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N-Methyl-L-prolinol
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Name

N-Methyl-L-prolinol

 EINECS 251-981-9
CAS No. 34381-71-0 Density 0.973 g/cm3
PSA 23.47000 LogP 0.01080
Solubility N/A Melting Point N/A
Formula C6H13NO Boiling Point 164.8 °C at 760 mmHg
Molecular Weight 115.175 Flash Point 63.3 °C
Transport Information N/A Appearance white to light yellow crystal powder
Safety 23-24/25-36-26 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 34381-71-0 (N-Methyl-L-prolinol) Hazard Symbols IrritantXi
Synonyms

2-Pyrrolidinemethanol,1-methyl-, (S)-;(-)-(S)-1-Methyl-2-pyrrolidinemethanol;(2S)-(Hydroxymethyl)-1-methylpyrrolidine;(2S)-1-Methylpyrrolidin-2-ylmethanol;(2S)-1-Methylpyrrolidine-2-methanol;(S)-(-)-(1-Methyl-2-pyrrolidinyl)methanol;(S)-(-)-1-Methylpyrrolidine-2-methanol;(S)-(-)-2-Hydroxymethyl-1-methylpyrrolidine;(S)-1-Methyl-2-pyrrolidinemethanol;(S)-1-Methylpyrrolidin-2-ylmethanol;(S)-2-(Hydroxymethyl)-1-methylpyrrolidine;(S)-N-Methylpyrrolidine-2-methanol;L-(-)-N-Methyl-2-pyrrolidinylmethanol;L-N-Methylprolinol;2-Pyrrolidinemethanol,1-methyl-, (2S)-;

Article Data 31

N-Methyl-L-prolinol Synthetic route

59936-29-7

(S)-N-(tert-butoxycarbonyl)proline methyl ester

34381-71-0

(S)-2-hydroxymethyl-1-methylpyrrolidine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether90%
50-00-0

formaldehyd

23356-96-9

(S)-1-Pyrrolidin-2-yl-methanol

34381-71-0

(S)-2-hydroxymethyl-1-methylpyrrolidine

Conditions
ConditionsYield
With formic acid In water for 20h; Heating;65%
With formic acid; water anschliessenden Erhitzen;
With hydrogen; platinum(IV) oxide In water for 24h;2.4 g
With formic acid
With formic acid Yield given;
475-11-6, 58123-62-9, 68078-09-1

N-methyl-L-proline

34381-71-0

(S)-2-hydroxymethyl-1-methylpyrrolidine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 4h; Heating;65%
147-85-3

L-proline

34381-71-0

(S)-2-hydroxymethyl-1-methylpyrrolidine

Conditions
ConditionsYield
With aq. sodium hydroxide; acetic anhydride In tetrahydrofuran; formic acid; water57%
Multi-step reaction with 2 steps
1: NaBH4, H2SO4
2: HCOOH
View Scheme
Multi-step reaction with 2 steps
1: NaBH4, conc. H2SO4
2: HCOOH
View Scheme
Multi-step reaction with 2 steps
1: acetic anhydride / 2 h / Ambient temperature
2: LiAlH4 / tetrahydrofuran / 48 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: 94 percent / H2O
2: 95 percent / diethyl ether
3: 90 percent / 3 eq. LiAlH4 / diethyl ether
View Scheme
27957-91-1

N-Methyl-L-proline Methyl Ester

34381-71-0

(S)-2-hydroxymethyl-1-methylpyrrolidine

Conditions
ConditionsYield
53%
With lithium aluminium tetrahydride In tetrahydrofuran
1148-11-4

N-Benzyloxycarbonyl-L-proline

34381-71-0

(S)-2-hydroxymethyl-1-methylpyrrolidine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran 1.) room temp., 1 h, 2.) reflux, 3 h;49%
64-18-6

formic acid

147-85-3

L-proline

34381-71-0

(S)-2-hydroxymethyl-1-methylpyrrolidine

Conditions
ConditionsYield
Stage #1: formic acid; L-proline With acetic anhydride
Stage #2: With lithium aluminium tetrahydride		48%
13200-83-4

(2S)-1-formylpyrrolidine-2-carboxylic acid

34381-71-0

(S)-2-hydroxymethyl-1-methylpyrrolidine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 48h; Heating; Yield given;
5211-23-4

N-carbobenzyloxy-L-proline methyl ester

34381-71-0

(S)-2-hydroxymethyl-1-methylpyrrolidine

Conditions
ConditionsYield
With lithium aluminium tetrahydride
68078-09-1

N-methylproline

A

3554-65-2, 30727-24-3, 34381-71-0, 99494-01-6

(R)-N-methylpyrrolidine-2-methanol

B

34381-71-0

(S)-2-hydroxymethyl-1-methylpyrrolidine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran Heating; Title compound not separated from byproducts;

N-Methyl-L-prolinol Chemical Properties

Molecule structure of N-Methyl-L-prolinol (CAS NO.34381-71-0):

IUPAC Name: (1-Methylpyrrolidin-2-yl)methanol 
Molecular Weight: 115.17352 g/mol
Molecular Formula: C6H13NO 
Density: 0.973 g/cm3
Boiling Point: 164.8 °C at 760 mmHg 
Flash Point: 63.3 °C
Index of Refraction: 1.468
Molar Refractivity: 32.95 cm3
Molar Volume: 118.3 cm3
Surface Tension: 32.2 dyne/cm  
Enthalpy of Vaporization: 46.74 kJ/mol
Vapour Pressure: 0.649 mmHg at 25 °C 
Storage Temp.: −20 °C
XLogP3-AA: 0.1
H-Bond Donor: 1
H-Bond Acceptor: 2
Rotatable Bond Count: 1
Exact Mass: 115.099714
MonoIsotopic Mass: 115.099714
Topological Polar Surface Area: 23.5
Heavy Atom Count: 8
Canonical SMILES: CN1CCCC1CO
InChI: InChI=1S/C6H13NO/c1-7-4-2-3-6(7)5-8/h6,8H,2-5H2,1H3
InChIKey: VCOJPHPOVDIRJK-UHFFFAOYSA-N
EINECS: 251-981-9
Product Categories: chiral;Chiral Reagent

N-Methyl-L-prolinol Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 23-24/25-36-26 
S23:Do not breathe vapour. 
S24/25:Avoid contact with skin and eyes. 
S36:Wear suitable protective clothing. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3
F: 8-10-23
Hazard Note: Irritant

N-Methyl-L-prolinol Specification

 N-Methyl-L-prolinol (CAS NO.34381-71-0) is also named as (1-Methyl-2-pyrrolidinyl)methanol ; (1-Methylpyrrolidin-2-yl)methanol ; 2-Pyrrolidinemethanol, 1-methyl- ; 1-Methyl-2-pyrrolidinemethanol ; 1-Methylpyrrolidine-2-Methanol . N-Methyl-L-prolinol (CAS NO.34381-71-0) is white to light yellow crystal powder.

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