2-Pyrrolidinemethanol, alpha,alpha-diphenyl-, (S)- (HCID 2724899)

Names & identifiers

Preferred name: 2-Pyrrolidinemethanol, alpha,alpha-diphenyl-, (S)-
IUPAC: diphenyl-[(2S)-pyrrolidin-2-yl]methanol
English name: (S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol
Molecular formula: C17H19NO
Molecular weight: 253.34

Names & synonyms

112068-01-6(S)-(-)-alpha,alpha-Diphenyl-2-pyrrolidinemethanolalpha,alpha-Diphenyl-L-prolinolK3HE3KC32M(S)-alpha,alpha-Diphenylprolinol(-)-alpha,alpha-Diphenylprolinol(2S)-alpha,alpha-Diphenyl-2-pyrrolidinemethanol(s)-alpha,alpha-diphenylpyrrolidinemethanol(-)-alpha,alpha-Diphenyl-2-pyrrolidinemethanol2-Pyrrolidinemethanol, alpha,alpha-diphenyl-, (2S)-2-Pyrrolidinemethanol, alpha,alpha-diphenyl-, (S)-.ALPHA.,.ALPHA.-DIPHENYL-L-PROLINOL

Show more names

(S)-DIPHENYLPROLINOL(S)-DIPHENYL(PYRROLIDIN-2-YL)METHANOLSDPPDiphenyl(2-pyrrolidinyl)methanol(S)-(-)-2-(DIPHENYLHYDROXYMETHYL)PYRROLIDINEalpha,alpha-DiphenylNebivolol Impurity 49Dextrodiphenylprolinol

(S)-.ALPHA.,.ALPHA.-DIPHENYLPROLINOL(-)-.ALPHA.,.ALPHA.-DIPHENYLPROLINOL(S)-.ALPHA.,.ALPHA.-DIPHENYLPYRROLIDINEMETHANOL(-)-.ALPHA.,.ALPHA.-DIPHENYL-2-PYRROLIDINEMETHANOL(2S)-.ALPHA.,.ALPHA.-DIPHENYL-2-PYRROLIDINEMETHANOL2-PYRROLIDINEMETHANOL, .ALPHA.,.ALPHA.-DIPHENYL-, (2S)-2-PYRROLIDINEMETHANOL, .ALPHA.,.ALPHA.-DIPHENYL-, (S)-RefChem:483466

Database identifiers

CAS: 112068-01-6
PubChem CID: 2724899
DTXSID: DTXSID50369275
UNII: K3HE3KC32M
EC Number: 601-153-1
Nikkaji: J370.862D

Properties

Computed structural properties

XLogP: 2.7
Topological polar surface area: 32.3 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 2
Rotatable bonds: 3
Heavy atoms: 19
Formal charge: 0
Complexity: 261

Physicochemical properties

Melting point: 77 · 77-80 °C(lit.)
alpha: -59 · -59 º (c=3, methanol 25 ºC)
Boiling point: 396.54 °C · 396.54°C (rough estimate)
Density: 1.0078 · 1.0078 (rough estimate)
refractive index: -66.5 ° · -66.5 ° (C=3, CHCl3)
storage temp.: Inert atmosphere,Room Temperature
solubility: Soluble in chloroform.
form: powder
pka: 13.15 · 13.15±0.29(Predicted)
color: white to off white ., crystal
optical activity: 20 · [α]20/D 67°, c = 3 in chloroform
Merck: 14 · 14,155
BRN: 17103 · 17103
InChI: 1S/C17H19NO/c19-17(16-12-7-13-18-16,14-8-3-1-4-9-14)15-10-5-2-6-11-15/h1-6,8-11,16,18-19H,7,12-13H2/t16-/m0/s1
InChIKey: OGCGXUGBDJGFFY-INIZCTEOSA-N
SMILES: OC([C@@H]1CCCN1)(c2ccccc2)c3ccccc3
CAS DataBase Reference: 112068 · 112068-01-6(CAS DataBase Reference)
FDA UNII: 3 HE3KC32M · K3HE3KC32M
NIST Chemistry Reference: -1 · S-(-)-1,1-diphenylprolinol(112068-01-6)
UNSPSC Code: 12352005 · 12352005
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
target organs: Respiratory system
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-37/39-24/25-36
WGK Germany: 3 · 3
F: 10 · 10-34
TSCA: No
HS Code: 29339900 · 29339900
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3

Safety & regulation

GHS classification

GHS Classification · 5 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (95.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 47 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)；Eye Irrit. 2 (100%)；STOT SE 3 (95.7%)

Safety data

F: 10-34
PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
tsca: No
hs_code: 29339900
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-37/39-24/25-36
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H315-H319-H335
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P264-P271-P280-P302+P352-P305+P351+P338

Chemistry & industry

Applications · 3 items

Usessuzuki reaction

Uses(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol is used to prepare the corresponding oxazaborolidines for the borane-mediated asymmetric reduction of ketones.

General Description(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol is a bifunctional organocatalyst.

Preparation methods · 1 item

PreparationInto a four-necked flask, add tetrahydrofuran, L-proline methyl ester hydrochloride, and phenyl magnesium chloride （dissolved in tetrahydrofuran) solution was added dropwise from a constant pressure dropping funnel, and the addition was completed in about 4 hours, and then stirred at 10-15°C for 3 hours. Add water, adjust the pH to 5-6 with 10% ammonium chloride aqueous solution, extract with dichloromethane, extract the aqueous layer twice with dichloromethane each time, and obtain the organic phase. Wash once with saturated sodium chloride aqueous solution. The organic phase was dried with anhydrous sodium sulfate for 4 hours and filtered. The obtained organic phase was distilled under reduced pressure to distill dichloromethane and tetrahydrofuran to obtain light yellow oily (S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol, yield 86.6%.