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120-94-5

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120-94-5 Usage

Chemical Properties

colorless transparent volatile liquid. Freely soluble in water, soluble in alcohol, ether and other organic solvents.

Uses

1-Methylpyrrolidine is a methylated pyrollidine and is involved as an essential part of the structure of cefipime. It is also an active component of cigarette smoke.

Preparation

n-methylpyrrolidine was successfully synthesized in an aqueous medium by using methylamine and 1,4-dibromobutane in the presence of catalyst k2co3 at a moderated temperature. here, n-methylpyrrolidine was firstly synthesized via the green chemistry process, in which both the water solvent and potassium carbonate catalyst were inexpensive and environmentally friendly. also, the reaction temperature was quite moderated at 90°C.green organic synthesis of n-methylpyrrolidine

Hazard

Flammable, dangerous fire risk. Irritant toskin and eyes.

Flammability and Explosibility

Highlyflammable

Safety Profile

Poison by intraperitoneal and intravenous routes. This material is strongly alkaline. Liquid and vapors are corrosive to the skin, eyes, or mucous membranes. A very dangerous fire hazard; keep away from sparks, heat sources, and powerful oxidizers. Keep in closed containers. To fight fire, use alcohol foam. When heated to decomposition it emits highly toxic fumes of NOx.

Check Digit Verification of cas no

The CAS Registry Mumber 120-94-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 0 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 120-94:
(5*1)+(4*2)+(3*0)+(2*9)+(1*4)=35
35 % 10 = 5
So 120-94-5 is a valid CAS Registry Number.
InChI:InChI=1/C5H11N/c1-6-4-2-3-5-6/h2-5H2,1H3/p+1

120-94-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Detail
  • Alfa Aesar

  • (B23799)  1-Methylpyrrolidine, 98%   

  • 120-94-5

  • 100g

  • 329.0CNY

  • Detail
  • Alfa Aesar

  • (B23799)  1-Methylpyrrolidine, 98%   

  • 120-94-5

  • 500g

  • 1186.0CNY

  • Detail
  • Sigma-Aldrich

  • (69110)  1-Methylpyrrolidine  ≥98.0% (GC)

  • 120-94-5

  • 69110-100ML

  • 259.74CNY

  • Detail
  • Sigma-Aldrich

  • (69110)  1-Methylpyrrolidine  ≥98.0% (GC)

  • 120-94-5

  • 69110-500ML

  • 1,807.65CNY

  • Detail
  • Aldrich

  • (M79204)  N-Methylpyrrolidine  97%

  • 120-94-5

  • M79204-5ML

  • 259.74CNY

  • Detail
  • Aldrich

  • (M79204)  N-Methylpyrrolidine  97%

  • 120-94-5

  • M79204-100ML

  • 259.74CNY

  • Detail
  • Aldrich

  • (M79204)  N-Methylpyrrolidine  97%

  • 120-94-5

  • M79204-500ML

  • 1,601.73CNY

  • Detail

120-94-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-Methylpyrrolidine

1.2 Other means of identification

Product number -
Other names Methylpyrrolidine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:120-94-5 SDS

120-94-5Synthetic route

pyrrolidine
123-75-1

pyrrolidine

methanol
67-56-1

methanol

1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

Conditions
ConditionsYield
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
39650-82-3

2,2-dimethoxy-1-methylpyrrolidine

1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

Conditions
ConditionsYield
With platinum on carbon; hydrogen at 25℃; under 3750.38 Torr; for 0.5h; Catalytic behavior; Reagent/catalyst;96%
methanol
67-56-1

methanol

4-Aminobutanol
13325-10-5

4-Aminobutanol

1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

Conditions
ConditionsYield
With alumina at 340℃; under 75007.5 Torr; High pressure; Flow reactor; Supercritical conditions;95%
pyrrolidine
123-75-1

pyrrolidine

1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

Conditions
ConditionsYield
In methanol93%
Butane-1,4-diol
110-63-4

Butane-1,4-diol

methylamine
74-89-5

methylamine

1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

Conditions
ConditionsYield
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℃;
pyrrolidine
123-75-1

pyrrolidine

formaldehyd
50-00-0

formaldehyd

1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

Conditions
ConditionsYield
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;
1-methyl-pyrrolidin-2-one
872-50-4

1-methyl-pyrrolidin-2-one

1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

Conditions
ConditionsYield
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
872-50-4

