2,6-diisopropylbenzenamine
Conditions | Yield |
---|---|
With potassium phosphate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ascorbic acid In water; acetonitrile at 20℃; for 2h; Sealed tube; Irradiation; Inert atmosphere; | 99% |
1,3-diisopropyl-2-nitrobenzene
2,6-diisopropylbenzenamine
Conditions | Yield |
---|---|
With borane-ammonia complex; copper(II) oxide In methanol at 50℃; for 0.333333h; | 96% |
With sodium tetrahydroborate In tetrahydrofuran; water at 20℃; for 16h; Inert atmosphere; Green chemistry; chemoselective reaction; | 88% |
With sodium tetrahydroborate; iron; water at 20℃; for 16h; | 88% |
With hydrogen; C27H27ClIrNO In methanol at 60℃; under 4560.31 Torr; for 6h; Autoclave; | 78% |
With C22H25ClF3NORu; hydrogen In methanol; water at 80℃; under 2280.15 Torr; Autoclave; | 67% |
2,6-diisopropylbenzenamine
Conditions | Yield |
---|---|
With formic acid; potassium hydroxide In ethanol at 70℃; for 1h; | 94% |
Conditions | Yield |
---|---|
93% |
N-(3-(2,6-diisopropylphenylamino)-3-methylbutan-2-ylidene)-2,6-diisopropylbenzenamine
A
3-[[2,6-bis(1-methylethyl)phenyl]amino]-3-methyl-2-butanone
B
2,6-diisopropylbenzenamine
Conditions | Yield |
---|---|
With sulfuric acid In ethanol; water at 40 - 65℃; for 3 - 4.5h; Inert atmosphere; | A 91% B 91% |
2,6-diisopropyl-1-azidobenzene
2,6-diisopropylbenzenamine
Conditions | Yield |
---|---|
With 1,3-diadamantane-4,5-dihydroimidazole chloride; potassium tert-butylate; bis(pinacol)diborane; copper(l) chloride In toluene at 25℃; for 4h; Schlenk technique; Inert atmosphere; | 91% |
N-methyl-N-allylamine
N-(2,6-diisopropylphenyl)benzimidamide
A
2,6-diisopropylbenzenamine
Conditions | Yield |
---|---|
With bis(trimethylsilyl)amide yttrium(III) In neat (no solvent) at 100℃; for 120h; Inert atmosphere; | A n/a B 85% |
2,6-di(isopropyl)-N-methyleneaniline
A
2,6-diisopropylbenzenamine
B
N,N-dimethyl-2,6-di(isopropyl)aniline
C
N-methyl-2,6-di(isopropyl)aniline
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether Heating; | A 4% B 9% C 79% |
With sodium tetrahydroborate |
2,4,6-tri-t-butylphenyldifluoroborane
A
2,4,6-tri(t-butyl)phenyl-2,6-di(isopropyl)phenyliminoborane
B
2,6-diisopropylbenzenamine
Conditions | Yield |
---|---|
In hexane byproducts: LiF; dropping a soln. of 2,4,6-tri-t-butylphenyl-difluoroborane in n-hexane to a suspension of freshly lithiated 2,6-di(isopropyl)phenylamine in n-hexane cooled with ice (under N2) followed by refluxing for 3 h; removal of the solvent under reduced pressure and subliming the iminoborane from the residue in anoil pump vacuum, elem. anal.; | A 79% B n/a |
2,6-diisopropylbenzenamine
Conditions | Yield |
---|---|
With methanol; oxalyl dichloride at 20℃; for 2h; | 78% |
2,6-di(isopropyl)-N-methyleneaniline
A
1,3-diisopropylbenzene
B
2,6-diisopropylbenzenamine
Conditions | Yield |
---|---|
With n-Butyl nitrite at 40℃; for 20h; | A 70% B n/a |
Conditions | Yield |
---|---|
With sodium chloride; aluminum (III) chloride under 37503.8 - 45004.5 Torr; Product distribution / selectivity; Friedel Crafts Alkylation; | 52% |
With aluminium trichloride; aluminium at 290℃; under 183877 Torr; |
Conditions | Yield |
---|---|
With sodium chloride; AlCl3(2,6-MIPA)2; 2-isopropyl-6-methylaniline at 260℃; under 37503.8 - 45004.5 Torr; for 5h; Product distribution / selectivity; Friedel Crafts Alkylation; | A 25% B 51% |
