Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydroxide; sodium perchlorate; chlorine at 24.9℃; Mechanism; Rate constant; Equilibrium constant; multistep reaction: 1.) water, 298 deg K, 2.) water, 298 deg K; reactions under var. conditions; | A 100% B n/a C n/a |
Conditions | Yield |
---|---|
In water at 24.9℃; Rate constant; Mechanism; Thermodynamic data; Irradiation; I=0.5 mol-1 L-1; various pH; ΔH(excit.), ΔS(excit.); | A 100% B n/a |
With water In 1,4-dioxane at 25℃; | |
With water In 1,4-dioxane at 25℃; Kinetics; Mechanism; |
acetamide
4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
A
ethylbis(dimethyl(2-penten-2-yl)silyloxy)borane
B
methylamine
Conditions | Yield |
---|---|
In 1,2,5-trimethyl-benzene dropwise addn. of acetamide to boron compd. soln., 160°C, 3.5h; heating (reflux), 10h; evapn.; all under Ar; distn.; elem. anal.; | A 100% B 98% |
Conditions | Yield |
---|---|
With borane-ammonia complex In methanol; water at 20℃; for 0.0833333h; | 99% |
With ammonia borane; Pd/MIL-101 In methanol; water at 20℃; for 0.025h; | 99% |
With sodium tetrahydroborate In methanol; water at 20℃; for 0.0666667h; Sealed tube; Green chemistry; | 99% |
piperidine
N-n-butyl-N-methylamine
A
1-butyl-piperidine
B
methylamine
Conditions | Yield |
---|---|
palladium at 160℃; for 5h; | A 98% B n/a |
piperidine
benzyl-methyl-amine
A
N-Benzylpiperidine
B
methylamine
Conditions | Yield |
---|---|
palladium at 130℃; for 10h; | A 97% B n/a |
A
1-methyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione
B
N,N'-dimethyl-guanidine
C
methylamine
Conditions | Yield |
---|---|
With hydrogenchloride for 10h; Heating; | A 15% B 96% C 4% |
N,N'-Dimethylurea
sodium p-toluenesulfonamide
A
N-Methyl-N'-toluene-p-sulfonylurea
B
methylamine
Conditions | Yield |
---|---|
at 160℃; for 3h; Product distribution; Rate constant; Equilibrium constant; Other temperature, other time, other ratio of reactants, activation energy, ΔH, ΔS;; | A 95.5% B n/a |
at 160℃; for 3h; | A 95.5% B n/a |
ethylenediamine
benzyl-methyl-amine
A
methylamine
B
N-benzylethylenediamine
Conditions | Yield |
---|---|
palladium at 120℃; for 10h; | A n/a B 95% |
4-Aminobutanol
4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
A
4,5-diethyl-2,2,3-trimethyl-6-oxa-1-azonia-2-sila-5-boratabicyclo{5.3.0}dec-3-ene
B
4,5-diethyl-2,2,3-trimethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclodecene
C
methylamine
Conditions | Yield |
---|---|
In neat (no solvent) addn. of boron compd. to equimolar amt. of aminoalkanol, room temp.; driving out CH3NH2 in a stream of Ar, 20-80°C, 4h;; distn. (vac.); elem. anal.; monocyclic : bicyclic isomer = 95:5; | A n/a B n/a C 95% |
6-methyl-8-nitro-1,6-naphthyridin-5(6H)-one
A
8-methylpyrido<2,3-d>pyridazin-5-one
B
methylamine
Conditions | Yield |
---|---|
With hydrazine hydrate at 130 - 140℃; for 5h; | A 94% B n/a C n/a |
4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
ethanolamine
A
4,5-diethyl-2,2,3-trimethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclooctene
B
methylamine
Conditions | Yield |
---|---|
In 1,2,5-trimethyl-benzene heating under Ar, 40-70°C, 4h; | A 93% B 93% |
In neat (no solvent) addn. of boron compd. to equimolar amt. of aminoalkanol, room temp.; driving out CH3NH2 in a stream of Ar, 20°C, 24h;; distn. (vac.); elem. anal.; | A 82% B 87% |
(2R)-2-aminobutan-1-ol
4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
A
(R)-4,5,7-triethyl-2,2,3-trimethyl-6-oxa-1-azonia-2-sila-5-boratabicyclo{3.3.0}oct-3-ene
B
(R)-4,5,7-triethyl-2,2,3-trimethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclooctene
C
methylamine
Conditions | Yield |
---|---|
In neat (no solvent) addn. of boron compd. to equimolar amt. of aminoalkanol, room temp.; driving out CH3NH2 in a stream of Ar, 20-25°C, 18h; distn. (vac.); elem. anal.; monocyclic : bicyclic isomer = 95:5; | A n/a B n/a C 91% |
