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23356-96-9

Basic Information
CAS No.: 23356-96-9
Name: L-(+)-Prolinol
Article Data: 99
Molecular Structure:
Molecular Structure of 23356-96-9 (L-(+)-Prolinol)
Formula: C5H11NO
Molecular Weight: 101.148
Synonyms: (2S)-2-Pyrrolidinylmethanol;(2S)-Pyrrolidin-2-ylmethanol;2-pyrrolidinemethanol, (2S)-;(S)-(+)-2-(Hydroxymethyl)pyrrolidine 99%;(S)-(+)-2-Pyrrolidinemethanol;
EINECS: 245-605-2
Density: 0.978 g/cm3
Melting Point: 42-44℃
Boiling Point: 211 °C at 760 mmHg
Flash Point: 86.1 °C
Solubility: Fully miscible in water. Soluble in chloroform.
Appearance: Colorless to light yellow liquid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36-37/39
PSA: 32.26000
LogP: 0.05950
Synthetic route
147-85-3

L-proline

23356-96-9

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

Conditions
ConditionsYield
Stage #1: L-proline With lithium aluminium tetrahydride In tetrahydrofuran for 1.25h; Heating / reflux;
Stage #2: With potassium hydroxide In tetrahydrofuran; water for 1.25h; Heating / reflux;
100%
Stage #1: L-proline With lithium aluminium tetrahydride In tetrahydrofuran Inert atmosphere; Cooling with ice; Reflux;
Stage #2: With potassium hydroxide In tetrahydrofuran at 20℃; Reflux;
99%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 72.5h; Reflux;99%
67-56-1

methanol

1-(N-benzyl-N-methylalanyl)-(S)-prolinol

A

methyl 2-(benzyl(methyl)amino)propanoate

B

23356-96-9

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

Conditions
ConditionsYield
With hydrogenchloride Heating;A n/a
B 96%
67-56-1

methanol

2-(Benzyl-methyl-amino)-1-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-3-methyl-butan-1-one

A

methyl 2-(N-benzyl-N-methylamino)-3-methylbutanoate

B

23356-96-9

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

Conditions
ConditionsYield
With hydrogenchloride Heating;A n/a
B 96%
67-56-1

methanol

1-(N-benzyl-N-methylphenylalanyl)-(S)-prolinol

A

2-(Benzyl-methyl-amino)-3-phenyl-propionic acid methyl ester

B

23356-96-9

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

Conditions
ConditionsYield
With hydrogenchloride Heating;A n/a
B 96%
67-56-1

methanol

2-(Benzyl-methyl-amino)-1-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-2-phenyl-ethanone

A

(Benzyl-methyl-amino)-phenyl-acetic acid methyl ester

B

23356-96-9

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

Conditions
ConditionsYield
With hydrogenchloride Heating;A n/a
B 96%

1-(N-benzyl-N-methylalanyl)-(S)-prolinol

A

101692-94-8

(rac)-N-benzyl-N-methylalanine

B

23356-96-9

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

Conditions
ConditionsYield
With hydrogenchloride In methanol Heating;A n/a
B 96%

2-(Benzyl-methyl-amino)-1-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-3-methyl-butan-1-one

A

42492-62-6

2-(benzyl(methyl)amino)-3-methylbutanoic acid

B

23356-96-9

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

Conditions
ConditionsYield
With hydrogenchloride In methanol Heating;A n/a
B 96%

1-(N-benzyl-N-methylphenylalanyl)-(S)-prolinol

A

14464-19-8

(rac)-N-benzyl-N-methylphenylalanine

B

23356-96-9

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

Conditions
ConditionsYield
With hydrogenchloride In methanol Heating;A n/a
B 96%

2-(Benzyl-methyl-amino)-1-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-2-phenyl-ethanone

A

(Benzyl-methyl-amino)-phenyl-acetic acid

B

23356-96-9

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

Conditions
ConditionsYield
With hydrogenchloride In methanol Heating;A n/a
B 96%
98-79-3

L-Pyroglutamic acid

23356-96-9

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

Conditions
ConditionsYield
With hydrogen; acetic acid In water at 100℃; under 52505.3 Torr; for 20h; Pressure; Temperature; Reagent/catalyst; Time; Autoclave;95%
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Chemistry

Molecular Structure of L-(+)-Prolinol (CAS NO.23356-96-9):

IUPAC Name: [(2S)-pyrrolidin-2-yl]methanol
Molecular Formula: C5H11NO
Molecular Weight: 101.15
H bond acceptors: 2
H bond donors: 2
Freely Rotating Bonds: 2
Polar Surface Area: 12.47 Å2
Index of Refraction: 1.454
Molar Refractivity: 28.02 cm3
Molar Volume: 103.3 cm3
Surface Tension: 36.5 dyne/cm
Density: 0.978 g/cm3
Flash Point: 86.1 °C
Enthalpy of Vaporization: 52.03 kJ/mol
Boiling Point: 211 °C at 760 mmHg
Vapour Pressure: 0.0423 mmHg at 25°C
Storage temp: 2-8°C
Sensitive: Air Sensitive
BRN: 79843
EINECS: 245-605-2
InChI
InChI=1/C5H11NO/c7-4-5-2-1-3-6-5/h5-7H,1-4H2
Smiles
N1[C@@H](CO)CCC1
Product Categories: Pharmaceutical Intermediates; Amines; blocks; Amino Alcohols; chiral;APIs; Proline [Pro, P]; Chemical Amines; Chiral Building Blocks; Glycidyl Compounds, etc. (Chiral); Synthetic Organic Chemistry; Amino alcohols; Amino Acids & Derivatives

Production

 L-(+)-Prolinol (CAS NO.23356-96-9) is obtained by reduction of the amino acid proline using lithium aluminium hydride.Because proline is cheaply available in high optical purity, enantiomerically pure. L-Prolinol is also widely available.

Safety Profile

Hazard Symbols: IrritantXi
Risk Codes: R36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Description: S26;S37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 3
F: 3-10-23
Hazard Note: Irritant/Air Sensitive

Specification

  L-(+)-Prolinol , with CAS number of 23356-96-9, can be called (S)-(+)-2-Pyrrolidinemethanol ; (S)-(+)-2-(Hydroxymethyl)pyrrolidine 99% ; 2-pyrrolidinemethanol, (2S)- ; (2S)-Pyrrolidin-2-ylmethanol ; (2S)-2-Pyrrolidinylmethanol . It is a colorless to light yellow liquid.  L-(+)-Prolinol (CAS NO.23356-96-9) is used in broad variety of chemical reactions as chiral ligand, chiral catalyst or chiral auxiliary reagent in the Hajos-Parrish-Eder-Sauer-Wiechert reaction, the Baylis-Hillman reaction, Noyori type reaction and the Michael reaction.