Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

00762

Sigma-Aldrich

(R)-4-Phenyloxazolidine-2-thione

≥98.0%

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C9H9NOS
CAS Number:
171877-37-5
Molecular Weight:
179.24
MDL number:
MFCD06658220
UNSPSC Code:
12352005
PubChem Substance ID:
329747134
NACRES:
NA.22

Quality Level

100

Assay

≥98.0%

optical activity

[α]/D -75±5°, c = 0.2 in chloroform

optical purity

enantiomeric ratio: 97.0:3.0 (LC)

SMILES string

S=C1N[C@@H](CO1)c2ccccc2

InChI

1S/C9H9NOS/c12-9-10-8(6-11-9)7-4-2-1-3-5-7/h1-5,8H,6H2,(H,10,12)/t8-/m0/s1

InChI key

LVIJIGQKFDZTNC-QMMMGPOBSA-N

Application

A highly selective and efficient chiral auxiliary which can be directly reduced to its corresponding aldehyde and the chiral auxiliary by reductive cleavage with diisobutylaluminum hydride.

Storage Class Code

13 - Non 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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCBH7584V
BCBJ2566V
1295800

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

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

Visit the Document Library

Velazquez. F.; Olivo, H. F.
Current Organic Chemistry, 6, 303-303 (2002)
M T Crimmins et al.
Organic letters, 2(6), 775-777 (2001-02-07)
[formula: see text] Asymmetric aldol additions using chlorotitanium enolates of thiazolidinethione propionates proceed with high diastereoselectivity for the "Evans" or "non-Evans" syn product depending on the nature and amount of the base used. With (-)-sparteine as the base, selectivities of

Articles

Evans-Type Auxiliaries

The asymmetric aldol reaction mediated by chiral auxiliaries is considered to be one of the most important methods for asymmetric C-C bond formation.

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