Conditions | Yield |
---|---|
With copper diacetate; water; triethylamine In dichloromethane; acetonitrile at 25℃; for 6h; | 97% |
Multi-step reaction with 2 steps 1: 85 percent / H2O2 / H2O / 20 °C 2: molecular sieves 4 Angstroem; Cu(OAc)2; Et3N / CH2Cl2 / 20 °C View Scheme |
Conditions | Yield |
---|---|
With aluminum oxide; potassium fluoride; copper(l) iodide In toluene at 100 - 110℃; for 22h; | 95% |
With caesium carbonate In N,N-dimethyl-formamide at 130℃; for 24h; Ullmann Condensation; | 90% |
With potassium phosphate; copper(l) iodide; tetrabutylammomium bromide In N,N-dimethyl-formamide for 22h; Ullmann coupling; Heating; | 87% |
p-cresol
2,4-dimethoxyphenyl(4-methylphenyl)iodonium tosylate
1,1'-oxybis(4-methyl-benzene)
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 50℃; for 6h; regioselective reaction; | 93% |
Conditions | Yield |
---|---|
With potassium phosphate In N,N-dimethyl-formamide at 80℃; for 4h; Ullmann Condensation; | 90% |
With potassium carbonate In water for 2.41667h; Ullmann Condensation; Reflux; Green chemistry; | 87% |
With potassium phosphate; 2-((o-toluidino)methyl)phenol; copper(l) chloride In acetonitrile at 81℃; for 24h; Catalytic behavior; Ullmann Condensation; Schlenk technique; Inert atmosphere; | 85% |
Conditions | Yield |
---|---|
With potassium phosphate; copper(l) iodide; 2,2,6,6-tetramethylheptane-3,5-dione; water In ethanol at 130℃; for 30h; Inert atmosphere; Sealed tube; chemoselective reaction; | 90% |
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.5 h / 20 °C 2: sodium hydroxide / dichloromethane / 22 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.5 h / 20 °C 2: sodium hydroxide; piperidine / dichloromethane / 14 h / 40 °C View Scheme |
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 40℃; | 88% |
para-bromotoluene
tert-Butyl(dimethyl)-(4-methylphenoxy)silane
1,1'-oxybis(4-methyl-benzene)
Conditions | Yield |
---|---|
With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 8h; | 81% |
Conditions | Yield |
---|---|
With potassium phosphate; tri-tert-butyl phosphine; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane at 100℃; for 20h; | 78% |
Conditions | Yield |
---|---|
With potassium phosphate; tri-tert-butyl phosphine; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane at 100℃; for 20h; | 72% |
piperazine
para-bromotoluene
A
p-cresol
B
1,4-bis(4-methylphenyl)piperazine
C
toluene
D
1,1'-oxybis(4-methyl-benzene)
Conditions | Yield |
---|---|
With Adipic acid; N'-phenyloxalyl bishydrazide; copper diacetate; sodium acetate; cetyltrimethylammonim bromide; 2,5-hexanedione; potassium hydroxide In water at 100℃; for 3h; Inert atmosphere; | A 21 %Chromat. B 68% C 13 %Chromat. D 11 %Chromat. |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 100℃; for 24h; | 65% |
Conditions | Yield |
---|---|
Stage #1: para-chlorotoluene With potassium phosphate; N,N'-bis(2,5-dimethylpyrrol-1-yl)oxalamide; copper(I) bromide In dimethyl sulfoxide at 20℃; Inert atmosphere; Sealed tube; Glovebox; Stage #2: p-cresol In dimethyl sulfoxide at 120℃; for 24h; Sealed tube; Inert atmosphere; Glovebox; | 62% |
para-bromotoluene
diethylamine
A
p-cresol
B
N,N-diethyl-p-toluidine
C
toluene
D
1,1'-oxybis(4-methyl-benzene)
Conditions | Yield |
---|---|
With Adipic acid; N'-phenyloxalyl bishydrazide; copper diacetate; sodium acetate; cetyltrimethylammonim bromide; 2,5-hexanedione; potassium hydroxide In water at 100℃; for 3h; Inert atmosphere; | A 18 %Chromat. B 28% C 5 %Chromat. D 26 %Chromat. |
1,1'-oxybis(4-methyl-benzene)
Conditions | Yield |
---|---|
With piperidine; sodium hydroxide In dichloromethane at 40℃; for 14h; | 11% |
furan
A
1,4-dihydro-1,4-epoxy-6-methylnaphthalene
B
