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06357

Sigma-Aldrich

(S)-4-Benzylthiazolidine-2-thione

≥95.0% (GC)

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About This Item

Empirical Formula (Hill Notation):
C10H11NS2
CAS Number:
171877-39-7
Molecular Weight:
209.33
MDL number:
MFCD06658216
UNSPSC Code:
12352005
PubChem Substance ID:
329748231
NACRES:
NA.22

Quality Level

100

Assay

≥95.0% (GC)

optical activity

[α]20/D -122±5°, c = 1% in chloroform

optical purity

enantiomeric ratio: ≥99:1 (LC)

SMILES string

S=C1N[C@H](CS1)Cc2ccccc2

InChI

1S/C10H11NS2/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

SLDUGQISGRPGAW-VIFPVBQESA-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

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK0649
BCCD1805
BCCC0431
BCBX7243
BCBX5576

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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
Velazquez. F.; Olivo, H. F.
Current Organic Chemistry, 6, 303-303 (2002)

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