3-Methoxy-pyridine-2-carboxylic acid (2,6-diisopropyl-phenyl)-amide
A
2,6-diisopropylbenzenamine
Conditions | Yield |
---|---|
In sulfuric acid at 25℃; controlled potential electrochem. reduction, (-)Hg/Pt(+), -1000 mV vs. s.c.e.; | A 50% B 30% |
3-Methoxy-pyridine-2-carboxylic acid (2,6-diisopropyl-phenyl)-amide
A
2,6-diisopropylbenzenamine
Conditions | Yield |
---|---|
With water In methanol at 25℃; electrochemical reduction; | A 50% B 30% |
Conditions | Yield |
---|---|
In benzene at 90℃; for 0.25h; Schlenk technique; Inert atmosphere; | A n/a B n/a C 40% |
N-(2,6-diisopropylphenyl)benzimidamide
A
2,6-diisopropylbenzenamine
B
benzonitrile
Conditions | Yield |
---|---|
With bis(trimethylsilyl)amide yttrium(III) In toluene at 100℃; for 120h; Inert atmosphere; | A n/a B 35% |
2,6-di(isopropyl)-N-methyleneaniline
A
1,3-diisopropylbenzene
B
2,6-diisopropylbenzenamine
Conditions | Yield |
---|---|
With n-Butyl nitrite; dichloromethane at 40℃; for 20h; Product distribution; other time, other temp., also with CCl4; | A 25% B n/a C 25% |
3-<(2,6-diisopropylphenyl)imino>-2,2,4,4-tetramethyl-2,4-disilapentane
A
2,6-diisopropylbenzenamine
B
2,6-diisopropylphenylisocyanide
C
2,6-diisopropylphenyl isocyanate
D
2,6-di(isopropyl)-N-methyleneaniline
Conditions | Yield |
---|---|
With tetrachloromethane In benzene-d6 at 20℃; for 2h; Product distribution; Decomposition; Photolysis; | A 5.6 % Chromat. B 82.2 % Chromat. C 6.3 % Chromat. D 5.9 % Chromat. |
N-(2,6-diisopropyl-phenyl)-3-hydroxy-picolinamide
2,6-diisopropylbenzenamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 35 percent / NaOMe / dimethylformamide / 24 h / Ambient temperature 2: 50 percent / aq. H2SO4 / 25 °C / controlled potential electrochem. reduction, (-)Hg/Pt(+), -1000 mV vs. s.c.e. View Scheme |
1-dodecyltetrazoleacetic acid ethyl ester
B
2,6-diisopropylbenzenamine
4-pyrrolidin-1-ylpyridine
B
2,6-diisopropylbenzenamine
Conditions | Yield |
---|---|
In not given in hydrocarbon soln.; elem. anal.; |
A
cis-stilben
B
2,6-diisopropylbenzenamine
Conditions | Yield |
---|---|
With H2O In diethyl ether excess of water (1/9 v/v H2O/acetone) added dropwise at room temp.; stirred for 20 min;; solvent removed; extd. with Et2O; filtered through Celite; solvent removed; identified by 1H NMR-spectroscopy;; |
A
trans,trans-2,2,7,7-tetramethylocta-3,5-diene
B
2,6-diisopropylbenzenamine
Conditions | Yield |
---|---|
With H2O In diethyl ether excess of water (1/9 v/v H2O/acetone) added dropwise at room temp.; stirred for 20 min;; solvent removed; extd. with Et2O; filtered through Celite; solvent removed; identified by 1H NMR-spectroscopy;; |
6-(dimethylamino)fulvene
A
6-(2,6-diisopropylanilino)fulvene
B
2,6-diisopropylbenzenamine
Conditions | Yield |
---|---|
Stage #1: 6-(dimethylamino)fulvene; lithium (2,6-diisopropylphenyl)amide In diethyl ether Inert atmosphere; Stage #2: With acetylacetone In diethyl ether at -40℃; Inert atmosphere; |
4-cyanophenylacetylene
A
2,6-diisopropylbenzenamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: tetrahydrofuran / 0.17 h / 20 °C 2: 20 °C View Scheme |
methanol
C36H54ClN3O2Si2
A
1,3-diisopropyl-4,5-dimethyl-1H-imidazol-3-ium chloride
B
2,6-diisopropylbenzenamine
Conditions | Yield |
---|---|
at 20℃; |
methanol
C35H51ClN4Si2
A