1-methyl-pyrrolidin-2-one

halo(tetradecyl)magnesium

halo(tetradecyl)magnesium

A

1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

B

(+/-)-1-methyl-2-tetradecylpyrrolidine
3447-09-4

(+/-)-1-methyl-2-tetradecylpyrrolidine

Conditions
ConditionsYield
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%
pyrrolidine
123-75-1

pyrrolidine

carbon dioxide
124-38-9

carbon dioxide

1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

Conditions
ConditionsYield
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.
pyrrolidine
123-75-1

pyrrolidine

trimethylbismuthine
593-91-9

trimethylbismuthine

1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

Conditions
ConditionsYield
With copper diacetate In dichloromethane for 24h; Ambient temperature;47%
1-[(S)-1-((R)-1-Methanesulfonyl-piperidin-2-ylmethyl)-hexyl]-1-methyl-pyrrolidinium; hydroxide

1-[(S)-1-((R)-1-Methanesulfonyl-piperidin-2-ylmethyl)-hexyl]-1-methyl-pyrrolidinium; hydroxide

A

1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

B

2-((E)-Hept-1-enyl)-1-methanesulfonyl-piperidine

2-((E)-Hept-1-enyl)-1-methanesulfonyl-piperidine

Conditions
ConditionsYield
at 170℃; for 3h;A n/a
B 41%
N-Methyl-1,4-diaminobutane
14475-60-6

N-Methyl-1,4-diaminobutane

1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

Conditions
ConditionsYield
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
tetrahydrofuran
109-99-9

tetrahydrofuran

methylamine
74-89-5

methylamine

1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

Conditions
ConditionsYield
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.
N-Methylpyrrole
96-54-8

N-Methylpyrrole

1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

Conditions
ConditionsYield
With palladium asbestos at 160℃; Hydrogenation;
With hydrogenchloride; platinum Hydrogenation;
With platinum(IV) oxide; acetic acid Hydrogenation;
1-pyrrolidinecarboxaldehyde
3760-54-1

1-pyrrolidinecarboxaldehyde

1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

Conditions
ConditionsYield
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.
N-n-butyl-N-methylamine
110-68-9

N-n-butyl-N-methylamine

1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

Conditions
ConditionsYield
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
16011-98-6

N,N'-dimethyl-butanediyldiamine; hydrochloride

1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

Conditions
ConditionsYield
Bei der trocknen Destillation.;
N,N-dimethyl-butanediyldiamine; hydrochloride
65592-37-2

N,N-dimethyl-butanediyldiamine; hydrochloride

1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

Conditions
ConditionsYield
Bei der trocknen Destillation.;
N,N,N'-trimethyl-butanediyldiamine; hydrochloride

N,N,N'-trimethyl-butanediyldiamine; hydrochloride

1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

Conditions
ConditionsYield
Bei der trocknen Destillation.;
N-methylputrescine dihydrochloride
89690-09-5

N-methylputrescine dihydrochloride

1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

Conditions
ConditionsYield
Bei der trocknen Destillation.;
tetra-N-methyl-butanediyldiamine; hydrochloride
78204-83-8

tetra-N-methyl-butanediyldiamine; hydrochloride

1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

Conditions
ConditionsYield
Bei der trocknen Destillation.;
N,N-dimethylpyrrolidinium hydroxide
68498-44-2

N,N-dimethylpyrrolidinium hydroxide

A

1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

B

methanol
67-56-1

methanol

Conditions
ConditionsYield
Destillation;
tetramethonium chloride dihydrate

tetramethonium chloride dihydrate

1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

Conditions
ConditionsYield
beim Erhitzen;
N,N-dimethylpyrrolidinium iodide
872-44-6

N,N-dimethylpyrrolidinium iodide

ethanolamine
141-43-5

ethanolamine

A

1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

B

1-pyrrolidineethanol
2955-88-6

1-pyrrolidineethanol

C

2-(4-dimethylamino-butylamino)-ethanol
100707-62-8

2-(4-dimethylamino-butylamino)-ethanol

D

dimethyl amine
124-40-3

dimethyl amine

1-Ethyl-1-methylpyrrolidinium iodide
4186-68-9

1-Ethyl-1-methylpyrrolidinium iodide

ethanolamine
141-43-5

ethanolamine

A

1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

B

1-ethylpyrrolidine
7335-06-0

1-ethylpyrrolidine

C

1-pyrrolidineethanol
2955-88-6

1-pyrrolidineethanol

D

N-Ethylmethylamine
624-78-2

N-Ethylmethylamine

1,4-dibromo-butane
110-52-1

1,4-dibromo-butane

methylamine
74-89-5

methylamine

1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

Conditions
ConditionsYield
In ethanol
1,4-Diiodobutane
628-21-7

1,4-Diiodobutane

methylamine
74-89-5

methylamine

1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

Conditions
ConditionsYield
With ethanol
3-(1-methyl-pyrrolidin-2-yl)-pyridine
22083-74-5