1,1'-oxybis(4-methyl-benzene)
Conditions | Yield |
---|---|
With sodium hydroxide In dichloromethane at 20℃; for 22h; Diels-Alder Cycloaddition; | A 11% B 11% |
p-cresol
carvacrol
A
(5-isopropyl-2-methyl-phenyl)-p-tolyl ether
B
1,1'-oxybis(4-methyl-benzene)
Conditions | Yield |
---|---|
at 440 - 450℃; |
Conditions | Yield |
---|---|
at 400℃; durch Ueberleiten ueber ThO2; | |
at 400℃; beim Ueberleiten ueber ThO2; | |
With copper diacetate; 4 A molecular sieve; triethylamine In dichloromethane at 20℃; |
Conditions | Yield |
---|---|
With p-cresol; copper at 200 - 240℃; |
2-(5-methyl-2-p-tolyloxy-benzoyl)-benzoic acid
A
benzene-1,2-dicarboxylic acid
B
1,1'-oxybis(4-methyl-benzene)
Conditions | Yield |
---|---|
in der Kalischmelze; |
aluminium tris(p-methylphenoxide)
A
p-cresol
B
2,7-dimethyl-xanthene
C
1,1'-oxybis(4-methyl-benzene)
Conditions | Yield |
---|---|
bei der trocknen Destillation; |
p-cresol
p-toluidine
A
4-Methyl-2-p-tolyl-phenol
B
1,1'-oxybis(4-methyl-benzene)
Conditions | Yield |
---|---|
With sulfuric acid at 95℃; Diazotization; |
tris(4-methylphenyl)sulfonium bromide
A
di-(p-tolyl)sulfane
B
toluene
C
1,1'-oxybis(4-methyl-benzene)
Conditions | Yield |
---|---|
With sodium isopropylate In isopropyl alcohol at 72℃; for 23h; Product distribution; Mechanism; var. of solvent, reagent, temp., time; D-incorporation into toluene; | A 100 % Chromat. B 33 % Chromat. C 35 % Chromat. |
Conditions | Yield |
---|---|
With copper(II) sulfate; acetic acid; zinc |
potassium p-cresolate
bis(4-methylphenyl)iodonium bromide
1,1'-oxybis(4-methyl-benzene)
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide |
Conditions | Yield |
---|---|
With potassium hydroxide at 150 - 160℃; |
para-bromotoluene
sodium 4-methylphenoxide
1,1'-oxybis(4-methyl-benzene)
Conditions | Yield |
---|---|
With copper(I) oxide In N,N-dimethyl acetamide at 166℃; |
Conditions | Yield |
---|---|
With copper diacetate; sodium hydride In dichloromethane 1.) r.t., 10 min, 2.) 50 deg C, 16 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With 3-Methylindole; copper diacetate; sodium hydride In dichloromethane 1.) r.t., 10 min, 2.) 50 deg C, 16 h; Yield given. Yields of byproduct given; |
methanol
A
4-Methylanisole
B
1-methoxy-3-methyl-benzene
C
1,1'-oxybis(4-methyl-benzene)
Conditions | Yield |
---|---|
With sodium hydroxide In water for 10h; Heating; Yield given. Title compound not separated from byproducts; |
1,1'-oxybis(4-methyl-benzene)
2,8-Dimethyl-5-hydroxy-5-oxo-Pv-dibenzo<1,4>oxaphosphorin
Conditions | Yield |
---|---|
Stage #1: 1,1'-oxybis(4-methyl-benzene) With aluminium trichloride; phosphorus trichloride Heating; Stage #2: With sodium hydroxide; dihydrogen peroxide In water for 0.25h; | 97.2% |
Multi-step reaction with 3 steps 1: phosphorus trichloride; aluminium trichloride / 22 h / 80 °C 2: 10.2 g / H2O / 0 °C 3: 92 percent / O2; KOH / H2O View Scheme | |
Multi-step reaction with 2 steps 1: PCl3, AlCl3 2: aq. Br2 View Scheme |
phenylphosphinic acid
1,1'-oxybis(4-methyl-benzene)
2,8-dimethyl-10-phenylphenoxaphosphinine 10-oxide
Conditions | Yield |
---|---|
With dmap; trifluoromethylsulfonic anhydride In cis-1,2-Dichloroethylene at 120℃; for 16h; Schlenk technique; Inert atmosphere; | 94% |
1,1'-oxybis(4-methyl-benzene)
methyl cyclohexane
Conditions | Yield |
---|---|
With platinum on activated charcoal; N-methyldiethanolamine trifluoromethanesulfonate; hydrogen at 150℃; under 7500.75 Torr; for 6h; Autoclave; | 93.2% |
With carbon nanotubes-supported ruthenium; hydrogen In dodecane; water at 220℃; under 37503.8 Torr; for 3h; Autoclave; | 89 %Chromat. |
With hydrogen at 130℃; under 15001.5 Torr; for 6h; Ionic liquid; Autoclave; Schlenk technique; | 94.3 %Chromat. |
