Conditions | Yield |
---|---|
With Ru on activatedcarbon cloth; activatedcarbon cloth In aq. phosphate buffer at 60℃; for 10h; pH=8.5; Time; Reagent/catalyst; Electrochemical reaction; | 98% |
rhodium hydrido (PEt3)3 complex for 4h; Product distribution; Heating; var. of catalyst, time; | 97% |
rhodium hydrido (PEt3)3 complex for 4h; Heating; | 97% |
2,2-dimethoxy-1-methylpyrrolidine
1-Methylpyrrolidine
Conditions | Yield |
---|---|
With platinum on carbon; hydrogen at 25℃; under 3750.38 Torr; for 0.5h; Catalytic behavior; Reagent/catalyst; | 96% |
Conditions | Yield |
---|---|
With alumina at 340℃; under 75007.5 Torr; High pressure; Flow reactor; Supercritical conditions; | 95% |
Conditions | Yield |
---|---|
In methanol | 93% |
Conditions | Yield |
---|---|
With hydrogen In water at 300℃; under 7500.75 Torr; for 6h; Time; Temperature; Reagent/catalyst; | 92% |
With hydrogen at 300℃; under 18751.9 Torr; for 6h; Catalytic behavior; Mechanism; Temperature; Time; Pressure; Reagent/catalyst; Autoclave; | 83% |
With aluminum oxide at 300℃; |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In 2,2,2-trifluoroethanol for 3.5h; Reflux; | 88% |
With acetic acid at 30℃; for 2h; | 82% |
With formic acid | |
With formic acid Eschweiler-Clarke reaction; Reflux; |
Conditions | Yield |
---|---|
With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran for 5h; Heating; | 85% |
With triphenylborane; methylphenylsilane In dichloromethane-d2 at 25℃; for 24h; Inert atmosphere; chemoselective reaction; | 78% |
With dihydrogen hexachloroplatinate(IV) hexahydrate In tetrahydrofuran at 60℃; for 3h; | 70% |
1-methyl-pyrrolidin-2-one
A
1-Methylpyrrolidine
B
(+/-)-1-methyl-2-tetradecylpyrrolidine
Conditions | Yield |
---|---|
Stage #1: 1-methyl-pyrrolidin-2-one With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride In dichloromethane at -78 - 0℃; for 1h; Inert atmosphere; Stage #2: halo(tetradecyl)magnesium In diethyl ether; dichloromethane at -78 - 20℃; for 1h; Inert atmosphere; Stage #3: With lithium aluminium tetrahydride In diethyl ether; dichloromethane at 20℃; for 1h; Inert atmosphere; | A n/a B 75% |
Conditions | Yield |
---|---|
With 5 wt% Pd/C; hydrogen; 1-butyl-3-methylimidazolium Tetrafluoroborate at 160℃; under 75007.5 Torr; for 6h; Autoclave; | 75% |
With hydrogen In neat (no solvent) at 200℃; for 24h; | 99 %Chromat. |
With hydrogen In octane at 150℃; for 30h; Autoclave; | 93 %Chromat. |
With hydrogen In hexane at 140℃; under 15001.5 - 45004.5 Torr; for 7h; Autoclave; Green chemistry; | 99 %Chromat. |
With 5 wt% Re/TiO2; hydrogen In octane at 200℃; under 45004.5 Torr; for 24h; Autoclave; chemoselective reaction; | 99 %Chromat. |
Conditions | Yield |
---|---|
With copper diacetate In dichloromethane for 24h; Ambient temperature; | 47% |
A
1-Methylpyrrolidine
Conditions | Yield |
---|---|
at 170℃; for 3h; | A n/a B 41% |
N-Methyl-1,4-diaminobutane
1-Methylpyrrolidine
Conditions | Yield |
---|---|
With R-selective imine reductase from streptosporangium roseum; NAD+-reducing hydrogenase from Ralstonia eutropha H16, variant E341A/S342R; putrescine oxidase from Rhodococcus erythropolis, variant E203G; water; hydrogen; oxygen; NADPH; catalase In aq. buffer at 25℃; for 4h; pH=7.5; | 30% |