pyrrolidine
benzyl-methyl-amine
A
N-benzylcyclohexylamine
B
N-phenyl(methylidene)cyclohexanamine
C
methylamine
Conditions | Yield |
---|---|
palladium at 120℃; for 10h; | A 10% B 90% C n/a |
2-aminobutanol
4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
A
4,5,7-triethyl-2,2,3-trimethyl-6-oxa-1-azonia-2-sila-5-boratabicyclo{3.3.0}oct-3-ene
B
4,5,7-triethyl-2,2,3-trimethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclooctene
C
methylamine
Conditions | Yield |
---|---|
In neat (no solvent) addn. of boron compd. to equimolar amt. of aminoalkanol, room temp.; driving out CH3NH2 in a stream of Ar, 20-25°C, 22h; distn. (vac.); elem. anal.; monocyclic: bicyclic isomer = 95:5; | A n/a B n/a C 89% |
N-methylisoephedrine
A
2-hydroxy-1-phenylpropylamine
B
formaldehyd
C
benzaldehyde
D
acetaldehyde
E
dimethyl amine
F
methylamine
Conditions | Yield |
---|---|
With water at 25℃; Product distribution; Mechanism; anodic oxidation, carbonate buffer, pH 10; effect of substituents investigated with different types of β-alkanolamines; | A 1.3% B 28% C 82% D 88% E 38% F 33% |
4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
m-Hydroxyaniline
A
C30H48B2N2O2Si2
B
methylamine
Conditions | Yield |
---|---|
In 1,2,5-trimethyl-benzene at 125-150°C, 26h under Ar; evapn.; elem. anal.; | A n/a B 88% |
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydroxide; sodium perchlorate; chlorine at 24.9℃; Mechanism; Rate constant; Equilibrium constant; multistep reaction: 1.) water, 298 deg K, 2.) water, 298 deg K; reactions under var. conditions; | A n/a B 87% C n/a |
2-methylamino-1-phenylpropanol
A
formaldehyd
B
benzaldehyde
C
acetaldehyde
D
benzoic acid
E
methylamine
Conditions | Yield |
---|---|
Mechanism; Product distribution; anodic oxidation; | A 12% B 65% C 68% D 12% E 87% |
4,5-diethyl-2,5-dihydro-3-isopropenyl-1,2,2-trimethyl-1,2,5-azasilaborole
ethanolamine
A
4,5-diethyl-3-isopropenyl-2,2-dimethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclooctene
B
4,5-diethyl-3-isopropenyl-2,2-dimethyl-6-oxa-1-azonia-2-sila-5-boratabicyclo{3.3.0}oct-3-ene
C
methylamine
Conditions | Yield |
---|---|
In neat (no solvent) addn. of boron compd. to equimolar amt. of aminoalkanol, room temp.; driving out CH3NH2 in a stream of Ar, 20-25°C, 22h;; distn. (vac.); standing at room temp.; crystn. of bicyclic isomer; elem. anal.; | A 57% B n/a C 87% |
4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
propan-1-ol-3-amine
A
4,5-diethyl-2,2,3-trimethyl-6-oxa-1-azonia-2-sila-5-boratabicyclo{4.3.0}non-3-ene
B
4,5-Diethyl-2,2,3-trimethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclononene
C
methylamine
Conditions | Yield |
---|---|
In neat (no solvent) addn. of boron compd. to equimolar amt. of aminoalkanol, room temp.; driving out CH3NH2 in a stream of Ar, 20-80°C, 24h;; distn. (vac.); elem. anal.; monocyclic : bicyclic isomer = 95:5; | A n/a B n/a C 87% |
pseudoephedrine
4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
A
(4S,5S)-2-Ethyl-4-methyl-5-phenyl-1,3,2-oxazaborolan
B
{(1S,2S)-2-[Dimethyl-((E)-1-methyl-but-1-enyl)-silanyloxy]-1-methyl-2-phenyl-ethyl}-methyl-amine
C
(7S,8S)-4,5-Diethyl-2,2,3,6,7-pentamethyl-8-phenyl-1-oxa-6-aza-2-sila-5-bora-3-cycloocten
D
methylamine
Conditions | Yield |
---|---|
In 1,2,5-trimethyl-benzene dropwise addn. of boron compd. to aminoalkanol soln. under Ar, 0.5h; heating to 140-150°C, 12h; evapn.; distn. (vac.); elem. anal.; | A n/a B n/a C 75% D 86% |
Conditions | Yield |
---|---|
With sodium hydroxide; benzyltrimethylazanium tribroman-2-uide In water at 70℃; for 2h; | 85% |
With potassium hydroxide; bromine ueber mehrere Stufen; | |
With potassium hydroxide; bromine | |