1,3-diisopropyl-4,5-dimethyl-1H-imidazol-3-ium chloride
B
2,6-diisopropylbenzenamine
Conditions | Yield |
---|---|
at 20℃; |
2,6-diisopropylbenzenamine
4-bromo-2,6-diisopropylaniline
Conditions | Yield |
---|---|
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 5℃; for 0.333333h; Inert atmosphere; | 100% |
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃; for 2h; | 99% |
With bromine In methanol; dichloromethane at 25℃; for 25.5h; Schlenk technique; Inert atmosphere; | 99% |
2,6-diisopropylbenzenamine
acetic anhydride
N-(2,6-diisopropylphenyl) acetamide
Conditions | Yield |
---|---|
at 0℃; | 100% |
98% | |
With silver trifluoromethanesulfonate at 60℃; for 0.1h; Kinetics; Concentration; Time; neat (no solvent); | 98% |
furfural
2,6-diisopropylbenzenamine
Conditions | Yield |
---|---|
With magnesium sulfate; toluene-4-sulfonic acid In dichloromethane at 20℃; Inert atmosphere; | 100% |
With sulfuric acid In toluene for 20h; Condensation; Heating; | 92% |
With formic acid In ethanol at 20℃; for 4h; Schlenk technique; Inert atmosphere; | 82% |
With formic acid In ethanol at 20℃; for 24h; | 76% |
2,6-diisopropylbenzenamine
2,6-di(isopropyl)-N-methyleneaniline
Conditions | Yield |
---|---|
at 100℃; | 100% |
2-methylchlorobenzene
2,6-diisopropylbenzenamine
Conditions | Yield |
---|---|
With di-μ-bromobis-(tritert-butylphosphine)dipalladium(I); sodium t-butanolate In toluene at 100℃; for 0.75h; Catalytic behavior; Time; Buchwald-Hartwig Coupling; | 100% |
With C34H39N3O4Pd; sodium t-butanolate In 1,4-dioxane at 100℃; for 0.166667h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere; | 99% |
With C28H29Cl2N3OPd; potassium tert-butylate In toluene at 110℃; for 15h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere; | 99% |
di-tert-butyl dicarbonate
2,6-diisopropylbenzenamine
Conditions | Yield |
---|---|
Stage #1: 2,6-diisopropylbenzenamine With triethylamine In tetrahydrofuran; water at 20℃; for 0.0833333h; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; water at 0 - 20℃; for 6h; | 100% |
In ethanol at 30℃; for 48h; | 97% |
In water for 48h; Inert atmosphere; | 73% |
2,6-diisopropylbenzenamine
2-bromoethylamine hydrobromide
N1-(2,6-diisopropylphenyl)ethane-1,2-diamine
Conditions | Yield |
---|---|
Stage #1: 2,6-diisopropylbenzenamine; 2-bromoethylamine hydrobromide for 96h; Reflux; Stage #2: With sodium hydroxide In diethyl ether | 100% |
In toluene for 18h; Heating; | 74% |
In toluene at 110℃; for 18h; | 70% |
In toluene at 100℃; for 48h; | 40% |
With sodium hydroxide In toluene at 110℃; for 12h; |
2,6-diisopropylbenzenamine
Conditions | Yield |
---|---|
acetic acid In ethanol at 20℃; | 100% |
With formic acid In methanol for 8h; Inert atmosphere; Molecular sieve; | 80.7% |
Conditions | Yield |
---|---|
With triethylamine In toluene | 100% |
With triethylamine In diethyl ether | 59% |
2,6-diisopropylbenzenamine
niobium pentachloride
Conditions | Yield |
---|---|
In dichloromethane inert atmosphere; stirring NbCl5 with excess amine (room temp., 10 h); solvent removal (vac.) drying (vac.); elem. anal.; | 100% |
2,6-diisopropylbenzenamine
tantalum pentachloride
Conditions | Yield |
---|---|
In dichloromethane inert atmosphere; stirring TaCl5 with excess amine (room temp., 10 h); solvent removal (vac.) drying (vac.); elem. anal.; | 100% |
1.4-dibromobenzene
2,6-diisopropylbenzenamine
