzenediazonium chloride
A
para-chlorotoluene
B
1,1,1,2-Tetrachlor-2-(p-tolyl)ethan
Conditions | Yield |
---|---|
With potassium chloride; copper dichloride In water; acetone | A n/a B 53% |
Conditions | Yield |
---|---|
With water; sodium iodide; nickel dichloride; zinc; sonication In N,N,N,N,N,N-hexamethylphosphoric triamide at 60℃; for 3h; | 100% |
With water; sodium iodide; nickel dichloride; zinc; sonication In N,N,N,N,N,N-hexamethylphosphoric triamide at 60℃; for 3h; Product distribution; | 100% |
With palladium on ceria; sodium hydroxide In isopropyl alcohol at 40℃; for 24h; Temperature; Solvent; Irradiation; Inert atmosphere; Sealed tube; | 97% |
Conditions | Yield |
---|---|
With Cs2O3; PCy3 adduct of cyclopalladated ferrocenylimine In 1,4-dioxane at 100℃; for 15h; Suzuki cross-coupling reaction; | 100% |
With [PdI(2-(2-thiophenyl)-4,4-dimethyloxazoline)(1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene)]; potassium carbonate In tetrahydrofuran; water at 90℃; for 18h; Catalytic behavior; Reagent/catalyst; Suzuki-Miyaura Coupling; | 100% |
With caesium carbonate; palladium diacetate; 1,3-di-([N-(2,4,6-Me3Ph)imidazolium-3-yl]Me)-2,4,6-Me3Ph*2Cl- In 1,4-dioxane at 80℃; for 1.5h; Suzuki reaction; | 99% |
Conditions | Yield |
---|---|
With johnphos; sodium t-butanolate; palladium diacetate In toluene at 20℃; for 19h; Arylation; | 100% |
With potassium tert-butylate; Pd(0) N-heterocyclic carbene-phosphine In 1,4-dioxane at 100℃; | 99% |
With potassium hydroxide; bis(tri-tert-butylphosphine)palladium(0); cetyltrimethylammonim bromide In water; toluene at 90℃; for 19h; | 99% |
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); 3-butyl-1-methyl-5-[9-(3-methyl-1H-imidazol-3-ium-1-yl)nonyl]-3H-1,2,3-triazol-1-ium diiodide; caesium carbonate In 1,4-dioxane Suzuki-Miyaura reaction; Inert atmosphere; Heating; | 100% |
With tris(dibenzylideneacetone)dipalladium (0); C3H3N2(C9H11)2*HCl; caesium carbonate In 1,4-dioxane at 80℃; for 1.5h; | 99% |
Stage #1: 4-methoxyphenylboronic acid With allyl(1,3-bis(2,6-diisopropyl-4-(3-((3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)oxy)propyl)phenyl)-imidazol-2-ylidene)palladium(II) chloride; potassium tert-butylate In ethanol at 30℃; for 0.5h; Inert atmosphere; Stage #2: para-chlorotoluene In ethanol at 30℃; for 4h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Suzuki Coupling; Inert atmosphere; | 99% |
para-chlorotoluene
1-phenyl-propan-1-one
1-phenyl-2-p-tolylpropan-1-one
Conditions | Yield |
---|---|
With sodium t-butanolate; Pd(dba)2*n-butylbis(1-adamantyl)phosphine In toluene at 80℃; for 20h; | 100% |
With [Ipent.H][Pd(η3-cin)Cl2]; sodium t-butanolate at 60 - 80℃; for 2h; Buchwald-Hartwig Coupling; Sealed tube; | 99% |
With sodium t-butanolate; [(N,N'-bis(2,6-di-iPr-phenyl)imidazol-2-ylidene)Pd(acac)Cl] In toluene at 100℃; for 0.5h; | 98% |
para-chlorotoluene
methyl [3,4-13C2]2-deoxyriboside
Conditions | Yield |
---|---|
With pyridine at 40℃; for 2h; Arylation; | 100% |
para-chlorotoluene
9-phenyl-9H-xanthen-9-ol
A
xanth-9-one
B
4-Methylbiphenyl
Conditions | Yield |
---|---|
With palladium diacetate; caesium carbonate; tricyclohexylphosphine In o-xylene for 4h; Heating; | A n/a B 100% |
para-chlorotoluene
(meta-(trifluoromethyl)phenyl)boronic acid
4’-methyl-3-(trifluoromethyl)-1,1’-biphenyl
Conditions | Yield |
---|---|
With potassium phosphate; N,N-diisopropyl 2-dicyclohexylphosphino-4-phenylbenzamide; tris(dibenzylideneacetone)dipalladium (0) In toluene at 110℃; for 5h; Suzuki cross-coupling reaction; | 100% |
