Skip to Content
Merck
All Photos(1)

Key Documents

298891

Sigma-Aldrich

(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone

99%

Synonym(s):

(4R,5S)-4-Methyl-5-phenyl-2-oxazolidinone

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C10H11NO2
CAS Number:
Molecular Weight:
177.20
Beilstein:
1211705
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

Assay

99%

form

solid

optical activity

[α]18/D +168°, c = 2 in chloroform

optical purity

ee: 98% (GLC)

mp

121-123 °C (lit.)

SMILES string

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

InChI

1S/C10H11NO2/c1-7-9(13-10(12)11-7)8-5-3-2-4-6-8/h2-7,9H,1H3,(H,11,12)/t7-,9-/m1/s1

InChI key

PPIBJOQGAJBQDF-VXNVDRBHSA-N

Application

Evan′s chiral auxiliary (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone reacts with carboxylic acids to produce corresponding acyl derivatives in the presence of a diisopropylcarbodiimide reagent. It can also employed in the preparation of N-sulfinyloxazolidinone reagent (chiral sulfinyl transfer reagent), which reacts with nucleophiles such as Grignard reagents, enolates, and metalated amides to produce the chiral sulfoxides, sulfinate esters, and sulfonamides.

Storage Class Code

11 - Combustible Solids

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 1

1 of 1

The Journal of Organic Chemistry, 57, 1179-1179 (1992)
Asymmetric synthesis of chiral organosulfur compounds using N-sulfinyloxazolidinones
Evans DA, et al.
Journal of the American Chemical Society, 114(15), 5977-5985 (1992)
DIC-mediated coupling of carboxylic acids to (4R, 5S)-4-methyl-5-phenyl-2-oxazolidinone
Graham JM, et al.
Synthetic Communications, 30(7), 1221-1226 (2000)
The Journal of Organic Chemistry, 57, 1744-1744 (1992)
Tetrahedron, 48, 7527-7527 (1992)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service