With water; bromine; calcium carbonate ueber mehrere Stufen; | |
With sodium hydroxide; sodium bromite In water at 70℃; for 0.5h; Yield given; |
Conditions | Yield |
---|---|
palladium at 120℃; for 20h; | A 85% B n/a |
2-(N,N-dimethylamino)ethanol
4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
A
(E)-3-<<2-(Dimethylamino)ethoxy>ethylboryl>-2-<<2-(dimethylamino)ethoxy>dimethylsilyl>-2-penten
B
methylamine
Conditions | Yield |
---|---|
In neat (no solvent) stirring under Ar, 0-20°C, 1-2h; heating to a maximum of 140°C, 10h; distn. (vac.); elem. anal.; | A 82% B 76% |
(2-hydroxyethyl)(methyl)amine
4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
A
4,5-diethyl-2,2,3,6-tetramethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclooctene
B
methylamine
Conditions | Yield |
---|---|
In neat (no solvent) dropwise addn. of boron compd. to aminoalkanol, 10 min; stirring in a stream of Ar, 20°C, 24h;; distn. (vac.); elem. anal.; | A 81% B 82% |
trimethyl-borane; compound with methylamine
A
trimethylborane
B
methylamine
Conditions | Yield |
---|---|
at 130.0°C, 77.4 Torr equilibrium; | A 81.95% B 81.95% |
at 130.0°C, 77.4 Torr equilibrium; | A 81.95% B 81.95% |
at 85.4°C, 52.5 Torr equilibrium; | A 38.86% B 38.86% |
at 85.4°C, 52.5 Torr equilibrium; | A 38.86% B 38.86% |
L(-)-ephedrine hemihydrate
4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
A
(7S,8R)-4,5-diethyl-2,2,3,6,7-pentamethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclooctene
B
methylamine
Conditions | Yield |
---|---|
In neat (no solvent) dropwise addn. of boron compd. to aminoalkanol under Ar, 5 min; heating to 110-150°C, 8.5h;; distn. (vac.); elem. anal.; | A 73% B 80.5% |
N-n-butyl-N-methylamine
benzyl-methyl-amine
A
N-Butyl-N-methylbenzenemethanamine
B
methylamine
Conditions | Yield |
---|---|
palladium at 120℃; for 10h; | A 80% B n/a |
Conditions | Yield |
---|---|
at 20℃; under 600.048 - 750.06 Torr; Addition; soid-gas reaction; ring cleavage; | 100% |
With water | |
In water for 1h; Ambient temperature; |
Conditions | Yield |
---|---|
With magnesium sulfate In methanol; dichloromethane for 7h; Heating; | 100% |
With water | |
In water 1.) 40 - 45 deg C, 15 min, 2.) room temp., 4 h; Yield given; |
Conditions | Yield |
---|---|
In water at 220℃; under 114000 Torr; for 4h; | 100% |
With ethanol at 220℃; | |
In 5,5-dimethyl-1,3-cyclohexadiene |
Conditions | Yield |
---|---|
at -20℃; under 75.006 Torr; Addition; solid-gas reaction; ring cleavage; | 100% |
In ethanol | 55% |
Conditions | Yield |
---|---|
In ethanol; water at 20℃; for 72h; Inert atmosphere; | 100% |
In water for 72h; Reflux; | 100% |
In water | 100% |
Conditions | Yield |
---|---|
In ethanol at 120℃; for 7h; Sealed tube; Microwave irradiation; | 100% |
With ethanol at 120℃; | |
With phenol at 190℃; |
4-methyl-benzaldehyde
methylamine
p-methylbenzylidene-methylamine
Conditions | Yield |
---|---|
at 20℃; for 12h; | 100% |
In methanol; dichloromethane for 18h; Molecular sieve; | 86% |
Conditions | Yield |
---|---|
With triethylamine In ethanol for 4h; Reflux; | 100% |
In ethanol; water Sealed tube; Reflux; | 94% |
In ethanol; water at 100℃; for 72h; Sealed tube; | 54% |
Conditions | Yield |
---|---|
at 20℃; for 12h; | 100% |
In water for 1h; Ambient temperature; | 95% |
at 20℃; for 15h; | 95% |
Conditions | Yield |
---|---|
at 0℃; under 187.515 Torr; Solid phase reaction; gas-solid reaction; | 100% |
at 20℃; for 12h; | 100% |
With ethanol; water at 40℃; |
Conditions | Yield |
---|---|
In ethanol; water at 40℃; for 2h; | 100% |
In ethanol at 0 - 40℃; | 90% |
In water for 10h; Ambient temperature; | 80% |
Conditions | Yield |
---|---|
In ethanol at 20℃; for 8h; | 100% |
In ethanol at 20℃; for 8h; | 100% |
With molecular sieve In ethanol; water for 0.5h; | 96% |
