1-Methyl-3-pyrrolidinol supplier

Name
1-Methyl-3-pyrrolidinol
EINECS 236-189-3
CAS No. 13220-33-2
Article Data13
CAS DataBase
Density 1.045 g/cm³
Solubility
Melting Point
Formula C₅H₁₁NO
Boiling Point 192.2 °C at 760 mmHg
Molecular Weight 101.148
Flash Point 70.6 °C
Transport Information
Appearance Colorless or light yellow liquid
Safety 26-36/37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 1-Methyl-3-pyrrolidinol;N-Methyl-3-hydroxypyrrolidine;N-Methyl-3-pyrrolidinol;NSC 89279;
PSA 23.47000
LogP -0.37930

Synthetic route

: 19398-47-1
1,4-dibromo-2-butanol

: 74-89-5
methylamine

A: 13220-33-2
1-methyl-3-pyrrolidinol

B: 1404453-61-7
1,4-bis(methylamino)butan-2-ol

Conditions

Conditions	Yield
In water at 100℃; for 16h; Inert atmosphere;	A 98% B 0.9 g

...Expand

: 2419-74-1
1,4-dichlorobutan-2-ol

: 74-89-5
methylamine

: 13220-33-2
1-methyl-3-pyrrolidinol

Conditions

Conditions	Yield
In water at 10 - 120℃; under 7500.75 Torr; for 10h; Temperature; Pressure; Autoclave; Sealed tube;	64.8%

: 4-methylamino-3-hydroxybutyronitrile

: 13220-33-2
1-methyl-3-pyrrolidinol

Conditions

Conditions	Yield
	56%

CH3 NH2: CH3 NH2

: 19398-47-1
1,4-dibromo-2-butanol

: 13220-33-2
1-methyl-3-pyrrolidinol

Conditions

Conditions	Yield
	25%

: 14891-10-2
ethyl-3-oxo-1-pyrrolidinecarboxylate

: 13220-33-2
1-methyl-3-pyrrolidinol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride

: 19398-47-1
1,4-dibromo-2-butanol

: 74-89-5
methylamine

: 13220-33-2
1-methyl-3-pyrrolidinol

Conditions

Conditions	Yield
With ethanol at 125 - 130℃;

: 554-15-4
1-methyl-2,5-dihydro-pyrrole

: 13220-33-2
1-methyl-3-pyrrolidinol

Conditions

Conditions	Yield
With sodium hydroxide; dimethylsulfide borane complex; dihydrogen peroxide Product distribution; var. hydroborating agents, olefin to hydroborating agent ratios, and times; other N-substituted-3-pyrrolines;

1.1-dimethyl-3-oxy-pyrrolidinium chloride: 1.1-dimethyl-3-oxy-pyrrolidinium chloride

: 13220-33-2
1-methyl-3-pyrrolidinol

: 14891-10-2
ethyl-3-oxo-1-pyrrolidinecarboxylate

: 60-29-7
diethyl ether

lithium alanate: lithium alanate

: 13220-33-2
1-methyl-3-pyrrolidinol

...Expand

: 40499-83-0
pyrrolidin-3-ol

: 50-00-0
formaldehyd

: 13220-33-2
1-methyl-3-pyrrolidinol

Conditions

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In tetrahydrofuran

: 13220-33-2
1-methyl-3-pyrrolidinol

: 1404453-62-8
1-methyl-1-oxypyrrolidin-3-ol

Conditions

Conditions	Yield
With dihydrogen peroxide In ethanol for 21h; Inert atmosphere;	100%

: 13220-33-2
1-methyl-3-pyrrolidinol

: 524-38-9
N-hydroxyphthalimide

: 160229-79-8
2-(1-methylpyrrolidin-3-yloxy)isoindoline-1,3-dione

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; for 6h; Inert atmosphere;	97%

: 103-82-2
phenylacetic acid

: 13220-33-2
1-methyl-3-pyrrolidinol

: 434332-38-4
1-methyl-3-pyrrolidinyl phenylacetate

Conditions

Conditions	Yield
With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;	91%

: 13220-33-2
1-methyl-3-pyrrolidinol

: 2309-07-1
Methyl ferulate

: (E)-methyl 3-(3-methoxy-4-((1-methylpyrrolidin-3-yl)oxy)phenyl)acrylate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; triphenylphosphine In tetrahydrofuran at 0℃; for 0.5h;	89%