With water; Catalase immobilized on Amberlite FP54; NAD+-reducing hydrogenase from Ralstonia eutropha immobilized on Amberlite FP54; NADH-dependent imine reductase from Myxococcus stipitatus immobilized on EziGI; putrescine oxidase from Rhodococcus erythropolis immobilized on EziGI In aq. buffer at 21℃; for 16h; pH=7.5; Flow reactor; Electrochemical reaction; Enzymatic reaction; | 3 mg |
Conditions | Yield |
---|---|
With aluminum oxide at 300℃; | |
With aluminum oxide at 400℃; | |
titanium(IV) oxide at 250 - 300℃; Yield given; | |
CrZMS-5 at 300℃; for 4h; | 48.0 % Chromat. |
Conditions | Yield |
---|---|
With palladium asbestos at 160℃; Hydrogenation; | |
With hydrogenchloride; platinum Hydrogenation; | |
With platinum(IV) oxide; acetic acid Hydrogenation; |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride; diethyl ether | |
With triethylsilane; ethyl iodide; dicarbonyldichlorobis(triphenylphosphine)ruthenium(II) In toluene at 100℃; | |
With hydrogen In 1,2-dimethoxyethane at 160℃; under 22502.3 Torr; for 20h; Inert atmosphere; Autoclave; Molecular sieve; | |
With Dimethylphenylsilane; [IrIII(triflato)(H)(κ2-((4-methylpyridine-2-yl)oxy)di(tert-butyl)silyl)(cis-cyclooctene)] In benzene-d6 at 49.84℃; for 0.25h; Catalytic behavior; Time; Temperature; Reagent/catalyst; Inert atmosphere; Glovebox; | > 99 %Spectr. |
Conditions | Yield |
---|---|
With sodium hypobromide Erwaermen des erhaltenen N-Brom-methylbutylamins mit konz. Schwefelsaeure erst auf dem Wasserbad, dann auf 135grad; | |
With C31H37ClN3NiO2(1-)*Li(1+); potassium tert-butylate In dimethyl sulfoxide at 110℃; for 3h; Catalytic behavior; Sealed tube; Inert atmosphere; | 24.5 %Chromat. |
N,N'-dimethyl-butanediyldiamine; hydrochloride
1-Methylpyrrolidine
Conditions | Yield |
---|---|
Bei der trocknen Destillation.; |
N,N-dimethyl-butanediyldiamine; hydrochloride
1-Methylpyrrolidine
Conditions | Yield |
---|---|
Bei der trocknen Destillation.; |
1-Methylpyrrolidine
Conditions | Yield |
---|---|
Bei der trocknen Destillation.; |
N-methylputrescine dihydrochloride
1-Methylpyrrolidine
Conditions | Yield |
---|---|
Bei der trocknen Destillation.; |
tetra-N-methyl-butanediyldiamine; hydrochloride
1-Methylpyrrolidine
Conditions | Yield |
---|---|
Bei der trocknen Destillation.; |
Conditions | Yield |
---|---|
Destillation; |
1-Methylpyrrolidine
Conditions | Yield |
---|---|
beim Erhitzen; |
N,N-dimethylpyrrolidinium iodide
ethanolamine
A
1-Methylpyrrolidine
B
1-pyrrolidineethanol
C
2-(4-dimethylamino-butylamino)-ethanol
D
dimethyl amine
1-Ethyl-1-methylpyrrolidinium iodide
ethanolamine
A
1-Methylpyrrolidine
B
1-ethylpyrrolidine
C
1-pyrrolidineethanol
D
N-Ethylmethylamine
Conditions | Yield |
---|---|
In ethanol |
Conditions | Yield |
---|---|
With ethanol |
3-(1-methyl-pyrrolidin-2-yl)-pyridine
A
1-Methylpyrrolidine
B
nicotirine
Conditions | Yield |
---|---|
With water; silver(l) oxide |
1-Methylpyrrolidine
1,3-dibromo-propane
1-(3-bromopropyl)-1-methylpyrrolidin-1-ium bromide
Conditions | Yield |
---|---|
Reflux; | 100% |
at 20℃; for 48h; Darkness; | 92% |
With benzene | |
In acetone at 20℃; for 168h; Darkness; |
Conditions | Yield |
---|---|
In toluene Heating; | 100% |
1-Methylpyrrolidine
propargyl bromide
1-propargyl-1-methylpyrrolidinium bromide
Conditions | Yield |
---|---|
In tetrahydrofuran; toluene at 0 - 20℃; for 4h; Inert atmosphere; | 100% |
