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294640

(S)-4-Benzyl-2-oxazolidinone

Name: (<I>S</I>)-4-Benzyl-2-oxazolidinone
Brand: ALDRICH

99%

Synonym(s):

(4S)-(-)-4-(Phenylmethyl)-1,3-oxazolidin-2-one, (4S)-4-(Phenylmethyl)-2-oxazolidinone, (4S)-4-benzyl-1,3-oxazolidin-2-one, (S)-(-)-4-benzyl-2-oxazolidinone, (S)-4-benzyloxazolidin-2-one

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About This Item

Empirical Formula (Hill Notation):

C₁₀H₁₁NO₂

CAS Number:

90719-32-7

Molecular Weight:

177.20

UNSPSC Code:

12352005

NACRES:

NA.22

PubChem Substance ID:

24857725

MDL number:

MFCD00064496

Beilstein/REAXYS Number:

3649667

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Properties

Quality Level

200

assay

99%

form

solid

optical activity

[α]20/D −63°, c = 1 in chloroform

optical purity

ee: 99% (HPLC)

mp

86-88 °C (lit.)

functional group

phenyl

SMILES string

O=C1N[C@H](CO1)Cc2ccccc2

InChI

1S/C10H11NO2/c12-10-11-9(7-13-10)6-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,11,12)/t9-/m0/s1

InChI key

OJOFMLDBXPDXLQ-VIFPVBQESA-N

Description

Application

Used for asymmetric synthesis of (3R)- and (3S)-piperazic acid.

Chiral auxiliary for asymmetric alkylation.

Chiral auxiliary used recently in a synthesis of (S)-equol. Preparation and functionalization of chiral, stabilized ylides.

pictograms

GHS08,GHS07

signalword

Warning

hcodes

H302,H373

pcodes

P260 - P264 - P270 - P301 + P312 - P314 - P501

Hazard Classifications

Acute Tox. 4 Oral - STOT RE 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Total synthesis and structural revision of (+)-amphidinolide W.

Arun K Ghosh et al.

Journal of the American Chemical Society, 126(12), 3704-3705 (2004-03-25)

An enantioselective first total syntheis of amphidinolide W (2) and a revision of its C6 absolute stereochemistry (1) are described. Amphidinolide W (1), a 12-membered macrolide isolated from Amphidinium sp., has shown potent antitumor properties against a variety of NCI

Total synthesis of (S)-equol.

Jennifer M Heemstra et al.

Organic letters, 8(24), 5441-5443 (2006-11-17)

The first enantioselective total synthesis of (S)-equol is reported. The described route relies on an Evans alkylation to form the stereocenter and an intramolecular Buchwald etherification to generate the chroman ring. Key features of this method include its brevity, its

Tetrahedron Letters, 33, 7613-7613 (1992)

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Global Trade Item Number

SKU	GTIN
294640-5G	04061826601341
294640-25G	04061833546048