: 13220-33-2
1-methyl-3-pyrrolidinol

: 1476-11-5
Z-1,4-dichlorobutene

: (Z)-1,1'-(but-2-ene-1,4-diyl)bis(3-hydroxy-1-methylpyrrolidinium) chloride

Conditions

Conditions	Yield
In acetonitrile at 20℃; Inert atmosphere;	88%

: 13220-33-2
1-methyl-3-pyrrolidinol

: 448-19-1
4-fluoro-2-methoxy-1-nitrobenzene

: 1001345-84-1
3-(3-methoxy-4-nitro-phenoxy)-1-methyl-pyrrolidine

Conditions

Conditions	Yield
With potassium hydroxide; tetrabutylammomium bromide In water; toluene at 18 - 60℃; for 18h;	87%
With potassium hydroxide; tetrabutylammomium bromide In water; toluene at 60℃; for 18h;	87%
With sodium hydride In acetonitrile at 80℃;

: 13220-33-2
1-methyl-3-pyrrolidinol

: N-(4-fluoro-2-methoxy-5-nitrophenyl)-8-(3-fluorophenyl)quinazolin-2-amine

: 8-(3-fluorophenyl)-N-(2-methoxy-4-((1-methylpyrrolidin3-yl)oxy)-5-nitrophenyl)quinazolin-2-amine

Conditions

Conditions	Yield
Stage #1: 1-methyl-3-pyrrolidinol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere; Stage #2: N-(4-fluoro-2-methoxy-5-nitrophenyl)-8-(3-fluorophenyl)quinazolin-2-amine In N,N-dimethyl-formamide at 20℃; for 0.5h;	86.1%

: 13220-33-2
1-methyl-3-pyrrolidinol

: 124-63-0
methanesulfonyl chloride

: 91832-73-4
1-methylpyrrolidin-3-yl methanesulfonate

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 16h;	81%
With triethylamine In benzene for 0.75h; Ambient temperature;
With triethylamine In dichloromethane at -10 - 20℃; for 2.08333h;
With triethylamine In dichloromethane at 20℃; for 1.5h; Cooling with ice; Inert atmosphere;
With sodium hydroxide In dichloromethane at 0℃;	124 g

: 13220-33-2
1-methyl-3-pyrrolidinol

: C20H15ClF3N3O4

: C25H24ClF3N4O4

Conditions

Conditions	Yield
With azodicarboxylic acid bis(2-methoxyethyl) ester; triphenylphosphine In tetrahydrofuran at 20℃; Cooling with ice;	78.5%

: 13220-33-2
1-methyl-3-pyrrolidinol

: (R)-(3-((5-bromopyrimidin-2-yl)amino)pyrrolidin-1-yl)(3-fluoro-4-nitrophenyl)methanone

: ((R)-3-((5-bromopyrimidin-2-yl)amino)pyrrolidin-1-yl)(3-((1-methylpyrrolidin-3-yl)oxy)-4-nitrophenyl)methanone

Conditions

Conditions	Yield
Stage #1: 1-methyl-3-pyrrolidinol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.25h; Stage #2: (R)-(3-((5-bromopyrimidin-2-yl)amino)pyrrolidin-1-yl)(3-fluoro-4-nitrophenyl)methanone In tetrahydrofuran; mineral oil at 0℃; for 1h; Enzymatic reaction;	73%

: 109-00-2
3-HYDROXYPYRIDINE

: 13220-33-2
1-methyl-3-pyrrolidinol

: 3-(1-methyl-3-pyrrolidinyloxy)-pyridine

Conditions

Conditions	Yield
Stage #1: With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at -20℃; for 0.166667h; Stage #2: 1-methyl-3-pyrrolidinol In tetrahydrofuran at -20℃; for 0.166667h; Stage #3: 3-HYDROXYPYRIDINE In tetrahydrofuran at 20℃; Mitsunobu reaction;	72.9%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran Mitsunobu reaction;
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran	260 mg (72.9%)

: 13220-33-2
1-methyl-3-pyrrolidinol

: 19833-96-6
2-Cyclopentyl-2-hydroxy-2-phenylacetic acid methyl ester

: 13118-11-1
3-(2-cyclopentyl-2-hydroxy-2-phenylacetyloxy)-1-methylpyrrolidine

Conditions

Conditions	Yield
With sodium In n-heptane for 3h;	72%

: 13220-33-2
1-methyl-3-pyrrolidinol

: 427-49-6
2-cyclopentyl-2-hydroxy-2-phenylacetic acid

: 13118-11-1
3-(2-cyclopentyl-2-hydroxy-2-phenylacetyloxy)-1-methylpyrrolidine

Conditions

Conditions	Yield
Stage #1: 2-cyclopentyl-2-hydroxy-2-phenylacetic acid With 1,1'-carbonyldiimidazole In toluene at 20℃; for 0.5h; Stage #2: 1-methyl-3-pyrrolidinol In toluene at 20℃;	71%
Stage #1: 2-cyclopentyl-2-hydroxy-2-phenylacetic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 18℃; Stage #2: 1-methyl-3-pyrrolidinol In N,N-dimethyl-formamide at 18 - 60℃; for 19h; Product distribution / selectivity;
With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 18 - 60℃; for 19h; Inert atmosphere;
Stage #1: 2-cyclopentyl-2-hydroxy-2-phenylacetic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: 1-methyl-3-pyrrolidinol In N,N-dimethyl-formamide at 60℃;	Ca.580 g