3-(1-methyl-pyrrolidin-2-yl)-pyridine

A

1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

B

nicotirine
487-19-4

nicotirine

Conditions
ConditionsYield
With water; silver(l) oxide
nicotin
54-11-5

nicotin

1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

1,3-dibromo-propane
109-64-8

1,3-dibromo-propane

1-(3-bromopropyl)-1-methylpyrrolidin-1-ium bromide
3722-27-8

1-(3-bromopropyl)-1-methylpyrrolidin-1-ium bromide

Conditions
ConditionsYield
Reflux;100%
at 20℃; for 48h; Darkness;92%
With benzene
In acetone at 20℃; for 168h; Darkness;
1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

methyl (2Z)-3-iodoprop-2-enoate
6214-23-9

methyl (2Z)-3-iodoprop-2-enoate

1-((E)-2-Methoxycarbonyl-vinyl)-1-methyl-pyrrolidinium; iodide

1-((E)-2-Methoxycarbonyl-vinyl)-1-methyl-pyrrolidinium; iodide

Conditions
ConditionsYield
In toluene Heating;100%
1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

propargyl bromide
106-96-7

propargyl bromide

1-propargyl-1-methylpyrrolidinium bromide
1337983-01-3

1-propargyl-1-methylpyrrolidinium bromide

Conditions
ConditionsYield
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
120-94-5

1-Methylpyrrolidine

2-chloroethyl methyl ether
627-42-9

2-chloroethyl methyl ether

N-2-methoxyethyl-N-methylpyrrolidinium chloride
1012794-01-2

N-2-methoxyethyl-N-methylpyrrolidinium chloride

Conditions
ConditionsYield
In ethyl acetate at 70℃;100%
1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

triethylene glycol di-(p-toluenesulfonate)
19249-03-7

triethylene glycol di-(p-toluenesulfonate)

1,8-bis[1-methylpyrrolidinium]-3,6-dioxaoctane di(p-toluenesulfonate)

1,8-bis[1-methylpyrrolidinium]-3,6-dioxaoctane di(p-toluenesulfonate)

Conditions
ConditionsYield
In acetonitrile at 75℃; for 60h;100%
1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

2-(2-(2-methoxyethoxy)ethoxy)ethyl p-toluenesulfonate
62921-74-8

2-(2-(2-methoxyethoxy)ethoxy)ethyl p-toluenesulfonate

1-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-1-methylpyrrolidinium p-toluenesulfonate
1492041-49-2

1-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-1-methylpyrrolidinium p-toluenesulfonate

Conditions
ConditionsYield
In acetonitrile at 120℃; for 3h;100%
1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

salicylic acid
69-72-7

salicylic acid

N-methylpyrrolidinium salicylate

N-methylpyrrolidinium salicylate

Conditions
ConditionsYield
In methanol at 20℃;100%
1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

zinc(II)-bis(5,15-(2,4,6-trimethylphenyl))porphyrin

zinc(II)-bis(5,15-(2,4,6-trimethylphenyl))porphyrin

C43H43N5Zn

C43H43N5Zn

Conditions
ConditionsYield
In chloroform-d1100%
1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

2-chloroethanesulfonyl fluoride
762-70-9

2-chloroethanesulfonyl fluoride

C7H15FNO2S(1+)*Cl(1-)

C7H15FNO2S(1+)*Cl(1-)

Conditions
ConditionsYield
In ethyl acetate at 20℃; for 0.0833333h; Menshutkin Reaction;100%
1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

1-bromo-butane
109-65-9

1-bromo-butane

N-methyl-N-butylpyrrolidinium bromide
93457-69-3

N-methyl-N-butylpyrrolidinium bromide

Conditions
ConditionsYield
for 48h; Inert atmosphere;99%
at 75 - 85℃; for 2.71667h;98%
In acetonitrile Inert atmosphere; Cooling with ice; Reflux;98%
1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

1-Chlorooctane
111-85-3

1-Chlorooctane

1-methyl-1-octylpyrrolidinium chloride

1-methyl-1-octylpyrrolidinium chloride

Conditions
ConditionsYield
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
120-94-5