In diethyl ether; toluene at 0 - 20℃; | 97% |
In toluene at 50℃; for 24h; | 88% |
1-Methylpyrrolidine
2-chloroethyl methyl ether
N-2-methoxyethyl-N-methylpyrrolidinium chloride
Conditions | Yield |
---|---|
In ethyl acetate at 70℃; | 100% |
1-Methylpyrrolidine
triethylene glycol di-(p-toluenesulfonate)
Conditions | Yield |
---|---|
In acetonitrile at 75℃; for 60h; | 100% |
1-Methylpyrrolidine
2-(2-(2-methoxyethoxy)ethoxy)ethyl p-toluenesulfonate
1-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-1-methylpyrrolidinium p-toluenesulfonate
Conditions | Yield |
---|---|
In acetonitrile at 120℃; for 3h; | 100% |
Conditions | Yield |
---|---|
In methanol at 20℃; | 100% |
Conditions | Yield |
---|---|
In chloroform-d1 | 100% |
Conditions | Yield |
---|---|
In ethyl acetate at 20℃; for 0.0833333h; Menshutkin Reaction; | 100% |
1-Methylpyrrolidine
1-bromo-butane
N-methyl-N-butylpyrrolidinium bromide
Conditions | Yield |
---|---|
for 48h; Inert atmosphere; | 99% |
at 75 - 85℃; for 2.71667h; | 98% |
In acetonitrile Inert atmosphere; Cooling with ice; Reflux; | 98% |
Conditions | Yield |
---|---|
at 120 - 180℃; for 1.08333h; microwave irradiation; | 99% |
In isopropyl alcohol at 4 - 82℃; for 25.5h; Inert atmosphere; Darkness; | 20% |
In toluene at 114.84℃; for 24h; Inert atmosphere; |
1-Methylpyrrolidine
C16H17IO4S
N-methyl-N-[3-(4'-iodophenoxy)-1-propyl]pyrrolidinium 4-methylbenzenesulfonate
Conditions | Yield |
---|---|
In acetonitrile at 60℃; | 99% |
In chloroform at 60℃; | 99% |
1-Methylpyrrolidine
N-methyl-N-[3-(4'-iodophenyl)-1-propyl]pyrrolidinium 4-methylbenzenesulfonate
Conditions | Yield |
---|---|
In acetonitrile at 60℃; for 16h; | 99% |
1-Methylpyrrolidine
methyl trifluoromethanesulfonate
1,1-dimethylpyrrolidinium trifluoromethanesulfonate
Conditions | Yield |
---|---|
In hexane at 0 - 75℃; for 1h; | 99% |
In dichloromethane at 0℃; for 0.166667h; | 92% |
1-Methylpyrrolidine
1-[2-(methylsulfonamido)ethyl]-1-methylpyrrolidinium methanesulfonate
Conditions | Yield |
---|---|
In ethanol at 100℃; for 24h; | 99% |
1-Methylpyrrolidine
2-Methoxyethoxymethyl chloride
methyl trifluoromethanesulfonate
Conditions | Yield |
---|---|
Stage #1: 1-Methylpyrrolidine; 2-Methoxyethoxymethyl chloride In dichloromethane at 0℃; for 0.0166667h; Stage #2: methyl trifluoromethanesulfonate In dichloromethane at 0℃; for 0.25h; | 99% |
1-Methylpyrrolidine
chloromethyl methyl ether
methyl trifluoromethanesulfonate
Conditions | Yield |
---|---|
Stage #1: 1-Methylpyrrolidine; chloromethyl methyl ether In dichloromethane at 0℃; for 0.0166667h; Stage #2: methyl trifluoromethanesulfonate In dichloromethane at 0℃; for 0.25h; | 99% |
1-Methylpyrrolidine
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 20℃; under 7500750 Torr; for 48h; Pressure; Temperature; Sealed tube; High pressure; Inert atmosphere; | 99% |
1-Methylpyrrolidine
1 ,6-dibromohexane
1,6-bis(N-methylpyrrolidinium)hexane bromide
Conditions | Yield |
---|---|
for 24h; Reflux; | 98% |
In acetone at 20℃; | |
In methanol at 20℃; for 96h; | |
With ethanol |
Conditions | Yield |
---|---|
In neat (no solvent) | 98% |
1-Methylpyrrolidine
1-chlorododecane
1-dodecyl-1-methylpyrrolidinium chloride
Conditions | Yield |
---|---|
for 0.333333h; Microwave irradiation; | 98% |
at 70 - 100℃; | |
In toluene at 114.84℃; for 24h; Inert atmosphere; |