With hydrogen In decalin at 200℃; under 75007.5 Torr; for 3h; |
Conditions | Yield |
---|---|
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 80 - 90℃; for 6.5h; Inert atmosphere; | 93% |
With bromine; ethylene dibromide; dibenzoyl peroxide Irradiation.Sonnenlicht; | |
With N-Bromosuccinimide; dibenzoyl peroxide | |
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 80℃; | |
With hydrogen bromide; dihydrogen peroxide In 1,2-dichloro-ethane for 12h; Cooling with ice; Irradiation; |
Conditions | Yield |
---|---|
With dihydrogen peroxide; sodium carbonate at 100℃; under 7500.75 Torr; for 18h; Reagent/catalyst; Pressure; | 93% |
With pyridine; cobalt(III) acetylacetonate; dihydrogen peroxide; sodium carbonate In acetic acid at 100℃; under 15001.5 Torr; for 6h; Reagent/catalyst; Temperature; Solvent; Pressure; | 92% |
With 2-chloroanthracene-9,10-dione; water; oxygen; trifluoroacetic acid In ethyl acetate for 72h; Irradiation; | 70% |
1,1'-oxybis(4-methyl-benzene)
2,8-dimethyl-10,10-dichlorophenoxatellurine
Conditions | Yield |
---|---|
With tellurium tetrachloride at 200℃; for 4h; | 93% |
sodium methylate
1,1'-oxybis(4-methyl-benzene)
4,4'-Bis-methoxymethyl diphenyl ether
Conditions | Yield |
---|---|
Stage #1: 1,1'-oxybis(4-methyl-benzene) With 2,2'-azobis(isobutyronitrile); bromine In benzene at 80℃; for 3h; Reflux; Stage #2: sodium methylate In methanol at 45℃; for 2h; Temperature; Reflux; | 92.8% |
Conditions | Yield |
---|---|
Stage #1: 1,1'-oxybis(4-methyl-benzene) With 2,2'-azobis(isobutyronitrile); bromine In tetrachloromethane at 80℃; for 4.1h; Reflux; Stage #2: sodium isopropylate In isopropyl alcohol at 50℃; for 3h; Reflux; | 92.8% |
benzoic acid
1,1'-oxybis(4-methyl-benzene)
2, 7-dimethyl-9-phenyl xanthen-9-ol
Conditions | Yield |
---|---|
With trichlorophosphate; zinc(II) chloride at 95℃; for 2h; Product distribution / selectivity; Friedel Crafts Reaction; | 91.8% |
With zinc(II) chloride; trichlorophosphate at 95℃; for 4h; | 66% |
With zinc(II) chloride; trichlorophosphate at 80 - 95℃; | |
With zinc(II) chloride; trichlorophosphate at 95℃; for 4h; |
sodium ethanolate
1,1'-oxybis(4-methyl-benzene)
4,4'-diethoxymethyldiphenyl ether
Conditions | Yield |
---|---|
Stage #1: 1,1'-oxybis(4-methyl-benzene) With 2,2'-azobis(isobutyronitrile); bromine In tetrachloromethane at 80℃; for 3.2h; Reflux; Stage #2: sodium ethanolate In ethanol at 46℃; for 2h; Reflux; | 91.2% |
oxalyl dichloride
1,1'-oxybis(4-methyl-benzene)
2,7-dimethylxanthen-9-one
Conditions | Yield |
---|---|
With aluminium trichloride In carbon disulfide at 0 - 20℃; for 18h; | 90% |
With aluminum (III) chloride In dichloromethane at 0℃; Friedel Crafts reaction; Inert atmosphere; Reflux; | 77% |
With carbon disulfide; aluminium trichloride |
benzoyl chloride
1,1'-oxybis(4-methyl-benzene)
2-<(p-methylphenyl)oxy>-5-methylbenzophenone
Conditions | Yield |
---|---|
With aluminium trichloride In carbon disulfide at 0℃; for 3h; | 90% |
Conditions | Yield |
---|---|
With hydrogenchloride; oxygen; 9-(2-mesityl)-10-methylacridinium perchlorate at 20℃; under 760.051 Torr; for 30h; Schlenk technique; Irradiation; Green chemistry; | 90% |
With 2,3-dicarboxyanthraquinone; oxygen for 48h; Irradiation; | 80% |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride; iron(III)-acetylacetonate; sodium t-butanolate In toluene at 140℃; for 24h; Inert atmosphere; | 88% |
Conditions | Yield |
---|---|
With sodium persulfate; copper diacetate; iron(II) sulfate; dimethyl sulfoxide In water; acetonitrile at 75℃; for 0.75h; | 87% |
With sodium persulfate; dimethylsulfide; copper diacetate; iron(II) sulfate In water; acetonitrile at 75℃; for 1.08333h; | 84% |