Conditions | Yield |
---|---|
With dichloro[1-(3-methylbenzyl)-3-(n-butyl)benzimidazol-2-ylidene]ruthenium(II); potassium acetate In water at 100℃; for 5h; Reagent/catalyst; | 100% |
With C36H35Cl2PRu; potassium carbonate In 1-methyl-pyrrolidin-2-one at 120℃; for 24h; regioselective reaction; | 86% |
para-chlorotoluene
1-(4-methoxyphenyl)ethanone
1-(4-methoxyphenyl)-2-(4-methylphenyl)ethanone
Conditions | Yield |
---|---|
With C40H48ClN3Pd; sodium t-butanolate In 1,4-dioxane at 100℃; for 4h; Reagent/catalyst; | 100% |
With [Ni(1,3-bis[2,6-bis(diphenylmethyl)-4-methylphenyl]imidazole-2-ylidene)(cin)Cl]; sodium t-butanolate In toluene at 80℃; for 16h; | 86% |
With (C5H5)Fe(C5H3C(CH3)NC6H4CH3)PdCl(CN2(C6H3(CH(CH3)2)2)2C2H2); potassium tert-butylate In toluene for 5h; Inert atmosphere; Reflux; | 80% |
With [Pd(IHept)(acac)Cl]; sodium t-butanolate In toluene at 100℃; for 16h; Glovebox; | 70% |
para-chlorotoluene
Conditions | Yield |
---|---|
Stage #1: para-chlorotoluene With potassium tert-butylate for 0.333333h; Cooling; Stage #2: With n-butyllithium In hexane at -35 - 20℃; for 5h; | 100% |
Conditions | Yield |
---|---|
In ethanol for 1h; Reflux; | 100% |
Conditions | Yield |
---|---|
Stage #1: para-chlorotoluene With iodine; magnesium In tetrahydrofuran at 57 - 80℃; for 5h; Inert atmosphere; Stage #2: 8-(4-oxocyclohexyl)-1,4-dioxaspiro[4.5]decane In tetrahydrofuran; toluene at 55 - 60℃; for 1h; Temperature; Solvent; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With Oxone; potassium bromide In dichloromethane; water at 20℃; for 24h; visible light irradiation; | 99% |
With ruthenium trichloride; sodium hypochlorite; tetrabutylammomium bromide In 1,2-dichloro-ethane at 25℃; for 2h; | 98% |
With ruthenium trichloride; sodium hypochlorite; tetrabutylammomium bromide In 1,2-dichloro-ethane at 25℃; for 2h; Rate constant; Mechanism; pH 9: other methylbenzenes; var. concentration of aq. NaOCl, ruthenium and tetrabutylammonium bromide; | 98% |
Conditions | Yield |
---|---|
With styrene; [2,2]bipyridinyl; sodium hydride; bis(acetylacetonate)nickel(II); aluminium(III) acetylacetonate In tetrahydrofuran for 3h; Ullmann coupling; Heating; | 99% |
With potassium tert-butylate; palladium diacetate; bis(pinacol)diborane; XPhos for 12h; Heating; | 99% |
With samarium; triphenylphosphine; nickel dichloride In N,N-dimethyl-formamide at 40℃; for 1.5h; | 98% |
Conditions | Yield |
---|---|
With bis(η3-allyl-μ-chloropalladium(II)); potassium tert-butylate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In 1,4-dioxane at 100℃; for 1.5h; Inert atmosphere; | 99% |
With dihydrogen dichloro-bis(di-tert-butylphosphinito-κP)palladium(2-); sodium t-butanolate In 1,4-dioxane at 110℃; for 4h; | 97% |
With potassium hydroxide; tert-butyl alcohol; cyclopalladated ferrocenylimine monophosphinobiaryl complex In water at 95℃; for 24h; Buchwald-Hartwig amination; | 97% |
Conditions | Yield |
---|---|
With (N,N'-diarylimidazol-2-ylidene)-based palladacycle; sodium t-butanolate In 1,4-dioxane at 70℃; for 0.5h; | 99% |
With tris(dibenzylideneacetone)dipalladium (0); potassium tert-butylate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In 1,4-dioxane at 100℃; | 98% |
With tris-(dibenzylideneacetone)dipalladium(0); keYPhos; potassium tert-butylate In tetrahydrofuran at 20℃; for 1h; Glovebox; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With potassium phosphate In dimethyl sulfoxide at 80℃; UV-irradiation; | 99% |