Conditions | Yield |
---|---|
In methanol | 98% |
Conditions | Yield |
---|---|
In acetonitrile at 60℃; for 72h; | 98% |
In acetonitrile for 24h; Reflux; | |
In acetonitrile at 0 - 25℃; for 24h; |
1-Methylpyrrolidine
Conditions | Yield |
---|---|
In acetonitrile for 72h; Menshutkin Reaction; Reflux; | 98% |
1-Methylpyrrolidine
2-nitrophenylmethyl bromide
1-methyl-1-(2-nitrobenzyl)pyrrolidinium bromide
Conditions | Yield |
---|---|
In ethyl acetate at 20℃; Inert atmosphere; | 97.8% |
1-Methylpyrrolidine
propan-1-ol
1-propyl-1-methylpyrrolidin-1-ium bromide
Conditions | Yield |
---|---|
With ethylene glycol; potassium bromide In water; acetonitrile at 40℃; for 1h; | 97.2% |
Conditions | Yield |
---|---|
With 5.4 wt% Au/CeO2; water; oxygen In 1,4-dioxane at 80℃; under 760.051 Torr; for 3.5h; Catalytic behavior; Reagent/catalyst; Temperature; Concentration; Schlenk technique; | 97% |
With iodosylbenzene In water for 36h; | 55% |
With tert.-butylhydroperoxide; [Mn(GBOA)2(H2O)2]*(Cl)2*4H2O In acetonitrile at 50 - 55℃; | 49.4% |
With carbonylchlorohydrido(4,5-bis((diisopropylphosphino)methyl)acridine)ruthenium(II); water; sodium hydroxide at 160℃; for 48h; Inert atmosphere; Schlenk technique; | 22% |
With water; oxygen at 80℃; under 760.051 Torr; for 24h; Green chemistry; regioselective reaction; | > 99 %Chromat. |
1-Methylpyrrolidine
4-acetamidophenyl 2-chloroacetate
1-(2-(4-acetamidophenoxy)-2-oxoethyl)-1-methylpyrrolidiniuim chloride
Conditions | Yield |
---|---|
In ethyl acetate for 48h; Reflux; | 97% |
In ethyl acetate for 48h; Reflux; | 97% |
IUPAC Name: 1-Methylpyrrolidine
Canonical SMILES: CN1CCCC1
InChI: InChI=1S/C5H11N/c1-6-4-2-3-5-6/h2-5H2,1H3
InChIKey: AVFZOVWCLRSYKC-UHFFFAOYSA-N
Molecular Formula: C5H11N
Formula Weight: 85.15
EINECS: 204-438-5
Product Categories: Building Blocks; Heterocyclic Building Blocks; Pyrrolidines
storage temp.: Flammables area
Water Solubility: fully miscible
Index of Refraction: 1.448
Molar Refractivity: 26.72 cm3
Molar Volume: 99.7 cm3
Surface Tension: 26.7 dyne/cm
Density: 0.853 g/cm3
Flash Point: −7 °F
Enthalpy of Vaporization: 32.27 kJ/mol
Boiling Point: 82.1 °C at 760 mmHg
Vapour Pressure: 79.6 mmHg at 25 °C
Appearance: clear to yellow liquid
Melting Point of 1-Methylpyrrolidine (CAS NO.120-94-5): -90 °C
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 178mg/kg (178mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 88, Pg. 82, 1946. | |
mouse | LD50 | intravenous | 47mg/kg (47mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 88, Pg. 82, 1946. |
Hazard Codes : F,C,N
Risk Statements : 11-22-34-51/53-35-20/22
R11:Highly flammable.
R22:Harmful if swallowed.
R34:Causes burns.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
R35:Causes severe burns.
R20/22:Harmful by inhalation and if swallowed.
Safety Statements : 16-26-36/37/39-45-61-29
S16:Keep away from sources of ignition.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
S29:Do not empty into drains.
RIDADR : UN 2924 3/PG 2
WGK Germany : 2
RTECS : UY1420500
HazardClass : 3
PackingGroup : II
APPEARANCE: clear to yellow liquid
ASSAY: 99.0% min
WATER: 0.5% max
1-Methylpyrrolidine (CAS NO.120-94-5), its Synonyms are Methylpyrrolidine ; N-Methylpyrrolidine ; N-Methyltetrahydropyrrole ; Pyrrolidine, 1-methyl- .
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