: 64471-47-2
(R)-α-phenyl-α-cyclopentyl-α-hydroxyacetate methyl ester

: 13220-33-2
1-methyl-3-pyrrolidinol

: 873912-87-9
N-methyl-3-pyrrolidinyl (-)-cyclopentylmandelate

Conditions

Conditions	Yield
With sodium In n-heptane for 2h;	70%

: 13220-33-2
1-methyl-3-pyrrolidinol

: 1007170-16-2
ethyl 6-(4-chloro-3-hydroxyphenyl)-5-(2,6-dimethoxyphenyl)pyridine-2-carboxylate

: 1007170-22-0
Ethyl 6-{4-chloro-3-[(1-methylpyrrolidin-3-yl)oxy]phenyl)-5-(2,6-dimethoxyphenyl)pyridine-2-carboxylate

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triethylamine; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Mitsunobu reaction; Inert atmosphere;	70%

: 13220-33-2
1-methyl-3-pyrrolidinol

: 349-57-5
3-nitro-5-(trifluoromethyl)phenol

: 1529769-19-4
1-methyl-3-(3-nitro-5-(trifluoromethyl)phenoxy)pyrrolidine

Conditions

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 15h; Cooling with ice;	67%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 25℃; for 15h; Cooling with ice;	67%

: 13220-33-2
1-methyl-3-pyrrolidinol

: 98-59-9
p-toluenesulfonyl chloride

: 60499-30-1
toluene-4-sulfonic acid 1-methylpyrrolidin-3-yl ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane for 5h;	66%
With potassium hydroxide In tetrahydrofuran at 0 - 25℃; for 16h;	65%
With potassium hydroxide In tetrahydrofuran at 0 - 25℃; for 16h;	44%
With dmap; triethylamine In dichloromethane at 20℃; for 16h;	31%
With triethylamine In dichloromethane

: 13220-33-2
1-methyl-3-pyrrolidinol

: 295320-15-9
2-(4-fluorophenyl)-1-(4-hydroxybenzyl)-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline

: 998-40-3
tributylphosphine

: 10465-81-3
1,1'-(Azodicarbonyl)dipiperidin

: 295320-23-9
2-(4-fluorophenyl)-1-[4-(1-methylpyrrolidin-3-yloxy)benzyl]-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
In tetrahydrofuran; dichloromethane	56%
In tetrahydrofuran; dichloromethane	56%

...Expand

: 13220-33-2
1-methyl-3-pyrrolidinol

: 79-44-7
N,N-Dimethylcarbamoyl chloride

: (RS)-1-methyl-3-pyrrolidinyl N,N-dimethylcarbamate

Conditions

Conditions	Yield
With sodium hydride In toluene Ambient temperature;	52%

: 13220-33-2
1-methyl-3-pyrrolidinol

: 32315-10-9
bis(trichloromethyl) carbonate

: (19Z,22Z)-octacosa-19,22-dien-11-ol

: 1-methylpyrrolidin-3-yl (9Z,12Z)-octacosa-19,22-dien-11-yl carbonate

Conditions

Conditions	Yield
Stage #1: bis(trichloromethyl) carbonate; (19Z,22Z)-octacosa-19,22-dien-11-ol With pyridine In toluene at 0 - 10℃; for 1.33333h; Stage #2: 1-methyl-3-pyrrolidinol In toluene at 0 - 20℃;	50%

...Expand

: 13220-33-2
1-methyl-3-pyrrolidinol

: 865886-86-8
5-hydroxy-1-(2-trimethylsilanylethoxymethyl)-1H-indazole-3-carboxylic acid ethyl ester

: 869782-61-6
5-(tetrahydro-2H-pyran-4-yloxy)-1-[2-(trimethylsilyl)ethoxy]methyl-1H-indazole-3-carboxylic acid

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran for 16h; Mitsunobu reaction;	49%

: 13220-33-2
1-methyl-3-pyrrolidinol

: 350-46-9
4-Fluoronitrobenzene

: 943751-42-6
1-methyl-3-(4-nitrophenoxy)pyrrolidine

Conditions

Conditions	Yield
Stage #1: 1-methyl-3-pyrrolidinol With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h; Stage #2: 4-Fluoronitrobenzene In tetrahydrofuran for 2h;	44%
With sodium hydride In 1-methyl-pyrrolidin-2-one

: 13220-33-2
1-methyl-3-pyrrolidinol

: 2-amino-N-(4-methoxypyridin-3-yl)-5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxamide

: 2-amino-N-(4-methoxypyridin-3-yl)-5-((1-methylpyrrolidin-3-yl)oxy)pyrazolo[1,5-a]pyrimidine-3-carboxamide

Conditions

Conditions	Yield
Stage #1: 2-amino-N-(4-methoxypyridin-3-yl)-5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxamide With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 0.0833333h; Stage #2: 1-methyl-3-pyrrolidinol With caesium carbonate In acetonitrile at 20℃; for 1h;	44%

: 13220-33-2
1-methyl-3-pyrrolidinol

: 1303954-15-5
2-chloro-8-cyclopentyl-1-propyl-1,7-dihydro-purin-6-one

: 1303953-67-4
8-cyclopentyl-2-(1-methylpyrrolidin-3-yl)oxy-1-propyl-7Hpurin-6-one

Conditions

Conditions	Yield
With sodium hydride In mineral oil for 3h; Inert atmosphere; Reflux;	41%

: 13220-33-2
1-methyl-3-pyrrolidinol

: 2-cyclopentyl-2-hydroxy-2-phenylacetic-1-[1-14C] acid

: 1-methylpyrrolidin-3-yl 2-cyclopentyl-2-hydroxy-2-phenyl-[1-14C]acetate

: 1-methylpyrrolidin-3-yl 2-cyclopentyl-2-hydroxy-2-phenyl-[1-14C]acetate

Conditions

Conditions	Yield
Stage #1: 2-cyclopentyl-2-hydroxy-2-phenylacetic-1-[1-14C] acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1-methyl-3-pyrrolidinol In N,N-dimethyl-formamide at 20 - 60℃;	A 41% B n/a

...Expand

: 13220-33-2
1-methyl-3-pyrrolidinol

: 4-(chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline

: 1972-28-7
diethylazodicarboxylate

: 4-(4-chloro-2-fluoranilino)-6-methoxy-7-(1-methylpyrrolidin-3-yloxy)quinazoline hydrochloride hydrate

Conditions

Conditions	Yield
With hydrogenchloride; triphenylphosphine In methanol; dichloromethane; isopropyl alcohol	40%

...Expand

: 13220-33-2
1-methyl-3-pyrrolidinol

: 1154427-47-0
3-[2-[2-(3-hydroxy-phenyl)-acetylamino]-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0(2,6)]dec-4-yl)-ethyl]-benzoic acid tert-butyl ester

: 1154427-56-1
3-[2-{2-[3-(1-methyl-pyrrolidin-3-yloxy)-phenyl]-acetylamino}-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0(2,6)]dec-4-yl)-ethyl]-benzoic acid tert-butyl ester

Conditions

Conditions	Yield
Stage #1: 1-methyl-3-pyrrolidinol; 3-[2-[2-(3-hydroxy-phenyl)-acetylamino]-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0(2,6)]dec-4-yl)-ethyl]-benzoic acid tert-butyl ester With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane Stage #2: With water In dichloromethane	34%

1-Methyl-3-pyrrolidinol Chemical Properties

IUPAC Name: 1-methylpyrrolidin-3-ol
Empirical Formula: C₅H₁₁NO
Molecular Weight: 101.1469g/mol
EINECS: 236-189-3
Structure of 3-Pyrrolidinol,1-methyl- (CAS NO.13220-33-2):

Index of Refraction: 1.496
Molar Refractivity: 28.31 cm³
Molar Volume: 96.7 cm³
Polarizability: 11.22×10^-24cm³
Surface Tension: 39 dyne/cm
Density: 1.045 g/cm³
Flash Point: 70.6 °C
Enthalpy of Vaporization: 49.85 kJ/mol
Boiling Point: 192.2 °C at 760 mmHg
Vapour Pressure: 0.132 mmHg at 25°C
Chemical Properties: Clear colorless to pale yellow liquid
Product Categories: Heterocyclic Compounds;Heterocycles;Building Blocks;Heterocyclic Building Blocks;Pyrrolidines
Canonical SMILES: CN1CCC(C1)O
InChI: InChI=1S/C5H11NO/c1-6-3-2-5(7)4-6/h5,7H,2-4H2,1H3
InChIKey: FLVFPAIGVBQGET-UHFFFAOYSA-N

1-Methyl-3-pyrrolidinol Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37/39
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.
WGK Germany: 3

1-Methyl-3-pyrrolidinol Specification

3-Pyrrolidinol,1-methyl- , its cas register number is 13220-33-2. It also can be called 1-Methyl-3-pyrrolidinol ; EINECS 236-189-3 ; NSC 89279 . 3-Pyrrolidinol,1-methyl- (CAS NO.13220-33-2) is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

Product Name

1-Methyl-3-pyrrolidinol

Synthetic route

1-Methyl-3-pyrrolidinol Chemical Properties

1-Methyl-3-pyrrolidinol Safety Profile

1-Methyl-3-pyrrolidinol Specification

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