1-Methylpyrrolidine

C16H17IO4S
1008460-14-7

C16H17IO4S

N-methyl-N-[3-(4'-iodophenoxy)-1-propyl]pyrrolidinium 4-methylbenzenesulfonate
1389264-96-3

N-methyl-N-[3-(4'-iodophenoxy)-1-propyl]pyrrolidinium 4-methylbenzenesulfonate

Conditions
ConditionsYield
In acetonitrile at 60℃;99%
In chloroform at 60℃;99%
1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

3-(4'-iodophenyl)-1-propyl tosylate

3-(4'-iodophenyl)-1-propyl tosylate

N-methyl-N-[3-(4'-iodophenyl)-1-propyl]pyrrolidinium 4-methylbenzenesulfonate
1389264-93-0

N-methyl-N-[3-(4'-iodophenyl)-1-propyl]pyrrolidinium 4-methylbenzenesulfonate

Conditions
ConditionsYield
In acetonitrile at 60℃; for 16h;99%
1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

methyl trifluoromethanesulfonate
333-27-7

methyl trifluoromethanesulfonate

1,1-dimethylpyrrolidinium trifluoromethanesulfonate
477934-00-2

1,1-dimethylpyrrolidinium trifluoromethanesulfonate

Conditions
ConditionsYield
In hexane at 0 - 75℃; for 1h;99%
In dichloromethane at 0℃; for 0.166667h;92%
1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

2-(N-methylmethylsulfonamido)ethyl methanesulfonate

2-(N-methylmethylsulfonamido)ethyl methanesulfonate

1-[2-(methylsulfonamido)ethyl]-1-methylpyrrolidinium methanesulfonate
1392481-56-9

1-[2-(methylsulfonamido)ethyl]-1-methylpyrrolidinium methanesulfonate

Conditions
ConditionsYield
In ethanol at 100℃; for 24h;99%
1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

2-Methoxyethoxymethyl chloride
3970-21-6

2-Methoxyethoxymethyl chloride

methyl trifluoromethanesulfonate
333-27-7

methyl trifluoromethanesulfonate

1-((2-methoxyethoxy)methyl)-1-methylpyrrolidinium trifluoromethanesulfonate

1-((2-methoxyethoxy)methyl)-1-methylpyrrolidinium trifluoromethanesulfonate

Conditions
ConditionsYield
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
120-94-5

1-Methylpyrrolidine

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

methyl trifluoromethanesulfonate
333-27-7

methyl trifluoromethanesulfonate

1-(metoxymethyl)-1-methylpyrrolidinium trifluoromethanesulfonate

1-(metoxymethyl)-1-methylpyrrolidinium trifluoromethanesulfonate

Conditions
ConditionsYield
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
120-94-5

1-Methylpyrrolidine

2-chloro-N-{4,11,17,24-tetraoxo-2,26-dioxa-5,10,18,23,32-pentaazatricyclo[25.3.1.112,16]dotriaconta-1-(31),12(32),13,15,27,29-hexaen-31-yl}acetamide

2-chloro-N-{4,11,17,24-tetraoxo-2,26-dioxa-5,10,18,23,32-pentaazatricyclo[25.3.1.112,16]dotriaconta-1-(31),12(32),13,15,27,29-hexaen-31-yl}acetamide

1-methyl-1-[({4,11,17,24-tetraoxo-2,26-dioxa-5,10,18,23,32-pentaazatricyclo[25.3.1.112,16]dotriaconta-1(31),12(32),13,15,27,29-hexaen-31-yl}carbamoyl)methyl]pyrrolidin-1-ium chloride

1-methyl-1-[({4,11,17,24-tetraoxo-2,26-dioxa-5,10,18,23,32-pentaazatricyclo[25.3.1.112,16]dotriaconta-1(31),12(32),13,15,27,29-hexaen-31-yl}carbamoyl)methyl]pyrrolidin-1-ium chloride

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; under 7500750 Torr; for 48h; Pressure; Temperature; Sealed tube; High pressure; Inert atmosphere;99%
1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

1 ,6-dibromohexane
629-03-8

1 ,6-dibromohexane

1,6-bis(N-methylpyrrolidinium)hexane bromide
13118-09-7

1,6-bis(N-methylpyrrolidinium)hexane bromide

Conditions
ConditionsYield
for 24h; Reflux;98%
In acetone at 20℃;
In methanol at 20℃; for 96h;
With ethanol
1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

