L-(+)-Prolinol

Iupac Name：[(2S)-pyrrolidin-2-yl]methanol

Molecular Weight：101.149

Modify Date.: 2022-10-28 03:01

Introduction: L-Prolinol is an intermediate in the synthesis of Physostigmine and Physostigmine derivative used for treatment of Alzheimer's disease. L-(+)-Prolinol Preparation Products And Raw materials Preparation Products View more+

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1. Names and Identifiers

1.1 Name: L-(+)-Prolinol
1.2 Synonyms: (-)-L-PROLINOL (+)-2-Pyrrolidinemethanol (2S)-2-(Hydroxymethyl)pyrrolidine (2S)-2-Pyrrolidinemethanol (2S)-2-Pyrrolidinylmethanol (2S)-prolinol (2S)-Pyrrolidin-2-ylmethanol (S)-(+)-2-(Hydroxymethyl)pyrrolidine (S)-(+)-2-Pyrrolidinemethanol (S)-(+)-PROLINOL (S)-(+)-Pyrrolidin-2-ylmethanol (S)-1-(Pyrrolidin-2-yl)methanol (S)-2-(Hydroxymethyl)pyrrolidine (S)-2-Pyrrolidinemethanol (S)-Prolinol (S)-Pyrrolidin-2-ylmethanol [(2S)-Pyrrolidin-2-yl]methanol [(S)-Pyrrolidin-2-yl]methanol 2-(S)-(Hydroxymethyl)pyrrolidine 2-Pyrrolidinemethanol 2-Pyrrolidinemethanol, (2S)- 2-Pyrrolidinemethanol, (S)- 2-Pyrrolidinemethanol, (S)-(+)- 2-Pyrrolidinylmethanol DL-Prolinol EINECS 245-605-2 H-L-PRO-OL H-PROLINOL H-PRO-OL L-(+)-2-Pyrrolidinylmethanol L(+)-Prolinol L-2-(Hydroxymethyl)pyrrolidine L-2-PYRROLIDINEMETHANOL L-PROLINOL L-Pro-ol MFCD00005255 Prolinol pyrrolidin-2-ylmethanol Pyrrolidine, 2-(hydroxymethyl)- rac-prolinol

1.3 CAS No.: 23356-96-9

1.4 CID: 640091

1.5 EINECS(EC#): 245-605-2

1.6 Molecular Formula: C5H11NO (isomer)

1.7 Inchi: InChI=1S/C5H11NO/c7-4-5-2-1-3-6-5/h5-7H,1-4H2/t5-/m0/s1

1.8 InChkey: HVVNJUAVDAZWCB-YFKPBYRVSA-N

1.9 Canonical Smiles: C1CC(NC1)CO

1.10 Isomers Smiles: C1C[C@H](NC1)CO

2. Properties

2.1 Density: 1.036

2.1 Melting point: 42-44 °C

2.1 Boiling point: 74-76℃ (2 torr)

2.1 Refractive index: 1.4853

2.1 Flash Point: 86℃

2.1 Precise Quality: 101.08400

2.1 PSA: 32.26000

2.1 logP: 0.05950

2.1 Appearance: Colorless to light yellow liqui

2.2 Storage: 2-8℃

2.3 Chemical Properties: Colorless to light yellow liqui

2.4 Color/Form: Pale-yellow to Yellow-brown Liquid

2.5 pKa: 14.77±0.10(Predicted)

2.6 Water Solubility: Very soluble

2.7 Stability: Stable at room temperature in closed containers under normal storage and handling conditions.

2.8 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Produe Method

3.2 Usage: L-Prolinol is an intermediate in the synthesis of Physostigmine and Physostigmine derivative used for treatment of Alzheimer's disease. L-(+)-Prolinol Preparation Products And Raw materials Preparation Products

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S26;S37/39

4.1 WGK Germany: 3

4.1 Safety: Hazard Symbols:?Xi
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

4.2 Sensitive: Air Sensitive

4.3 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.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Serious eye damage, Category 1

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H302 Harmful if swallowed H318 Causes serious eye damage H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P310 Immediately call a POISON CENTER/doctor/\u2026 P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in CDCl3

1H NMR : 400 MHz in CDCl3

IR : liquid film

Mass

7. Synthesis Route

23356-96-9Total: 41 Synthesis Route

98-79-3 356 Suppliers

23356-96-9 250 Suppliers

17342-08-4 176 Suppliers

Literatures:
US2004/225133 A1, ; Page 6-7 ;
Yield: null

147-85-3 624 Suppliers

23356-96-9 250 Suppliers

Literatures:
HUMAN BIOMOLECULAR RESEARCH INSTITUTE Patent: WO2006/25920 A2, 2006 ; Location in patent: Page/Page column 56-57 ; WO 2006/025920 A2
Yield: ~99%

498-63-5 28 Suppliers

23356-96-9 250 Suppliers

Literatures:
Kawabata, Takeo; Kuroda, Akio; Nakata, Eizo; Takasu, Kiyosei; Fuji, Kaoru Tetrahedron Letters, 1996 , vol. 37, # 24 p. 4153 - 4156
Yield: ~35%

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8. Precursor and Product

precursor:

128269-65-8

82379-40-6

142-47-2

1148-11-4

171753-91-6

98-79-3

147-85-3

171561-58-3

153870-19-0

5817-26-5

62024-36-6

1451214-36-0

32159-21-0

171561-60-7

171561-65-2

854917-80-9

153870-09-8

128257-10-3

171561-67-4

153870-06-5

6216-63-3

128257-13-6

498-63-5

2133-40-6

128257-12-5

View all

product :

182277-12-9

183014-03-1

403477-64-5

460746-46-7

130418-90-5

63126-45-4

22795-99-9

86661-32-7

338945-22-5

53912-80-4

146405-63-2

69610-40-8

460748-84-9

61350-66-1

51368-34-4

65921-41-7

34381-71-0

91790-91-9

174213-51-5

51207-66-0

174213-76-4

72500-25-5

851394-30-4

186202-18-6

127075-47-2

View all

9. Other Information

9.0 Usage: It is an active pharmaceutical intermediate.

10. Computational chemical data

Molecular Weight: 101.149g/mol
Molecular Formula: C₅H₁₁NO
Compound Is Canonicalized: True
XLogP3-AA: -0.3
Exact Mass: 101.084063974
Monoisotopic Mass: 101.084063974
Complexity: 56
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 32.3
Heavy Atom Count: 7
Defined Atom Stereocenter Count: 1
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBiIAAAAAAAAAAAAAAAAAAAAWAAAAAAAAAAAAAAAAAAAAAAHgAQCAAACCjhgAYAAALAAgAAAAAAAAAAAAAAAAAAAIAIAAACEAIAgAAEQAAEEACQAACQEAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==