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Sigma-Aldrich

(2S)-N-[(1S,2S)-2-Hydroxy-1,2-diphenylethyl]-2-pyrrolidinecarboxamide

≥99% (HPLC)

Synonym(s):

(2S,1′S, 2′S)-Pyrrolidine-2-carboxylic acid (2-hydroxy-1,2-diphenyl-ethyl)amide

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About This Item

Empirical Formula (Hill Notation):
C19H22N2O2
CAS Number:
529486-26-8
Molecular Weight:
310.39
MDL number:
MFCD10000880
UNSPSC Code:
12352005
PubChem Substance ID:
329760409
NACRES:
NA.22

Assay

≥99% (HPLC)

optical activity

[α]/D -25±2°, c = 2 in ethanol

mp

127-131 °C

storage temp.

2-8°C

SMILES string

O[C@H]([C@@H](NC(=O)[C@@H]1CCCN1)c2ccccc2)c3ccccc3

InChI

1S/C19H22N2O2/c22-18(15-10-5-2-6-11-15)17(14-8-3-1-4-9-14)21-19(23)16-12-7-13-20-16/h1-6,8-11,16-18,20,22H,7,12-13H2,(H,21,23)/t16-,17-,18-/m0/s1

InChI key

JVOUIFUIIPEWLM-BZSNNMDCSA-N

Application

(2S)-N-[(1S,2S)-2-Hydroxy-1,2-diphenylethyl]-2-pyrrolidinecarboxamide can be used as a catalyst:
  • In the synthesis of α-hydroxyamino carbonyl compounds by reacting aldehydes with nitrosobenzenes via N-nitroso aldol reaction.
  • In the direct aldol reactions of aldehydes with chloroacetones, methylthio- and fluoroacetones.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

Signal Word

Danger

Hazard Statements

H301 + H331,H410

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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L-Prolinamide-catalyzed direct nitroso aldol reactions of α-branched aldehydes: A distinct regioselectivity from that with L-proline
Guo H, et al.
Chemical Communications (Cambridge, England), 429-431 (2006)
l-Proline amides catalyze direct asymmetric aldol reactions of aldehydes with methylthioacetone and fluoroacetone
Xu X, et al.
Tetrahedron Asymmetry, 18(2), 237-242 (2007)
L-Proline amide-catalyzed direct asymmetric aldol reaction of aldehydes with chloroacetone
He L, et al.
Tetrahedron, 62(2-3), 346-351 (2006)

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