4-bromoethylbutanoate
2969-81-5

4-bromoethylbutanoate

1-(3-Ethoxycarbonyl-propyl)-1-methyl-pyrrolidinium; bromide

1-(3-Ethoxycarbonyl-propyl)-1-methyl-pyrrolidinium; bromide

Conditions
ConditionsYield
In neat (no solvent)98%
1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

1-chlorododecane
112-52-7

1-chlorododecane

1-dodecyl-1-methylpyrrolidinium chloride
114569-86-7

1-dodecyl-1-methylpyrrolidinium chloride

Conditions
ConditionsYield
for 0.333333h; Microwave irradiation;98%
at 70 - 100℃;
In toluene at 114.84℃; for 24h; Inert atmosphere;
1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

water
7732-18-5

water

boric acid
11113-50-1

boric acid

Conditions
ConditionsYield
In methanol98%
3-chloroprop-1-ene

3-chloroprop-1-ene

1-allyl-1-methylpyrrolidinium chloride
1059624-28-0

1-allyl-1-methylpyrrolidinium chloride

Conditions
ConditionsYield
In acetonitrile at 60℃; for 72h;98%
In acetonitrile for 24h; Reflux;
In acetonitrile at 0 - 25℃; for 24h;
1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

(1R,5S)-2-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethyl methanesulfonate

(1R,5S)-2-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethyl methanesulfonate

1-{2-[(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2yl]ethyl}-1-methylpyrrolidin-1-ium methanesulfonate

1-{2-[(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2yl]ethyl}-1-methylpyrrolidin-1-ium methanesulfonate

Conditions
ConditionsYield
In acetonitrile for 72h; Menshutkin Reaction; Reflux;98%
1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

2-nitrophenylmethyl bromide
3958-60-9

2-nitrophenylmethyl bromide

1-methyl-1-(2-nitrobenzyl)pyrrolidinium bromide
1350913-72-2

1-methyl-1-(2-nitrobenzyl)pyrrolidinium bromide

Conditions
ConditionsYield
In ethyl acetate at 20℃; Inert atmosphere;97.8%
1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

propan-1-ol
71-23-8

propan-1-ol

1-propyl-1-methylpyrrolidin-1-ium bromide
608140-09-6

1-propyl-1-methylpyrrolidin-1-ium bromide

Conditions
ConditionsYield
With ethylene glycol; potassium bromide In water; acetonitrile at 40℃; for 1h;97.2%
1-Methylpyrrolidine
120-94-5

1-Methylpyrrolidine

1-methyl-pyrrolidin-2-one
872-50-4

1-methyl-pyrrolidin-2-one

Conditions
ConditionsYield
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
120-94-5

1-Methylpyrrolidine

4-acetamidophenyl 2-chloroacetate
17321-63-0

4-acetamidophenyl 2-chloroacetate

1-(2-(4-acetamidophenoxy)-2-oxoethyl)-1-methylpyrrolidiniuim chloride
1234188-70-5

1-(2-(4-acetamidophenoxy)-2-oxoethyl)-1-methylpyrrolidiniuim chloride

Conditions
ConditionsYield
In ethyl acetate for 48h; Reflux;97%
In ethyl acetate for 48h; Reflux;97%

120-94-5Relevant articles and documents

-

Nakajima

, p. 1218 (1961)

-

-

Searles et al.

, p. 4917,4918 (1956)

-

Gas-Phase Elimination Kinetics of (Dimethylamino)alkyl Acetates. The Ion-Pair Mechanism through Neighboring Group Participation.

Chuchani, Gabriel,Rotinov, Alexandra,Dominguez, Rosa M.,Gonzalez, Neil

, p. 4157 - 4160 (1984)

The gas-phase elimination kinetics of some amino esters and a keto acetate have been studied in the temperature region of 260.0-411.5 deg C and in the pressure range of 21.5-170.0 torr.These eliminations, in vessels seasoned with allyl bromide, are predominantly unimolecular and homogenous and obey a first order rate law.The rate coefficients for the reactions are expressible by the following Arrhenius equations: for 3-(dimethylamino)-1-propyl acetate (1), log k1 (s-1) = (12.97 +/- 0.20) - (202.1 +/- 2.5) kJ mol-1 (2.303RT)-1; for 4-(dimethylamino)-1-butyl acetate (4), log k1 (s-1) = (11.91 +/- 0.43) - (163.5 +/- 4.8) kJ mol-1 (2.303 RT)-1; for 4-oxo-1-pentyl acetate (7), log k1 (s-1) = (12.77 +/- 0.36) - (202.8 +/- 4.6) kJ mol-1 (2.303RT)-1.The presence of the (CH3)2N group in these acetates appears to provide anchimeric assistance in the elimination; methyl acetate and the corresponding heterocyclic products arise from an intimate ion-pair mechanism.The CH3CO substituent is believed to influence the pyrolysis rate of 5-acetoxy-2-pentanone by a weak steric acceleration.