N,N'-bis(2,6-diisopropylphenyl)-p-phenylenediamine
Conditions | Yield |
---|---|
Stage #1: 1.4-dibromobenzene; 2,6-diisopropylbenzenamine With tri-tert-butyl phosphine; sodium t-butanolate; palladium diacetate In toluene at 110℃; for 14h; Stage #2: With water; ammonium chloride In toluene Product distribution / selectivity; | 100% |
Stage #1: 1.4-dibromobenzene; 2,6-diisopropylbenzenamine With tri-tert-butyl phosphine; sodium t-butanolate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) In toluene at 110℃; for 14h; Stage #2: With water; ammonium chloride In toluene Product distribution / selectivity; |
C25H35OP
2,6-diisopropylbenzenamine
((CH3)3C)3C6H2PHC6H4CHNC6H3(CH(CH3)2)2
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In toluene for 13h; Reflux; | 100% |
Conditions | Yield |
---|---|
With 4-methyl-morpholine; chloroformic acid ethyl ester In ethyl acetate at 0 - 20℃; for 15h; Inert atmosphere; Schlenk technique; | 100% |
With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran |
2,6-diisopropylbenzenamine
9-(3-(1-(2,6-diisopropylphenyl)-1H-imidazol-2-yl)phenyl)-9H-carbazole-2-carbonitrile
N-(2,6-diisopropylphenyl)-9-(3-(1-(2,6-diisopropylphenyl)-1H-imidazol-2-yl)phenyl)-9H-carbazole-2-carboximidamide
Conditions | Yield |
---|---|
Stage #1: 2,6-diisopropylbenzenamine With trimethylaluminum In toluene at 0 - 20℃; for 2.75h; Stage #2: 9-(3-(1-(2,6-diisopropylphenyl)-1H-imidazol-2-yl)phenyl)-9H-carbazole-2-carbonitrile In toluene at 90℃; for 60h; | 100% |
Conditions | Yield |
---|---|
With acetic acid In methanol for 8h; Reflux; | 100% |
With acetic acid In methanol for 12h; Reflux; |
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane at 20℃; Inert atmosphere; | 100% |
5,6,7,8-Tetrahydroquinolin-8-one
2,6-diisopropylbenzenamine
2,6-bis(1-methylethyl)-N-(5,6,7-trihydroquinolin-8-ylidene)phenylamine
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In water; toluene for 12h; Reflux; | 100% |
pentacarbonyl(tetrafluoroborato)rhenium
2,6-diisopropylbenzenamine
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 12h; | 100% |
2,6-diisopropylbenzenamine
isobutyraldehyde
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane at 20℃; | 100% |
With magnesium sulfate In toluene at 70℃; Inert atmosphere; Schlenk technique; | 97% |
at 20℃; for 72h; Inert atmosphere; Molecular sieve; | 89% |
2,6-diisopropylbenzenamine
benzene-1,2-dicarboxylic acid
Conditions | Yield |
---|---|
In methanol at 20℃; for 2h; Inert atmosphere; Reflux; | 100% |
2,6-diisopropylbenzenamine
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); n-butyllithium; XPhos In toluene at 60 - 100℃; | 100% |
Conditions | Yield |
---|---|
With triethylamine In ethyl acetate at 50℃; for 3h; Schlenk technique; Inert atmosphere; | 99.7% |
carbon disulfide
2,6-diisopropylbenzenamine
N,N'-bis(2,6-diisopropylphenyl)thiourea
Conditions | Yield |
---|---|
With sodium carbonate; triethylamine In water at 20 - 90℃; for 19h; Reagent/catalyst; | 99.1% |
With triethylamine In water at 20 - 90℃; for 15h; | 93% |
With triethylamine In water | |
With triethylamine In water Inert atmosphere; Schlenk technique; |
pyridine-2-carbaldehyde
2,6-diisopropylbenzenamine
2-(((2,6-diisopropylphenyl)imino)methyl)pyridine
Conditions | Yield |
---|---|
In dichloromethane for 20h; Dean-Stark; Reflux; | 99% |