With tris-(dibenzylideneacetone)dipalladium(0); 4-dicyclohexylphosphino-12-(2',6'-dimethoxy)phenyl-[2.2]paracyclophane; sodium t-butanolate In 1,4-dioxane at 100℃; for 6h; Buchwald-Hartwig amination; Inert atmosphere; | 93% |
With palladium diacetate; (R)-1-[(SP)-2-(diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; sodium t-butanolate In toluene at 85℃; for 2h; | 89% |
Conditions | Yield |
---|---|
With (R)-1-[(SP)-2-(diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 110℃; for 16h; Mechanism; Product distribution; other amines; other aryl halides and tosylates; var. chelating alkylphosphines, var. time, var. temp., further solvent; | 99% |
With (R)-1-[(SP)-2-(diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 110℃; for 16h; | 99% |
With potassium tert-butylate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane at 100℃; for 5h; | 99% |
Conditions | Yield |
---|---|
With C40H42NP; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In 1,4-dioxane; water at 20℃; for 1.16667h; Reagent/catalyst; Inert atmosphere; Sealed tube; Reflux; | 99% |
With potassium tert-butylate; C46H69ClP2Pd In tetrahydrofuran at 20℃; for 6h; Reagent/catalyst; Schlenk technique; Inert atmosphere; | 96% |
With palladium diacetate; monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; sodium t-butanolate In toluene at 100℃; for 24h; | 95% |
Conditions | Yield |
---|---|
With caesium carbonate; palladium diacetate; 1,3-di-([N-(2,4,6-Me3Ph)imidazolium-3-yl]Me)-2,4,6-Me3Ph*2Cl- In 1,4-dioxane at 80℃; for 4h; Suzuki reaction; | 99% |
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); 3-(dicyclohexylphosphino)-2-(2,6-dimethoxyphenyl)-1-methyl-1H-indole In 1,4-dioxane at 100℃; for 24h; Suzuki-Miyaura Coupling; Schlenk technique; Sealed tube; Inert atmosphere; | 97% |
With bis(1,5-cyclooctadiene)nickel (0); potassium phosphate; tricyclohexylphosphine In tetrahydrofuran at 20℃; for 30h; Suzuki coupling; | 92% |
Conditions | Yield |
---|---|
With potassium tert-butylate; Pd(0) N-heterocyclic carbene-phosphine In 1,4-dioxane at 100℃; | 99% |
With palladium diacetate; sodium t-butanolate; ruphos In neat (no solvent) at 110℃; for 12h; Buchwald-Hartwig Coupling; Green chemistry; | 99% |
With dichloro(3-chloropyridinyl)(1,3-(diisopropylphenyl)-4,5-bis(dimethylamino)imidazol-2-ylidene)palladium(II); potassium tert-butylate In 1,4-dioxane at 80℃; for 18h; Catalytic behavior; Solvent; Temperature; Reagent/catalyst; Buchwald-Hartwig Coupling; Inert atmosphere; Schlenk technique; Sealed tube; | 99% |
para-chlorotoluene
4-methylphenylboronic acid
(4,4'-dimethyl-1,1'-biphenyl)
Conditions | Yield |
---|---|
With caesium carbonate; palladium diacetate; 1,3-di-([N-(2,4,6-Me3Ph)imidazolium-3-yl]Me)-2,4,6-Me3Ph*2Cl- In 1,4-dioxane at 80℃; for 4h; Suzuki reaction; | 99% |
With potassium phosphate; poly{[1,1'-bis-(1,4-phenylene-C(PPh2))ferrocene]-derivative}; bis(1,5-cyclooctadiene)nickel (0) In tetrahydrofuran for 24h; Suzuki cross-coupling; Heating; | 99% |
With potassium phosphate; ferrocenylmethylphosphine; bis(1,5-cyclooctadiene)nickel (0) In tetrahydrofuran at 20℃; for 48h; Suzuki-Miyaura cross-coupling; | 98% |
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium (0); N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene hydrochloride In tetrahydrofuran; 1,4-dioxane at 80℃; for 3h; Phenylation; | 99% |
With [1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene; Ni(1,5-bis-cyclooctadiene)2 In various solvent(s) Kumada-Corriu cross-coupling reaction; | 88% |
