ChemicalBook > CAS DataBase List > (S)-(-)-ALPHA,ALPHA-DIPHENYL-2-PYRROLIDINYL METHYLTMS ETHER

(S)-(-)-ALPHA,ALPHA-DIPHENYL-2-PYRROLIDINYL METHYLTMS ETHER

Product Name
(S)-(-)-ALPHA,ALPHA-DIPHENYL-2-PYRROLIDINYL METHYLTMS ETHER
CAS No.
848821-58-9
Chemical Name
(S)-(-)-ALPHA,ALPHA-DIPHENYL-2-PYRROLIDINYL METHYLTMS ETHER
Synonyms
S-Diphenylprolinol trimethyl silyl ether;(S)-Diphenylprolinol Trimethyl Silyl Ether,99%e.e.;(2s)-2-[diphenyl[(trimethylsilyl)oxy]methyl]pyrrolidine;(S)-(–)-α,α-DiphenyL;(S)-Hayashi-Jorgensen Catalyst;Jorgenson-Hayashi organocatalyst;[(DIPHENYL)TRIMETHYLSILOXYMETHYL]PYRROLIDINE;(S)-(-)-[(DIPHENYL)TRIMETHYLSILOXYMETHYL]PYRROLIDINE;-diphenyl-2-pyrrolidine methanoltrimethylsilyl ether
CBNumber
CB8838775
Molecular Formula
C20H27NOSi
Formula Weight
325.52
MOL File
848821-58-9.mol
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(S)-(-)-ALPHA,ALPHA-DIPHENYL-2-PYRROLIDINYL METHYLTMS ETHER Property

Boiling point:
412.7±35.0 °C(Predicted)
Density 
1.0459 g/mL at 25 °C
refractive index 
n20/D 1.5513
Flash point:
110 °C
storage temp. 
2-8°C
pka
10.01±0.10(Predicted)
form 
liquid
color 
Yellow
optical activity
[α]22/D -50°, c = 1 in chloroform
Hydrolytic Sensitivity
7: reacts slowly with moisture/water
λmax
193nm(lit.)
InChI
InChI=1S/C20H27NOSi/c1-23(2,3)22-20(19-15-10-16-21-19,17-11-6-4-7-12-17)18-13-8-5-9-14-18/h4-9,11-14,19,21H,10,15-16H2,1-3H3/t19-/m0/s1
InChIKey
RSUHWMSTWSSNOW-IBGZPJMESA-N
SMILES
N1CCC[C@H]1C(C1=CC=CC=C1)(C1=CC=CC=C1)O[Si](C)(C)C
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Safety

Hazard Codes 
Xi,Xn,F
Risk Statements 
36/37/38-67-65-48/20-38-11-63
Safety Statements 
26-62-36/37-16
RIDADR 
UN1294 - class 3 - PG 2 - Toluene, solution
WGK Germany 
3
TSCA 
No
HS Code 
29339900
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
677183
Product name
(S)-(–)-α,α-Diphenyl-2-pyrrolidinemethanol trimethylsilyl ether
Purity
95%
Packaging
1g
Price
$178
Updated
2025/07/31
Sigma-Aldrich
Product number
677183
Product name
(S)-(–)-α,α-Diphenyl-2-pyrrolidinemethanol trimethylsilyl ether
Purity
95%
Packaging
5g
Price
$530
Updated
2025/07/31
TCI Chemical
Product number
D3843
Product name
(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol Trimethylsilyl Ether
Purity
>98.0%(GC)(T)
Packaging
1g
Price
$201
Updated
2025/07/31
TCI Chemical
Product number
D3843
Product name
(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol Trimethylsilyl Ether
Purity
>98.0%(GC)(T)
Packaging
5g
Price
$804
Updated
2025/07/31
Sigma-Aldrich
Product number
706442
Product name
(S)-(?)-α,α-Diphenyl-2-pyrrolidinemethanoltrimethylsilyl ether solution
Purity
0.05 M in toluene
Packaging
25ml
Price
$97.9
Updated
2023/01/07
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(S)-(-)-ALPHA,ALPHA-DIPHENYL-2-PYRROLIDINYL METHYLTMS ETHER Chemical Properties,Usage,Production

Chemical Properties

Light yellow liquid

Uses

Organocatalyst for 3-component reactions, and Robinson annulation of α,β-unsaturated aldehydes.