N,N,N',N'-Tetramethylphosphorodiamidic chloride
methylamine
Pentamethylphosphoramide
Conditions | Yield |
---|---|
at 20℃; for 48h; | 100% |
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane at 0℃; for 1h; | 83% |
64% |
3,4-dimethoxy-benzaldehyde
methylamine
N-(3,4-dimethoxybenzylidene)methanamine
Conditions | Yield |
---|---|
With 4 A molecular sieve In toluene at 0℃; | 100% |
With benzene | |
In methanol at 40℃; for 5h; | |
In ethanol at 50℃; | |
In benzene for 2h; Reflux; |
Conditions | Yield |
---|---|
In ethanol at 0 - 5℃; for 2h; | 100% |
at 20℃; for 12h; | 100% |
With benzene zuletzt unter Abdestillieren des gebildeten Wassers; |
Conditions | Yield |
---|---|
at 0℃; under 375.03 Torr; Addition; solid-gas reaction; | 100% |
acrylic acid methyl ester
methylamine
methyl 3-(methylamino)propanoate
Conditions | Yield |
---|---|
In diethyl ether at 4℃; Addition; | 100% |
With C12H18NO3S(1+)*HO4S(1-) at 25℃; for 0.0833333h; Ionic liquid; Neat (no solvent); chemoselective reaction; | 99% |
In ethanol at -10℃; | 86% |
Conditions | Yield |
---|---|
In ethanol at 20℃; for 48h; Molecular sieve; Inert atmosphere; | 100% |
In ethanol at 20℃; for 48h; Molecular sieve; Inert atmosphere; | 100% |
With triethylamine In ethanol for 1h; Molecular sieve; | 97% |
Conditions | Yield |
---|---|
at 20℃; for 12h; | 100% |
In ethanol at 0 - 40℃; | 90% |
In water for 10h; Ambient temperature; | 86% |
Conditions | Yield |
---|---|
In ethanol at 0 - 40℃; | 100% |
In water for 10h; Ambient temperature; | 80% |
With water |
4-dimethylamino-benzaldehyde
methylamine
4-(dimethylamino)-N-methylbenzylimine
Conditions | Yield |
---|---|
at 20℃; under 750.06 Torr; Solid phase reaction; gas-solid reaction; | 100% |
at 20℃; for 12h; | 100% |
With benzene |
Conditions | Yield |
---|---|
In ethanol; water Reflux; | 100% |
In methanol; water Heating; | 98% |
In water at 20℃; for 2h; Inert atmosphere; | 93% |
Conditions | Yield |
---|---|
In ethanol at 20℃; for 15h; | 100% |
In ethanol; water at 20℃; for 1h; | 100% |
In ethanol at 0 - 20℃; for 15h; | 95% |
1-isothiocyanatonaphthalene
methylamine
1-methyl-3-naphthalene-1-yl-thiourea
Conditions | Yield |
---|---|
at 20℃; under 750.06 Torr; Addition; solid-gas reaction; | 100% |
With ethanol |
p-nitrophenyl isothiocyanate
methylamine
1-(4-nitrophenyl)-3-methyl-thiourea
Conditions | Yield |
---|---|
at 20℃; under 750.06 Torr; Addition; solid-gas reaction; | 100% |
Conditions | Yield |
---|---|
With ammonium chloride In ethanol at 200℃; for 20h; | 100% |
With water at 200 - 220℃; unter Druck; | |
With sodium hydrogensulfite In water Bucherer reaction; Autoclave; |
methylamine
3-(bromomethyl)benzonitrile
3-((methylamino)methyl)benzonitrile
Conditions | Yield |
---|---|
In THjfF (tetrahydrofuran) at 20℃; for 3h; Inert atmosphere; | 100% |
In tetrahydrofuran at 20℃; for 24h; | 96% |
In water at 0 - 20℃; for 3.16h; | 82% |
methylamine
4-Bromophenyl isothiocyanate
1-(4-bromophenyl)-3-methyl-thiourea
Conditions | Yield |
---|---|
at 20℃; under 750.06 Torr; Addition; solid-gas reaction; | 100% |
With ethanol |
methylamine
2,3-dimethyoxybenzaldehyde
(2,3-dimethoxy-benzylidene)-methyl-amine
Conditions | Yield |
---|---|
at 20℃; for 12h; | 100% |
In ethanol at 0 - 40℃; | 90% |
With benzene zuletzt unter Erwaermen und Entfernen des gebildeten Wassers; | |
In benzene for 2h; Reflux; | |
In ethanol; water |
methylamine
2,4-Dichloro-5-nitropyrimidine
2-chloro-4-(methylamino)-5-nitropyrimidine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; methanol at -78 - 20℃; for 3h; | 100% |
With N-ethyl-N,N-diisopropylamine In dichloromethane at -60℃; for 1h; | 85% |
With N-ethyl-N,N-diisopropylamine In ethanol; dichloromethane at 0℃; for 0.5h; | 85.4% |
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