With N-heterocyclic carbene-based nickel(II) complex In tetrahydrofuran at 20℃; for 12h; Kumada reaction; | 83% |
With 1-[2-(diphenylphosphino)phenyl]ethanol; bis(acetylacetonate)nickel(II) In diethyl ether at 20℃; for 0.333333h; | 97 % Chromat. |
Conditions | Yield |
---|---|
With PdCl(π-allyl)(cyclohexyl-(1-methyl-2,2-diphenylcyclopropylphophine)); sodium t-butanolate In tetrahydrofuran; toluene at 100℃; for 0.25h; Reagent/catalyst; Buchwald-Hartwig Coupling; Inert atmosphere; | 99% |
With palladium diacetate; sodium t-butanolate; ruphos In neat (no solvent) at 110℃; for 12h; Buchwald-Hartwig Coupling; Green chemistry; | 99% |
With sodium t-butanolate; tris(dibenzylideneacetone)dipalladium (0); P(i-BuNCH2CH2)3N In toluene at 100℃; for 20h; Buchwald-Hartwig amination; | 98% |
Benzophenone imine
para-chlorotoluene
N-(diphenylmethylene)-p-toluidine
Conditions | Yield |
---|---|
With potassium tert-butylate; bis(dibenzylideneacetone)-palladium(0); 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In 1,4-dioxane at 100℃; for 4h; | 99% |
With 1,8-bis(diisopropylphosphino)triptycene; potassium phosphate; palladium diacetate In toluene Buchwald-Hartwig amination; | 99% |
With potassium tert-butylate; Pd(0) N-heterocyclic carbene-phosphine In 1,4-dioxane at 100℃; | 98% |
With (±)-[2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]bis(triphenylphosphite)nickel(0) toluene solvate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 100℃; Inert atmosphere; | 97% |
With bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; 1,3-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene In Dimethyl ether at 55℃; for 18h; Amination; | 94% |
styrene
para-chlorotoluene
E-1-methyl-4-styryl-benzene
Conditions | Yield |
---|---|
With tetrabutylammonium acetate; palladium diacetate; DavePhos In 1,4-dioxane at 80℃; for 24h; Heck reaction; Inert atmosphere; Sealed tube; | 99% |
With tetrakis[μ-1-[(3-methoxyphenyl)methyl]-2-phenyl-3-[2-oxo-2-[(2-phenolato-kO)aminokN]ethyl]-1H-imidazoliumato-kC4]tetrapalladium; tetrabutylammomium bromide; sodium acetate at 140℃; for 12h; Heck Reaction; | 99% |
With potassium phosphate; catacxium A; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 120℃; for 24h; Substitution; Heck reaction; | 98% |
para-chlorotoluene
bis(pinacol)diborane
p-tolylboronic pinacol ester
Conditions | Yield |
---|---|
With sodium acetate; bis(dibenzylideneacetone)-palladium(0); XPhos for 12h; Miyaura Borylation Reaction; Heating; | 99% |
With potassium phosphate tribasic heptahydrate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); XPhos In ethanol at 20℃; for 0.5h; Catalytic behavior; Reagent/catalyst; Solvent; | 98% |
With potassium acetate In isopropyl alcohol at 82℃; for 2h; Suzuki-Miyaura Coupling; | 94% |
Conditions | Yield |
---|---|
With 4-diphenylphosphino-13-dicyclohexylphosphino-[2.2]paracyclophane; water; palladium diacetate; caesium carbonate In 1,4-dioxane at 150℃; for 5h; Buchwald-Hartwig coupling; Microwave irradiation; | 99% |
With copper(l) iodide; potassium carbonate; trans-N,N'-dimethylcyclohexane-1,2-diamine at 110℃; for 23h; | 96% |
With copper(l) iodide; potassium carbonate; trans-N,N'-dimethylcyclohexane-1,2-diamine at 110℃; for 23h; | 96% |
Product Name: 4-chlorotoluene (CAS NO.106-43-4)
Molecular Formula: C7H7Cl
Molecular Weight: 126.58g/mol
Mol File: 106-43-4.mol
EINECS: 203-397-0
Melting Point: 6-8 °C(lit.)