Synthesis

75-77-4

22348-32-9

848821-58-9

To a solution of (S)-diphenylprolinol (4.00 g, 15.8 mmol, 1.00 eq.) in dichloromethane (40 mL) was added imidazole (3.22 g, 47.4 mmol, 3.00 eq.) at 0 °C. Trimethylchlorosilane (5.00 mL, 39.5 mmol, 2.50 eq.) was added slowly and the reaction mixture was subsequently stirred at room temperature for 12 hours. Upon completion of the reaction, the reaction mixture was diluted by addition of methyl tert-butyl ether (MTBE, 100 mL) and filtered to remove insoluble material. The organic phase was washed sequentially with water (50 mL) and saturated aqueous sodium chloride solution (2 x 50 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the colorless oily product (2S)-2-[diphenyl[(trimethylsilyl ester)oxy]methyl]-pyrrolidine (11, 5.00 g, 15.3 mmol, 97% yield). The product was characterized by 1H NMR (400 MHz, CDCl3), 13C NMR (101 MHz, CDCl3) and HR-MS (ESI), and the data were consistent with the expected structure.

References

[1] Journal of the American Chemical Society, 2014, vol. 136, # 52, p. 18140 - 18148
[2] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 18, p. 4996 - 5001
[3] Angewandte Chemie - International Edition, 2005, vol. 44, # 27, p. 4212 - 4215
[4] Patent: WO2010/144293, 2010, A1. Location in patent: Page/Page column 29
[5] Journal of Organic Chemistry, 2010, vol. 75, # 22, p. 7829 - 7841

(S)-(-)-ALPHA,ALPHA-DIPHENYL-2-PYRROLIDINYL METHYLTMS ETHER Preparation Products And Raw materials

Raw materials

Preparation Products

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(S)-(-)-ALPHA,ALPHA-DIPHENYL-2-PYRROLIDINYL METHYLTMS ETHER Suppliers

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View Lastest Price from (S)-(-)-ALPHA,ALPHA-DIPHENYL-2-PYRROLIDINYL METHYLTMS ETHER manufacturers

Zhuozhou Wenxi import and Export Co., Ltd
Product
(S)-()-α,α-Diphenyl-2-pyrrolidinemethanoltrimethylsilyl ether solution 848821-58-9
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-06-27
Career Henan Chemical Co
Product
(S)-(-)-ALPHA,ALPHA-DIPHENYL-2-PYRROLIDINYL METHYLTMS ETHER 848821-58-9
Price
US $2.00/KG
Min. Order
1g
Purity
98%min
Supply Ability
ask
Release date
2020-01-08

848821-58-9, (S)-(-)-ALPHA,ALPHA-DIPHENYL-2-PYRROLIDINYL METHYLTMS ETHERRelated Search:

S-2-[[[(1,1-diMethylethyl)diMethylsilyl]oxy]bis(3,5-diMethylphenyl)Methyl]-Pyrrolidine S-2-[bis[3,5-bis(trifluoroMethyl)phenyl] [(triethylsilyl)oxy]Methyl]-Pyrrolidine (S)-[(diphenyl)-t-butyldimethylsiloxymethyl]pyrrolidine (S)-2-{Bis[3,5-bis(trifluoromethyl)phenyl]hydroxymethyl}pyrrolidine S-2-[bis[3,5-bis(3,5-diMethylphenyl] [(triethylsilyl)oxy]Methyl]-Pyrrolidine S-2-[bis[3,5-bis(trifluoroMethyl)phenyl][[(1,1-diMethylethyl)diMethylsilyl]oxy]Methyl]-Pyrrolidine S-2-[diphenyl[(triethylsilyl)oxy]Methyl]-Pyrrolidine (S)-(-)-2-[Bis(3,5-dimethylphenyl)hydroxymethyl]pyrrolidine Pyrrolidine, 2-[bis(3,5-dimethylphenyl)[(trimethylsilyl)oxy]methyl]-, (2S)- Pyrrolidine, 2-[diphenyl[(trimethylsilyl)oxy]methyl]-, (2R)- (S)-2-[(Bis(3,5-bis(trifluoromethyl)phenyl)trimethylsilanyloxy)methyl]pyrrolidine, (S)-2-[(Bis(3,5-bis(trifluoromethyl)phenyl)trimethylsilyloxy)methyl]pyrrolidine, (S)-α,α-[3,5-Bis(trifluoromethyl)phenyl]prolinol trimethylsilyl ether (S)a,a-Bis(3,5-dimethylphenyl)prolinol trimethylsilyl ether hydrochloride, (S)-2-[Bis(3,5-dimethylphenyl)(trimethylsilyloxy)methyl]pyrrolidine hydrochloride (S)-2-DIPHENYLMETHYLPYRROLIDINE (S)-(-)-ALPHA,ALPHA-DIPHENYL-2-PYRROLIDINYL METHYLTMS ETHER (S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol

  • (S)-(–)-α,α-Diphenyl-2-pyrrolidineMethanol triMethylsilyl ether 95%
  • (S)-()-α,α-Diphenyl-2-pyrrolidineMethanoltriMethylsilyl ether solution 0.05 M in toluene
  • (S)-(-)-α,α-Diphenyl-2-pyrrolidoneMethanoe triMethylsilys ether
  • (S)-(-)-[(DIPHENYL)TRIMETHYLSILOXYMETHYL]PYRROLIDINE
  • [(DIPHENYL)TRIMETHYLSILOXYMETHYL]PYRROLIDINE
  • (S)-(-)-alpha,alpha-Diphenyl-2-pyrrolidineMethanol triMethylsilyl ether 95%
  • (S)-(?)-α,α-Diphenyl-2-pyrrolidinemethanoltrimethylsilyl ether solution
  • (S)-2-[Diphenyl(Trimethylsilanyloxy)Methyl]Pyrrolidine
  • Jorgenson-Hayashi organocatalyst
  • (S)-(-)-alpha,alpha-Diphenyl-2-pyrrolidinemethanoltrimethylsilyl ether solution 0.05 M in toluene
  • (S)-Diphenylprolinol Trimethyl Silyl Ether,99%e.e.
  • (S)-(-)-ALPHA,ALPHA-DIPHENYL-2-PYRROLIDINEMETHANOL TRIMETHYLSILYL ETHER, 95%
  • (2s)-2-[diphenyl[(trimethylsilyl)oxy]methyl]pyrrolidine
  • (s)-(-)-α,α-diphenyl-2-pyrrolidine methanol trimethylsilyl ether
  • (2S)-2-[Diphenyl[(trimethylsilyl)oxy]methyl]pyrrolidine, (S)-α,α-Diphenylprolinol trimethylsilyl ether, (S)-2-[Diphenyl(trimethylsilanyloxy)methyl]pyrrolidine
  • (S)-(-)-ALPHA,ALPHA-DIPHENYL-2-PYRROLIDINYL METHYLTMS ETHER
  • Pyrrolidine, 2-[diphenyl[(trimethylsilyl)oxy]methyl]-, (2S)-
  • -diphenyl-2-pyrrolidine methanoltrimethylsilyl ether
  • (s)-(-)-lmdiphenyl-2-pyrrolidine methanoltrimethylsilyl ether
  • S-Diphenylprolinol trimethyl silyl ether
  • (S)-2-((2,2-diphenylethyl)diMethylsilyloxy)pyrrolidine
  • (S)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine
  • Diphenyl-(2S)-pyrrolidin-2-ylmethoxy-trimethyl-silane
  • (S)-(-)-alpha,alpha-Diphenyl-2-pyrrolidinemethanoltrimethylsilyl ether solution
  • )-α,α-DiphenyL
  • (S)-Hayashi-Jorgensen Catalyst
  • alpha,alpha-Diphenyl-L-prolinol Trimethylsilyl Ether
  • (S)-(–)-α，α-Diphenyl-2-pyrrolidinemethanol trimethylsilyl ether
  • )-α,α-Diphenyl-2-pyrrolidinemethanol trimethylsilyl ether
  • (S)-()-α,α-Diphenyl-2-pyrrolidinemethanoltrimethylsilyl ether solution
  • (S)-(&#x2013
  • (<i>S</i>)-(–)-α,α-Diphenyl-2-pyrrolidinemethanol trimethylsilyl ether
  • (<i>S</i>)-(?)-α,α-Diphenyl-2-pyrrolidinemethanoltrimethylsilyl ether solution
  • 848821-58-9
  • C20H27NOSi