With formic acid In methanol at 20℃; for 10h; | 95% |
With toluene-4-sulfonic acid In diethyl ether at 27℃; for 12h; Inert atmosphere; Schlenk technique; | 95% |
2,6-diisopropylbenzenamine
phenyl isothiocyanate
N'-phenyl-N-(2,6-diisopropylphenyl)thiourea
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 2h; | 99% |
With [{Ph2P(Se)NCH2CH2NPPh2(Se)}Ti(NMe2)2] In toluene at 25℃; for 1h; Schlenk technique; Glovebox; Inert atmosphere; | 99% |
With [κ2-{(Ph2P-(=Se))}2NCH2(C5H4N)ZnCl2] In toluene at 25℃; Schlenk technique; Inert atmosphere; | 85% |
for 2h; Ambient temperature; Yield given; |
2,6-diisopropylbenzenamine
Acetic formic anhydride
N-(2,6-diisopropylphenyl)formamide
Conditions | Yield |
---|---|
In tetrahydrofuran at -20℃; for 0.25h; | 99% |
at 0 - 20℃; for 1h; | 94% |
In tetrahydrofuran at 20℃; | |
In dichloromethane at 0℃; for 3h; | |
In tetrahydrofuran at 20℃; for 15h; Cooling with ice; |
di-tert-butyl dicarbonate
2,6-diisopropylbenzenamine
2,6-diisopropylphenyl isocyanate
Conditions | Yield |
---|---|
With dmap In acetonitrile at 25℃; for 0.166667h; | 99% |
Stage #1: di-tert-butyl dicarbonate; 2,6-diisopropylbenzenamine With dmap In acetonitrile for 0.166667h; Stage #2: With sulfuric acid In water; acetonitrile for 0.0666667h; | 90% |
isocyanate de chlorosulfonyle
2,6-diisopropylbenzenamine
[[[2,6-bis(1-methylethyl)phenyl]amino]carbonyl]sulfamoyl chloride
Conditions | Yield |
---|---|
In diethyl ether at -15℃; for 1h; | 99% |
In diethyl ether at -15℃; for 1.5h; | 75% |
In diethyl ether | 53.79 g (99%) |
In diethyl ether | 53.79 g (99%) |
pyridine-2-carbaldehyde
2,6-diisopropylbenzenamine
2,6-bis(1-methylethyl)-N-(2-pyridinylmethylene)phenylamine
Conditions | Yield |
---|---|
In dichloromethane for 17h; Reflux; | 99% |
With air In dichloromethane for 17h; Reflux; | 99% |
In dichloromethane for 20h; Reflux; Dean-Stark; | 99% |
Reported in EPA TSCA Inventory.
1. Introduction of 2,6-Diisopropylaniline
2,6-Diisopropylaniline, with CAS number of 24544-04-5, can be called 2,6-Bis(1-methylethyl)aniline; 2,6-Bis(1-methylethyl)benzenamine; 2,6-Diisopropylphenylamine ; N-(2,6-Diisopropylphenyl)amine. 2,6-Diisopropylaniline is stable under normal temperatures and pressures, but incompatible with strong oxidizing agents, acids, acid chlorides, acid anhydrides, chloroformates. The colorless to pale orange liquid slightly soluble in water and the solubility is less than 0.20g/L.
2. Properties of 2,6-Diisopropylaniline
H bond acceptors: 1
H bond donors: 2
Freely Rotating Bonds: 3
Polar Surface Area: 26.02 Å2
Index of Refraction: 1.525
Molar Refractivity: 58.85 cm3
Molar Volume: 191.8 cm3
Surface Tension: 33.9 dyne/cm
Enthalpy of Vaporization: 49.49 kJ/mol
Vapour Pressure: 0.0147 mmHg at 25°C
Density: 1.2 g/cm3
Melting Point: -45 °C(lit.)
Flash Point: 208.2 °C
Boiling Point: 420.7 °C at 760 mmHg
Water solubility: <0.20 g/L
Product Categories: Amines; C11 to C38; Nitrogen Compounds; Aniline Derivatives; o-alkylated Anilines
3. Toxicity of 2,6-Diisopropylaniline
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rat | LD50 | oral | 3204mg/kg (3204mg/kg) | LIVER: OTHER CHANGES BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE BLOOD: CHANGES IN SPLEEN | Fundamental and Applied Toxicology. Vol. 3, Pg. 285, 1983. |
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