Boiling point: 158.5 °C at 760 mmHg
Storage Temperature: 0-6°C
Flash Point: 46.2 °C
Density: 1.075 g/cm3
Refractive index: n20/D 1.52(lit.)
Water Solubility: <0.1 g/100 mL at 20 ºC
Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
Index of Refraction: 1.523
Molar Refractivity: 35.97 cm3
Molar Volume: 117.6 cm3
Surface Tension: 32.4 dyne/cm
Enthalpy of Vaporization: 37.89 kJ/mol
Vapour Pressure: 3.39 mmHg at 25°C
XLogP3-AA: 3.3
H-Bond Donor: 0
H-Bond Acceptor: 0
Structure Descriptors of 4-chlorotoluene (CAS NO.106-43-4):
IUPAC Name: 1-chloro-4-methylbenzene
Canonical SMILES: CC1=CC=C(C=C1)Cl
InChI: InChI=1S/C7H7Cl/c1-6-2-4-7(8)5-3-6/h2-5H,1H3
InChIKey: NPDACUSDTOMAMK-UHFFFAOYSA-N
Product Categories: Analytical Chemistry; Standard Solution of Volatile Organic Compounds for Water & Soil Analysis; Standard Solutions (VOC); Pesticides&Metabolites; Aryl; C7; Halogenated Hydrocarbons; Alpha Sort; CAlphabetic; Volatiles/ Semivolatiles; Alphabetic; C; CH
4-chlorotoluene is used as the intermediates of organic reagents, pharmaceutical intermediates,and 4-chlorotoluene also used in the process of synthesis of Chlorobenzaldehyde
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
guinea pig | LD50 | unreported | 3750mg/kg (3750mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: EXCITEMENT LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 46(2), Pg. 67, 1981. |
mouse | LC50 | inhalation | 34gm/m3/2H (34000mg/m3) | "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 38, 1982. | |
mouse | LD50 | oral | 1900mg/kg (1900mg/kg) | "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 38, 1982. | |
mouse | LD50 | unreported | 4gm/kg (4000mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION BEHAVIORAL: EXCITEMENT | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 46(2), Pg. 67, 1981. |
rat | LD50 | oral | 2100mg/kg (2100mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) LUNGS, THORAX, OR RESPIRATION: CYANOSIS GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS | Office of Toxic Substances Report. Vol. OTS0513162, |
rat | LD50 | unreported | 4gm/kg (4000mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 45(12), Pg. 64, 1980. |
Safety Information of 4-chlorotoluene (CAS NO.106-43-4):
Hazard Codes: Xn,N,T,F
Risk Statements: 20-51/53-39/23/24/25-23/24/25-11-10
R20:Harmful by inhalation.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
R39:Danger of very serious irreversible effects.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.
R11:Highly flammable.
R10:Flammable.
Safety Statements: 24/25-61-45-36/37-16-7
S24/25:Avoid contact with skin and eyes.
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36/37:Wear suitable protective clothing and gloves.
S16:Keep away from sources of ignition.
S7:Keep container tightly closed.
RIDADR: UN 2238 3/PG 3
WGK Germany: 2
RTECS: XS9010000
Hazard Note: Harmful
HazardClass: 3
PackingGroup: III
HS Code: 29036990
4-chlorotoluene , its CAS NO. is 106-43-4, the synonyms are Synonyms 1-Chloro-4-methylbenzene ; 1-Methyl-4-chlorobenzene ; 4-Chloro-1-methylbenzene ; 4-Chlorotoluene ; Benzene, 1-chloro-4-methyl- ; Toluene, p-chloro- ; p-Chlorotoluene ; p-Tolyl chloride .
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