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ChemicalBook > CAS DataBase List > N-Methyl-L-prolinol

N-Methyl-L-prolinol

Uses
Product Name
N-Methyl-L-prolinol
CAS No.
34381-71-0
Chemical Name
N-Methyl-L-prolinol
Synonyms
(S)-(1-Methylpyrrolidin-2-yl)Methanol;(S)-1-METHYL-2-PYRROLIDINEMETHANOL;[(2S)-1-Methylpyrrolidin-2-yl]Methanol;N-METHYLPROLINOL;(S)-(-)-1-MethyL;N-METHYL-L-PROLINOL;1-METHYL-L-PROLINOL;N-methylI-L-prolinol;N-METHYL-L-PYRROLINOL;N-Methyl-L-Prolinol HCl
CBNumber
CB6675789
Molecular Formula
C6H13NO
Formula Weight
115.17
MOL File
34381-71-0.mol
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N-Methyl-L-prolinol Property

Boiling point:
67-69 °C12 mm Hg(lit.)
alpha 
-49.5 º (c=5, MeOH)
Density 
0.968 g/mL at 25 °C(lit.)
refractive index 
n20/D 1.469(lit.)
Flash point:
146 °F
storage temp. 
2-8°C
form 
Liquid
pka
14.77±0.10(Predicted)
color 
Colorless to yellow
optical activity
[α]19/D 49.5°, c = 5 in methanol
BRN 
79851
InChI
InChI=1S/C6H13NO/c1-7-4-2-3-6(7)5-8/h6,8H,2-5H2,1H3/t6-/m0/s1
InChIKey
VCOJPHPOVDIRJK-LURJTMIESA-N
SMILES
N1(C)CCC[C@H]1CO
CAS DataBase Reference
34381-71-0(CAS DataBase Reference)
NIST Chemistry Reference
N-Methyl-L-prolinol(34381-71-0)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
23-24/25-36-26
WGK Germany 
3
8-10-23
HazardClass 
IRRITANT
HS Code 
29339900
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H227Combustible liquid

Precautionary statements

P403+P235Store in a well-ventilated place. Keep cool.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
302767
Product name
(S)-(?)-1-Methyl-2-pyrrolidinemethanol
Purity
96%
Packaging
5g
Price
$85.01
Updated
2025/07/31
Sigma-Aldrich
Product number
302767
Product name
(S)-(?)-1-Methyl-2-pyrrolidinemethanol
Purity
96%
Packaging
25g
Price
$386.14
Updated
2025/07/31
TCI Chemical
Product number
M2058
Product name
(S)-(1-Methylpyrrolidin-2-yl)methanol
Purity
min. 98.0 %
Packaging
5G
Price
$32
Updated
2025/07/31
TCI Chemical
Product number
M2058
Product name
(S)-(1-Methylpyrrolidin-2-yl)methanol
Purity
min. 98.0 %
Packaging
25G
Price
$125
Updated
2025/07/31
TRC
Product number
M339030
Product name
(S)​-​(-​)​-​1-​Methyl-​2-​pyrrolidinemethanol
Packaging
10g
Price
$105
Updated
2021/12/16
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N-Methyl-L-prolinol Chemical Properties,Usage,Production

Uses

N-Methyl-L-prolinol is a reagent used in the synthesis of novel 4-hydroxytamoxifen analogs used as estrogen-related receptor γ (ERRγ) inverse agonists.

Chemical Properties

white to light yellow crystal powde

Uses

Precursor to phosphine ligands for catalytic asymmetric Grignard cross-coupling reactions.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

147-85-3

34381-71-0

(2) 5.0 g (0.0434 mol) of L-proline was dissolved in 92 mL of 97% formic acid and the reaction temperature was maintained at 5°C-10°C. 30 mL of acetic anhydride was added slowly and the reaction mixture was stirred continuously for 2 hours. After completion of the reaction, the reaction was quenched by adding 35 mL of ice water at room temperature. The solvent was removed by evaporation to afford (S)-(-)-N-formylproline ([α]D2?: -105°, c = 2.885, methanol), the product was a clarified, viscous, light yellow oil, which could be used for the next reaction without further purification. Under nitrogen protection, 20 mL of tetrahydrofuran solution of (S)-(-)-N-formylproline was slowly added to 125 mL of tetrahydrofuran suspension of 8.23 g (0.217 mol) of lithium aluminium hydride, and the rate of addition was controlled to maintain mild reflux. After addition, the reaction was continued at reflux for 48 hours. At the end of the reaction, it was cooled to room temperature and the reaction was quenched by careful addition of 8.3 mL of water, 8.3 mL of 15% aqueous sodium hydroxide solution and 25 mL of water in that order. The off-white mixture obtained was filtered and the filtrate was dried over magnesium sulfate and concentrated to an oil. Purification by bulb-to-bulb distillation (oven temperature 40°C-55°C, 0.15 Torr) afforded 2.823 g of N-methyl-L-prolinol in 57% yield (as L-proline).

References

[1] Patent: US4321387, 1982, A
[2] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 19, p. 2891 - 2896
[3] Tetrahedron Letters, 1995, vol. 36, # 43, p. 7885 - 7888
[4] Journal of the American Chemical Society, 1991, vol. 113, # 24, p. 9286 - 9292
[5] Tetrahedron Letters, 1983, vol. 24, # 33, p. 3513 - 3516

N-Methyl-L-prolinol Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from N-Methyl-L-prolinol manufacturers

Jinan Ruitong Biotech Co., Ltd.
Product
(S)-Methylpyrrolidine-2-methanol 34381-71-0
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1
Release date
2025-08-29
ZHENGZHOU JIUYI TIME NEW MATERIALS CO,.LTD
Product
N-Methyl-L-prolinol 34381-71-0
Price
US $2.00-5.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
100kg
Release date
2025-06-30
Zhuozhou Wenxi import and Export Co., Ltd
Product
N-Methyl-L-prolinol 34381-71-0
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-11

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