Poisoning and Reuse of Supported Precious Metal Catalysts in the Hydrogenation of N-Heterocycles Part?I: Ruthenium-Catalysed Hydrogenation of 1-Methylpyrrole

Heged?s, László,Sz?ke-Molnár, Kristóf,Sajó, István E.,Srankó, Dávid Ferenc,Schay, Zoltán

, p. 1939 - 1950 (2018)

Abstract: Poisoning phenomena of heterogeneous, supported precious metal catalysts caused by nitrogen were investigated in the liquid-phase hydrogenation of 1-methylpyrrole (MP) to 1-methylpyrrolidine (MPD) over ruthenium on carbon, in non-acidic medium (methanol), at 10?bar and 25–60?°C. Reusing a spent, unregenerated 5% Ru/C catalyst, it was found that the activity of catalyst and the conversion of model substrate were strongly dependent on the amount of catalyst and the number of recycling, respectively. During the first reuse of this ruthenium catalyst, surprisingly, it showed high activity already at room temperature contrary to the fresh catalyst which worked at only 60?°C. This unexpected catalytic behaviour was studied by XRD and XPS methods which revealed the existence of a fine RuO2 layer on the surface of the catalytic metal in the fresh catalyst. Graphical Abstract: [Figure not available: see fulltext.].

Preparation and GC-MS-Identification of N-Methyl-Δ3-pyrroline

Mahboobi, Siavosh,Fischer, Erich Chr.,Eibler, Ernst,Wiegrebe, Wolfgang

, p. 423 - 424 (1988)

The preparation of N-methyl-Δ3-pyrroline by 1) reduction of N-methyl-pyrrole followed by gc-separation or by 2) condensation of cis-1,4-dichloro-2-butene with methylamine is described.The title compound is identified by GC-MS.

A Lewis Base Nucleofugality Parameter, NFB, and Its Application in an Analysis of MIDA-Boronate Hydrolysis Kinetics

García-Domínguez, Andrés,Gonzalez, Jorge A.,Leach, Andrew G.,Lloyd-Jones, Guy C.,Nichol, Gary S.,Taylor, Nicholas P.

supporting information, (2022/01/04)

The kinetics of quinuclidine displacement of BH3 from a wide range of Lewis base borane adducts have been measured. Parameterization of these rates has enabled the development of a nucleofugality scale (NFB), shown to quantify and predict the leaving group ability of a range of other Lewis bases. Additivity observed across a number of series R′3-nRnX (X = P, N; R′ = aryl, alkyl) has allowed the formulation of related substituent parameters (nfPB, nfAB), providing a means of calculating NFB values for a range of Lewis bases that extends far beyond those experimentally derived. The utility of the nucleofugality parameter is explored by the correlation of the substituent parameter nfPB with the hydrolyses rates of a series of alkyl and aryl MIDA boronates under neutral conditions. This has allowed the identification of MIDA boronates with heteroatoms proximal to the reacting center, showing unusual kinetic lability or stability to hydrolysis.

Zirconium-hydride-catalyzed site-selective hydroboration of amides for the synthesis of amines: Mechanism, scope, and application

Han, Bo,Jiao, Haijun,Wu, Lipeng,Zhang, Jiong

, p. 2059 - 2067 (2021/09/02)

Developing mild and efficient catalytic methods for the selective synthesis of amines is a longstanding research objective. In this respect, catalytic deoxygenative amide reduction has proven to be promising but challenging, as this approach necessitates selective C–O bond cleavage. Herein, we report the selective hydroboration of primary, secondary, and tertiary amides at room temperature catalyzed by an earth-abundant-metal catalyst, Zr-H, for accessing diverse amines. Various readily reducible functional groups, such as esters, alkynes, and alkenes, were well tolerated. Furthermore, the methodology was extended to the synthesis of bio- and drug-derived amines. Detailed mechanistic studies revealed a reaction pathway entailing aldehyde and amido complex formation via an unusual C–N bond cleavage-reformation process, followed by C–O bond cleavage.

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