With sodium persulfate; racemic methyl phenyl sulfoxide; copper diacetate; iron(II) sulfate In water; acetonitrile at 75℃; for 0.75h; | 84% |
Multi-step reaction with 2 steps 1: 1,2-dibromo-ethane; dibenzoyl peroxide; bromine / Irradiation.Sonnenlicht 2: CHCl3 / Erhitzen des Reaktionsprodukts mit wss. Essigsaeure und anschliessend mit wss. HCl View Scheme |
1,1'-oxybis(4-methyl-benzene)
4-nitro-benzoic acid
2,7-dimethyl-9-(4-nitrophenyl)-xanthen-9-ol
Conditions | Yield |
---|---|
With zinc(II) chloride; trichlorophosphate at 95℃; for 4h; | 86% |
Conditions | Yield |
---|---|
With zinc(II) chloride; trichlorophosphate In neat (no solvent) at 100℃; for 24h; Inert atmosphere; | 85% |
1,1'-oxybis(4-methyl-benzene)
4-(4'-methylphenoxy)benzonitrile
Conditions | Yield |
---|---|
With sodium azide; copper(ll) sulfate pentahydrate; [bis(acetoxy)iodo]benzene In acetonitrile at -40 - 25℃; Inert atmosphere; | 83% |
Conditions | Yield |
---|---|
With oxygen; palladium diacetate at 55℃; | 82% |
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; copper dichloride 1.) Et2O, cyclohexane, RT, 16 h, 2.) Et2O, cyclohexane, 5 deg C, 3 h; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With sodium tetrahydroborate; 10 wt% Pd(OH)2 on carbon; ammonia In water; m-xylene at 150℃; for 24h; Inert atmosphere; Sealed tube; | A 82% B n/a C 88 %Chromat. |
4-(1,1-dimethylethyl)benzoic acid
1,1'-oxybis(4-methyl-benzene)
2,7-dimethyl-9-(4-t-butyl)phenylxanthene-9-ol
Conditions | Yield |
---|---|
With trichlorophosphate; zinc(II) chloride for 2h; Friedel Crafts Reaction; | 81% |
With zinc(II) chloride; trichlorophosphate at 95℃; for 4h; | 70% |
ammonium formate
1,1'-oxybis(4-methyl-benzene)
2,7-dimethylxanthen-9-one
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; sulfuric acid; palladium diacetate; trifluoroacetic acid at 45℃; | 80% |
MF: C14H14O
MW: 198.260 g/mol
EINECS: 216-423-0
Flash Point: 121.3 °C
Index of Refraction: 1.56
Melting Point: 47-49 °C(lit.)
Enthalpy of Vaporization: 50.35 kJ/mol
Boiling Point: 285.5 °C at 760 mmHg
Vapour Pressure: 0.0048 mmHg at 25°C
IUPAC Name: 1-methyl-4-(4-methylphenoxy)benzene
Density of P-(p-Tolyloxy)toluene (1579-40-4): 1.029 g/cm3
Synonyms: 1,1’-Oxybis(4-methyl-benzen ; 1,1’-Oxybis(4-methylbenzene) ; 1,1’-Oxybis[4-methyl-benzen ; Benzene, 1,1'-Oxybis*4-methyl- ; Benzene, 1,1'-Oxybis[4-methyl- ; Bis(4-methylphenyl) ether ; Bis(4-methylphenyl)ether ; P-(p-Tolyloxy)toluene
Product Categories: Ethers ; Organic Building Blocks ; Oxygen Compounds
Following is the molecular structure of P-(p-Tolyloxy)toluene (1579-40-4):
1. | skn-rbt 500 mg/24H SEV | NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) OTS0545443 . | ||
2. | orl-rat LDLo:2250 mg/kg | NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) OTS0537676 . | ||
3. | ihl-rat LC :>184 ppm/4H | NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) OTS0537676 . | ||
4. | skn-rbt LDLo:7940 mg/kg | NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) OTS0545443 . |
Reported in EPA TSCA Inventory.
Moderately toxic by ingestion and inhalation. Low toxicity by skin contact. A severe skin irritant. When heated to decomposition it emits acrid smoke and irritating vapors.
Safety Information of P-(p-Tolyloxy)toluene (1579-40-4):
Hazard Codes: Xi,N
Xi: Irritant N: Dangerous for the environment
Risk Statements: 36/37/38-50/53
36/37/38: Irritating to eyes, respiratory system and skin
50/53: Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment
Safety Statements: 26-36-61
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
61: Avoid release to the environment. Refer to special instructions safety data sheet
RIDADR: UN 3077 9/PG 3
WGK Germany: 2
RTECS: DA6625000
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